This as-told-to essay is based on a transcribed conversation with Steve Yegge, a 56-year-old from Washington, about working at Amazon — founded in 1994 — from 1998 to 2005. The following has been edited for length and clarity.

When I was still finishing up college, I started working for a software company, and one of my college friends told us the saddest news ever: She was going to work at an online bookstore.

It sounded like she was going to be a librarian, but it turned out she was onto something: She was one of the first Amazon employees.

Later on, another friend upped and went to Amazon, saying he got an offer he couldn't refuse. I started poking around and was next to leave — I joined Amazon in 1998 as a technical program manager.

I worked my way up and eventually found myself working on a secret project for Jeff Bezos himself. He was a hands-on leader with an unmistakable magnetism to him, but he didn't seem to care about anything other than his mission. Despite the fact that I disagreed with the company's practices, Bezos himself was difficult to dislike.

It's hard not to like a person who's that smart.

I could tell Bezos was on to something big when I started at Amazon

When I joined the company in the late 90s, Amazon was hiring like crazy. Bezos was on a mad mission to get big fast. As soon as I got there, I started interviewing other candidates. At times, I was scheduled for two interviews at the same time, so I'd run back and forth between the rooms to ask them questions.

The Amazon office was unlike the conventional startup atmosphere I was used to. The building was grungy and the offices were dark and dingy.

Despite that, once you stepped into the building, there was a crackle in the air. You could feel that something really big was going on — and it was all centered on Jeff.

I worked across multiple parts of the company, including on a secret project for Jeff

To get hired at Amazon, I asked my friend who left before me to deliver my résumé. After interviewing, I wound up in the technical program management organization. My job for the first year was to help coordinate projects that spanned across multiple teams.

Then, I spent roughly two and a half years in customer service tools and led the engineering team for a year and a half of that time. The craziest things would happen in that part of the company: There'd be transportation mishaps, and we'd send people the extraordinarily wrong thing, but then we'd go overboard trying to make things right for the customer. We had all the best stories. I then became an engineering manager in developer tools.

Toward the end of my time at Amazon, Jeff asked me to work on a secret project. He was always dreaming up stuff and assigning tasks that seemed impossible. The project was meant to be something like Reddit.

I didn't know enough about distributed computing to pull off what Jeff wanted in his desired timeframe. I felt the project wasn't feasible at the time, but I was scared to deliver that message to Jeff.

Meanwhile, Google offered me a great package, so I left Amazon in 2005 to work there.

I didn't like working at Amazon, but I actually really liked Jeff

Jeff was a very hands-on leader. He'd often come to our customer service meetings and look at the data showing why customers were contacting us.

I've worked under other CEOs, including Google's Larry Page and Eric Schmidt, and they didn't typically pull senior employees together for impromptu chats, but Jeff would do this quite often. He'd reset us and change how everyone in the company thought about things.

He challenged people every day, but I never saw him get mad or swear in my almost seven years there. He had this electric presence, a magnetism to him that was unmistakable.

However, I found Amazon could be a horrible place to work. I'm still a customer and don't boycott them because of their practices, though I disagree with some of them.

While I worked at Amazon, there was this pressure that everybody had to work all the time, and people avoided asking for time off. Some employees would berate others. A friend of mine worked in a closet because that's the only place where there was room for a desk.

From what I could tell, Jeff is a hear-no-evil, see-no-evil kind of person who was focused on the mission. It didn't matter if the toilet was dirty or if engineers were being paged all night long. He seemed to only care if it started slowing him down. Maybe that's the kind of leader you have to be. Successful leaders don't take no for an answer.

Working with Jeff and his leadership team was normally calm and serious with a sense of urgency, like in a war room. People were very cautious with their words around him. When people raised concerns to him, he'd sometimes laugh in their faces.

I felt like Amazon employees could never say if something bad was happening at Amazon. You could be brave and raise issues, but you were swimming against the stream.

In 2011, years after I left Amazon, I accidentally publicly shared a private post about working at Google and Amazon where I described Jeff as a control freak. The post blew up and made it into the Wall Street Journal. I heard through the grapevine Jeff was aware of the post and got a laugh out of it.

Jeff was likable, so I was glad to hear he wasn't angry. He consistently came across as calm and keenly interested in everything everyone has to say. He wasn't afraid to ask questions or appear ignorant. He was never difficult to work with, even though he could be difficult to work for at times because of his super-high expectations.

He tries to keep things very real, and it's kind of hard not to like somebody like that.

In response to Business Insider's request for comment, an Amazon spokesperson said, "Business Insider declined to share the information needed to verify this individual's account from over 20 years ago." They added, an "anecdote from one person isn't representative of what it was like to work at Amazon then or what it's like now."

BI reached out to representatives for Jeff Bezos but received no response.

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• Building relationships well is widely considered to be a desirable soft skill in the workplace.
• You might call it 'networking.' But Langni Zeng has been calling it 'biz rizz.'
• Zeng, who learned people skills at McKinsey, shared her top tips for developing 'biz rizz.'

This as-told-to essay is based on a transcribed conversation with 25-year-old Langni Zeng, based in LA. The following has been edited for length and clarity.

During my college years studying business at Queen's University in Canada a lot of my fellow students' parents were VPs at big organizations.

There's a certain culture to their backgrounds around the way you dress, how you speak, and what you talk about. One big culture shock for me was learning how to pick wine at dinner.

My dad is an engineer, and my mum is a former lecturer, so I wasn't very exposed to corporate America. I didn't grow up around corporate functions or know what investment banking or the consulting space was like.

At college, I learned more about consulting and saw it as a good field for someone like me who wanted to be a generalist and work on problem-solving. I took part in consulting extracurriculars and landed an internship at McKinsey for the summer of my third year.

After the internship, I joined McKinsey full-time as a business analyst in 2021.

I stayed at McKinsey for around two years and then left to take on a director of strategy and business operations role for a tech company. My tenure at McKinsey strengthened my ability to build relationships in professional environments, a skill that has helped me throughout my career. I've also been using a fun term to describe this skill: biz rizz.

Mentors helped me with relationship-building skills

When I started at McKinsey, I was linked up with a professional development manager who helped staff me on projects. In consulting, you don't really have a set manager and team — it's all project-based. Every few weeks or months, you're working with new people, clients, and often in new cities.

There are obviously hard skills consultants should have, like making Excel models and analysis, but also soft skills — the ability to build relationships with clients. Some of this was formally taught, such as in a training session about trust, but I also developed soft skills organically.

One of my biggest barriers to developing relationships in the workplace was confidence and comfort. At McKinsey, you can be 21 sitting in a room with C-Suite executives, which can be intimidating. You overthink in those situations about what's appropriate to say.

When my parents found out I had this job, they advised me to keep my head down, but I think professional relationship-building is important. I tried figuring out how to network and make small talk.

I was lucky to have great mentors on my first projects. One of my managers coached me to present to a C-suite executive. One of my mentors told me to think about the executive as my friend's uncle or someone I know in real life to make things feel more familiar.

At first, I struggled to relate during some conversations with my peers. Travel came up a lot; I didn't grow up skiing in the Alps or playing golf. Going to business school helped train me for these conversations, and my background wasn't as big of a constraint as I thought. I think the key is to be authentically yourself.

Having 'biz rizz' has helped me throughout my career so far

I used feedback from the teams I worked with to gauge how well I was developing my relationship-building skills.

On one project, I was tasked with preparing a celebration at the end of our off-site. It was a circle of appreciation. Everyone had to say what they appreciated about someone they were assigned, like a secret Santa.

I wrote a funny poem with silly rhymes about the person I was assigned, who was a client. I was more experienced at that point, so could confidently gauge what was appropriate. Earlier in my career, I wouldn't have done something like that. Afterward, the key stakeholder from that client referenced the poem for months after the off-site.

Soft skills like this can strengthen your reputation and relationships at work. They have been helpful beyond my time at McKinsey.

In a previous job, I was a director of strategy and business operations for a tech company. I was trying to facilitate change management and worked with leaders across different functions. You have to build trust-based relationships to get people to align with your vision. This can be hard when you're younger or new, but my time at McKinsey taught me how to engage with senior stakeholders.

At times when I've done coffee chats or mentorship sessions with students, a lot of their questions are about what grades they need or tactical skills they should build to get a certain job. That's all important, but another really important part is how you network and build a personal brand.

Here are some of my top tips for building 'biz rizz'

I've been casually using the term 'biz rizz' among friends for years. "Rizz" became a popular slang term used to refer to charisma, so we'd use 'biz rizz' to describe professional relationship-building. I posted a TikTok about this last year, which really took off.

One of my relationship-building tips is to end every interaction with the question, "How can I help?" or tell them, "If there's anything you need, let me know." This can be seen as strategic because people like it when you help them, but it's also a generally positive thing I'd do with people in my network.

Another big piece is communication. People really respond to a good speaker who is concise and eloquent. I was not naturally a good speaker, but being part of an international case competition team at college and doing presentations at McKinsey helped me with this.

Be authentically positive. Don't think of networking as a ploy to advance your interests, but think about how you can have the most fun working with people.

Many people perceive networking as kissing up to senior leaders, but I think it goes beyond that. I've learned so much and gotten so many opportunities from it.

Do you have a story to share about professional networking? Contact this reporter at [email protected]

• Deborah Fleischaker worked for the Department of Homeland Security and ICE under President Biden.
• Fleischaker witnessed the Trump administration make changes to immigration guidelines she worked on.
• She said she's feels that federal workers are being vilified and finds it sad to watch.

This as-told-to essay is based on a transcribed conversation with 52-year-old Deborah Fleischaker, from Washington, D.C. The following has been edited for length and clarity.

On election night, I knew I was out of a job.

I'd been working for the Department of Homeland Security as a political appointee under the Biden administration. I was hopeful about staying in my position under a Harris administration, but when Trump was elected, there was no question I was going to be leaving in January.

Political appointees serve at the direction of the president, and I didn't think President Donald Trump would ask me to stay on, or that I would stay on if asked.

I've always appreciated working for the underdog. I took my first job at the DHS in 2011. It was a departure from my background in nonprofits — I enjoyed trying to support both the system and the people in it.

I held multiple career and political positions within the DHS until January 2025, including as the chief of staff at Immigration and Customs Enforcement, or ICE.

Since leaving my job, I've been following updates on immigration policies in the news. It's been hard to watch changes being made, including to guidelines I was particularly proud to work on. I'm also disheartened to see how — in my view — government employees are being vilified right now.

I wanted to help shape policies in a political capacity during my career

I hadn't aspired to do government work, but it sounded interesting. My first role was in the Office for Civil Rights and Civil Liberties in the Department of Homeland Security. I ended up loving it and stayed for almost a decade.

I handled allegations of civil rights violations in DHS activities and ICE issues. I worked through the first Trump administration and wasn't thrilled about some of the changes.

After the Biden administration came in, I worked for the DHS Office of Policy on policies that put up guardrails around immigration enforcement near courthouses, schools, and medical facilities.

I became the assistant director of regulatory affairs and policy at ICE in 2021, shifting from government employee to political appointee, which is an ally of the party in power. I've held political roles ever since, including ICE's chief of staff and chief privacy officer.

There's an assumption that ICE employees are cold and on one side of politics, but that's not my experience. Many of us were trying to do the right thing, even if we didn't agree on what that was.

You can understand that immigration requires enforcement, including detention and removal, but also support legal pathways to migration. I tried to walk that line.

The Trump administration has rescinded a policy I was particularly proud of

I'm particularly proud of the guardrails around enforcement I worked on at ICE, such as the sensitive locations policy. It made me sad to see it reversed in the first week of the Trump administration.

I feel that previous administrations were able to enforce immigration laws with the policy in place. I don't think making people scared to go to the local police, hospitals, or schools is good for communities. Since the guidelines were rescinded, there have been reports of school attendance dropping among immigrant communities.

It's hard to watch the policy changes unfold because I know the blood, sweat, and tears that have gone into creating previous policies. I've been taken aback by the speed and scope of change since the Trump administration came in, even though intellectually, I could have predicted some of it.

I feel my former colleagues in government jobs are being vilified

I was sad to leave my job after the election. There was so much more I wanted to do and so many ways I thought ICE and DHS could continue to improve. There are lots of people in the department who I respect and would be honored to work with again.

I could have gotten another career job at the DHS, but I've decided to work as a self-employed consultant, mostly on immigration. We'll see if I like it.

The vast majority of government employees are nonpartisan, hardworking people who are trying to do the right thing with taxpayer money. But especially now, I feel they're being vilified through accusations of waste, fraud, and abuse by Trump and DOGE. There are certainly changes to the civil service I would agree with, but I think we should do that work carefully and thoughtfully.

It's incredibly disheartening to watch the hard work and careers of thousands of people be disparaged.

I'm proud of the work I did over the past four years and the relationships I've made throughout the department, including with people I have different political viewpoints from.

When asked to respond to Fleischaker's statements that the White House had suddenly reversed ICE guidelines, was vilifying federal workers and disparaging the hard work and careers of thousands of workers, a spokesperson for the White House replied that the Biden administration's handling of the United States border security was "incompetent" and "Biden officials who oversaw that four-year disaster have no authority or standing to comment on the Trump administration." DOGE, ICE, and the Department of Homeland Security did not respond to BI's request for comment.

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• Tim Jordan, M.D., a counselor who supports young girls, also provides CEOs with parenting support.
• He said successful parents make the mistake of overscheduling their kids in extracurriculars.
• They also overindulge their child's requests for new things, feeling that they can't say no.

This as-told-to essay is based on a transcribed conversation with Tim Jordan, M.D., 70, a counselor for teenage girls from St. Louis. The following has been edited for length and clarity.

I've been a counselor for around 30 years. For the past 15 or so years, my practice has been exclusively for middle school, high school, and college-aged girls.

I've been married to my wife for 43 years. We both started out in medical careers but then developed our own business focusing on parenting classes, talks, and weekend retreats.

For many years, we've worked with YPO, a membership community for chief executives, creating family events to support members with parenting and giving talks in their various chapters around the world.

I've noticed executives are very hungry for information about parenting. Although their business lives are set, and they're pretty successful, they're still open to learning more about raising their kids.

Across my experience meeting chief executives and helping families through my counseling practice, I've spotted some key mistakes successful parents make when raising their kids.

1. Overscheduling kids in extracurricular activities

Successful parents want their kids to be successful. They want them to be at the top of their class or on the best soccer team.

Everything is about their children's future, as opposed to what their kids like to do.

I once saw a high schooler in my counseling practice who was so burned out. She was on the cheer team, so had to go to practices and games, but she also did competitive dance, which was what she really loved. She wanted to quit cheerleading but said her parents wouldn't let her because they were concerned about how dropping out would impact her college prospects.

Parents are coming from a place of fear that their kids will get left behind. They want their kid to have a leg up. It's a rampant fear in our culture.

I think it's important for kids to pick their activities but also have some free time.

I recently spoke to another family with a daughter in sixth grade. She does volleyball and gymnastics, among other things. I told her dad there was something missing in her list of activities: play and downtime. Time to do things she enjoys, like reading or doing artwork — not because it's going to be in her portfolio, but because she likes to draw.

Unsupervised play is a great way for kids to learn, but they have little time for it these days.

2. Trying to be the driving force behind your child's motivation

When parents push their kids, they'll ask me, "How do I motivate my daughter?"

I tell them they're asking the wrong question. It's not your job to motivate your kids. A better question would be, "How do I support my child's intrinsic motivation?"

A good way to support a child's motivation is to ask them questions to make them think about why they want A's at school or why they like soccer.

Once, my wife and I were speaking to a girl who was a gymnast. We asked what she liked about gymnastics. She started talking, but her dad interjected and told her to show us her trophies.

We could tell her awards weren't what drove her, so we repeated the question. She said her favorite thing was the floor routine. She liked it when all eyes were on her, and she entertained people. That was her intrinsic motivation for loving gymnastics. We derive more satisfaction from things if we're doing them for our reasons instead of to please others.

Listen to why your kid enjoys something and use that understanding to encourage them. You're not always going to be there to push and micromanage your kids. They need to learn to push themselves by focusing on why they want to do things and how it's meaningful to them.

3. Overindulging your child's requests for new things

I've found that the executives I work with are very worried about whether their kids will be spoiled or if they'll have ambition. Many of these parents worked hard but are conscious that their kids don't have to do that because they're born into affluence.

Some have even said they're worried flying first class could spoil their child.

My wife and I tell them it's amazing their child can receive education through wonderful trips. That won't spoil them, but what will is if you immediately comply every time your child asks for something new.

Affluent parents sometimes think they should grant requests because they can afford it, but I encourage the attitude that the money parents have created is theirs, not their children's. Kids aren't entitled to one cent of it unless the parents gift it to them.

Get your kids to earn things and put some sweat equity into it. It will allow them to develop a work ethic.

Once when we were out with my son, he wanted a new Lego pirate ship. We told him we weren't willing to buy it and he could use his allowance money. However, it was around $75, which shocked him. We encouraged him to rake some leaves and do jobs in the neighborhood if he really wanted it.

4. Not sharing your stories

Kids look up to their moms and dads and see the finished product. They see a successful business or happy marriage, but they haven't seen the parent as an awkward 12-year-old struggling with self-doubt or when a parent didn't make the basketball team.

Every entrepreneur I've talked to has had at least one business failure, if not many. Successful parents can show their children that things aren't always smooth by sharing stories of failure.

I think parents don't tend to think about sharing their stories with their children. But when a child makes a mistake and is really bummed out, sharing a relatable story shows you know how they feel. Kids love hearing stories and it connects them on a deeper level with their parents. It makes them feel safe to share things in return.

Do you have a story to share about parenting as a chief executive? Contact this reporter at [email protected]

• Waabi, Raquel Urtasun's AI company, has raised $280 million across two funding rounds.
• Having a strong cap table has been part of Waabi's strategy for success, Urtasun said.
• Uber's Dara Khosrowshahi and Nvidia's Jensen Huang have been key supporters, she said.

This as-told-to essay is based on a transcribed conversation with Raquel Urtasun, the founder and CEO of Waabi, an autonomous driving startup headquartered in Toronto, Canada. The following has been edited for length and clarity.

I've been working in AI for 25 years after first being exposed to AI research in my undergrad.

I started my career in academia, focusing on technology capable of human reasoning. Around 15 years ago, I became interested in self-driving technology.

I joined Uber in 2017 and became the chief scientist of its self-driving unit. I wanted to push self-driving technology in the real world. However, I felt like the industry was using a capital-intensive approach that I didn't think could scale self-driving vehicles. I saw an opportunity to build my own company with an AI-first approach.

In 2021, I founded Waabi. We're an AI company focused on developing self-driving trucks. We've raised over $280 million, receiving investment from best-in-class investors like Nvidia and Uber.

Waabi raised large amounts during our two rounds of funding so far, but I'm not building the company for an exit. I want to transform the world. Having the best people in the industry supporting us has been a huge help in the endeavor.

I started Waabi with a focus on unleashing the power of AI

I spent nearly four years at Uber. It was a great stepping stone for entrepreneurship. I learned so much about building a business and being an executive. Dara Khosrowshahi, Uber's CEO, became a mentor to me, which has been an asset in my career.

Had I started Waabi as an academic, I don't think I would be as successful today.

I started Waabi because I didn't think the industry's capital-intensive approach, which has historically involved fleets of vehicles driving physical distances for tests, would generate scalable technology that could be deployed in the real world.

Instead of a system with bits and pieces of AI playing a small role, I wanted to build a single AI system that can safely perform all the necessary tests for self-driving.

This meant building an Al-generated simulation system for testing and training vehicles that was the same as the real world. My background in AI helped me foresee this technology years ahead.

Waabi is headquartered in Toronto, where there's a lot of AI talent. We have trucks in Texas that are driving autonomously on public roads for commercial operations, both through a partnership with Uber Freight and also direct-to-customer.

We've raised more than $280 million and are backed by investors like Uber and Nvidia

We've done two rounds of financing. Our Series A was led by Khosla Ventures. It was too large to be a "seed" round, but it was done in the company's first week. We raised $83.5 million.

Our Series A investors are all excited about Waabi. Vinod Khosla, who founded Khosla Ventures, is himself very bullish about our potential. This support is so valuable because as a company continues its journey, your current investors and your reputation help to tell your story.

In our brief three-and-a-half-year history, we've hit ambitious milestone goals. When I pitched during our Series A, I mentioned our plans for the simulator and trucks, and we managed to hit our milestones exactly as I pitched. This resonated well with investors for our second round.

There have been some challenges. There was an accident with an autonomous vehicle in 2023. The market was quite tough after that, and investors were concerned about how one incident could significantly reduce the value of the investment.

There were also concerns about whether the population wanted self-driving in the first place. Investors will always ask you about risks, so we explained them. Our safety approach, which is simulation-first and avoids adding risk to the roads before the technology is ready, resonated with investors.

Our cap table explained

We announced our second round of financing last June and raised $200 million. It was a very oversubscribed round, and we had to say no to people. We ended up raising more than we intended to.

We were very strategic about the types of investors we wanted to bring to our cap table so that we'd have the best in class to help us in the company's next stage.

On one side, there was the AI bucket. We had investment from Khosla Ventures — who really understood generative AI before anybody else and have also invested in OpenAI — as well as Nvidia.

With logistics, we wanted a forward-looking shipper, which was Ingka Investments, the investment arm of Ingka Group, who operate IKEA. We also had participation from Uber, who jointly led the round.

Additionally, we wanted original equipment manufacturers (OEMs), which is very important when you build technology for self-driving. We had Volvo Group Venture Capital, Scania Invest, as well as Porsche Automobil Holding SE, invest in us.

Our differentiated technology is one reason behind our success. Investors were coming around to Gen AI for the physical world and saw Waabi as at the forefront of that.

Having tremendous supporters has been very helpful

Nvidia is one of our investors, but we also partner with them to build the generative AI compute that drives our trucks.

My personal relationship with Nvidia goes back a decade. Jensen Huang has always been a big supporter of my research. When I was an academic, he'd come to academic events. He's very personable and someone I look up to in terms of building a business.

We have a tremendous roster of supporters behind us, including Jensen and the team, Geoffrey Hinton, and Dara Khosrowshahi. It's very important to have a diverse set of voices you can bounce ideas off of. For me, building a company is not really about the money you raise, it's about who's on your cap table and helping you build the best possible company.

I'm not building Waabi for an exit but to transform the world.

• Michael W. Sonnenfeldt started TIGER 21 so he could learn about wealth preservation from peers.
• The network now has nearly 1,600 members who all have a minimum net worth of $20 million.
• The biggest concern members have is probably how to not screw up their kids, Sonnenfeldt said.

This as-told-to essay is based on a transcribed conversation with 69-year-old Michael W. Sonnenfeldt, the founder of TIGER 21, a membership organization for high-net-worth individuals. The following has been edited for length and clarity.

I'd sort of made it in life by the time I was 31 years old.

I achieved significant success in the real estate development world by developing the Harborside Financial Center — my partner and I bought an industrial warehouse when I was 25, with a vision to turn it into a modern computer center, and we sold it a few years later.

My next venture wasn't successful, and I lost money. I then went on to build a real-estate merchant bank called Emmes, which I sold in 1998.

When I sold Harborside, I didn't know the term "wealth preservation." At 30 years old, you're more focused on your next deal than preserving wealth, but losing money on my next venture was a wake-up call for me, and I wanted to avoid losing the capital I'd created after selling Emmes.

In 1999, I started TIGER 21, an organization for high-net-worth individuals to connect and discuss their finances and lives. I wanted to learn from other smart people about how they were grappling with wealth preservation.

Within the organization, ultrawealthy members are able to confidentially share and receive feedback on their investment portfolios, as well as discuss how not to screw up their children. It's produced some magnificent learnings.

I started TIGER 21 to support entrepreneurs who'd sold businesses

Although I'm the founder and chairman of TIGER 21, my first role is "member No. 1."

I started the group with six people who I'd connected with through Vistage, a coaching organization for business executives. These people, like me, had sold their businesses at a similar time and were no longer CEOs.

I invited these members to form a new group focused on the transition from entrepreneurship to investing and wealth preservation.

The group was born out of the realization that once you sell your business, you need a new body of knowledge about the next stages of your life. It's not just about finances but also legacy, children, health, and community.

Our members are primarily first-generation wealth creators, such as executives or entrepreneurs who've sold a business. They didn't grow up with that wealth, so managing it is new to them.

Some members have inherited wealth and have to manage it. The mix of wealth creators and inheritors helps wealth creators get insight into how their children might react to their wealth, and inheritors can connect with the entrepreneurial spirit of their ancestors who created that wealth.

Members share issues they're facing and talk about their investment portfolios

In 1999, the original threshold to be a TIGER 21 member was a minimum of $10 million of investable assets. Now, our community is for members with a minimum net worth of $20 million. We have nearly 1,600 members.

Net worth is just one factor in our rigorous application process. We look for individuals who meet the "five Cs" of membership: character, contribution, capacity, conditions, and capital.

A TIGER 21 membership costs roughly $33,000 a year, plus an initiation fee of $5,000.

At the core of the community experience is a full-day monthly meeting in small groups. We start with a world update or "personal board of directors" segment. Everyone in the group shares how the news in the last 30 days has impacted their views on investing and life.

Then, groups will discuss a few key issues that members have mentioned they're grappling with, like a family issue or investment consideration.

We tend to have a speaker at every meeting sharing on a topic, like biodiversity or China. Lastly, there's a portfolio defense. One group member will present their investment portfolio to the others for about an hour and a half. Everyone is bound by confidentiality.

Members also discuss parenting and passing wealth onto children

If you plan on leaving money to your children, you have to think about the estate tax impact, but there are also non-financial issues about how you treat each child. Do you treat them equally, how do you set up an estate plan?

These issues are talked about in every group, but we've also set up a family office division to address this. It's for principal leaders of single-family offices — private businesses established by families for financial management — who meet separately from our core groups to discuss themes like estate planning, family governance, and succession planning. It costs $50,000 a year with a one-time $5,000 initiation fee to be part of this division.

Throughout all of TIGER, the No. 1 concern probably isn't how to preserve wealth, but how to not screw up your kids. I'd say that some part of every meeting always touches on a situation happening with a member's children and how to address it productively.

I was in a family office group recently where two members shared their parenting approaches. One member talked about making their kids rake leaves or do odd jobs and telling them they'd have to pay for their first car because they wanted their kids to appreciate the meaning of labor and wealth. Another member shared their family "charter," outlining the family's values.

We discuss best practices all the way around.

It doesn't matter how much money you have, if you do something smart, it'll pay off. And if you do something stupid, it'll kick you in the butt.

Do you have a story about networking you'd like to share with Business Insider? Email the reporter at [email protected]

• Dhruv Loya came to the US to study in 2020, but he struggled to find a job for after he graduated.
• He landed a job at Tesla but had to field questions about visa sponsorships along the way, he said.
• International students face job searching hurdles when it comes to visa sponsorships, he said.

This as-told-to essay is based on a transcribed conversation with 22-year-old Dhruv Loya, from Buffalo, New York, about job searching and landing a role at Tesla. The following has been edited for length and clarity.

I did over a year of job hunting before I landed my first job after college, working for Tesla.

I started looking for jobs in the summer of 2023. Back in 2020, I moved from Pune, India, to study biomedical engineering at the State University of New York at Buffalo. I spent a lot of money, took student loans, and received financial support from my parents to study in the US, but it was really difficult for me to land a job. I applied to hundreds of listings, but I often didn't hear back or got rejected.

Although I have a job now, I'm aware that it's a very tough time for students looking for work. There are particular difficulties for international students who rely on companies to sponsor their visas.

I kept getting ghosted or rejected for jobs. Being an international student made things even tougher.

I didn't know exactly what I wanted to do after college, but growing up, I always wanted to get into a company where I could use my tech skills to do something innovative with an impact.

I did several internships while at university and also had an on-campus job helping students and faculty with tech problems. I wanted to use my time at college to figure out my future career.

In the summer of my third year, I started applying for full-time jobs. I wanted to be employed by December so I could enjoy my last semester and the following summer without worrying about finding a job.

I had an interest in entry-level sales engineer roles but wasn't having much success because I didn't have sales experience. I pivoted toward quality engineering roles because I'd done an internship in this area.

When I applied for jobs, I got ghosted or received automated rejection emails. I tried changing my résumé templates and making YouTube videos to sell myself to recruiters, but nothing seemed to be working.

Things seemed to improve in the fall of 2023 when I started optimizing my résumé for ATS, the tracking software employers use to assess whether your résumé matches the job description. I got ChatGPT premium and asked it to do an ATS analysis on my résumé using the job descriptions for the roles I was applying to. I'd try to keep my score at about 85% because I thought this could help me avoid automated rejections.

I don't know for sure if ChatGPT helped, but when I started using the tool, I saw a difference and received more callbacks.

But I faced another obstacle too. During the application process or interviews with recruiters, there would be a question about whether I'd need a visa sponsorship now or in the future.

Because I was a STEM student, I had access to three years of OPT — optional practical training — with my student visa. This meant I wouldn't need sponsorship for three years after graduation, but I'd still answer yes to the question because it asked if I needed sponsorship in the future. After admitting this, I'd receive rejection emails.

Being unemployed was difficult, but I eventually landed a job at Tesla

When I graduated in May 2024, I still didn't have a job. My parents didn't come to my graduation because they decided to financially support me in my unemployment instead of spending money on the trip from India. I was very upset about it.

My lease expired in August, and I had nowhere to go. I stayed with friends instead of spending money on rent.

I was job hunting on borrowed time. I had 90 days to find a job on my OPT, which took me to late October.

A friend who I studied with got a job at Tesla and recommended me to the recruiter. I sent my résumé, and they interviewed me.

When I spoke to the recruiter, I mentioned I'd have authorization to work for three years through OPT, and it was fine if they didn't sponsor me after that. They gave me a job offer in October 2024 to work as a Powerwall technical support specialist. The role involves troubleshooting the Tesla battery product, which stores solar energy for powering people's homes. It's also more customer-facing than the quality engineering jobs I was applying for previously.

I'm hoping I can move up in the company and get a role where I'd be sponsored and take on more engineering and managerial responsibilities. However, if I have to move back to India after three years, I'd happily do that.

It's a difficult time for students to find work

In the end, getting a job wasn't as tough as the journey. Tesla was hiring new people, and the timing was right.

I have many friends who are struggling to find jobs right now, both international and domestic students. In 2023, there were so many layoffs at big companies that more people were put back in the market.

Companies are trying to cut costs, and it seems to me like they're avoiding sponsorships for international candidates. There are a limited number of visas available in the US, so there's much uncertainty around whether candidates will actually get a visa, even when the company is spending so much money on them.

I don't think mass-applying to hundreds of jobs is effective in the current job market. Instead, candidates should focus on quality over quantity. Be strategic, reach out to people, and try to get referrals. Connections and referrals can significantly improve job search outcomes.

• Lee McKeeman found out he was autistic in his late 30s while he was working at Meta.
• Being autistic has made it hard to navigate office politics and communication at work, he said.
• His neuro differences have also set him apart in positive ways, such as with hyperfocus, he added.

This as-told-to essay is based on a transcribed conversation with 42-year-old Lee McKeeman, from Texas, about navigating Big Tech as an autistic person. The following has been edited for length and clarity.

As a child, I felt different, but I didn't know why.

When I was a teenager, I found out I had ADD — my mom took me for an evaluation after my teachers gave her feedback that I was sometimes disruptive.

Later in my life, one of my wife's relatives suggested I had some autistic behaviors. As time went on, I read more about autism and became interested in getting an evaluation.

Finding someone who evaluated adults was difficult, but I managed to get an evaluation in my late 30s. It confirmed I was autistic and also had sensory processing disorder. At the time, I was an engineer at Meta.

I've worked in tech my entire career, including for Big Tech companies: Amazon, Meta, and Google. Though I haven't always known I'm autistic, looking back, I can see that it's impacted my ability to handle office politics and communicate in the workplace. However, my neuro differences have also come with superpowers that help me stand out as an employee.

I've struggled to navigate the workplace because of my neuro differences

I got my first full-time job in 2004, shortly after finishing a computer science degree. Multitasking can be difficult for autistic people, and unlike in school, where I had to manage multiple classes and tests, I found it relieving to enter the workforce and have one focus. I showed up, did my job, and went home.

However, it wasn't clear to me how to approach job searching. I didn't know about salary expectations and didn't negotiate my first offer. I'm generally uncomfortable with conflict and wasn't willing to ask questions or look foolish. I feel like this is part of social differences related to autism.

Once I was in the workplace, I found navigating office politics challenging. Early on, I didn't know how to ask for more money or get promoted. I thought that if I kept working, things would go fine, which I now realize is naive.

I joined Amazon in 2012 after a recruiter reached out to me. I hadn't worked at large tech companies in the past and wasn't used to rigorous processes around promotions.

At one point, I was trying to get promoted as an engineer, but there was always some reason it didn't work out. I think some of those gaps were about salespersonship — self-advocacy and visibility — and knowing the right people. I struggled with these things because of a lack of social and situational awareness.

I felt I was doing good technical work and that if I solved senior engineer-worthy problems, then I was succeeding. However, I was often doing this in isolation, and I didn't understand the importance of showing other people or getting their input.

In 2021, I joined Meta as an engineer. They had a team-matching process, which I really struggled with. It took me months to find a team to join. I didn't know how to approach a new work environment. I'd been at Amazon for almost nine years. I knew how things worked and how to join a team there, whereas now I felt the expectations of me weren't very clear.

I've been working at Google for the last two and a half years. Last year, I was in discussions with managers about improving my performance, and I felt like I was at risk of losing my job.

With autism, I notice that my performance ebbs and changes, and I can get tired quickly. Sometimes, this is because of autistic burnout, but outside this, if I'm struggling with a problem and don't know how to get help, it quickly exhausts me. I worked with a psychiatrist to try to build up my capacity, which I think helped me to overcome some of my challenges.

I struggle to understand some requests. Like when asked to "pull something out" of a document, I wonder whether I'm meant to put that content in a new document or just remove it.

I can be very verbose, thinking that if I provide a lot of extra detail when communicating, I won't be misunderstood. However, this can be distracting for others. One manager suggested I write a TLDR above my message, which has been helpful, but it's still a work in progress for me.

My neuro differences have also helped me stand out in positive ways

Hyperfocus is one of the superpowers that comes with my neuro differences. Where other people might give up investigating a problem, I'll keep digging until I solve it because of my curiosity.

I spend days digging into issues. If it's not high-priority, people can think I'm "wasting" time, but at times when I'd get all my tasks done and solve something additional, it would impress people. It's distinguished me from others during my career.

Since I see things differently when it comes to problem-solving, I often make suggestions when reviewing other people's work. Being able to identify unseen problems is a very valuable skill in my line of work.

However, I've had to learn to get better at communicating those suggestions in a way that can be heard since I've been told I'm too blunt or inflexible when giving feedback.

Getting support is crucial for people with neuro differences

I'm part of a group for autistic individuals at Google. Having support and asking if others have experienced similar problems to me is helpful. You don't have to have an official diagnosis to be a part of groups like this, but getting an evaluation was empowering for me to feel I belonged.

I also use other resources like occupational therapy and psychiatry for support with different aspects of my neuro differences.

If you have neuro differences, finding support is critical. Learning about yourself and how to support yourself can be really powerful.

It's exhausting to think you just need to work harder and be like everyone else to succeed.

Do you have a Big Tech career story you'd like to share? Email the reporter at [email protected]

• After eight months at Harvard, Steven Wang dropped out to focus on dub, his investing business.
• Though he says it was the right move, he's sad to have missed out on the college experience.
• Wang says he doesn't regret trading his personal life to go all in on his entrepreneurial passions.

This as-told-to essay is based on a transcribed conversation with Steven Wang, a 22-year-old entrepreneur based in New York. The following has been edited for length and clarity.

My parents immigrated to the US from China before I was born. Watching them build new lives and careers inspired me to try new things.

I've always loved creating, which has manifested into different entrepreneurial projects throughout my life, from selling origami cranes in first grade to leaving high school for around two years to launch a VR education company.

I eventually completed high school and went to Harvard for college. Eight months into my freshman year, when a new product idea came my way, I dropped out of full-time education again to work on a copy-trading platform called "dub."

Dropping out of college was the right decision. Throughout my life, I've traded my social life to pursue ideas I believe in. Even though I've missed out on some things, like the college experience, I don't regret it.

I'd already taken time away from education before college

The VR wave took off in the mid-2010s when I was in high school. I started working on Realism, a VR education company, with two friends, and we got into an accelerator program at MIT.

We raised money, which convinced me to drop out of high school at 16. My friends and I moved to Boston from Michigan and lived together in a one-bedroom apartment for a year on stipends from the money we raised.

Realism was acquired in 2020. This experience showed me you have to work hard and give up everything to pursue what you want.

I worked at Apple during this time as well

In 2019, I also got a full-time engineering project manager job at Apple. As a kid, I was a Steve Jobs fanboy and wanted to learn how Apple built teams and managed people. I remember making mock-up designs for new versions of the Apple Watch and bringing them to the interview.

I was lucky to get an offer despite little prior employment experience. At 17, I was the youngest person I met while working there.

During my break from school working on Realism and at Apple, I lived in Boston and California with roommates and mentors. After about eight months at Apple, I decided to return to high school and complete my senior year at age 18.

I'd missed out on a lot of the social development that school offers, so I viewed going back as a personal challenge. COVID-19 hit around that time and ruined the second half of my senior year, but before that, I enjoyed building new relationships from the ground up.

Despite my time away from high school, I got into Harvard

During high school, I took some philosophy classes that opened my eyes to different ways of viewing the world. There was a whole new world of academia that I wanted to explore in more depth.

I applied to a few colleges and was lucky enough to get into Harvard. I was drawn there because of its strength in humanities, but I knew I wanted to return to entrepreneurship after earning my degree. I worked part-time as a product manager for a friend in Silicon Valley who needed help with a project during my studies.

My time at Harvard coincided with an exciting stock market period, during which meme stocks and crypto took off. This experience got me back into investing, which I'd been interested in from a very early age.

I dropped out of Harvard to focus on a new business

I wanted to build a product around the big retail investor movement I witnessed in college, so I started working on a project in my second semester as part of a business class. The product lets retail investors copy the trades of other investors automatically.

There was a demo day at the end of the semester where you pitched your product in front of mentors and venture capitalists. I invited some of Realism's investors to watch. They told me they were keen to back whatever I did next.

In June 2021, I left Harvard to focus on the product. I'd been studying for eight months.

I didn't tell my mom I'd dropped out at first. She was very against me leaving high school, but she saw the same spirit in me that moved her and my dad to come to the US. I think her immigrant mindset helped her accept it. This time, she only knew I left school after relocating to New York in July.

Leaving college was the right choice

I've been focused on building "dub" ever since. We have a team of around 25 and have raised over $17 million, including from Uber's CEO and Robinhood's founding COO. I had three cofounders at one point, but we've since parted ways, and I've been a solo founder for the past two and a half years.

Think of "dub" as a brokerage where you can trade, but instead of trading single stocks, you pick other investors you can copy-trade. When the person you copy makes a trade, the platform automatically mirrors that for you. We want users to be able to invest in the ideas and people they believe in.

Dropping out of Harvard was the right choice for me. I've never been happier. My company's growth means there are so many things to do, which exhilarates me. I feel blessed to spend every waking minute on it.

I missed out in some ways, but I don't regret it

I saw my friends finish college and sometimes felt jealous of their experience. I fantasize about going back to study philosophy, but for now, I've traded my personal life to pursue something I believe in.

If the investor craze hadn't happened, I'd probably have finished my degree and entered the workforce. Building great products gives me the most joy in life, and when I saw the opportunity to do that, I couldn't let it go.

• Alex Acker became a professional basketball player when he was selected in the 2005 NBA draft.
• He said basketball helped him financially support relatives but that he struggled with overspending.
• To address the issue of athletes going bankrupt, Acker started an alternative investment fund.

This as-told-to essay is based on a transcribed conversation with 42-year-old Alex Acker, based in Como, Italy, about managing wealth as a professional athlete. The following has been edited for length and clarity.

My dad taught me the fundamentals of basketball when I was growing up.

I can remember playing the game with an orange instead of a basketball. That's how poor we were. We'd have to shoot the orange and catch it before it hit the ground.

Basketball got me a college scholarship. I met some elite NBA athletes who came to my college one summer and played pickup ball with us. I held my own and they took my name over to the NBA. In the 2005 NBA draft, I was selected by the Detroit Pistons.

When I got my first check, I understood that I was a professional athlete and had to take it seriously. I was with the big boys and had to bring it every day.

I was never playing for the money. I loved the sport and knew money would come. But I wanted to serve my family. They were struggling, and I knew I could be a breadwinner.

Looking back, I can see I made mistakes when managing my finances early on in my career. Hearing the stats about athletes going broke pushed me take steps and improve things.

Basketball helped me to financially support my family

During college, I lived off the stipends that I received as a collegiate athlete, and some of my relatives would live with me in my apartment for months at a time.

I'd ask my coaches to help me make money on the side with a job, but they didn't really understand how serious our situation was.

I was the youngest among my siblings, but once I got drafted, they all looked at me like I was the one in charge. They didn't realize that my contract wasn't guaranteed because I was a second-round pick, so I still had to work for a spot on the team.

I was able to get a contract with the team, but my family and I didn't have the financial education to understand what would happen with the money. From the amount I was paid, taxes were deducted, and some was allocated to my pension plan. I wasn't seeing the full amount that my relatives thought I was seeing.

During my first year with the Pistons, my family lived with me in a three-bedroom apartment in Detroit. Some people think athletes have a crazy spending limit, but I was a pretty normal individual with one car, paying rent and providing for my family.

I made mistakes with my money

I think a lot of athletes don't understand they have the power to vet the individuals who handle their finances. Especially at an early age, athletes tend to just go with the flow and can get taken advantage of.

I remember thinking everyone around me had my best interests in mind and I allowed others to handle payments for things like watching my house and gardening without paying much attention to the details.

Initially, my family members could see all the details about what I was spending money on and how much I had. This negatively affected some relationships, and I wish I had told them I had it from here so they weren't burdened by trying to advise me financially.

I also had some issues with friends. I had to check my circle and understand I couldn't keep paying for everything when I was with them. I can't throw all the blame on them for this. As Kevin Hart once pointed out, it's lonely when you're the only one who can afford the things you want to do. But I had to learn that I couldn't keep up those spending behaviors.

I've taken steps to learn more about financial markets

I received a wake-up call when I heard statistics about athletes going broke, which said that 60% of NBA athletes and 78% of NFL players experience severe financial issues after leaving their leagues.

It spurred me to think harder about my wants versus my needs. I asked myself questions like, "Do I need to buy another car, or do I need 10 pairs of shoes?"

I made lifestyle changes. Instead of indulging in partying, I used my free time to educate myself about financial markets, learning how to ask the right questions and prepare for life's uncertainties.

I retired from basketball in 2021. I wanted to do something about the problem of athletes going broke, so in 2024, I launched an alternative investment fund called Amongst Elite Capital for athletes, entertainers, and others, with two co-founders.

For athletes who are thinking of trying entrepreneurship after retirement, my advice is not to be scared of taking losses. I had to take small L's to get to this point, and it all lined up to where I am today.

Do you have a unique story about wealth management that you'd like to share with Business Insider? Email the reporter at [email protected]

• Alessandro Palombo has lived in Dubai and he's launched two businesses in Singapore.
• He said people in Dubai often display their wealth, while Singapore has billionaires in flip-flops.
• The lifestyle in Dubai can be transient, meanwhile, Singapore can feel small, he said.

This as-told-to essay is based on a transcribed conversation with Alessandro Palombo, 36, an entrepreneur based in Lisbon, about doing business in Dubai and Singapore. The following has been edited for length and clarity.

I lived in Dubai for around four years, and I have two businesses in Singapore.

I started my career in the legal field but pivoted into startups. I currently live in Lisbon and focus on running a fund advisor for a Golden Visa fund helping non-Europeans gain residency and citizenship in Portugal.

I first moved to Dubai in 2019. I used the city as my headquarters and often traveled from there for work and my startups. I had team members in Asia, so there was good connectivity from Dubai to them. I also frequently visited Singapore for business trips.

I launched two businesses, including a fund advisor, in Singapore in 2024. I travel frequently to manage both companies and plan to spend at least a quarter of my time there moving forward.

Having experienced life in both Dubai and Singapore, here is a comparison of what I think of both locations. Overall, I think they are both great places for doing business. Dubai is better suited for doing business with Europe or the US, and Singapore is a great place if you're doing business in Asia.

Displays of luxury are more understated in Singapore than in Dubai

People in Dubai often display their wealth, while in Singapore, there were billionaires in flip-flops — it's more understated.

In Dubai, you can get lost among hundreds of luxury shops at the Dubai Mall. It shows you the best of every luxury brand in one place.

While luxury is embedded into a holiday experience in Dubai, it isn't at the center of your experience when you live there. When visiting for a week, you're typically taken to high-end attractions and restaurants, but living in Dubai reveals its more grounded side. You can dine in more authentic Lebanese restaurants for 25 euros, around the same in dollars a head.

Meanwhile, in Singapore, I've personally met more wealthy and powerful people than I did in Dubai. This could be due to coincidences around my network, but I have a feeling it attracts more people who have already made it as opposed to people who are trying to make it. I've met several wealthy people who were dressed in ordinary clothes but had significant assets, including luxury cars.

In Dubai, business meetings often happen in lavish offices, but in Singapore, I've seen more personal touches, like a CEO's private room with an extraordinary cigar collection and premium liquor — items that reflect wealth but aren't immediately visible.

Consider where your clients are based when deciding which city is best for your business

I think both locations are great for digital nomads and entrepreneurs.

In Dubai, the killer value proposition is 0% personal income tax. It's one of the very rare places in the world where your earnings, capital gains, and dividends are not taxed. It's a major advantage for people who have wealth to preserve and for digital nomads. However, there is a 5% VAT.

If you're doing business with Europe or the US, Dubai would be a better fit because of the time zone.

Meanwhile, Singapore offers an unmatched ease of doing business in Asia without the language barriers present in countries like China, where Mandarin is essential. However, if you have clients in Europe, the time difference can make things difficult.

In Singapore, personal income tax is reasonable, and there are thoughtful tax exemptions for startups. Plus, there is no capital gains tax or foreign-source income tax. Singapore is such an efficient city. Compared to Dubai, it's faster to open a bank account. The tax guidelines are clear, and they enable you to do business easily.

That said, there are challenges around entrepreneurship in both locations. In Dubai, pathways for securing a visa can involve establishing a company or obtaining a freelance license. While feasible, it's more complex than it appears, and it's often useful to have assistance from trusted local partners. In Singapore, incorporation is straightforward, but obtaining the required Employment Pass involves additional steps.

There are some potential downsides to life in both cities.

In Dubai, I think the lifestyle can be quite transient. There's a large expat population, and since many people see their time there as temporary, it can limit deep connections.

I'd avoid the hottest summer months in Dubai. If you open your door in July, it's like a huge hairdryer blowing hot air on you. Meanwhile, in Singapore, it's hot and humid all year round. In both places, expect to be spending a lot of time in buildings with air conditioning.

Both cities can be expensive, but I think Singapore is more expensive, particularly the cost of cars and real estate.

Singapore is also a very small city. In Lisbon, where I live now, I can drive to many beautiful places in my car like beaches and hiking spaces, but in Singapore, you don't have to drive for long before you've left Singapore and are entering Malaysia. In the medium to long term, you may feel the smallness of the space. I haven't lived in Singapore, but when I visit, I often end up in the same four or five streets.

Overall, Singapore and Dubai are great examples of international hubs, and I really like both cities.

Do you want to share a review of cities you've lived in for work and business purposes? Email [email protected]

• Stephany Kirkpatrick said no to a job offer from Goldman Sachs so she could explore new territory.
• She decided to work at SoulCycle; an opportunity that equipped her to become an entrepreneur.
• Had she accepted the Goldman offer, she likely would not have become a founder, she said.

This as-told-to essay is based on a transcribed conversation with Stephany Kirkpatrick, a 43-year-old from New York, about turning down an offer from Goldman Sachs to work at SoulCycle. The following has been edited for length and clarity.

When I got a job offer from Goldman Sachs, many people counseled me to take it. They likened it to Harvard. If you get in, you go.

By 2018, I'd spent 15 years working in the financial advice industry. I started my career as a financial planner in the retirement planning ecosystem. In 2011, I joined a New York-based startup called LearnVest. We were acquired in 2015, and I spent another three years working there.

In 2018, I received a job offer from Goldman Sachs to lead a software and business team. The role was similar to what I was already doing, and the obvious next step to continue my career in financial services.

Counter to every piece of advice I received from friends and family members, I thought about what would make me happy instead.

Choosing SoulCycle over Goldman allowed me to do something new

I could've accepted the Goldman job and been the subject matter expert, but in my heart of hearts, I wanted to test my boundaries.

In the spring of 2018, I turned down the offer from Goldman Sachs and accepted a job at the fitness company SoulCycle. The skills I gained at SoulCyle helped me start my own business, and I have no regrets about taking that risk.

The Goldman Sachs offer came after someone I had worked with at LearnVest reached out to me. They wanted me to meet someone building a new project at Goldman.

As you get further into your career, you do less formal applications, and it more likely your network is helping you connect with the right people at the right time.

I spoke with the connection at Goldman and realized the work would be very similar to what I'd done before.

Saying yes to this opportunity would mean I'd probably spend another 10 years doing the same work because I don't like to change jobs often. It became clear to me that this wasn't what I wanted.

I questioned whether I wanted to be a middle-aged financial expert or explore new territory.

Around that time, a person in my network who worked at SoulCycle reached out to me because of my digital and operating experience at LearnVest. I connected with the then-CEO, Melanie Whelan, and we had an informal conversation.

Working with Whelan checked all my boxes: I wanted to work for a female CEO since I'd worked for a female founder at LearnVest, and I wanted to work somewhere based in New York in an industry I could get excited about.

The job paid wildly less money than what I'd earned before. It would be a huge departure from what I'd been able to save. My husband and I had to sit down and discuss what it would mean for our lifestyle, and he supported my choice to take the job.

I also spoke with the chief commercial officer; we immediately clicked and shook hands. Shortly after, I became the GM of digital strategy.

At the time, SoulCycle was considering entering the at-home market. I learned about brick-and-mortar and supply chains and applied what I was good at: being a digital entrepreneur.

It pushed me to figure things out, like how to build bikes that go nowhere, what it would take to make content, and how to learn about the market. I had to build my network in the company and tap into the expertise of others. It was scary to walk into a place where I didn't know all the answers, but it unlocked incredible career growth for me.

After SoulCycle I founded my own business

I loved working at SoulCycle, but I couldn't stop thinking about an idea I'd had at my last job: how people have reduced access to money in a brokerage or high-yield savings account on nights, holidays, or weekends. This is a fundamental flaw in the infrastructure that powers financial services.

One day, I was catching up with an investor friend and brought it up to her. She told me I had a fundable idea and she wanted to write me an inspiration check.

I left SoulCycle in September 2019 and started my own business, Orum. We aim to improve payment speed and orchestration for businesses using API solutions. I've been working on Orum for the past five years. The team has grown to about 40 people, and we've raised $82M to date.

I don't think I'd be a founder if I hadn't turned down the Goldman offer

Looking back, I remember feeling excited about taking the SoulCycle job, but because I'm a people pleaser, I also felt a little bit of shame that I wasn't doing the thing people expected of me.

No one told me not to work at SoulCycle, but taking less money to do something I didn't know I was going to be good at was a little unsettling.

However, the opportunity has made me a better founder today. At both SoulCycle and LearnVest, I basically had to look at a blank piece of paper and pursue a strategy to test our hypothesis. I had to ask and answer how quickly we could learn whether to do this or that, and that's what startups are all about.

Had I stayed in financial services instead of moving to SoulCycle, I truly think I would've stayed there for the next 10 years. I don't think I'd be any less happy, but it's very unlikely that I would have had the courage or reason to take the leap of faith to become a founder.

I'm excited about where Orum is right now and have zero regrets.

Do you have a story about turning down a prestigious job offer or leaving a prestigious company? Email [email protected]

• While struggling with parenting duties, Babette Lockefeer considered quitting her business.
• Her husband didn't agree with her decision to stop work and be a stay-at-home mom.
• Lockefeer was angry at first but later realized she wouldn't be happy if she wasn't working.

This as-told-to essay is based on a transcribed conversation with Babette Lockefeer, 35, from the Netherlands, about navigating motherhood alongside her career. The following has been edited for length and clarity.

Four months after my second child was born, I wasn't living life as I'd envisioned it.

I was in the midst of a big project for my business as a leadership and team facilitator and struggling to balance my career and motherhood. I felt overwhelmed, stressed, and sleep-deprived.

In the summer of 2021, I told my husband I wanted to quit the business. He immediately said no.

At first, I was angry. I'd always valued doing important work and my career, and I was willing to stop doing that for our family, but felt he wasn't letting me.

Over time, I realized he was right: I wouldn't have been happy as a stay-at-home mom. Talking with my husband and processing my feelings helped me realize that being a mother wasn't a detriment to my career. I had to deal with some insecurities and make some changes at home to understand I could do both.

I was always a high achiever at work

I started my career in 2014 as a consultant at McKinsey. I spent two and a half years there, but in 2016, I joined Alibaba as a global leadership associate. I spent around half a year in their Dutch office, helping Dutch e-commerce players connect to the Chinese market.

In the summer of 2017, my husband, who I'd met as a student, and I moved to China, and I worked for Alibaba in Hangzhou.

I really enjoyed it. We had monthly trainings where we learned more about China, e-commerce, and leadership. The training made me realize that my real interests lay in leadership development. In 2018, I left Alibaba and started my own business in the leadership space, TheoryY.

I was also pregnant with my first child at that time. Five months after his birth, in December 2019, we decided to leave China and move back to the Netherlands.

Soon after we returned, the COVID-19 pandemic hit. I got pregnant again and had a second child in February 2021. Because of the pandemic, it was difficult to have family assistance with childcare or access to day care.

Around 10 weeks after giving birth, I started a new project with my business after being referred to a new client. Our newborn wasn't fond of sleeping, so we had a lot of broken nights.

For me, motherhood was about having a healthy attachment with my children, being present, and attending to all of their needs.

This was impossible to achieve all the time. I was too tired, overwhelmed, and full of doubt. With hindsight, I still did a good job as a mother, but I'd internalized the perfect mother myth.

Society's picture of an ideal mother is in direct conflict with that of an ideal employee. The employee is always available and wants to go the extra mile, but the mom also needs to be fully committed and always have the space to attend to her children's needs.

I was always a high achiever at work, but now, I had less time and energy to go the extra mile. I was working fewer hours than before having children, but when I was with my kids I wasn't always present because I was thinking about work. I felt like I wasn't doing a good job on the work front or the motherhood front.

My husband didn't think quitting would make me happy

My husband worked full-time. He was very involved as a dad. When our second child was born, he took some parental leave, spread across the year, plus six weeks of birth leave. But because I was self-employed and had more flexibility, I was always picking up things that fell off the wagon — which was a lot of the time during COVID.

I would spread my hours around, sometimes working in the evenings so I could still do the tasks I was hired to do. We never had a consistent schedule, and I felt like I was firefighting. Whenever a child was ill or had a doctor's appointment, the mental load was predominantly on my shoulders.

When I spoke to my husband about quitting, he said he didn't think it was the right decision. He also wanted to spend time with our kids and thought it wasn't fair if he was the sole breadwinning parent.

He also said he didn't think I'd be happy as a stay-at-home mom. I disagreed, saying I wasn't happy as it stood.

I spoke with my husband, processed my feelings and decided to continue working

From our first conversation, it was clear we weren't aligned, so we continued to discuss it.

I shared that I felt I was undervalued and wasn't appreciated by him unless I was achieving something professionally. He told me he still appreciated me now that I was a mom and wasn't on a steep career trajectory at the time.

I decided to continue working, but we also changed some practical things about our household. When our third child was born in July 2023, my husband was granted 26 weeks of parental leave by his new company, and he took all of it, taking full end-to-end responsibility for the household for the first time.

It allowed me to trust him fully with the kids and family chores going forward, so our dynamic has become more equal. We don't split things 50-50 all the time, but regularly discuss how best to divide responsibilities between us.

Looking back, I'm grateful that my husband could see that, in the long term, it wasn't a good idea for me to quit working. I need the intellectual stimulation that comes from a job, and my work fills me with the energy to show up as the mom and partner I want to be.

Do you have a story about balancing parenting with your career? Email Charissa Cheong at [email protected]

• When Dapo Bankole moved to Canada in 2012, he had years of IT experience under his belt.
• But he struggled to find a professional job for months and did minimum wage work to make ends meet.
• Bankole said he thinks companies weren't hiring him because he lacked Canadian experience.

This as-told-to essay is based on a transcribed conversation with Dapo Bankole, 47, about moving to Canada from Nigeria. The following has been edited for length and clarity.

My Canadian Dream began in 1993. I was living in Nigeria, where I was born, and had to sit an exam. My brother's friend drove me there. A few months later, I asked after him and was told he moved to Canada.

It was the first time I heard about someone relocating to a new country. I dreamed of doing the same.

I studied biochemistry at university and completed a postgraduate program in computer science. I worked in IT for around 12 years in Nigeria, where I gained experience in computer engineering, billing administration, and team management

My desire to relocate heavily influenced my life. When I courted my wife, I told her about my dream because I didn't want it to be a problem for her. I started getting myself ready to move by gaining IT certifications through a Canadian society.

In 2012, I moved to Canada with my wife and two children after successfully applying for permanent residency in the country.

But it ended up taking me around nine months to find a professional job. I struggled to get my foot in the door and provide for my family's basic needs. I feel I was overlooked because I didn't have Canadian work experience.

I applied for professional jobs in Canada but didn't hear back

We arrived in Canada in 2012 and stayed with my sister, who had moved there ahead of me, for two months before we got an apartment.

My wife worked in a bank in Nigeria, but when we moved she decided to pursue her hobby of making clothes, so she went back to school to go into fashion design. Meanwhile, I started job-hunting.

I applied for professional jobs, such as analyst and project manager positions, but it mostly was crickets. I wasn't hearing anything back.

Peers who were also immigrants asked to look at my résumé. I'd put Nigeria all over the place, someone suggested I remove it. When I did, I started getting follow-up calls.

I felt I wasn't getting opportunities because of my lack of Canadian work experience. Recruiters didn't say it directly — it was subtle. In phone conversations, recruiters would ask where my experience was based. I'd explain it wasn't in Canada, and the conversation would continue, but they'd never get back to me.

It became glaring that companies weren't hiring me because I lacked local experience, but I'd never get it if they didn't hire me. It's a chicken-and-egg situation.

I took on minimum-wage work. We struggled with our basic needs.

After a month or so of job-seeking, I started applying to lower-wage jobs as well. Living in Canada wasn't cheap, and I needed to stop depleting my savings.

I worked at a call center for CA $10 an hour for around two months. Then, I got a job as a grocery store clerk doing night shifts. I also did evening shifts unloading cargo from planes at the airport.

I kept my days free to pursue more professional opportunities. I didn't want to get stuck in a low-wage job. But it meant I hardly saw my kids. They were asleep when I got home and went to school when I was asleep. They started speaking to me less, and it made me question why we left Nigeria.

We were comfortable in Nigeria, but we lived in a basement in Canada. We struggled to cover our basic needs. There was a day when I only had around $10 left and had to decide whether I'd use it to buy food or put gas in the car. I'd never been in that situation.

Moving back to Nigeria at that stage would have meant starting all over again there, so we decided to push through the pain of integration.

I received help from a mentorship program and was eventually hired as a business analyst

During my struggle to get a professional job, my confidence levels crashed and I started to doubt myself.

Through an organization that offered loans to immigrant professionals, I received some money to attend a short training course. I interacted with professionals on the course who listened to me. I found myself leading conversations and felt my confidence being restored.

I also joined a mentorship program that reaches out to companies on your behalf. They didn't have a magic wand that automatically gave people jobs, but it leveraged social capital on behalf of immigrants like me.

They helped me get an unpaid opportunity, which led to a full-time offer for a business analyst job. I was able to keep doing my night shift work to make money in the interim and actually kept my grocery store job for months afterward for extra income.

Even though the road isn't completely smooth, it always becomes easier once you have that initial foot in the door.

I stayed in the business analyst role for around two years before I was headhunted by another company to work as a senior business analyst. In 2015, I started my own business. My team of six builds software and consults with organizations on software and implementation.

Employers should give people like me a chance

The program I did gave me an in-route for Canadian experience, but I don't think it's right to filter out candidates who don't have Canadian experience.

You don't need Canadian experience to succeed in Canada. You only need experienced people who are ready to do whatever it takes to fit in and deliver on the work priorities. We should give people a chance to prove themselves.

Immigration shouldn't make people suffer. It should help them transfer their skills, which can positively impact the economy.

Do you have a story about how relocating to a new place impacted your career? Email Charissa Cheong at [email protected]

• Manufacturing engineer Douglas Dorsey started working at Boeing in 1984 and retired in 2017.
• Dorsey worked on the Boeing 777 and 787 Dreamliner, where he said things began to unravel.
• He reflects on his time on the shop floor and how Boeing plans to repair its reputation.

This as-told-to essay is based on a transcribed conversation with Douglas Dorsey, from Washington, about his career as a manufacturing engineer at Boeing. The following has been edited for length and clarity.

I started my career at Boeing in 1984, and I worked there for over 30 years.

I was a manufacturing engineer. My responsibilities included writing instructions and coming up with assembly sequences for aircraft.

During my career, I worked on several aircraft projects for Boeing, including the Advanced Tactical Fighter program, the Boeing 777, and the 787 Dreamliner. It was always interesting and challenging. I worked with dedicated employees and on cutting-edge programs.

I retired in 2017 feeling proud to have worked there. I was a "lifer" with Boeing blue blood running through my veins.

However, while working on the Boeing 787 program in the 2000s, I noticed that outsourcing manufacturing tasks to suppliers became a really big problem for Boeing. When I worked on the shop floor, I saw the negative impacts of outsourcing to suppliers, such as slower production and delivering incomplete parts.

Even after retiring, I've stayed up to date with Boeing. I've followed the news on malfunctions and strikes, but I think management is taking baby steps in the right direction.

I saw chaos unfold at Boeing due to mismanagement and outsourcing

During the good old days, I had a positive opinion of Boeing. In my first decade at the company, the chain of command was clear. You knew what your job responsibilities were and could count on your line managers. Most importantly, there was no drama with executives, and we had confidence in those in command.

But in 1997, upper management was thrown into chaos when Boeing merged with McDonnell Douglas, with McDonnell Douglas executives taking top positions at Boeing. Harry Stonecipher, who was briefly Boeing's CEO, resigned in 2005 after he was found having an affair with an employee.

It was like a corporate soap opera played out in the media. As an employee, the news was distracting and felt like evidence of the level of disorder at the top of the company.

At the same time, the Boeing 787 program was underway. The 787 was launched as a complete departure from how Boeing airplanes had traditionally been constructed. To reduce the time from program launch to when the planes were in service, Boeing would have "risk-sharing partners" deliver complete aircraft sections to the final assembly site.

787 program managers and employees implicitly understood this new production method, and we cautiously believed it might work. But it began to unravel bit by bit and ended in a three-year delay.

I wondered why we were accepting substandard work on 787

I was a project manufacturing engineer for the 787, creating work instructions, and a liaison manufacturing engineer, working on the shop floor to resolve issues with existing work instructions.

At the beginning of each new airplane program, program leadership and supply chain management divided major sections of the aircraft among various subcontractors, suppliers, and risk-sharing "partners." When suppliers were late in delivering their components or delivered them incomplete, this became "traveled work," which had to be completed by Boeing employees during final assembly.

I spent much of my time on the program trying to accommodate parts that had a "non-conformance" tag on them and had to be reworked and installed into the build.

I wondered what was going on and why we were accepting substandard, incomplete work.

As an engineer, I wasn't privy to the decisions going on in the upper chambers of management, but I could see the chaos filtering down. It felt like the company wasn't listening to its mechanics about how to improve processes.

I remember group meetings where employees, including myself, questioned decisions by management and offered constructive criticism that was politely but bluntly blown off.

The 787 was sadly delayed three years.

Confusing supply chains seem to still cause problems

In 2024, there was an incident with a Boeing 737 Max plane, where a door plug blew out after take off.

Although I retired in 2017, I think this was caused by mismanagement of traveled repair work. The plug door was manufactured by Spirit AeroSystems, a Boeing subsidiary that was sold off in 2005.

An investigation found that because the part 737MAX9 fuselage is shipped in whole, mechanics at Boeing rarely work on the plug doors. When the plug door frame had to be repaired and the plug door replaced, two separate groups of mechanics working on the door made mistakes.

As a result, a plug door malfunctioned, and Boeing's reputation was damaged alongside it, causing the FAA to increase its oversight of 737MAX9 planes' production processes.

It's always disappointing when the company you worked for makes major news headlines for a mistake. However, it doesn't change my general opinion of Boeing. I know there are many dedicated employees who are committed to doing their jobs properly and safely.

Boeing is taking baby steps in the right direction

I still know some Boeing employees and followed the recent strike. I think employees have gotten a good package, but they didn't get a return to the legacy defined-benefit pension plan. When I retired, I still benefited from the traditional pension plan and also had a 401(k).

Back in 2014, Boeing promised employees that they'd build the 777-9 in Washington. Part of the strike package is also building the next new plane in Washington. These promises show that Boeing management is waking up to the matter of outsourcing.

Boeing is also bringing Spirit AeroSystems, which it sold in 2005, back in-house. All the workers will be merged back under one camp.

The lines of communication between two in-house teams are often simpler and more direct than with a supplier. When I was on the 777 program in the 1990s, I would call my counterparts at the Wichita site to resolve issues and exchange information. I couldn't do this with a supplier because all communication had to be through supply chain management.

I think this shows Boeing acknowledging it went down a bad path when it sold the supplier.

I see these actions as baby steps in the right direction. Kelly Ortberg, Boeing's CEO, is trying to steer the company on a new course, but I think it's going to take a long time.

Editor's note: In response to Business a request for comment from Business Insider, a Boeing spokesperson highlighted remarks by CEO Kelly Ortberg during the company's third quarter report:

"Much has been written about how we got to where we are, but most also recognize that Boeing was once a benchmark for what good culture looks like. And I believe we can return to that legacy. I know culture change starts at the top. Our leaders, from me on down, need to be closely integrated with our business and the people who are doing the design and production of our products. We need to be on the factory floors, in the back shops, and in our engineering labs. We need to know what's going on, not only with our products but with our people."

• Matt Phillips is an assistant VP in AT&T's benefits department.
• He shared 5 tips for making the most of your employee benefits.
• He touched on how to avoid redundant dependant coverage and utilizing HSAs.

This as-told-to essay is based on a transcribed conversation with Matt Phillips, 45, the assistant vice president of benefits, health operations at AT&T, from Dallas. Business Insider verified his employment with documentation. The following has been edited for length and clarity.

The benefits enrollment process is a two-way street. My department spends a lot of time on our package, but employees also need to understand and engage with those benefits so they can make the most of them.

I've worked in the HR benefits department at AT&T for over 10 years. We spend a lot of time trying to educate and inform employees on what they need to know about their benefits.

Prior to that, I worked as an actuarial consultant, where I consulted on post-employment benefits, such as pension and retiree health, and also worked for a nonprofit.

Since joining AT&T in 2013, I've worked in multiple areas of our benefits department, including in strategy and in running savings plans. Five years ago, I moved into my current role, overseeing all health and well-being operations.

Here are some of my top tips about benefits enrollment for employees:

1. Ask yourself key healthcare questions and consider virtual options

Asking yourself key questions can help you pick the best health plan during enrollment season.

For example, do you want to pay more or less now for your health plan?

Choosing a high-deductible plan that's cheaper in terms of what comes out of your paycheck exposes you to higher out-of-pocket costs throughout the year. I think a good idea is to pair a plan like this with an additional ancillary medical plan, like a critical illness, hospital indemnity, or accident insurance plan.

For example, my son runs cross country, and in 2022, he fractured his tibia. There were significant costs for urgent care, imaging, and a specialist appointment, but through my accident plan, I got a payment from the insurer to provide more financial security at this time.

Also, virtual care has come a long way. I often hear employees say they don't have time for preventive check-ups with primary care physicians. However, it's possible to establish an ongoing relationship with a primary care physician virtually, so I'd encourage employees to look into virtual benefits options.

This can also include virtual mental health counseling. If you feel you don't have time in your day to go see a therapist or coach, you may be able to do it over the phone.

2. Go beyond a medical plan

I spend a lot of time telling employees not to just focus on their medical plan but to ensure they're taking advantage of all the other benefits available to them.

For example, at AT&T we offer employees a robust legal plan. If you may need to do something like write a will or set up an estate plan, a legal plan can help provide services around that.

My family has also benefited from an elder care planning service under my benefits plan. The company paid for a professional to come and meet with my wife, her cousin, and me about making a plan for caring for my wife's aging aunt.

While you do have to specifically enroll in something like a legal plan, companies may give other benefits to all employees automatically. Our dependant care and mental health benefits are given to all employees without a need for enrollment, for example. Ask the HR or benefits person at your company what you're entitled to that you don't even have to enroll in.

3. Max out your 401(k) contributions and use retirement planning tools

My advice for those thinking about retirement is to make sure you're not leaving any free money on the table.

Look into your company's 401(k) match and make sure you're maxing that out.

Many employers also have a retirement planning tool that can help you. We have an online one where you can say, "I want to retire at this age, I want this much money in retirement," and it helps you build a plan for how much you should contribute to hit that goal by the time you retire.

People should also be thinking about healthcare expenses for retirement. That's likely to become a larger share of your out-of-pocket expenses once you leave a company, especially if you retire before you become Medicare-eligible. Make sure you speak about this with your advisor and think about leveraging a Health Savings Account for that.

You don't lose your HSA when you leave a company. You can contribute tax-free, interest is tax-free, and if you use it on qualified healthcare expenses, it comes out tax-free. Plus, your employer might offer to contribute to or match your HSA contributions as part of a benefits plan.

4. Avoid redundant dependant coverage

When both spouses work and have children, it doesn't make sense to cover the children under both benefits plans. You'll end up paying double out of your paychecks but not necessarily getting double the benefits out of it.

If one parent's insurer agreed to cover or make a payout for a claim, then the other parent's insurer likely wouldn't, on the basis that the family has already received coverage and potentially a payout for the claim. Insuring dependents under both parents' plans could cover potential gaps in one parent's coverage, but it's often not worth it.

Instead, parents should compare potential costs under each plan and pick the best option.

5. Reach out to people in your company who can help you

There's usually someone in your company you can contact to talk about benefits options. If it's not your direct HR person, because you're at a really large company, they will have hired resources to help you. Call that phone number, download that app, or chat with that person.

Your company will hopefully have invested in those resources to help you navigate the process; you just need to reach out and take them.

Are you a professional or consultant with advice for employees to maximize their employment? Email Charissa Cheong at [email protected]

• Aaron Goldsmid, head of product at Deel, has previously worked for Facebook, Amazon, and Twitter.
• Early in his career, Goldsmid said he over-indexed on emulating senior leaders.
• He also said he focused more on hitting OKRs than investing in relationships.

This as-told-to essay is based on a transcribed conversation with Aaron Goldsmid, a 44-year-old from San Francisco about mistakes he made early in his career. Business Insider verified his previous employment at Microsoft, Facebook, Twitter, and Amazon with documentation. The following has been edited for length and clarity.

I had a somewhat atypical journey into tech. My parents were Broadway performers, and I was the first person in my family to go to college.

I became interested in computer science in high school and broke into tech straight after studying computer science at Columbia.

Through the college recruiting process, I got a job at Microsoft in 2002 and spent nearly six years there, largely working in the security space.

During the 2010s, I held tech roles at Amazon from 2011 to 2012, Facebook from 2012 to 2014, and Twitter from 2014 to 2015, as well as working at several smaller companies.

I've been fortunate to work at some of the most iconic tech companies during interesting periods. I've taken tools from each opportunity and now apply them to my current job as the head of product for Deel, a payroll and HR platform.

Because my parents didn't have 9-to-5s, I sometimes struggled to determine how to succeed in the corporate world. I didn't have anyone telling me about things like checking boxes to get to the next level in my career and how frictional relationships can impact the workplace.

Now that I have two decades of career experience under my belt, I understand how to avoid some of the mistakes I made early on and plan a career more intentionally.

Mistake 1: Thinking one job ahead instead of two

When I informally coach folks about careers, I usually advise them to think two jobs ahead.

Instead of thinking about what you dislike about your current job and whether your next role will solve that, think two jobs ahead. I tell early career techies to ask themselves how their next role will get them to the role after that.

After leaving Microsoft, I moved from Seattle back to New York, where I grew up. I wanted to secure a job in the city, and because the tech scene wasn't as mature in New York in the early 2000s, I took a role at NBCUniversal, helping build their video streaming service.

I did good work in that role, but I'm not sure it necessarily advanced my career. I then joined a startup because they gave me a very fancy title, but I ended up leaving before completing one year because I felt there were problems at the company, and I realized I'd chased a title instead of thinking things through.

As I advanced in my career, I knew I needed to focus on the skills I needed to acquire rather than the prestige of a position.

When I joined Kiva, a microfinance nonprofit, in 2018, I didn't view it as a permanent job. I took the job to gain skills outside a product and engineering capacity.

During my time there, I learned about business development and communicated with UN officials and central bank leaders. Not only did I get to experience the challenges faced by other teams, but I also got to know different contours of the product, business, and customer experience.

When I moved into my next role, a general manager at the communications company Twilio, I had a broader scope of experience and could operate more effectively.

You can accelerate quickly into a senior role, but taking a less fancy role and diversifying your experience might mean your upside long-term is much higher. If you're thinking two jobs ahead, evaluate what opportunities will help you more in the long run. It's a marathon, not a sprint.

Mistake 2: Not investing in relationships

Early in my career, because I didn't know how corporations worked, it was easy to think that everyone in a company was aligned and felt the same way, which is foolish.

When I worked at Twitter on their growth team, my job was to play in other people's sandboxes and tweak things. The company was having a difficult growth time, and we had to be hyper-focused on hitting our OKRs. This sometimes came at the detriment of my team's relationship with the rest of the product engineering org.

We had to step into other team's territories and move quickly. I felt I needed to hit a goal at all costs, and the problem was "at all costs." We often weren't on the same page as that team and had to go back and repair relationships afterward. In hindsight, I needed to do a better job of explaining why we were doing something from the outset.

Not everyone is trying to achieve a company's mission in the same way, and so by investing in relationships, you can more clearly communicate how you align with others in a company. Even if they don't align with you, they'll respect your process.

Mistake 3: Over-emulating senior leaders

Early in my career, I didn't have a role model in the corporate environment, so I questioned what "good" looked like and how I should show up.

Folks who are early in their career will often look at people who they think are successful and think, "I want to be just like them."

But sometimes, early-career workers have a hard time distinguishing the reasons for a person's success from their bad habits. They might not know things that the company has been willing to work around or that hold that person back.

Early in my career, I over-indexed on emulating senior leaders. For example, I'd see some of them making sweeping statements like "This is the future, or, this isn't the future." They can get away with that because they've proven themselves, but I'd do the same, and it would fall on deaf ears. I hadn't yet earned that level of credibility and still needed to "show my work" before I earned that trust.

As a senior leader at Deel, I'm very conscious about how I present myself to early career folks. In larger meetings, I remind myself that there will be people on the call who view my role through a limited set of interactions. I don't want to pass on any bad behavior or shortcomings for them to emulate.

Do you have a career story you want to share with Business Insider? Email [email protected]

Silicon Valley is the undisputed global tech hub. The small corner of California is the birthplace of Apple, Google, and OpenAI — companies that have, for better or worse, changed modern life.

Far away, in the southern Indian state of Karnataka, another tech hub has been finding its footing in the international market. The city of Bengaluru is the startup capital of India and shares similar DNA to California's Silicon Valley.

Bengaluru grew into an IT hub in the wake of the rapid expansion of its electronics manufacturing industry from the 1940s to the 1960s. Back in the US, Silicon Valley was home to the semiconductor industry in the 1950s and owes its name to the silicon transistors produced there in the 1960s.

By the mid-1980s, Apple, Oracle, and Microsoft had a presence in the Valley, while in Bengaluru, large companies like Infosys and Texas Instruments moved in.

Bengaluru is widely referred to as the "Silicon Valley of India," producing tech unicorns and housing offices for companies like Amazon, Google, and Dell. After taking over Twitter, Elon Musk shut the company's offices in Delhi and Mumbai but kept the Bengaluru office. Earlier this year, Virgin Atlantic launched daily direct flights from London to Bengaluru.

However, the city's status as a tech metropole is under pressure as rapid growth tests the local infrastructure. Estimates place the current population at roughly 14 million, compared to 8 million in 2010.

Heavy traffic, water shortages, and rising property prices have led to online speculation that Bengaluru may be crumbling and debates about whether another city will emerge as a new tech hub in India. During a water crisis earlier this year, some tech companies in Bengaluru had to tell employees to stay home.

Business Insider spoke to four current and former Bengaluru residents in and outside the tech industry who shared their experiences of how India's "Silicon Valley" is holding up under the pressures of rapid urbanization and whether they believe it can maintain its place as a global tech hub.

Vikram Chandrashekar

Vikram Chandrashekar, 50, was born in Bengaluru and has worked at Oracle for the past 27 years. He told BI he is happy for the job opportunities Bengaluru's status as a tech hub has brought, but is nostalgic for the city of his youth.

A lake he visited when he was younger, across from a guava and mango orchard, has now been replaced by housing.

Chandrashekar said the IT boom drew people to the city, bringing a larger airport, a more diverse culture, and better internet connectivity. He is also grateful to the startup ecosystem because he has access to new services and products faster than the rest of the country.

He said local people have benefited from job opportunities, but they still complain about the issues urbanization has caused. Chandrashekar doesn't plan to leave his hometown and thinks creating other tech hubs in India to redirect the growing population is a solution.

Read Vikram Chandrashekar's full story here.

Dhruv Suyamprakasam

Dhruv Suyamprakasam grew up joining his dad on business trips to Bengaluru and Hyderabad, another large tech hub in India. When Suyamprakasam became a founder himself, he moved to Bengaluru twice.

However, the founder said the city wasn't a golden ticket to success, and Suyamprakasam decided it was better to build his startup in his local city.

Suyamprakasam first moved to Bengaluru in 2010 after launching a medical startup with his relative.

It turned out to be a mistake. Suyamprakasam said Bengaluru's tech ecosystem's "fail-fast" mentality put too much pressure on their medical startup. He also felt excluded for being from a smaller city, not speaking Hindi, or not having studied at India's top engineering school.

Suyamprakasam said access to talent and venture capital are huge advantages of Bengaluru, while smaller cities can offer lower costs and more space.

Still, Bengaluru doesn't compare to Silicon Valley's vast capital and power. The founder said Bengaluru can be great on its own merits, but it needs to start being more inclusive.

Read Dhruv Suyamprakasam's full story here.

Batool Fatima

Batool Fatima, 50, moved to Bengaluru nearly 25 years ago from Hyderabad. Like Chandrashekar, the founder of a local nonprofit organization saw the city known for greenery and lakes change before her eyes.

Fatima said she is concerned that the city may not be able to support further population growth and that residents must work on improving the city's problems.

She said more intellectuals and non-tech workers have moved to Bengaluru which has been beneficial. But there have been reports of tensions between locals and immigrants who don't speak the language.

The influx of people has also caused environmental strains, including a recent water crisis. Fatima said the shortage disproportionality impacted high-rise buildings, a telling example of the lack of planning around urban growth.

The philanthropist said she wanted companies to invest in solutions to protect Bengaluru's natural resources, like funding wetland wildlife reserves. She also said community action, like residents collecting stormwater drainage, is more helpful than complaining about the government.

Fatima said developing nearby suburbs could reduce the strain on the city's center and allow the tech hub to continue to thrive.

Read Batool Fatima's full story here.

Spencer Schneier

Spencer Schneier is from New York, but spends half his year in Bengaluru and the other half in San Francisco running a tech startup.

The pandemic opened Schenier's eyes to the idea of leaving the US. In 2020, Schneier worked with two Indian cofounders and joined them on a trip to Mumbai and Bengaluru. While traveling, he decided to launch a startup from Bengaluru to help businesses expand overseas.

Schneier told BI he chose the city because it gave him access to customers, other founders, and small businesses to learn from. He said the Indian startup ecosystem was more conservative than the US, but the next generation of investors is really promising.

Now Schneier spends half his time in San Francisco and half in Bengaluru. He loves the Indian city's moderate climate and generosity. The tech CEO said he struggles with traffic and bureaucracy in the city, but feels he is part of a larger trend of people moving to India to start businesses.

Schneier told BI he believes the appeal of Bengaluru's talent density and local generosity will gain popularity.

Read Spencer Schneier's full story here.

In the tussle between economic growth and sustainability, can Bengaluru have it all?

Bengaluru has undergone significant changes in its transition from a serene "Garden City" to the Silicon Valley of India. Residents said the rapid urbanization has brought both opportunities and challenges.

The opportunities — a booming tech and startup industry, jobs, and diversity — draw people to the city and keep locals living there. But residents BI spoke to are keenly aware of the tradeoffs, pointing to environmental degradation, rising costs of living, and traffic.

The tension between Bengaluru's growth as a tech hub and the cost for its inhabitants lies at the heart of the city's future.

Harini Nagendra, a professor at Azim Premji University in Bengaluru, said, "There's a city which is growing, and there's obviously the economic prosperity it brings, but there's also the ecological degradation that you see everywhere."

Nagendra echoed Batool Fatima's suggestion of a collaborative solution with companies and residents maintaining their local environments.

Narendar Pani, an economics professor at the National Institute of Advanced Studies in Bengaluru, said the city's growth also hinges on education – better education in urban planning and the ongoing strength of city's educational institutions.

"When people look at Bangalore's future, they think about roads and water," he said. "Water is important, but I think more than the roads, a much more critical element is education."

He, like other residents who spoke to BI, expressed a cautious hopefulness that Bengaluru would solve its problems and continue to grow.

"I belong here, so I would like to think the ideas will come," he said.

• Batool Fatima moved to Bengaluru, "India's Silicon Valley," nearly 25 years ago.
• She said the city felt like a dream when she arrived but now it's struggling with urbanization.
• After a water crisis this year, some people are leaving Bengaluru but Fatima plans to stay.

This as-told-to essay is based on a transcribed conversation with Batool Fatima, 50, about environmental issues facing Bengaluru, the city known as "India's Silicon Valley." The following has been edited for length and clarity.

I was born and raised in Hyderabad. Like Bengaluru, it's one of India's tech hubs.

I moved to Bengaluru in 2000 after I got married because my husband lives there. I also visited frequently as a child because my father used to work there.

It was like a dream city for us then. It was more advanced than Hyderabad, with wider roads and a lot of greenery and lakes.

Over the years, the rapid expansion of certain industries in Bengaluru, such as IT and ITES, fueled significant construction and population growth. The landscape changed in front of our eyes. Development has had a positive impact, creating opportunities for both locals and migrants.

But Bengaluru is dealing with water scarcity issues and some people seem to be leaving the city because of problems with infrastructure. Rather than leaving, I want to work on solutions. The community must come together to prioritize sustainability and the city's natural resources to preserve its future.

People who've moved to Bengaluru help to sustain the city

I've been working in the nonprofit sector since 2011. In June 2024, I started my own nonprofit, Sheya Foundation. We're invested in equitable access to healthcare and education, and I'm also very interested in climate issues.

Bengaluru is seen as an IT city. It's an aspirational city to live in because it's known for its pleasant climate and career opportunities.

With the development of the city's tech sector, a lot of intellectuals have moved in, many who care about the city and climate. However, there have also been environmental and economic strains.

There's an economic strain on people who don't work in IT and don't make high salaries. With wealthier tech workers in the city, the cost of living has risen dramatically, and houses have become more unaffordable. I'm seeing young people dropping out of school to start work because of the impact of higher costs on families.

Other people who aren't IT employees have moved to the city to work in industries serving the tech community, such as hospitality and schools. These people are helping to sustain the city.

There have been some tensions between local people and those who've come from elsewhere because of cultural differences. Recent reports suggest a rise in confrontations between locals and people who don't speak the language.

I'm not from Bengaluru and haven't encountered any negativity myself. But I speak Telegu, which many local people also understand, so I feel at home here.

I'm concerned about water scarcity in the city, but there are solutions

Water scarcity has become a particularly visible issue in Bengaluru.

The number of lakes in the city has decreased significantly in recent decades due to urbanization. Too many high rises are coming up too fast, and I don't think there's enough planning going into water facilities to sustain residents.

Bengaluru dealt with a huge water crisis earlier this year. It particularly affected people in high-rise buildings because the buildings are over-reliant on borewells that dried up during the crisis.

The water crisis didn't affect me too badly. Where I live, there's only one borewell for our group of villas, so we agreed to ration it and only use the water for half an hour per house each day. Since June, we've had good rain, so we no longer need to restrict ourselves.

The water issues seem to have calmed down across the city. But we'll have to see if there'll be a year-on-year impact during the summer months.

We need to be ruthless about not encroaching on our lakes. If we're going to be lax on this aspect, people are going to leave. I've read on the news that some people left during the summer because of a lack of water.

I'd like to see companies investing in solutions for Bengaluru. For example, they should work with the government to develop vegetation wetlands.

Residents also need to assess what we are doing to treat water as a precious commodity instead of complaining about what the government isn't doing. The community has to collaborate with the government by doing things like looking into stormwater drainage for their houses.

We need to work on solutions for the city rather than try to create a new Bengaluru elsewhere

Public infrastructure has struggled to keep pace with Bengaluru's growing population. I feel the city is bursting at the seams and may not be able to support further population growth.

But that doesn't mean I want it to stop developing as a tech hub. Bengaluru contributes significantly to India's GDP and helps generate high-paying jobs. Maintaining it as a tech hub allows players in the tech ecosystem — multinational companies, startups, research institutions, and a skilled workforce — to continue collaborating, driving innovation and job creation.

The state government has been developing nearby suburban regions like Yeshwanthpur and Bidadi, which can reduce congestion in the city's core while enabling Bengaluru to continue excelling in tech. In my opinion, that's a more viable solution than relocating the IT sector to other regions in India.

It's not going to be easy to move a tech hub from Bengaluru to another city. When I visit, Hyderabad, my hometown, which is also known for IT, there are similar issues there in terms of traffic, water, and property prices.

I want to keep using my foundation to build community awareness. I love Bengaluru, and I'd rather stay here and work on solutions than leave.

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• When Vikram Chandrashekar was growing up in Bengaluru, it was quiet and full of natural beauty.
• Chandrashekar said urbanization is a good thing, but it changed the city too quickly.
• He enjoys living in a tech hub, but said locals are struggling with the pressure on infrastructure.

This as-told-to essay is based on a transcribed conversation with Vikram Chandrashekar, 50, who was born in Bengaluru, India, about how the city has changed over his lifetime. The following has been edited for length and clarity.

Bengaluru has become known as the "Silicon Valley of India," but it was once known as a "Garden City."

I was born in Bengaluru and have lived in J.P. Nagar, a neighborhood in the south of the city since I was seven. Back then, it was a remote area with a lot of trees and gardens.

There was a huge lake with a guava and mango orchard across from it. We used to get off the school bus, grab a mango, wash it in the lake, and eat it.

Now, there are houses where the lake used to be, and the majority of the orchard is gone. As the tech sector developed in Bengaluru over the decades, there was a lot of urbanization. As a result, there's less greenery on the streets and more high-rise buildings.

Urbanization is good, but it transformed Bengaluru too quickly and too soon — the city's been catching up ever since. It's left some people feeling frustrated about things like traffic, housing costs, and this year's water crisis.

I've witnessed Bengaluru's transformation into a tech hub

Bengaluru used to be a place where retirees wanted to live. It was a quiet place with a relatively moderate climate.

There's a long history of science and tech development in Bengaluru. The Indian Institute of Science and Raman Research Institute is here. We also have a decadeslong history of aerospace research and electronics manufacturing.

In the 80s and 90s, IT companies like Infosys, Wipro, and Texas Instruments moved into Bengaluru. In the mid-2000s, the startup ecosystem grew as it became more accessible and normalized to start a business.

IT created a lot of job opportunities, just like it did in Silicon Valley. Today, there's a large startup ecosystem and community of venture capitalists. It's probably the best place to launch a startup in India, which means more people have come to the city, creating a need for more space, public transport, and residences.

It also created a lot of urbanization, which gave people more access to resources. We had a larger airport, restaurants with various cuisines coming into the city, and affordable internet access due to more competition between companies.

Because of the startup ecosystem, we get new services and products faster than other Indian cities. I've benefited positively from urban development in these ways.

There are benefits and drawbacks to Bengaluru's transformation

I'm employed in the IT sector. I've been working at Oracle for the past 27 years, and my current role is solutions architect.

People in Bengaluru have undoubtedly benefited from the job opportunities created by the tech boom, but I think local people are split on the effects of urbanization.

It's common to see negative comments about Bengaluru on social media or people complaining to their friends. I think the three biggest issues they raise are the water crisis, housing prices, and traffic.

Traffic is definitely an issue. Public transport isn't sufficient as it stands. Before the pandemic, I'd take the metro to work four days a week because it made me less angry than driving in traffic.

Residential pricing has increased from what it used to be, but so have housing prices in other cities. I'm living in a house that belonged to my parents, so I don't have to pay rent, and this isn't an issue for me.

Bengaluru has had long-standing issues with water. There are too many people and a limited water supply due to a decreasing number of lakes. Earlier this year, there was a very bad water crisis because it got very hot and there was little rain.

People were consciously trying to conserve water, and the government brought in water tankers for people to get water at a price. I've never struggled with water supply in the past: I have access to a well, rainwater harvesting, and facilities to store water from the public supply. But this year, I noticed the public water supply was running out more frequently, so even I had to buy water a few times. It was a bad feeling which made me see how the city was changing.

Things have definitely improved since the summer, and hopefully, people will be more prepared for next summer.

I support carpooling, using public transport, and rainwater harvesting to address infrastructure issues in Bengaluru. We should also plant trees for the next generation. Tree roots can help absorb rainwater when there's flooding, so it's important to conserve every tree.

Creating other prominent tech hubs like Bengaluru is a good solution, but progress has been slow

Despite the concerns people have, I don't think people are leaving Bengaluru.

Jobs are a big reason why. There are opportunities in tech and other industries serving that community, such as schools, public transport, and cooking.

There are problems, but they're probably not as bad as social media portrays them to be. I'm frustrated by the traffic and water crisis, but I'll probably continue to live in Bengaluru.

For many years, people have talked about creating alternate cities to Bengaluru within the state, or cities like Hyderabad or Mumbai replacing it, but I feel progress on this has been small.

The solution probably lies in creating other cities like Bengaluru that can distribute the load across various places, but even in other countries, this doesn't happen. One or two cities always take most of the burden.

There are cities near Bengaluru, like Mysore and Mangalore, that could be developed and house more tech parks, but people have to be willing to move there. I think companies have to move first so that good infrastructure, like schools and jobs, can develop, incentivizing people to move. Why not create more Bengaluru's across the country?

It's going to take a long while for anything to change, so I still think Bengaluru will continue to be "India's Silicon Valley."

It would be like trying to move the capital city.

A whole ecosystem would need to be shifted, and that's not going to be easy.

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