New Beginnings

New Beginnings

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As you may have heard from my previous post, I’ve left Apple. Part of my decision to leave was motivated by the fact that even before joining Apple, I knew I wanted to work at a startup.

So, let’s cut to the chase: I’m headed to an insurance tech startup called Vouch where I’ll lead the Data team as an engineering manager. Today’s my first day, and I couldn’t be more excited.

You won’t be surprised to hear that I was systematic in the search to find my next role. Why go to a startup? How did I find Vouch? Why did I pick Vouch from all the options I had on the table? Below I’ll try to answer these questions.

Space and Product:

While I leaned towards fintech and fintech adjacent companies given my interests and my background in economics, that wasn’t a hard requirement. Finding a startup whose product depended on understanding risk and reward using data was key, though. Ideally, the data processing systems my team and I would build would be critical to the day to day operations of the business, not a support function nor an afterthought.


I was looking for one of two kinds of software engineering roles:

  1. An individual contributor position at a startup with 5-20 people, where the promise of fast growth implied the opportunity to take a leadership role within a few months to a year. This was appealing because of the prospect of getting firsthand experience finding product market fit.
  2. A manager role at a larger startup with roughly 50-100 people, with a working product but growing pains, the kind of place where my experience in scaling systems and leading teams would be relevant from day one.

In both cases, I’d be early enough to wear many hats, at times by necessity and at times out of curiosity.


I wanted to stay in San Francisco. Say what you want about Miami, Austin, and wherever else you imagine people are leaving the Bay Area for1 but this city is amazing. Even with all its problems, I don’t want to leave. I enjoy being surrounded by nature, the culture, and the vibrant tech scene. I’m also one of those weirdos who loves the year round 50s and 60s. Needless to say, I’m long SF.

For the right opportunity, I would have considered a commute across the Bay Bridge or even down to the Peninsula, but those were points against the companies I talked to outside of the city.

Separately, while I’m bullish about the rise of remote work (and in fact have a strong reason to want it to become mainstream), after working from my apartment for a year, I’m really craving the human interactions that come from being at an office and meeting people face to face. Finding a company with a strong office culture was important to me.


Amazing leadership, great investors, and ambitious, smart peers, were the top requirement in my book.

The best interviews I had were more about me interviewing the team I’d join than them interviewing me. In some cases, I even ended up emailing back and forth with some of my interviewers for days after our meetings, going deeper into nuanced points of our conversations.

Considering The Future:

These days, it seems unusual for people in tech to stay at the same company for a long time. My almost six years at Apple put me at the top of the distribution for people I know in my age group. One possible implication of this is that many young people see their current and next jobs as springboards to something else that they really want to do.

In my case, I know that eventually I want to start my own company. While I already have ideas I’d like to develop, I didn’t want to jump from years at a 100k+ person behemoth like Apple with its structure and its processes into the mess of optionality that is a startup of 1. A better strategy, I thought, was looking for a smaller company that could act as a stepping stone, where I could learn about how things work at a small scale before taking on that challenge on my own.

I made this goal clear to my interviewers at the various companies I talked to, but my entrepreneurial ambition wasn’t taken as a positive everywhere. It was important to me to find peers and superiors that understand where I want to go, and to land a role where that goal could inform the kinds of projects I’d be involved in. Having people who could coach me in that direction would be icing on the cake.

Finding The Role

Because I wanted to find a role at a small company, rather than looking for intriguing teams at FAANG or late-stage startups, I knew that I’d have to put in the work to find a good fit. The challenge in my case was finding places with an interesting product and clear growth potential. I wasn’t going to find the best opportunities by searching on LinkedIn or AngelList, which would be too noisy.

Instead, I decided to build a list of reputable venture capital firms whose portfolios I could scan to seed my top-of-funnel. Every VC loves to boast about having a slice of the most successful startups; some VCs even have their own internal job boards2 and talent consultants3 who help match you with their portfolio companies. Iterating through the public portfolios of a16z, USV, YCombinator, Ribbit, First Round, etc, I built a list of over a hundred companies where I could see myself (assuming there was a relevant opening), all at the right stage and with interesting enough products.

While word of mouth could have been a useful channel, COVID meant that the network I’d feel comfortable reaching out to was smaller than usual - I hadn’t talked to most friends of friends in months, and I had few opportunities to catch up with acquaintances where I could casually mention I was starting to look. I added a few suggestions from my closest friends to my list, along with things I learned about through social media, but the bulk came from the seeding process described above. Vouch came in through YC’s Top Companies list, where they are ranked at number 70, above well known names like Substack, Optimizely, Heroku and Lambda School.

After assembling the list and narrowing it to companies that were hiring for relevant roles, my next step was sharing it with a few friends to see if I could network my way into any of the options via warm introductions. My brother happened to know someone who was connected to Vouch and I got a warm intro to their team.

Why Vouch?

Vouch checked the boxes in terms of role and location — they were looking for an SF-based engineering manager to build out their data team. Insurance tech wasn’t exactly what I originally had in mind, but it was fintech adjacent, and the kind of data problems I’ll be tackling along with the regulated environment made it a pretty good fit.

A unique perk I realized early in the interview process is that in addition to learning of Vouch’s successes and mistakes from my day to day experience, my job would also force me to find patterns in the data about what makes some companies riskier than others, learning about the challenges and blunders of startup founders and their teams. No other company I talked to had this characteristic, which can be thought of as a knowledge multiplier in the exact area that I want to learn the most right now.

I was also glad to find that the Vouch team seemed supportive of my long term goals of starting a company, with a leadership team eager to hear about my aspirations and who I’m looking forward to learning a lot from. Vouch scored bonus points for having leaders with successful exits, backing from some of the best investors in the fintech space, and standing partnerships with institutions like Silicon Valley Bank.

One of the most important criteria for my next role was a product I believe will make a positive impact. Vouch checked that box, too. I’m certain that making better insurance products more accessible to startups is a net positive for the world. The insurance business is rooted in a mutually beneficial market dynamic, where the insurer and the buyer of a policy get to share the risk of uncertain future outcomes. The buyer gets an upper bound for his losses while the seller gets to collect a premium. Unlike the buyer, for whom the risk can be existential, the insurer can treat a single policy’s risk as a small bet in a broader portfolio, lowering the volatility of the system as a whole, and thus creating value. Enabling entrepreneurs to take on more risk is one way to push out the frontier of what products are feasible to build, as it lowers the cost of failure.

Hopefully I’ll be able to share some of my early learnings in a future blog post. I’m sure there are plenty of exciting aspects of my new role that I haven’t even realized yet.

If these challenges sound amazing to you too, of course we’re hiring.

This is the second in a series I’m writing about my recent career transition out of Apple. See part one, on things I learned in my time at Apple, and make sure to check back in a few days for upcoming pieces on things to ask in interviews with startups, how to evaluate an offer from a startup, and tips on how to make your job transition as smooth as possible, etc.

Photo: Tunnel, Zürich, Switzerland, by me. Previously posted on Europa V, Zürich MMXX.

  1. Surprise, they’re all going to Tahoe, the East Bay, and SoCal

  2. The fact that there’s at least two startups who are building this product is fascinating in and of itself. 

  3. I learned about this too late in the process, but in retrospect it could have been a helpful channel. While talent consultants and applicants don’t have the most aligned incentives, it is an interesting relationship, where a single conversation can get you multiple double opt-in intros. I wonder how much of the attention I got came from having Apple on my resume, though. 

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