My journey as a search founder

The term you’ve probably heard before is a search fund  - where an entrepreneur raises money to acquire and run a company. The goal is to find an existing opportunity with potential for an exit, kind of like house flipping in the real estate market. 

I consider myself a search founder, constantly seeking my next venture-scale business idea to build from the ground up. I’ve worked in startups for the last decade, experiencing the roller coaster ride of entrepreneurship as both an employee and a founder - and I’ve been lucky to experience everything from stagnant growth to fundraising to acquisitions to an IPO.

During the pandemic, I had a lot of isolated time for reflection. I realized my primary skill set and passion is around being an entrepreneur. Whether as the founder of a company or working as an employee, I find myself rethinking the status quo, iteratively building things, and creating organizational change with others.

Now I’m pursuing an MBA at the University of Chicago Booth, with the primary focus of discovering my next startup idea to work on after graduating. Most of my peers in business school are taking part in a more known recruitment cycle like banking or consulting. I’m choosing a far riskier path, without any guarantees. So, I want to hold myself accountable and share my journey with you here.

How I got started in Silicon Valley 

I started my career in San Francisco as an app product designer in 2013 - it was my dream job at that time and I felt so lucky to be there. After working at a product consultancy called AKQA for a year after college, I realized I liked going deeper on one problem rather than giving other companies short-term advice. I used a new job marketplace called Hired to find my first startup job, at an early-stage fitness app company called Fitstar. 

I loved my new startup life at Fitstar. We shipped an iOS app to millions of subscribers, then launched the platform on web, Android, and Apple Watch. I was learning from smart people, working on a product I loved, and even got to design a personal passion project of mine - Fitstar Yoga. 

Six months after joining, Fitstar got acquired by Fitbit, and suddenly I was a product designer at one of the best-known consumer brands in the world. The product design team alone at Fitbit was made up of 60+ designers, split into specialists in ‘human factors engineering’ and ‘user interaction design’. Again, I was given a growth opportunity to learn from some of the best designers and engineers in Silicon Valley. 

Fitbit went public in 2015, just a few months after I joined. We celebrated the ringing of the NYSE bell at 6 AM in the brand new San Francisco office with champagne and Fitbit-designed mini cakes. I had experienced the full upward trajectory of the quintessential startup story in less than a year - from joining a scrappy team of 10, to being acquired and given meaningful ownership, to seeing the Fitbit founders do a roadshow and go public. I was in awe of the non-traditional career path I had been fortunate enough to find myself in.

I worked hard for the next two years, becoming more specialized in mobile app development, and building a network of as many smart entrepreneurs and product people in San Francisco as I could. 

Becoming a founder

I left Fitbit in 2017, looking to move away from San Fransisco and live as a digital nomad. I had a few consulting projects lined up with early-stage female founders I met in SF - like Simple Habit and Modern Fertility. I got a virtual mailbox to maintain residency in California (don’t ask me why I chose that state 🤷), sold all my things, and found an international insurance plan.

The first city I moved to was Mexico City, where I spent four months with my partner. Friends from San Francisco and around the U.S. were curious, wondering how we managed to live this international lifestyle but maintain a Silicon Valley salary (this was before remote work became ubiquitous during the pandemic). 

We started to realize there could be a business model around this working style - living remotely, working in SF. To test it out, we bought a domain (moonlightwork.com), put up a Squarespace site with a Typeform, and posted it to HackerNews and Twitter. Within a few days, we had thousands of signups from developers looking for highly paid software work. 

Over the next two years, we hustled to bootstrap the remote work marketplace while living in 8 cities around the world. Once we figured out a sustainable subscription model, we raised money from institutional venture capitalists and hired a remote team. We moved to New York City, with a roadmap to double down on growth and automation. (If you’re interested to read more about the Bootstrap journey, read my interview with IndieHackers here)

When it came time to raise a second round of funding, it was early 2020. Coronavirus was on the horizon, VCs were cooling off on investments, companies stopped hiring, and Moonlight had not achieved the hockey-stick subscription growth we promised to investors. The team was burnt out from three years of building, evangelizing, acquiring, and scaling the business - and our investors offered to introduce us to three potential acquirers. 

After a few weeks of negotiations and conversations, we got an acquisition offer from one of the startups. We took the offer and the deal closed - Google-backed PullRequest bought Moonlight and gave us offers to join the team and keep growing the platform. All considered, we were ecstatic to end the Moonlight journey with an acquisition. 

I joined PullRequest for three months through the transition, then left to join theSkimm as Lead Product Manager up until I started business school.

On the search for something new

Being an entrepreneur is addicting. It’s the opportunity to discover a secret insight and imagine a future that’s different from today, then work relentlessly to make it happen. 

I think there are lots of ways to take on an entrepreneurial role, even as an employee working within a larger organization. During my time at theSkimm, I was able to identify an opportunity with a forgotten mobile app, create a new strategy and roadmap, then hire a team to re-launch the subscription platform. This opportunity to create change kept me as activated in many ways as being a founder, but with the stability of a great paycheck and supportive benefits. But in the end, I was working towards someone else’s dream, which has its limitations. 

A year and a half after selling Moonlight, I finally have the headspace to start thinking about something new. What’s the next opportunity I want to devote myself to? 

The must-haves in my next startup:

• A product that needs to exist in the world and that solves a large problem

• An end-user who I care deeply about

• A clear path to monetization that doesn’t require ads

• Venture-scale growth 

The big unknowns I’m looking to discover this year:

• What problem I’ll be solving

• The exact industry (broadly within fintech)

• Who my co-founder(s) will be

• Yes, I realize these are really important unknowns!

So, I’ll be writing about my discoveries here. I won’t have all the answers and I’ll surely be wrong in my assumptions. If you read something I get right or wrong, if you want to get involved, if you have ideas, please tell me about it. 

Your feedback is always welcome, and thank you (really, thank you!) for following my journey. 

Oh, and wish me luck! I’ve got about 18 months to figure this all out before I finish business school in May 2023:)