I remember the exact moment I knew MovieLaLa was going to die. We were burning through cash, our user growth had flatlined, and I was sitting in a board meeting with investors who looked like they wanted to personally escort me out of the building. It was brutal. That wasn't my first startup, and it wouldn't be my last, but that feeling of impending doom is something you never forget.
People love to talk about the glory of Silicon Valley – the billion-dollar valuations and the flashy headlines about world-changing ideas. They don't talk as much about the gut-wrenching failures and the sleepless nights spent under constant, crushing pressure. I’ve been through the wringer four times as a founder. Two of those companies, MovieLaLa and RemoteTeam, ended in acquisitions. The other two, MojiLaLa and Leo AR, were a different kind of education. I want to tell you what I actually learned from the trenches, not the stuff you read in business books.
The First Hurdle: Getting Anyone to Care
With MovieLaLa, my first real swing at building a company, we had what I thought was a brilliant idea: a social network for movie lovers. We got into the Founder Institute, raised $750,000 from some big names, including Marc Benioff, and even got featured on TechCrunch. On paper, we were killing it. In reality? We were struggling to find a product that people would actually use every day. We had a lot of sign-ups, but not a lot of active users. That's a death sentence for a social app.
Here’s the thing about product-market fit: it’s not a checkbox you tick. It’s a moving target. We pivoted so many times I lost count. We tried being a movie recommendation engine, a place to buy tickets, a social game. Nothing quite stuck. The acquisition by Gfycat was less of a triumphant victory and more of a soft landing. It was a relief, but also a hard pill to swallow. I learned that a great idea and a great team aren
The Siren Song of a Hot Trend
After MovieLaLa, I jumped into the world of stickers and augmented reality. First with MojiLaLa, a marketplace for sticker artists, and then with Leo AR. This was when AR was the talk of the town. Everyone was buzzing about the potential. We built some incredibly cool technology. With Leo AR, you could place 3D objects in the real world, bring your NFTs to life, and create all sorts of amazing content. We got into the Betaworks Vision accelerator and the 500 Startups program. The tech was impressive, and we had a lot of fun building it.
But I made a classic mistake: I fell in love with the technology, not the problem it solved. We had a solution in search of a problem. People would download Leo AR, play with it for a few minutes, and then churn. It was a fun novelty, but it wasn t solve a burning pain point for a large enough audience. MojiLaLa had a similar fate. It was a great platform for artists, but the market for paid stickers just wasn't big enough to build a venture-scale business.
I learned that timing is everything, but you can't build a business on a trend alone. You need to find a real, painful problem that people are willing to pay to solve. And you need to be brutally honest with yourself about whether you've found it.
The Right Problem at the Right Time: RemoteTeam
My fourth startup, RemoteTeam, was different. I had been managing remote teams for over a decade, and I knew firsthand how painful it was to hire, onboard, and correctly pay international employees. It was a mess of a frustrating mix of spreadsheets, wire transfers, and legal headaches. I knew there had to be a better way.
This time, I wasn't chasing a hot trend. I was scratching my own itch. I was solving a problem that I understood deeply. And it turned out, I wasn't the only one. When the pandemic hit, the world went remote overnight, and suddenly, every company was facing the same challenges we were.
We built a platform to streamline the entire process of managing a global workforce. We made it easy to pay contractors in their local currency, handle compliance, and offer benefits. We weren't just building cool tech; we were solving a real, expensive problem for businesses. The demand was insane. We were growing so fast we could barely keep up.
In 2021, Gusto, a giant in the HR and payroll space, came knocking. They saw what we had built and how it fit perfectly with their mission to simplify payroll for small businesses. The acquisition was a no-brainer. It was a true win-win. We had built something of real value, and Gusto was the perfect home for it to grow.
What I Learned from It All
Looking back, the biggest lesson I've learned is this: focus on the pain. Don't get distracted by shiny objects or the latest tech fads. Find a real, burning problem that people are desperate to solve, and then build the best possible solution for it. That's it. That's the secret.
My journey as a founder has been a rollercoaster of highs and lows. I've made more mistakes than I can count. But each one has been a lesson. And those lessons are what have allowed me to become a better entrepreneur and investor. It's what I write about in my book, Becoming Top 1%, and it's the foundation of my approach to angel investing, which you can read more about in my post on how I became the #1 angel investor.
So if you're a founder out there in the trenches, my advice is this: don't give up. Keep learning and keep iterating. Most importantly, keep solving real problems. The road is long and hard, but it's worth it.
Frequently Asked Questions
What was the biggest challenge in this case?
Almost always, the biggest challenge is people and alignment, not technology or strategy. Getting the right team focused on the right problem is harder than any technical challenge I've encountered.
What would you do differently looking back?
I'd move faster on the things that were working and cut the things that weren't sooner. Most founders, myself included, hold onto failing strategies too long because of sunk cost. Speed of learning is everything.
Can these results be replicated?
The specific numbers will vary, but the underlying patterns and principles are transferable. The key is understanding the context behind the results, not just copying the tactics. Every company has unique constraints that shape what works.
How long did it take to see results?
Most meaningful business results take 3-6 months to materialize. Anyone promising overnight success is selling something. The companies in my portfolio that grew fastest were the ones that stayed patient and consistent.