Crashing Cannes to Save My Startup

I’m on a triple-decker yacht in the South of France, dressed to fit in while servers offer champagne and caviar. Nobody here knows that I’m broke, with an eight-month pregnant wife and an equally broke co-founder an ocean away. Oh, and I’m not even on the guest list. I had slipped aboard via the servants’ plank.

But now I’m talking to a high-net-worth investor, pitching my startup like next week's rent money depends on it. Because it does.

The Hole We Dug Ourselves

Rewind a few months. I was on the phone with my team on Christmas Eve.

“We’re almost out of cash,” I tell them. It feels like announcing a death sentence.

I had invested $50,000 of my own money into the startup, and hadn’t taken a salary yet despite working full time for a year, living off what remained of my savings from employment at a big tech company. A few angels, friends, and coworkers from my old network had chipped in, but we blew a hole in the balance sheet when we fired a third co-founder we found to be untrustworthy. Why? Because we’d signed a contract with this exit clause: he immediately receives accrued salary if we let him go. A devastating rookie mistake.

We owed him five months of back pay. That nearly killed us outright. Combine that with the fact that our Techstars demo day “investor interest” evaporated; multiple venture capital firms (and angels) expressed interest in our funding round, but everyone wanted to follow, and nobody would lead. We were staring at zero.

I found a credit card startup that offered a 6 month intro APR of 0%, and that became our next source of funding. Did I mention my wife was pregnant with our second child?

Pivoting with Nothing Left

We had been building a B2B SaaS product aimed at big real estate investment players. That strategy was slow, expensive, and unlikely to generate sufficient revenue to survive before we flatlined. At the cliff’s edge, we decided to pivot to what had always been the end goal: a capital marketplace where real estate investors can discover new lenders and receive quotes from a marketplace, a strategy where revenue could show up faster. Instead of building it on top of a well-adopted SaaS for managing related processes, we needed to sprint toward that outcome now.

Our second software engineer (the first being my Co-founder & CTO) agreed to stick around for 90 days in exchange for a big boost in equity to help us launch. Ninety days to build the platform, make noise, and find cash. If we couldn’t find cash at that point, we’d close up shop.

Pivots are hard to make when you are generating growth. When you’re nearly dead? Surprisingly easy to act decisively. Whether the new strategy works is the new wildcard, but a wildcard is far superior to losing it all.

Scrambling Becomes the Playbook

We had already earned an invitation to the global finals of a proptech startup pitch contest in Cannes, France that would take place in the Spring, courtesy of a win at the New York regional. Unfortunately, the invitation didn’t cover travel or lodging. I called the organizers and begged for help with flights and hotels. They refused—until I told them we’d have to withdraw. They compromised: one hotel room covered.

I booked a flight to Marseille and a three-hour train ride to Cannes because it was cheaper than flying directly to Cannes. Every dollar mattered. While preparing to launch (and pitch), I cold-called over 100 lenders to “join” our marketplace for day one. Many told me to scram. Some felt like an enterprise sale: slow and tangled decision process. Twenty agreed to join in. Later, I would realize how bad that conversion ratio really was, and how it was due to my own ineffective sales pitch. No real estate lender actually cared about “joining a platform” or the aspirational non-sense I was peddling about opening up a new customer acquisition channel.

It proved much more effective to just offer to send more leads through lenders’ existing lead channels (something we could support with a bit more work and customer service on our side). But for launch optics, we needed lenders, and I hadn’t learned how to improve the ratio yet, so my cold calls and follow-ups and meetings continued, while working on the product strategy with our engineers, working on my pitch, prepping a marketing campaign for our launch, researching new investors, and managing expectations with the few investors we had taken on.

We secured a spot in another pitch contest, this one for “fintech” startups, the same week as Cannes, doubling our potential investor and media exposure during the last stretch of our 90-day runway. Score!

Momentum as Our Only Currency

My Co-founder & CTO took on another job on the side, coding and reviewing code for our web app at night to keep the lights on. In addition to lenders entering the Supply side of our marketplace, we quietly onboarded a few borrower in a closed beta test. Deals were entered… and stalled. None of those early deals converted into revenue, but the live activity revealed real friction points, insights no survey or customer interview could have uncovered. We prioritized ruthlessly, and had enough of the platform put together for our launch moment (we hoped).

I pitched at the fintech event in New York, meeting a few venture investors who showed interest in us. A few days later I was in Cannes, France, pitched on stage during the first day of the conference, hit the yacht and party circuit, and hustled every corner of the conference hall. No investor wrote a check, and once again I thought we were cooked. But the buzz, press, and pitch contest coverage let us roll out a successful crowdfunding campaign within a few weeks of returning home that bridged us for another several months, by which time we started to see revenue trickle in from the marketplace play, and as revenue signaled some level of product-market fit, the fine tuning game began.

The company survived this period, not because anyone saved us, but because we manufactured just enough momentum to keep moving.

Ask my wife to tell the story of my luxury yacht party in France and she’ll playfully complain about being left at home. But if not for the support of stalwart teammates and family members, the music stops at that moment.

We made many more boneheaded founder mistakes in the years to come, but we had looked down the barrel of a bankrupt Christmas, reached down deep, and made it through the toughest period we ever faced to that point. But that’s enough founder mistakes to cover for now.

Today’s Founder Mistakes

1. Co-founder contracts can sink you. That accrued salary clause was insane. Get advice on things like this the first time around. Don’t sign important docs until you have a lawyer or seasoned entrepreneur review them with you.

2. Hire for culture and character first (before connections or skills). One untrustworthy hire can drain a company’s money, reputation, or morale.

3. Marketplaces live or die by demand. Nobody woke up wanting to “join a platform” or “embrace future customer acquisition channels” today. Find something on their existing checklist to eliminate, or send growth in a way they can already handle.

4. “Yes” isn’t real until it’s on paper. Soft VC interest isn’t money. From a cash burn standpoint, treat every investor handshake as zero until you have money in your account.

5. Momentum buys time. Press, contests, and even beta users, even without revenue, can boost your fundraising momentum if you leverage them.

6. You can’t fake desperation. It forces you to find a path or burn out trying. The grind of cold calls, late nights, and crashing yacht parties was our path. Yours will look different. But founders willing to go all-in fight the hardest.

Format feedback

We’re trying out a new format today: Story first; Lessons at the end.

Do you prefer the lessons grouped together like this, or would you prefer that I interrupt the narrative to sprinkle the founder lessons throughout the text? Let me know in the comments.