Billions or Bust 

I remember it like it was yesterday. The moment I knew the company I’d come to love was dead. 

Amidst a massive, 3-day business debate with the other two leaders, I felt completely alone. Leaning back in my chair, I stared at the ugly gray storage cabinets while fighting back tears. Not sad tears; tears of anger boiling over. As a business, we were at a major crossroads, spiraling.

Just a few months earlier, we had taken on a new investor out of sheer desperation. We knew it was bad money, giving up the power in our company in exchange for very little, but we wanted the connections and needed to make payroll. I believed we could be a profitable business, potentially worth millions, by staying true to our vision. But the sway of the new investors had us throwing away a million dollars in revenue for a Silicon Valley pipe dream. With them in the driver’s seat, it was a billion dollars or bust.

So, founder vs founder, we argued. In my gut I felt abandoning our business model at that stage was risky, irresponsible, even stupid. But it was two executives versus one, and the pressure to be like other tech giants—but better—was crushing. Hands clammy, adrenaline coursing through my veins, I felt voiceless in the fight. I was literally outmanned. 

My stomach sank deep into that black, cushionless office chair. I wondered, “What will Cladwell become? How do we protect our team and their jobs?” The gray cabinets just silently stared back.

That day, I lost the fight. At the mercy of the investors, we abandoned our mission and changed directions entirely. Within the year, the deal I doubted drove us straight into the ground. The business and team we worked so hard to build crumbled into pieces. We went bust.

But at the end, when the others resolved to walk away, I couldn’t. I couldn’t shake the feeling that, for me, it wasn’t quite over. What they saw as the right moment to say goodbye, I saw as the right moment to start fresh. 

And so it began…again.