#founder-assessment

#founder-assessment

The money was supposed to feel like something. You work your whole life thinking about the payoff. The day you can finally relax. The moment you don't have to worry about making payroll or whether that big invoice will come through.

If you're looking at a founder and they got dirty white sneakers, you're a real builder. They don't have time to buy nice sneakers; they just put on the same pair of sneakers, and they get dirty.

I got laid off nine months ago, and it was AI-related. I had to sit there and say, 'This is a blessing, because I get a head start on everyone else that's going to have to go through this in a little while.'

I don't take founders here for exercise. I take them here because the controlled environment of a boardroom practically demands rehearsed answers. The trail does not. I don't prepare a script for these walks. In fact, that's the point. The pitch is already done; I know the metrics. Now I want to know the human.

Every search, purchase, loyalty swipe, location ping and scroll feeds systems that now shape pricing, product decisions, hiring and marketing strategies. Most founders understand this in theory, but few grasp the practical consequence: whether they intend to or not, they and their customers are already casting votes with their data. And those votes? They're usually cast passively, on someone else's terms.

Awards may be encouraging and occasionally useful for visibility, but they are weak indicators of validation and poor predictors of long-term success. In the longevity and healthspan industry, where timelines are long and claims are easy to overstate, venture capital ultimately follows alignment and evidence, not applause received at glitzy industry events.

In an era obsessed with shortcuts, overnight success, and polished social media profiles, adversity is often treated as something to avoid. Something unfortunate. Something that signals failure. That assumption is completely wrong. Adversity is not a flaw in the entrepreneurial journey; it is, in fact, the training ground, the pressure that sharpens one's judgment, accelerates their adaptability and forges the kind of resilience no accelerator, MBA or funding round can manufacture.

We're fortunate to stand on the work of giants. Every time we cross a suspension bridge or hear a brilliant piece of music, we experience the spark of someone else's genius. We don't need to understand every theory to benefit from it - and the same is true in building a business. You don't need a computer science degree to think like an engineer - but doing so can help you build smarter, faster and with fewer mistakes.

A colleague and I launched a new company after our previous employer closed. We divided responsibilities so she handled manufacturing and distribution while I managed digital content and marketing. My side of the business grew steadily. But within six months, her operational area began to falter. I began to step in to keep physical projects moving, and key infrastructure on her side wasn't maintained. Despite having access to shared digital project management tools, she frequently framed it as a communication problem.

The founder of one of our portfolio companies created a company with approximately $200 million in revenue purely on instinct. The founder had spent a large amount of time around the products and relationships with customers, so that he could literally go out onto the production floor and identify the machine that would be broken down in a week, and he would reject a price recommendation from his financial staff because "it didn't feel right!"