Building Antifragile Startups and Sales Teams (incl. video)

Back in 2020, Sequoia Capital published its now-famous memo Coronavirus: Black Swan of 2020. It spread like wildfire. The memo captured the moment perfectly — but it didn’t explain the solution.

At the time, I felt compelled to fill that gap. I had written my master thesis on antifragility in software development with PwC and was fascinated by the idea that some systems actually benefit from stress. So I created a seven-part video series on what antifragility means for startups and sales teams.

Five years later, those ideas feel just as relevant — maybe even more so. Here’s a look back at what I shared then.

First a video - including all of 8 videos that I had recorded during COVID:

1. Skin in the Game 👫

My first video explored skin in the game — making sure decision-makers share in the upside and downside of their choices.

When decision-makers have skin in the game, they think long term. In sales, that meant giving teams more ownership of decisions that directly impacted customers and revenue. The closer the decision-maker is to the market, the better the decision.

2. Redundancy 💰

Next, I talked about redundancy — the buffer that allows you to survive shocks before you can learn from them.

In 2020, cash reserves became a lifeline. I argued that startups needed more than just financial redundancy. They needed diversification in lead sources, customers, and markets so that one downturn didn’t cripple them.

3. Optionality 📊

In video three, I discussed optionality — having choices that protect you from downside risk and increase your chance to capture upside opportunities.

I used examples from venture capital, FC Barcelona’s passing strategy, and Microsoft’s product portfolio. The lesson for startups: always have multiple ways to generate revenue and test ideas, so you’re never locked into one path.

4. Flexibility 🔀

Optionality is useless without flexibility. My fourth video argued that startups should lean into their natural advantage: fast, decentralized decision-making.

I shared the story of a client that quickly pivoted to create DriverBubble — a physical product to keep taxi drivers and passengers safe — in under a month. That kind of speed and responsiveness was exactly what 2020 demanded.

5. Falsification 🕵️‍♀️

By mid-2020, every forecast had been proven wrong. So in video five, I encouraged founders to stop clinging to prediction and instead stress-test assumptions.

I recommended asking:

• What happens if this key deal doesn’t close?

• What happens if a critical team member leaves?

• What happens if churn spikes?

Rather than relying on perfect forecasts, I suggested building buffers and redundancies to absorb surprises.

6. The Lindy Effect 👵

The sixth video explored the Lindy Effect — the idea that things that have lasted a long time will likely keep lasting.

I encouraged founders and sales leaders to build on durable ideas and frameworks rather than chasing every shiny new thing. SPIN Selling, email newsletters, and in-person connections all had staying power that was easy to underestimate in the rush toward disruption.

7. Tinkering 🔬

Finally, I wrapped the series with tinkering — the art of constant experimentation.

I encouraged founders to have a clear vision but to test it with small, cheap experiments before committing serious resources. Or as Jim Collins put it, “fire bullets before cannonballs.”

For SaaS sales, this meant testing new markets with just a few customers, learning quickly, then doubling down once the model worked.

Five Years Later

Looking back, I’m glad I captured those thoughts when I did. The last few years have only reinforced the need for startups and sales teams to be antifragile — to not just survive uncertainty but to get stronger because of it.

The principles of skin in the game, redundancy, optionality, flexibility, falsification, Lindy thinking, and tinkering are as relevant today as they were in 2020.

If anything, they’ve become my default framework for thinking about growth, resilience, and go-to-market strategy.