Descending Mount McKinsey and Other Storytelling Woes

Short is hard.

Je n'ai fait celle-ci plus longue que parce que je n'ai pas eu le loisir de la faire plus courte.

If I had more time, I would have written a shorter letter.

My team is so sick of hearing me say that. Maybe because I've been saying it for months. Maybe it's because I've been misattributing it to Mark Twain. It was actually Blaise Pascal and he said it in French, which nobody wants me to translate.

The point is: distilling what you're trying to say into punchy, crisp, clear language is hard. Giving yourself permission to say what you mean? Harder.

That's something we've really struggled with at Daring Ventures. Saying what you mean succinctly is as much about being confident as it is about being concise.

This is about the complicated journey from knowing what you mean to actually saying it. It's a universal tragedy in three acts that everyone performs when they try to explain themselves. Most people die in Act II, suffocated by their own sophistication.

October 2024. Our first real thesis was three bullets: "Not so niche" niches. FUBU (For Us, By Us). "Back to the future" innovations.

It sounded fucking stupid. We knew it. But here's what kills me now: we were completely right. We just had the worst possible words for it.

"Not so niche" meant expert-driven markets that VCs can't size properly. "FUBU" meant founders with lived experience building for communities they understand. "Back to the future" meant taking human judgment that's always existed and giving it digital leverage.

We were saying "we back experts who build for experts in markets where expertise matters." We just said it like college kids who'd watched too much Netflix.

The tragedy? We had the answer on day one. Every element of our current thesis was there: overlooked markets with hidden scale, founders with authentic domain expertise, digitizing existing human judgment patterns. We were tourists speaking the truth in broken vocabulary, which in venture capital is worse than being wrong with perfect diction.

Remember Susan Fowler's Uber post? Sexual harassment, HR coverups, threats. The internet explodes. Travis hires Eric Holder. Everyone pretends shock that the "Boober" company might have issues.

Peak dogwhistle era. We all knew but agreed to act scandalized.

Seven years later, Roy Lee puts "suspended for cheating" in his LinkedIn like it's a Rhodes Scholarship.

That's the gap between dogwhistle and airhorn. One demanded investigation and denial. The other makes confession the product.

Then came our institutional raise. Suddenly we needed to sound "sophisticated."

Enter: DignityTech. Then OpportunityTech. Then "Human-Centric Value Creation in Relationship-Mediated Markets." I wrote that last one. Stone cold sober. It took thirty slides to explain what used to take thirty seconds.

We built frameworks. We had 2x2 matrices for deciding which 2x2 matrices to use. Our simple truth became "we leverage non-consensus insights to identify asymmetric opportunities in nascent markets positioned for exponential growth trajectories."

The worst part? We thought we were evolving. We were actually drowning. Every framework added another layer between us and what we meant. We became fluent in a language nobody speaks outside conference rooms.

The mirror moment came during an LP meeting. Twenty minutes into our prepared spiel about differentiated approaches and market dynamics, they stopped us: "But what do you actually do?"

I sat there, pitch deck laden with footnotes between us, and realized I couldn't answer simply anymore.

July 2025. Eight months of linguistic gymnastics later, we finally said fuck it.

The mirror moment had actually happened weeks earlier in that LP meeting. But this was the moment we gave ourselves permission to do something about it. Three people who'd been playing dress-up finally admitted thatd the costume didn't fit.

We killed the frameworks. Stopped apologizing for our insight. Started saying "Conviction Bias" instead of "systematic pattern recognition in underserved verticals." Planned daily content for August. Not because we had more to say, but because we needed practice speaking Human again.

Turns out our original FUBU thesis was fine. We'd just been pitching it in founder-speak instead of LP-speak. Those eight months weren't about changing our strategy. We just had to learn that what gets founders excited sounds like nonsense to MBAs, and what MBAs want to hear makes founders roll their eyes. Same idea, different words.

Now we say: "When everyone has the same tools, domain expertise is the only moat." Simple. Clear. True.

The deepest irony is that if we'd pitched "FUBU for B2B" with total confidence on day one, it probably would have worked. But we had to take the journey. We needed to fail at other framings to appreciate the simple truth. We needed the intellectual framework to defend against attacks. We needed to learn institutional language to fund our anti-institutional insight.

Pascal's quote isn't about brevity for the sake of brevity. It's about the courage to strip away everything you're hiding behind.

We're back where we started: backing outsiders with expertise. We just learned to say it in a way that gets us checks instead of confused looks.