Is venture capital broken, or are we just doing it wrong? Jack Altman brings a rare founder-turned-VC perspective after scaling Lattice to $3 billion and stepping back as CEO while on top. Now managing Alt Capital with investments in Figma, Rippling, and Flexport, Jack delivers brutal honesty about what's really happening in startup investing.

The Dating Analogy That Changes Everything Jack compares investor-founder relationships to dating - and the analogy is disturbingly accurate:

"I think it is a little bit like dating. Even your cherished execs come and go faster than preferred board members."

You're literally stuck with each other longer than most marriages. This changes how you should think about choosing investors entirely.

Why Everyone Missed Airbnb (And What It Means for Pattern Matching) In a moment that should humble every investor, Jack reveals the industry's dirty secret:

"There's a lot of founders that I think, you know, like the Airbnb rounds in the early days, special as Brian Chesky is, everybody missed it."

Pattern matching is fundamentally broken. The best founders don't fit existing patterns - they create entirely new ones.

The Altman Family IT Department Jack finally answers the question everyone's been wondering: who does mom call when the computer breaks?

"As kids, Sam was the one playing with computers, and so he was solving. And the IT problems used to be harder than they are now. So it was Sam."

But the deeper revelation is about their upbringing - "extremely showered with love and support" with classic 90s participation trophies for everyone.

Why AI Won't Be Winner-Take-All While everyone debates which AI company will dominate, Jack uses a brilliant payroll industry analogy to explain why they're asking the wrong question:

"I think a more accurate mental model for it is like overlapping bubbles, Venn diagram style."

Look at ADP, Paychex, Gusto, Rippling - all billion-dollar companies doing essentially the same thing but serving different niches.

The Market Sizing Confession In rare VC honesty, Jack admits what everyone thinks but won't say:

"I think all of us, whether you're an investor, a founder, a prospective employee, I think we all suck at trying to guess how big a market's gonna actually be."

Get two things wrong by 5X? You're off by 25X. The math is humbling.

The Anti-Scale Fund Strategy While everyone chases billion-dollar mega-funds, Jack is doing the exact opposite:

"I'm not somebody who is a big believer in platform teams. The way I want to work with people is just to be like a high quality, personal relationship partner."

His contrarian bet: staying human-scale in an industry obsessed with getting bigger.

The People-First Investment Philosophy Jack's most controversial take on deal evaluation:

"I'm not waiting for the pitch, I'm waiting for people."

While other VCs build thesis-driven investment memos, Jack admits he's completely founder-first. The market, opportunity, timing - all secondary to the person building it.

This episode cuts through VC marketing speak to reveal what early-stage investing actually looks like when you've been on both sides of the table.

Companies Mentioned:

Alt Capital
Lattice
Figma
Rippling
Flexport
Retell
Airbnb
OpenAI
ADP
Paychex
Gusto
Paycom
Paycor
Paylocity
Bamboo HR
Ultimate Software

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