The Operator-VC Trap

Venture capital constantly debates the value of operational experience.

That badge of honor—"I was an operator"—once opened doors and closed deals.

Investors wore their battle scars proudly: I’ve been in your shoes.

ChatGPT arrived in 2022, and everything sped up.

Smaller teams. Faster revenue. Product cycles in days, not weeks.

Today's startups operate differently.

Operating Skills

When builders stop building, skills erode.

The instincts that once set them apart slowly lose relevance.

A handful of operators-turned-investors could return to a C-suite tomorrow and dominate.

But they are the exception. Most lose their edge far sooner than they admit.

The lost edge can be technical skills, risk tolerance, or willingness to grind — many startups today are on “996” schedules (9 a.m. to 9 p.m., six days a week).

Staying Relevant

I wake up every day paranoid about losing my edge in product.

Tech is more like Hollywood than we admit. No one remembers your hit from a decade ago.

You're either building or decaying. No middle ground.

That applies to PMs, designers, engineers. I spent years at the top of the App Store. It doesn’t matter now.

Maybe you're reading this from a completely different industry, but you know exactly what I mean.

Because the truth is universal: if you care about your craft, you’re either getting better or falling behind.

Self-Awareness

The most underrated skill for operator-turned-investors is self-awareness.

Knowing when your past experiences no longer apply, and resisting the temptation to offer generic, outdated advice

That SXSW 2011 go-to-market strategy —free tacos for downloads or whatever it was—is probably irrelevant today.

Spend weekends building something instead of writing your 500th IC memo.

You won’t regret it, and you’ll become a better investor.