Portfolio Companies On The Naughty and Nice List

Ho ho ho – gather ’round, here’s a seasonal CEO tale,
A short little story of VC and PE boards,
Creating their portfolio company lists of naughty and nice.

Santa has his system; so do boards when they meet,
Reviewing the numbers, the forecasts, the heat.
When growth starts to wobble or systems don’t scale,
That’s usually when a new chapter sets sail.

Because I don’t get called when all’s humming along,
I get called when something’s fundamentally wrong.
Strong product? Yes.
Great people? Sometimes.
But discipline, rigor, and rhythm?- not prime.

So here’s what boards tend to see at first glance,
When a company lands in a governance trance:

Naughty looks like:
Big dreams, small controls,
Hero-led execution and operational holes.
Metrics everywhere, but no shared source of truth,
SMB instincts chasing enterprise-proof.

Quarterly promises drift out of view,
Forecasts feel hopeful, but rarely come true.
Culture runs fast, but accountability’s thin,
And strategy bends to whichever voice wins.

But fast-forward a bit – with the right kind of grind –
And here’s what “nice” tends to look like in kind:

Nice looks like:
Culture before strategy, strategy before speed,
Clear ICP focus and boards that can lead.
Enterprise trust (yes, compliance is real),
Security, scale, and controls that appeal.

Finance as a weapon, not vibes or delay,
A cadence that drives how decisions get made.
From chaos to clarity, noise into signal,
Growth less emotional – more repeatable.

No magic. No myths. No silver-bell tricks.
Just systems, accountability, and hard-earned fixes.
The work isn’t flashy, but it compounds with time,
Turning “almost enterprise” into something refined.

So to VC partners, PE partners, board members too,
And talent partners searching for CEO leadership – this one’s for you.

If there’s a company that’s promising, but stuck in between,
Not broken – just overgrown, undisciplined, unseen –
You know where to find me when the timing is right.

Until then, happy holidays, enjoy some peace and some quiet,
And may all your portfolio companies
End up nice.

-Jim

P.S. Image: Sitting around the Board table – Venture Capitalists and Private Equity moguls Marc Andreessen & Ben Horowitz – Andreessen Horowitz, John Doerr – Kleiner Perkins, Reid Hoffman – Greylock / LinkedIn, Bill Gurley – Benchmark, Michael Moritz – Sequoia Capital, Stephen Schwarzman – Blackstone, Henry Kravis & George Roberts – KKR, Leon Black – Apollo Global Management, and David Rubenstein – Carlyle Group. Sora AI-Generated.