Who Actually “Runs the Money” at a VC Firm

We’ve spent close to 20 years peeling back the onion about how the VC world works and sharing what we learn with you.

But oddly enough, we’d never ventured into what is one of the most critical parts of the ecosystem.

It’s one that doesn’t get much airtime…and when it does?

It gets overwhelmed by the flurry of deals, fund launches, and portfolio company updates that you get in your inbox and on the socials.

Well, that changed earlier this year. And this month, we celebrated.

With Carta’s support, we gathered 14 of New York City’s top VC fund CFOs and finance leaders onto one rooftop, in one room, for one night, to celebrate our newest program @ Venture5: Office of the Venture CFO.

The conversations from the dinner were private, but what we can share is what we’ve learned in interviewing the fund finance and operations leaders who are helping drive firm strategy, fundraising, and returns:

A fund CFO structured a secondary that returned real cash to LPs at an effective tax rate under 5%, all without triggering a single ROFR across 20+ portfolio companies
The new QSBS rules quietly changed the math on every early-stage exit + a redemption “foot fault” that can wipe the benefit out entirely
A less stressful fund tax planning schedule that any GP or CFO can follow

Presented by Carta

Building the ERP for private capital

Nobody built software for the Fund CFO. While Fortune 1000s have ERPs, Fund CFOs rely on spreadsheets and legacy providers.

Carta closes this gap. By connecting the startup, investor, and LP, we’ve moved fund administration into a single source of truth. It’s the first ERP for Private Capital—giving you total control over your data.

Learn more

Hard Won Knowledge (that venture press seldom covers)

This is where it gets fun, because the interviews have delivered the kind of practical, hard-won knowledge the venture press almost never covers. A few of the standouts:

A liquidity playbook for a market that won’t give you exits. Mike Witkowski (Eniac, previously Primary) walked us through what he believes was a first-of-its-kind secondary: an affiliate transfer into a disregarded tax entity, then sold to StepStone.

This resulted in meaningful cash back to LPs, the QSBS exclusion preserved, the ROFR/co-sale maze across 20+ portfolio companies avoided entirely, and an effective tax rate for LPs that came in under 5%.

He also laid out his “three pillars” of GP-engineered liquidity, and noted that in one 2015-vintage fund, roughly 90% of the liquidity returned to LPs was GP-engineered, not waited for. His one-liner for getting a deal like that done: never talk to your lawyers and your tax team separately, get ‘em in one room.

→ Read the full conversation with Mike Witkowski

The QSBS rules quietly changed, so don’t foot-fault your way out of them. Matt Guiney (Flybridge) broke down the new graduated exclusion: 60% at a three-year hold, 80% at four, 100% at five.

And the trap that’s easy to miss: a company redeeming its own stock within a year on either side of your round can taint the QSBS on your shares.

He also gave us tax-season advice you will be able to use whether or not you have a full-time CFO: every day you move into February, you drop two. Want to know why?

→ Read the full conversation with Matt Guiney

EVERYTHING IS TAKING LONGER. PLAN FOR IT.

Presented by Carta

Peter Walker runs the Insights team at Carta, focused on discovering key data and narratives across the private capital ecosystem. In a former life, he was a marketing executive for a media analytics startup and led the data visualization team at the Covid Tracking Project.

The transcript below has been edited for length and clarity.

“Plan on delays being the case. If they don’t happen, congrats — you’re one of the lucky few.”

Venture5: Any closing thoughts for CFOs right now?

Peter Walker: Everything is taking longer. Everything. The initial meetings, the LP due diligence, the fundraise itself. There needs to be a backup plan that says: if we don’t hit first close when we expect to, but instead it takes three or four months longer, what is our route of action? What plays do we put in place so we’re not surprised?

I’m consistently surprised at how delays in fundraising arrest the motion of a fund. You should b e planning on delays being the case. If they don’t happen, congrats — you’re one of the lucky few.

Venture5: So delays out of your control are the rule, not the exception right now?

Peter Walker: One hundred percent. We don’t know if we’re going to be in another conflict in another quarter. The world is not quiet. Your fundraise might not be smooth and easy. And I don’t think it’s smart for funds to say, “SpaceX is IPO-ing in June, so once everyone’s excited about that we’ll go back out to market.” That’s not necessarily a good idea.

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Fund sizing + force ranking: Dan Rochkind explained why Lerer Hippeau moved its target ownership from around 10% to 11–12% on Fund 9, which closed at roughly $200M: seed rounds went from $2–4M “not that long ago” to $4.5–8M today, so hitting the same ownership simply required bigger checks.

“Our strategy didn’t change. The math did.” He also shared how the firm force-ranks its portfolio, so every follow-on dollar is weighed against the next-best place it could go.

→ Read the full conversation with Dan Rochkind

Meet the CFOs