Plenty. Just in SaaS, I was, Byron Deeter at Bessemer was, obviously the entire Andreesen partner team was, David Skok at Matrix (OK not Bay Area) was as were many of the partners there, etc.

Having said that, I think I’ve learned that as appealing as that is in a VC, to have an investor that has walked in your shoes — it’s not a panacea.

The most important thing in picking a VC is trust. Who can you really trust? I think in general, we can trust other founders more. For many good reasons. Because we share the same values, in many cases. We’ve been through it. And we tend to care about each other in a way non-founders don’t really get. But that’s not the only way to build trust. Of all the VCs who have invested in my startups, I only really trust one.

The second most important thing is who can help the most. And this varies by stage. If you are seed stage, an ex-CEO VC can often help the most. Bring in the best talent, the best advice, etc. But even as early at the Series A stage, I’m not sure CEOs need “operational” help from their VCs all that much. Certainly by $5m-$6m in ARR, most CEOs don’t really need help on the tactical side. They need help recruiting VPs and bringing in additional capital, but on the nuts-and-bolts of their business, they now have the 1.0 at least pretty well figured out. And generally, don’t want as much advice from the investors and board on the operation of the business itself.

I think I add extra value having been a SaaS CEO and founder at the late seed stage in particular. But when I recommend VCs for the next round, a bunch of variables go into the recommendation. Being an ex-founder isn’t one of them. Not really.

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