175. From Operator to Accelerator MD to Fund Manager (John Fein)

So you participated in 5 startups, after which you scaled an organization from zero to 1,500 employees and $2B/year in revenue. Talk about your background and experience at United Health.

Tell us a bit about your decision to raise a fund.

When I started raising fund I, I had calls w/ 30+ GPs and my target was $5M but I told him, under no circumstances would I raise more than $10M, even if things went really well. He responded that the difference between a $5M and a $10M is significant and that the story and strategy would be very different for the two. So I know that you started with a $7M target and ended at $18M... how did your strategy change and did you get any pushback from early LPs as the fund got larger?

How did the process play out... in what ways was it different than what you expected?

How early do you go?

How did you create urgency w/ prospective LPs to make a decision. From personal experience, I found a number of large LPs that preferred to wait until final close

You've gone on the record stating that you'll avoid investing in arrogant founders, where many VCs specifically look for this character trait in entrepreneurs. Do you think it's the best economic decision to avoid working w/ arrogant founders?

Everyone says they're a founder-focused VC... but when I speak w/ founders I find that there are very few that are actually qualify. What does this mean from your standpoint and how are you serving founders in ways that others aren't?

What are some of the key strengths of your pipeline and dealflow.... how are you seeing more deals and higher quality deals than others?

The feedback cycle in venture is really long... you won't truly know how your fund stacks up against others from you vintage for many years. How do you track progress and assess if you're winning over the near term?