I’m now totaling 63 deal memos with >40% published just in August 2020. In the last 31 days I published 26 pieces, nearly one every day. Users, sessions, bounce rates, and session duration have all improved, and inbound email has doubled from July to August. I’ve started a paid subscription newsletter for startup investors to support each other and received my first subscriber within 48 hours of launch. Most promisingly, I’m getting inbound emails almost once every other day.

I went on a prolific tear of content in August sort of like an amateur jogger on runner’s high: I published every day simply because I could. This was the first month where I felt my writing feedback loop was tight enough that I was effortlessly motivated to write every day. My apologies to those who may have been overwhelmed with the deluge of content—this will be corrected in the coming month.

Starting in September, I will be capping deal memo publishing to three times a week. At the same time, I thought I’d summarize and share some unsolicited $0.02 from the month that’s been.

Three Takeaways

1. Takeaway for Startup Investors

Common sense and experience made me a good startup investor, but patience and discipline will make me great.

I was recently asked whether SapientX, one of my portfolio companies from late 2018, was still worth investing in its 2020 round. This lead me down an exercise of calculating my returns.

Executive summary: According to the numbers, and using fairly conservative estimates, I am a better-than-average startup investor and venture capitalist, but still on a journey to enter the top quintile.

Detailed Summary: Of the investments that have had follow-up raises, I’ve experienced 76.46% on average over 7 investments since 2017. (Of note, 4 investments have not had follow-up funding so they are not included in return calculations.) This averages to >20% IRR every year, compounded (1.2^3=1.728.) Compare to:

  • Compare to median VC industry of 11.7%.
  • Compare

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