Welcome to VC Insider! This is where I share what I couldn’t say on the VC side of the table.
I am a recovering, ex-venture capitalist.
At age 30, I was hired to lead all operations, strategy, and business development for a Corporate Venture Capital Fund for a $1B company.
Of our six (6) early-stage investments:
Two (2) were acquired at 9-figure valuations
One (1) received significant growth equity funding from a private equity firm and is still in operation
One (1) remains in operation at a 9-figure valuation
But in 2018, the Venture Capital industry had me feeling jaded and unfulfilled.
I couldn’t understand:
Why it is totally acceptable for VCs to throw enormous amounts of money into a startup at the most inefficient point of its existence
Why VCs never leave to go “walk the walk”
Why industry cliché was richer than industry data
How (1) solid companies couldn’t secure funding but (2) terrible — or fraudulent — companies could get funding all the time
How 7 or 8-figure checks could still be written on “gut feel”
How VCs at different funds could exchange very transparent notes on deal flow but refuse to teach startups how to successfully navigate our world
Why LPs put money into funds that are chasing the wrong companies for investment
How VCs can give horrible advice and not be held accountable
Why VCs aren’t more honest and direct in our guidance to the opportunities we decline
I found this very unfair to the startup community and the very people we were supposed to be empowering.
And as a VC, I was part of the problem.
So, I had a crazy, career-altering idea…
“What if I left the fund side to go work for and with the types of companies I would have invested in as a VC?”
It was a huge risk, but I wanted to
Gain empathy for those who are on the other side of the table
Educate entrepreneurs on the real inner-workings of VC
Teach Founders how to navigate Venture Capital by sharing “VC Secrets”
See if I could accelerate, contribute to a high-growth company
Have the flexibility to launch my own entrepreneurial efforts
Above all, I wanted to pursue and speak freely to the above topics and transparently document my journey.
So, I did the unthinkable and intentionally left a dream job in VC.
Since leaving VC, my efforts have been highly focused on
Strategic partnerships with early stage companies
Equity investments off my employers’ balance sheet
Acquisition due diligence
Retail health and real estate investments
Educating and advising entrepreneurs on how to navigate venture capital
Now, almost 5 years later, I wouldn’t change a thing about my journey.
I am very proud to be a part of an awesome team in the role I’m in now at eHealth.
I love sharing with founders what I know to be effective when engaging VCs,
I love talking about how to spot value in overlooked areas on the fund management side and on the operational side within retail health.
I love building partnerships and strategy in retail health.
I love coaching and advising game-changing companies.
I love monitoring the longitudinal results of AMOS and how accurate my AMOS predictor has been over the last 3+ years.
I love sharing VC Secrets with Founders and explaining “The Why to the What”
I love talking about the 2 rejected investments that hurt the most: Startup X which gained about 20x and Startup Y (case coming soon).
I love talking about startups’ exit probabilities and sharing that knowledge with founders so that they can better prepare for their fundraising.
People, ideas, and truth will always motivate me more than money and comfort.
VC Insider allows me to share what I’ve learned on my journey with you.
Q: Why the gorilla emoji and logo?
A: It’s a nod to one of my favorite books, Ishmael, which challenged my thinking on spirituality, economics, human engagement, sustainability, and culture.
I try to challenge the VC / Startup norms in a way that’s practical and easy to understand, so the gorilla references are my reminder of that.
Also, in a world full of random people, don’t be a troll. Be a gorilla. Be a lion. Be bold. Be brave. Be curious. But don’t cut down other people. It just screams that you’re unhappy. Find joy in taking your own path.