About Chris, VC Insider, & Stuff for the Dissenters
“I had to leave the story to tell the story.”
Four years ago, I intentionally left a dream job running a corporate venture capital fund to get operating experience with the types of companies I would have invested in.
It was a huge risk, but I wanted to gain empathy for those who are on the other side of the table.
And I learned a lot. Most of it the hard way.
I had a boss quit on my first day.
I closed multi-million dollar deals.
I lost multi-million dollar deals.
I was on the favorable side of layoffs.
I was on the unfavorable side of layoffs.
My picture was displayed in Times Square the day we went public.
I saw our stock hit an all time high and then lose 67% of its value in a matter of months — twice.
I sat on the emotional roller coaster of stock options.
I built AMOS.
I watched investments we made at our VC fund exit for enormous amounts of money. I watched founders we'd invested in give up way too early.
All of these experiences have better strengthened me as a coach and advisor to startups and venture funds.
And, I am beyond excited for the VC Insider journey.
Q&A / FAQs
Q: Why should I invest in you to advise my startup?
A: Would you rather:
Spend the next 6 - 12 months in pitching to VC’s and trying to figure out what they want via trial and error? OR
Work with me for 30 days and come away with exactly what a VC wants you to deliver, training in how to deliver it, and be coached to spot the dirty tricks VC’s will use to gain leverage over you?
If #2 above is your vibe, then let’s talk.
Dissenter: OK, but you didn’t have to leave VC to be an adviser, right?
A: In the words of my favorite living author, Michael Lewis, “I had to leave the story to tell the story.”
VCs don’t like to share their secrets, and I find that very unfair to the startup community.
VC’s at different funds regularly talk to each other and exchange very transparent notes on deal flow, but why do we never teach startups how to successfully navigate our world?
Why aren’t we more honest and direct in our guidance to the opportunities we decline?
I wanted to freely speak to these topics. That was a big motivator for me in leaving.
Also, AMOS. I believed enough in AMOS to step away from a fund to build my own intellectual property without any ties to a fund.
Q: What were your roles once you left VC?
My roles were based on:
Strategic partnerships with early stage companies
Equity investments off my employers’ balance sheet
Acquisition due diligence
Retail health and real estate investments
Q: What qualifies you to be an expert in the field of VC and startup fundraising?
A: I view myself as an advisor, coach or sparring partner. I love to share with founders what I know to be effective when engaging VCs, and what I did on the fund management side to spot value in overlooked areas.
I love talking about startups’ exit probabilities and sharing that knowledge with founders so that they can better prepare for their fundraising.
My goal is to use my platform to invite others on my journey, not to position myself as an “expert” — I think that term is overused, and it feeds peoples’ egos.
Dissenter: You’re not even working for a VC fund right now. Why should I take you seriously?
A: Since 2018, I’ve remained active in coaching and advised companies worth upwards of $250M on the very services I offer here.
I built AMOS and consulted with venture funds.
I’d encourage you to look at how accurate my AMOS predictor has been over the last 3+ years.
Dissenter: Your fund was modest in size and you only made a few investments.
A: I appreciate this question. Yes, the fund size was modest and we were judicious in terms of our number of portfolio companies — like many corporate VC funds.
Corporate money, strategic money and “smart” money often have very specific charter restrictions. This means incredible opportunities with high probability of exit will be rejected because there’s not enough strategic alignment with the parent company.
I brought deals to the board with the recommendation to invest that were declined because of charter fit.
The two rejected investments that hurt the most: Startup X which gained about 20x and Startup Y (case coming soon).
Q: Will you ever go back to operating a Venture Capital fund?
A: It is very possible. My experiences on the operating side of emerging companies will make me a more effective, empathetic fund operator if/when I do return.
Q: Will you ever launch a startup of your own?
A: I already have. It’s a very strong startup concept in the health and wellness space (shocker), and I will share more about this in 2023.
Q: Do you advise / consult with funds on their portfolio strategy?
A: Yes! Man, there are so many funds out there right now chasing the wrong companies for investment. Some of the strategies are so bad. I’m glad to assist. Let’s talk.
Q: Do you raise money on behalf of a startup client?
A: No, I do not get hired to raise money on behalf of a startup client.
When I advise my startup clients, I do make VC introductions when and where appropriate based on VC/Founder fit, but I do not raise money on behalf of my clients.
Dissenter: VC Insider seems like another one of those self-serving solopreneur websites. Is that the case?
A: No worries, you are certainly allowed to have your opinions.
People, ideas, and truth are what motivate me. VC Insider allows me to share with you what VCs are thinking about as they engage with you.
I love the VC / Startup space, but, too often (1) Solid companies get passed on simply because the founders are not coached on how to work with VCs; and (2) terrible — or fraudulent — companies get funded because the founders know how to work with VCs.
I believe I can set Founders up for greater success through coaching and advising.
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.