This VC is NOT Killing It

“They are killing it over there at XYZ-32 Fund.” But, are they really? The answer is “no.” As an economist, I believe that markets are efficient and that there are rarely outliers. So, the odds are, “they” are not “killing it” 99% of the time.

What does “killing it” even mean? It must be some loose rendition of “crushing it.” I guess if you “crush” it hard enough, you’ll “kill” it? This sounds like an intellectually weak way to gloss over the reality of how hard it is to succeed, ignore transparency and vulnerability, and display the ultimate veneer of success to project a status of #winning.

It feels to me like VCs are the worst at this. Startups are just as bad, but to be honest, they are just following the leaders (VCs). I wonder how much better off we would all be if we just aired our vulnerabilities instead of projecting our desired end state of success over our current harsh realities.

The State of Vulnerability at What If Ventures — July 2020

A lot of VCs write a quarterly update to their LPs, boasting of their latest success. Since I don’t have any LPs, or any money, and I’m not “killing it,” I’ve decided to write a regular vulnerability statement and post it here.

  1. What If Ventures, today, is an AngelList syndicate because I failed at raising a committed capital fund back in the summer of 2019. I shouldn’t have been surprised. At that time, I was nine months sober and asking investors to make a 10-year commitment of $20mm. Something clearly wasn’t adding up.
  2. I personally do not have any money; I hustle as a freelancer on TopTal to pay my bills while I run a mental health startup investing syndicate. It’s a grind, but it’s good for me in many ways.
  3. When asked how I add value, I tell founders that I don’t. Founders create value, investors provide capital, and occasionally, I’m able to make an introduction or bring in a few extra investor dollars, but that’s not adding much value. Are there VCs out there who can add a ton of value simply because of who they are? Sure! If you can land one of them, then by all means, go for it and congratulations! I really hate this question. My default answer is “I don’t add value.”
  4. I failed to syndicate two deals during the first half of 2020. Two failures in a row right after three wins led me to question what we are doing and if it is sustainable.
  5. One investor bailed on our syndicate last month after I spent time recording a podcast episode with him about his recent exit in the mental health space. He took a few other investors with him. All in all, that week, we lost five investors. It made me mad, and I was rude to him. I could have handled it better. Sometimes I lose track of the bigger picture. Losing five while gaining 400 is a good thing, not a bad thing, but my ability to focus on the negative is still a problem.
  6. I got into an argument with Internet trolls, again. I’m the worst at this. Really, I need help.

I’m sure there is more, and I know there will be more to report next quarter. I intend to write a vulnerability update once a quarter in place of an investor update. Partly because I don’t have any actual investors, which was alluded to in #1 above.


Getting real, and embracing vulnerability doesn’t feel natural for me. I was not always able to see things this way. Frankly, I was the worst offender of the group that pretended to be killing it for many years. As I suppressed trauma, pain, guilt, shame, anger, and other struggles, I found myself wading deeper into addiction as I sought to cope with feeling like what Adam Duritz of Counting Crows describes in the song “Have You Seen Me Lately.” I was continually losing myself and had no sense of who I was.

When I “hit bottom” as they say (I hate that terminology), I found myself in rehab in the summer of 2018. Today, I’m approaching two years of sobriety. As I trudge the road of happy destiny and a way of living that embraces rigorous honesty, vulnerability, and transparency, I find myself hoping that others could find their way here without having to go through the pain that I went through. I realize that vulnerability, is the key and that I need to apply this to my business. Yes, the business of “killing it” in venture capital.

Why Vulnerability Matters

I know everyone applauds Dr. Brene Brown and it’s sort of become a rite of passage in a mental health conversation to say you love her or rattle off a quote or two from her. She’s great, don’t get me wrong, but why is she so great?

She was recently asked by Tim Ferris to theorize why her story resonates so well. Her answer was that people seem to feel most connected to her when they are able to watch her struggle with her own work.

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Brene Brown and Tim Ferrie

She models vulnerability in a way that is real and resonates with people. That’s her secret sauce. We as investors, as business leaders, and as entrepreneurs need to be modeling vulnerability to our constituents as well, including founders, employees, and other investors.

However, as investors we are often asking our founders to come to us when they struggle, tell us their weaknesses, and be authentic with us so we can help. I just don’t see how we can expect that of them if we are unwilling to lead by example.

“If we want authenticity, we have to initiate it…. We will never know our full potential unless we push ourselves to find it. It’s this self-discovery that inevitably takes us to the wildest places on earth.”

-Travis Rice from the movie, “The Art of Flight”

Why should business leaders demonstrate extreme vulnerability? Here are my thoughts:

  1. We, as humans, crave authenticity, and we are great at detecting it as well as detecting inauthenticity. We are actually wired to do so; it’s built into our DNA. Society has moved to perfecting the art of portraying a perfect life on social media as the standard, so when we see authenticity, we identify with it and cling to it immediately (unless we are really unhealthy, and that’s a different conversation).
  2. Leaders should model transparency and vulnerability to show others how to do it. As investors we expect founders to be transparent with us about their business but we have created an environment where “killing it” is the only acceptable outcome, so founders have an incentive to tell us things are fine, using vanity metrics, when things are far from fine.
  3. Educate our investors, supporters, and mental health ecosystem friends on where we are struggling, where we need help, and how those who want to support us can pitch in if they are so inclined.
  4. Provide a road map for others who are recovering from addiction and mental illness. Many of these people are getting back on their feet through entrepreneurship in the midst of a cancel culture that wants to see them fail again and again. I believe that sharing my experiences, the bumps in the road, and my hardships may help someone who comes along the path after me to have a little easier time, or at least some comfort.

A Challenge to All VCs and Founders

Get vulnerable. Find the right way to open up to people about your shortcomings and weaknesses. Yes, in business. Yes, with investors. Yes, with subordinates and peers as well.

Be curious about your failures. Don’t hide from them; rather, turn toward them and embrace them so they can unlock truths about who you are, what you are, and how you are doing and lead you to greater success.

It’s so obvious and off-putting when people posture around their strengths and overplay their hands. It’s a turn off. But the opposite is also true. When people are open and honest about their weaknesses, it draws people in to want to help. This strategy is not just a “strategy;” it’s a way of living, and the byproducts for me have been sobriety and a few people who have decided to work with us.

I’ve found that in radical transparency and rigorous honesty that I often do not get what I want because people turn away, but I’ve also found that the people who matter the most to me react better than I could have ever imagined. It’s really a litmus test of sorts. If I can be transparent with you, and you stick around, then this relationship is going to work out (whether that be an investor, a friend, a founder, or someone at my home AA group).

Take Action

Right now, text or call someone, maybe it’s a founder in your portfolio, or maybe it’s one of your investors or even just a friend and tell them you care about them, and then share something vulnerable about yourself with them. When you hang up the phone, your life will be on a completely different, and much better, path.

Want to know more about What If Ventures? Just let us know here, and we will reach out to set up a call and share more.

About the Author: Stephen Hays — After decades of addiction and struggling with bipolar disorder, Stephen was fortunate to receive help and has focused his attention on funding solutions to the problems he lived with. You can read more about his story here.

About What If Ventures What If Ventures exists to invest in mental health and addiction focused startups. The fund was launched in 2019 by Stephen Hays. Investors can apply to join the deal distribution email list here.

Stigma: Mental Health Podcast — We created a podcast in 2019 to tell the stories of those living with, recovering from and impacted by mental illness and addiction. To date we have 55 episodes with clinicians, mental health founders, others in recovery, and many more. This is how we fight stigma, by educating others and encouraging more people to share their story. Will you join us?