What If: Mental Health Rolling Fund

Hi, I’m Stephen. I’m the founder of What If Ventures.

Addiction and mental illness almost took my life in 2018. In 2020, I launched an AngelList syndicate to back mental health startups. Since January, I’ve backed 6 mental health startups, deploying over $3,200,000 into the space, supporting startups that are touching more than 3,000,000 lives. I’m just getting started.

Now, What If Ventures, is live as a rolling fund on AngelList.

Here’s our deck, if you’re into that kind of thing.

About Me

I’m a West Point trained leader with an MBA from Vanderbilt. I spent 7 years as an investment banker before launching my first venture vehicle (captive family office fund) in 2015. I made 25 investments from that vehicle, but in 2018 I ended up in rehab for addiction.

While I was in rehab, getting sober for the first time in 20 years, I was diagnosed with bipolar disorder. When I got out of rehab I wondered if I was the only person like this. It turns out, I’m not alone, in fact there are incredible entrepreneurs trying to build solutions to help people like me.

A few months after rehab, I decided to raise a seed fund to back these entrepreneurs. However, most investors struggled with the concept of giving 10-year dated capital to someone who was 9 months out of rehab (it’s OK to laugh, it’s kind of funny that I needed to actually have this explained to me).

One investor, now an advisor of mine, encouraged me to start a syndicate, and use that to prove myself and my thesis while providing investors more security against any mistakes I could make personally. In January 2020, I launched What If Ventures as a syndicate on AngelList focused on mental health startups. Through August 2020, we have invested in 6 mental health startups, deployed just over $3,200,000 and invested in some of the premier names in our space while creating a significant amount of thought leadership content through our mental health podcast, Stigma Podcast.

If you want to read more details on my addiction and recovery journey, then go here.

Track Record

To date I’ve invested in 32 startups. Here is a full list of them (including a list of exits). Of those investments, 6 have exited, 1 has been shut down, 25 are operating and 5 have raised follow-on capital at valuations above $100mm and another 6 have raised follow-ons at valuations above $50mm.

Mental Health Investments

Pre-Rehab Investments


I believe that mental health impacts every human and that most of us are starting to admit how important it is to proactively address the health of our mind. As stigma decreases, and more people talk about mental health, the demand for mental health resources is increasing while the supply of high quality, effective resources has remained stagnant for quite some time. This has resulted in a supply & demand imbalance creating a ripe opportunity for investment.

Just as the fitness revolution began small, not that long ago, so the mental health revolution has begun. It will spawn an ecosystem of solutions and opportunities. You may be wondering if this market is too niche. It’s not. There are over 1,100 startups in this space.

Now you’re probably thinking this sounds great, but what about the exits and what kind of valuations can companies in this space get?

Our Approach: We Built an Ecosystem

In just 7 months, with zero capital, and without paid search, we became the leading brand in the mental health startup investing space. If you go to Google and search “mental health VC,” then you’re going to see us first. This is great news, because this means founders find us first too. This is a result of not just the deals we’ve done, but our thought leadership, content creation and community building. To date, we have created:

  1. Content Strategy — We launched the Stigma Podcast in August 2019 and have grown to nearly 10,000 downloads per month (and nearly 70 episodes) with top founders, clinicians, thought leaders, and many others joining us regularly. This content platform has become an important component of our top of funnel deal sourcing strategy. Founders value our ability to get their story in front of customers, payers, investors and partners.

  2. Thought Leadership — We’ve written several white papers on the industry that are consistently sourced and cited by journalists, other investors, and founders (we love seeing our data show up in pitch decks that we receive via random inbound). Here are a few of those content pieces: Approaching 1,000 Mental Health Startups in 2020, Who is Investing in Mental Health Startups?, Explosion of Mental Health Startup Funding in Q1 2020.

  3. Mental Health Startup Community Slack Channel — We created a home for founders, investors, employees, aspiring entrepreneurs, clinicians and more to share ideas and collaborate. We have nearly 1,200 members in the slack community at the time of this blog post.

  4. Shared Personal Experience — There is no teacher greater than experience. I almost lost my life to the problems I’m trying to solve today. Many of the founders in this space have lived with addiction or mental health differences as well. I relate to the founders in a way that many others can’t and won’t because of the incredible level of transparency and vulnerability required in the broader recovery community.

Deal Selection Criteria

I have a simple set of criteria that I begin with…

  1. Could / Would this solution have helped me with my own recovery / mental health journey? If Yes, then I look at three more things.

  2. Does this solution increase care capacity in the system? Meaning, if this solution just repurposed or re-brands existing capacity and calls it something else, then I’m not that interested. Remember, the supply/demand imbalance is my thesis. We want to solve for supply of effective care.

  3. Does this solution deliver care in a new or improved way that adds value to all stakeholders from patients, to payers, and providers?

  4. Does this founding team have two key qualities: First, are they world class leaders who can build a team? I lean heavily on my West Point training to identify great leaders and coach them to success. Second, what is their purpose for solving in this space? If they are driven simply by money, then I’m not that interested. If they are driven by a desire to improve the human experience, then I’m all about helping them one way or another.

What is a Rolling Fund?

rolling fund is an open-ended venture capital fund that allows a GP to start by raising a small amount of capital and begin investing immediately, then scale up over time while allowing LPs to invest on a quarterly subscription basis requiring less of an up front commitment and the option to opt in or out any time.

Here is an AngelList blog post explaining the fund structure.

Here is a deck by AngelList explaining it in more detail.

Here is our pitch deck which has a section on how these funds work.

Fund Details

  • Target quarterly fund size: $2,000,000

  • Investment focus: Early stage mental health and addiction solutions

  • First close: October 1st — for deployment during Q4 2020

  • Targeting 2–3 investments per quarter

  • First right on syndicate: Our fund investors, no matter how small, get first access to any excess allocations that will be shared with our syndicate as well as a reduction of syndicate carry fee by 50% for any deals they participate in.

  • 2% management fees (which is redeployed into the fund) / 20% carry (+ 1% AL rolling fund fees)

  • Commitments: We are seeking quarterly commitments for at least one year, with a very modest minimum check size that is disclosed on the fund page.

Are You In?

Link to invest: https://angel.co/v/back/what-if-ventures/

Have questions?

Join our webinar on Friday August, 14th co-hosted with AngelList to learn more about us, our approach, and the rolling fund structure. Go here to sign-up. It’s totally cool if you’re just coming by to learn more about rolling funds.

Sign-up: https://forms.gle/XzgP8paiQaMgXXwR9

About the Author: 

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.


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