Why I’m Leaving My First Startup

What If…? It’s Time?


Disclaimer: Based on some of the reactions from others reading this, it is important I clarify a few points. The clarification is at the end.


Four years ago I sat in an office trying to figure out how to bring the different disciplines in my college together. Sitting across from me was Matt Murrie, my conversation partner, egger-on-er, and in a year from then, my cofounder. We talked about apathy in the classroom on both the student’s and educator’s side. We talked TED. We talked about what we could do about it all.

From that conversation grew the idea of What If…?: an interdisciplinary gathering, where people would share eight minute questions and an exploration on that question. The presenters and off-stage presenters (audience) would be filled with students, professors, and community members — all asking questions, exploring possibilities, and getting the motivation to go out and create something new. We were co-authoring the future.

Participants at What If…? 02014

To think how far we’ve come in the last few years is astounding. We started in an office. Our first two Conferences were at Westminster College. The first year it was mostly spent convincing people to trust our model (they loved it). The second year we had brought in our first non-Westminster sponsor: Schlafly Beer (audience loved it, someone in the administration didn’t). We also had a presenter (Bjorn Cooley) who believed in us enough to fly out without knowing us first, a splattering of installation artwork, and our first workshop. The third year we amped everything up by bringing in speakers who were out building crazy things; working with two awesome interns; talking with an outstanding advisory board; pulling together a more diverse audience; bringing in two bands; and revving up the engagement, action section, and production value. We rocked our Conference and we rocked it in a local rock hall, the Blue Note.

On the side, we’ve participated in Startup Weekends, pitch contests, other conferences, tested smaller events, worked with passionate high schoolers who wanted to help build our audience, and we even started a book with Simon & Schuster (which is still happening).


Everything has been utterly amazing.
But, it’s time for me to step out.

Lots of entrepreneurial phrases tell you to listen to your customers — your customer’s voice will lead you in the right direction. While it is true that you should listen, the phrases give the perception that you should do what your customers want and overlook any definitional holdings. One of my friends and mentors told me a story I’ll paraphrase:

I was at a public library and saw someone walking out with a cake pan. Curious, I asked a librarian why people could get cake pans at the library. She responded that, due to funding setbacks, the library had to examine its offerings. They realized: while the library had the lofty goal of having books of higher education, people want cake pans.

What do we learn from this? The story does not show us all libraries should start offering cake pans. It does show us that the market is changing and the definition of “library” is either modified or a new type of library has arrived. I think most importantly it does not show us that cake pans are the best way to save the library. Perhaps they would have done better by instead rebranding, or finding a new place for books in our lives, or reaching out to philanthropists, or doing a multitude of other things. They found something that works better than nothing — which keeps them afloat — but the nature of these decisions become limited based on their resources.

Which really is what we do in entrepreneurial ventures anyway — maximize value using our very limited resources.

For small companies with extremely limited resources (like we are at What If…?), it becomes easy to focus on what is immediately profit bearing. Or, focus on whatever people latch on to. We run an idea-based company. We have this core idea and core model that is like water. Each project we do is like a different glass/cup/container. We can pour our water into many molds, and based on the opacity of the mold, you can see the same thing inside.

Quirky.com Workshop at What If…? 02014

Over the years, we’ve poured our model into many molds. For a few of the projects, we even modified our core, our water. Each time we learned something new. But through the process, I’ve realized the gap between where we are and where I’d like to see us is quite the chasm — perhaps a multi-decade chasm. Part of the problem is that we are very limited in the short term. So while we’ve gone further on nothing than most people I know could have done with a few thousand dollars and we certainly have an idea people believe in, our financial and social capital is still extremely limited.

I’m not complaining. This was the hand we were dealt with from the beginning. It only matters in that it will take longer for us to succeed. But, when I look at my age, 24 years in October, I can’t see myself at 34 or 44 doing similar things even if it means I’m wealthy or in control of the company (often decision points for people sticking with something).

I need a change.

Breakout participant at What If…? 02014

The line of thought that got me here started a few weeks ago. Matt (again, cofounder) asked me to meet ASAP to talk about direction, sequencing, and funding. He also wanted to rehash our equity agreement. All reasonable as we were prepping our pitch to potential investors.

Interpersonally, Matt and I have been having some problems. After the Conference, my sporadic depression kicked into overdrive and I became pretty worthless. My work took a hit. Deadlines stretched out. Emails were not sent in a timely manner. Bad mojo for working well.

At about the same time my cofounder and I had our very serious conversation, I started a regimen of low dose anti-depressants. Over the last month my condition increased greatly. The voracity I lived my life with in college is returning. It is an absolutely amazing feeling.

The return of my former passion and drive coupled with the few interpersonal frustrations coupled with the time of year, allowed me to take a very serious look at everything in my life. I know that the next steps for the company are to (1) procure a financial investment so we can facilitate events in large metropolitan areas with high priced tickets, (2) offer our model and brand out for a flat rate, and (3) facilitate workshops for organizations. All of this leads to the gravy boat.

But is this what I want to do?

Back to the entrepreneurial phrases and culture. When our drive focuses so much on the users, I think we forget to ask ourselves “What do we want to do? What do we find valuable?”. For some of us it’s the money. For others it is making an impact. One is certainly not exclusive from the other. When I asked myself this, I realized my passion for What If…? has decreased — not because of our mission, but because of the long steps we’ll have to go through to get there. I would rather make a different impact, build the networks to facilitate this, and (smartly) sprint through my goals.

So, my reasons for leaving?

  1. It’s going to take too long to make the impact I want to see based on our current financial and social capital.
  2. My passion for the labor, not mission, decreased.
  3. As we transition from egalitarian roles to more hierarchical roles (this is usually needed as companies grow and take on outside investment), I am unwilling to play a subordinate role.
  4. There exist other paths to exciting things that will help the world.
  5. I have to get out of mid-Missouri.
Me at the 02014 What If…?Conference

I can overcome each problem, though the first two are the hardest. What leads me away are the relevant alternatives. And, my role in What If…? won’t decrease to zero. I’ll stay on to finish the release of the videos we’ve produced, I’ll help the next web designer/developer get into my code, and I’ll always be available for support. I still love the company and I still love all of our passionate believers.

Regarding equity, I chose to decrease my stake from 50%. This helps Matt with investors and can make both of our stakes more valuable in the long term. Part of what I have left over I will sell one day. Part of it I’ll keep for rest of the company’s existence.

In terms of overall direction for the company, Matt will do well with it. We’ve been planning some of those conferences in large metro areas (lookout LA) and that work will continue.

It is also hard to leave because of the many people we’ve built partnerships with. We’ve been working with many great people and I hope my leaving doesn’t tarnish those relationships.

What am I going to do now that I don’t have the What If…? Conference? A few things.

  1. I started a company, Dasein Design, to handle my web development freelancing clients. In addition to freelancing, I’ll also turn out a few other things I’ve stashed away over the years. This will be about 20h of my week and pay my bills.
  2. The other 20h of regimented time will be set towards grad school or my next venture. For a long time I’ve been passionate about technology’s role in our future and building tools that help new creators. I’ll spend the next few months learning as much as I can in the technical areas I’m lacking. Then, apply to the MIT Media Lab, Carnegie Mellon’s Human Computer Interaction Institute, and other programs in Human Computer Interaction or Artificial Intelligence. On the side I’ll finish some of the research I started in college and work on an interactive project.
  3. Leftover time will be spent wandering, reflecting, working on other projects (e.g. my friend who’s running for state rep in Kansas), and enjoying my wonderful girlfriend.

The few people I’ve talked with about my decision ask me “are you sure?”. The question reminds me of a Kundera quote:

Any schoolboy can do experiments in the physics laboratory to test various scientific hypotheses. But man, because he has only one life to live, cannot conduct experiments to test whether to follow his passion (compassion) or not.
-Unbearable Lightness of Being

No. I’ll never be sure this was the right decision.

It is a hopeful one.


Disclaimer in full:

  1. The story about the library points to the difficulties of a growing brand. What is it that the founders see that no one else does? And, what is it that the founders were wrong about that should be changed? In no way is it to say that libraries (or startups) have the ultimate authority on how we, or if we, consume books. In some ways, we’ve been limited because we have to pursue more profit bearing practices. However, that sentiment has no bearing on if we’ve made the right or wrong choices. The Kundera quote at the end puts this thought well.
  2. When I say that Matt and I had interpersonal problems, I mean that due to my depression and our joint financial frustrations, tensions ran high sometimes. These were situational and just as frequent as other startups.
  3. When I mention I’m unwilling to take a subordinate role, that is a personal choice not a comment on how successfully Matt will take the company forward. These kinds of choices need to be made as a company grows. You can read more about how startup teams can evolve in Noam Wasserman’s Founder’s Dilemmas.
  4. The article used to say “My cofounder and I have different visions of the company in the short term.” I removed this because it is ultimately misleading. We have a similar vision in the short term. The difficulty we face, like other entrepreneurs face, is that our dreams are always bigger than reality and our pocketbooks.
  5. My leaving is amicable. My cofounder and I have worked things out and the transition will be fairly smooth. We’re all going in good directions.
  6. I’ve changed a few other lines to clarify my points. Seeing as this can be a sensitive topic anyway, clarity is of the utmost importance. Part of this was removing “better” from my description of my new path. “Better” is better for me, not a comment on the amazing work What If…? does.
  7. And in case you aren’t sure: What If…? is a good thing in the world. It is a big idea. Democratizing critical thinking and question asking is vitally important to our success as individuals, communities, and as a species.