Hindsight is Twenty20 - Why I Left My Venture-Backed Startup

Hindsight is Twenty20 - Why I Left My Venture-Backed Startup

I get asked “Why did you leave your company?” often. This is my story.

Last year, a company that I founded, Twenty20, was acquired.

Most founders would be thrilled.

For me, it was quite different because two years prior I had left the company.

I’m often asked by friends and family why I left. But I’ve been slow to share my story publicly.

It’s been meeting other leaders wrestling with similar “Should I stay or should I go?” questions that has helped me finally share how I knew it was my time to go.


My Story

The irony is not lost on me of founding a company named Twenty20 and then in hindsight seeing so clearly how amazing the entire experience of that company was for me. Because it was.

Every day was a new challenge. Each challenge an opportunity to grow. The possibilities were endless.

We created products that had a real impact in people’s lives. Hundreds of thousands of people sold their artwork for the very first time because of us.  For many of them, this was their very first taste of entrepreneurship. We had raving fans always willing to give us feedback and new ideas to explore.

Oh, and the team that we built. We’d grind it out at the office by day and then to cap off the evening with sunset volleyball. Then back at it again the next morning.

It certainly wasn’t all easy nor happy. Not at all. Most days felt like pure chaos. Way too many inputs. Nowhere near enough time to manage it all. Building a company is relentlessly demanding work. But in that struggle, I found my true passion.

After years of being a product and marketing guy, I fell in love with leading and building an organization of people.

I found myself gravitating toward being a support to our team leads. I led our executive team meetings and planning. I interviewed every prospective employee, meeting incredibly talented people who I had the privilege of sharing our vision on where we were headed, and for some inviting them to join us. I defined and built company culture.

This new people-focused lens to my work was exhilarating. A new frontier on which to learn, experiment, and grow.

Then everything changed with a single phone call.

The Pivot

Two weeks before that fateful call, I had led our executive team through our quarterly planning offsite. We entered the room all aware of the current landscape: Revenue was below target. Our runway was shortening, but we also likely had financial options available to us.

We began that day addressing the elephant in the room: Are we going to do a layoff to cut costs? Or press onward for the quarter?

We chose the latter without much debate needed. We believed there were other levers to pull in reversing the recent trend. Plus we needed time yet to better grasp our options for accessing additional capital.

We built out the quarter’s objectives. Days later they were shared with the team at our all-hands. The mood was tense but optimistic. We had time, a strategy, and the team to execute it.

Or so it seemed.

I wasn’t on the phone call when the pivot occurred, but the resulting directive was clear. We were to cut costs and to do so aggressively.

The coming days were poured into financial models and scenarios to sort the path forward.

At one point, a question was asked: “What if we had to trim down to just six people?”

I laughed, thinking it was a joke.

But, no, even that was under consideration.

That day we employed 56 people.

Fifty six people that I had poured years of my life into leading and supporting. Fifty six people that I had interviewed and invited to join my team. Fifty six people that I had told they were working at a business that was different, that cared for them, that would be open and honest with them. Suddenly 50 of their jobs were at risk. It had been just two weeks since I stood before them sharing our Q3 plan involving no cuts.

I tried my best to reassure myself that it’s business, not personal. It didn’t help. I felt sick.

In the end, the number of people we let go wasn’t quite that drastic, but we still laid off over 60% of the team that July. The plan forward was simple: get lean and grind out a path to profitability over the next two years.

What Am I Committed To?

Along with our plan, as an executive team we discussed the need for each of us to be completely committed going forward.

But, was I committed to this for the next two years?

As I wrestled with the question I was feeling a lot. Frustration. Disappointment. Regret. Sadness. I didn’t want those emotions to drive my decision making. But I know enough about what I was feeling to know there was truth there.

Beneath the sadness and regret was the great joy of building and leading the team. A joy cut short. A love, now lost. A good portion of the team remained and yet I knew that exhilaration would never

Beneath the frustration and disappointment, a realization that my work at Twenty20 and Twenty20’s work on me was complete. It was in supporting, guiding, coaching, mentoring, and leading people that I feel most alive. It was clear that staying meant a return to product leadership - work that I knew was no longer mine to do.

It was time to leave.

I told the executive team, we built a timeline for transition, and a few weeks later I said goodbye to my team.

There were other leaders and teams who needed me more. And I them.

Further Hindsight

Years on now, I still miss that team. I’ve also remained assured in my decision to move on.

Life shaping decisions are never easy. Yet I’m increasingly convinced that they are quite simple. At the fork in the road, emotions will swirl. They will be uncomfortable enough that your logical brain will try to take over the decision. But the truth of the person you are and the person that you are are becoming, is in the need beneath the feelings.

Only by identifying the need can you then ask the question of each path: Can you meet this need of mine?

When the status quo is a “no” and the unknown path offers its truest reply of “possibly” then it’s time to venture out. Time to see what’s possible.