Taking A Leap OF Faith

Come to the edge,” he said.

“We can’t, we’re afraid!” they responded.

“Come to the edge,” he said.

“We can’t, We will fall!” they responded.

“Come to the edge,” he said.

And so they came. And he pushed them.

And they flew.

— Guillaume Apollinaire

I have bittersweet news. I’ve made a very tough decision to leave Primary and take a pause from “institutional” VC life. I’ve been mulling over this for months but finally made the call after I turned forty in October.

First — I’d like to thank my Partners, Ben and Brad, and the rest of the team at Primary for making the last year and a half so memorable. They’re building one of the top seed firms in NYC. I know this approach will pay off many times over in the years to come. If I was going to continue my career as a pure institutional VC, Primary is the place I’d want to do it. And I’m excited to remain part of the extended Primary family as a Board Partner.

I’d also like extend a heartfelt thanks to the founders I was lucky to serve in the Primary portfolio. It has been an honor working together. I’m excited to watch you and your companies thrive, evolve and have a big impact in the coming years.

With that, “Why am I leaving and what’s next?”

My decision to make a slight career pivot was ultimately driven by a desire to align more tightly with two of my core values — selfless service and intense collaboration. These values have really come into focus over the last five years. Meditation, sobriety and coaching have had a big influence on me and my worldview during this time.

Service

Since I became a coach two years ago, I’ve been having off the record conversations about power dynamics with founders inside and outside the Primary portfolio. I kept on hearing a similar refrain. One well-known serial entrepreneur said, “If a term sheet, bridge round or pro-rata is on the line, it absolutely changes the interaction and relationship. Walls go up.”

I also heard repeatedly that founders value coaching and leadership development but they don’t want their lead VCs to deliver these experiences as an internal capability. They’d rather partner with best-of-breed third parties who are truly neutral. We collectively spent some time and energy on trying to make the coaching stuff work within Primary and ultimately concluded that it’s not the right platform from which to do that.

Given all of these dynamics, it was difficult for me to show up at Primary as a board member AND a coach. I couldn’t play the role I felt would allow me to have the biggest impact. My inner and outer worlds were out of alignment. I’m now at a point in my life where I want service to be at the core of what I do. More specifically I want to help founders become great leaders and humans.

Collaboration

Institutional seed investing (especially in NYC) was a very different game when I joined Lerer Ventures in early 2011. NYC Tech was just coming of age. Often three or four seed funds and a group of angels would partner to invest in and support a company. Many of us were talking weekly, sharing deal flow, discussing trends and learning the business together. We were co-investing as partners and friends. This period of collaboration was the most fun I’ve ever had in my career.

Today, seed investing is more competitive than ever before. There are now more than five hundred seed funds in every flavor, sector and geography. Large multi-stage funds are coming down market and investing earlier. Fund sizes have also swelled. The only way to make the fund math work is by targeting 10–20% ownership. Because of this, there is typically one institutional winner, maybe two at the very most. Collaboration among seed funds isn’t what it used to be.

Over the last six months, I have come to the conclusion that a ‘winner take all’ style of investing isn’t necessarily for me at this stage of my career. Don’t get me wrong, I love and thrive off good competition. It’s in my blood. However, I’m now at a point in my life where I want to invest in a manner that enables me to collaborate more broadly and thoughtfully.

My Own Pond

I recently explained to my friend Satya Patel that I’ve felt like a fish out of water for years. He responded, “The time has come for you to create your own pond.”

So what does my pond look like? The honest answer is I’m going to take some time to figure it all out. I should have a better answer in ninety days. But my immediate plan is two fold: to coach founders and leaders in transition, and to actively make angel investments with a likely focus on NYC. I can see myself doing these professionally for a long time.

This initial path leverages my superpowers and builds on eighteen years of operating and investing experience. It also builds on two years of intense and daily training to be a coach. Most importantly, it aligns with my mission to help founders perform at higher levels, build more resilient and humane organizations, and bring their grandest visions to life.

That’s why I’m psyched for what’s next. I have a fresh opportunity to step fully into the role that I’ve wanted to play for a long time: coach, angel investor, advisor, mentor and evangelist.

Taking The Leap

Taking a pause on the familiar world of institutional VC is a big move personally and professionally. It has taken me many months to muster up the courage since I’m walking away from an exceptional situation and great partners at Primary. However, I believe that I’ll be kicking myself years from now if I don’t listen to my inner voice and somehow combine my passions for coaching and investing. Thankfully, I found the confidence and courage to take the leap.

Here’s the best part. I’m not going anywhere. Rather, I’m making a change that will allow me to bring my best self to this ecosystem, collaborate broadly and have the biggest impact. While I’m starting out as an ‘army of one,’ I don’t plan to be a lone wolf. Hopefully, I can do this important work alongside you.

You can follow my adventures at here at schlaf.me and/or connect directly at steveschlaf@gmail.com. I’d love to hear from you. Until then!