A week ago I sat down at my computer. Still staring at the blank screen, my heart rate began to spike. The butterflies in my stomach were going wild, and my inner voice started agitating: Are you really going to do this? Are you really going to walk away from months of hard work? Are you really ok walking away from millions of dollars?
Deep down inside, I knew the answer to each question was yes.
I accessed my email, opened a draft, and hit send. The recipients—50 investors, including many friends, former colleagues, and people I respect—had committed to invest millions in a new venture fund I was on the verge of launching. They were expecting an email from me telling them it was time to wire their capital. But the one they got told them I wasn’t moving forward with the fund.
In other words, I walked away at the 11th hour, right before launching what was supposed to be the dream I had worked so hard for, and that they had all supported me in making happen.
It ended in a second. As soon as I hit send, I felt a flood of joy and relief and sadness. I looked up to my wife and said, “Holy shit, I did it.” I got up from our kitchen table and gave her a big hug. At that moment, I felt like a new person. The weight of the world was lifted off my shoulders.
But this wasn’t an easy choice. This was one of the most difficult decisions of my life. I deeply believe in combining early stage capital and “holistic leadership development.” I also believe that I’m among a small group of people who can actually marry these two worlds. It aligns with my experience, unique combination of skills and personal values. I know it would work. In fact, I still get excited just thinking about our mission, vision, and strategy.
If I have conviction in myself and the thesis why did I walk away from the fund? Why did I risk my social capital and reputation with my investors? Why did I leave behind months and years of hard work? I agonized for weeks. I had countless calls with my coach, therapist, advisors, and even some of my investors. I took long walks through the city with friends. I had many discussions with my wife (god bless her!). And I spent hours journaling and sitting in silence. No matter how many times I analyzed the situation, I arrived at the same conclusion.
Overall, I realized a core identity of mine (investor) had to step back to make room for a new one to take center stage (coach). Being a VC is one of the most privileged positions in the world. You get to meet with and invest in incredible people while having an opportunity to make “fuck you money.” There’s power, prestige, influence and cash. All the things the ego loves and society supposedly values. I felt it was time to finally let this part of me go. I was scared shitless.
But if I’m being honest, it wasn’t just one but a confluence of factors that led me to walk.
I was lonely and craved collaboration. Solo Capitalists are all the rage right now. Some people are wired to work alone. Not me. I’m a social creature. I get energy by exchanging ideas, exploring alternative perspectives, and learning from others. I ultimately realized that I highly value having sparring partners and working towards a common goal with talented people who complement me.
I was burnt out. The previous two years were a mad sprint for me. I launched High Output, built a thriving coaching practice, created The Founder Library and Tapestry, raised a $5M angel fund, and invested in nearly 50 companies. I worked every chance I could and thought about work even when I wasn’t working. In fact, when I had “free time” I was reading about technology, coaching, and leadership. It finally caught up to me. I was spent emotionally, mentally, physically.
I needed a break from the echo chamber. I’ve been in technology for two decades. It’s a big part of my identity. I love being in the ecosystem. However, over the past six months something shifted. When I opened Twitter, browsed Product Hunt or read the tech press, a rush of anxiety would wash over me. Unicorns. Decacorns. Building in public. Crypto. Tweetstorms. Clubhouse rooms. NFT mania. New rolling funds. Victory laps galore. Endless expert opinions. All of this began to drain me; I sensed it was time to unplug and reset.
I was taking on too much. Investing. Coaching. Parenting. Writing. Fundraising. Operating. When I finally stepped back a few weeks ago, it occurred to me that I was really building three companies—an investment fund, a coaching company and a family. I was trying to do too many things. My attention and energy were spread too thin. Context switching and multitasking were leading to mediocre performance and diminishing returns. I wasn’t at the top of my game. I began to sense a strong desire within me to simplify and focus.
I love coaching. Helping founders develop professionally and personally fills me with energy, purpose, and meaning. I find the work challenging, fascinating, and impactful. I love learning about a founder’s goals, challenges, tendencies, blind spots, and edges. And then helping them get to where they want to go. There’s also unlimited territory to explore in the profession. The quest to sharpen my craft feels endless. Most important, I’ve proven to myself that I can make a great living and support my family by helping others.
I value my LPs time and capital as much as my own. Raising money, especially from many friends and advisors, is a big responsibility that I don’t take lightly. I couldn’t possibly accept their money AND deliver a 3-5x fund without being fully bought in. When the money hits the bank I want to be ALL IN with every fiber of my body. Anything less would be a disservice to them and myself
I was making a long-term commitment. Fund lifecycles are 10-15 years. This is a very long-term game with very long feedback cycles. In 10 years, I’ll be 51 years old. I just didn’t have the conviction that I wanted to be a VC for the next decade of my life and career. I knew I wasn’t ready to commit because I didn’t have a whole body yes.
I believe cash is a commodity in this market. Everyone and their college roommate is a fund manager these days. Founders. Creators. Influencers. Athletes. Twenty somethings. The barriers to start a fund and deploy capital have (for many people, not for everyone) collapsed. That’s a good thing for entrepreneurs. They have most of the power in this market. That’s now reflected by deal volume, velocity, and valuations. Raising a seed fund is the consensus move these days. I began to wonder if now is the ideal time to start a fund given all the mania surrounding tech and venture.
Finally, I wasn’t having fun and felt out of alignment. I was more often in a state of stress and anxiety than I was in a state of flow and joy. Every morning I’d review my calendar, see a wall of back to back to back meetings, and realize I wasn’t energized for the day ahead. Having fun is essential. I believe it’s an important ingredient of high performance. Why do something if you’re not truly engaged and enjoying the process? Life is too short.
So what’s next for me? You might be wondering if I’m leaving the venture business for good or if I’m going all in on coaching. Honestly, I’m not sure.
My plan today is to take the rest of this year to coach and advise, sharpen my skills, and blog about personal growth, leadership, and coaching. These activities will fulfill my desire to support founders as leaders and humans. I also plan to spend time with my family, reconnect with old friends in NYC, and collaborate with potential business partners who are passionate about supporting founders in radical ways. That’s all to say, I'm not sure where I'm heading or with whom, but I am excited for the adventures that lie ahead.
This much I know: stepping into my identity and power as a coach, writer and builder feels right. I’m excited to see what doors, people, and opportunities emerge as I channel all my energy and focus toward supporting founders.
So why have I chosen to share all of this with you?
We only hear stories of the founders who plow forward. Not enough people talk about those who arrive at the precipice, stare down into the void, take a deep breath, and courageously turn around at the sound of an inner knowing.
Stepping away from a great situation, seeing a dream fade, and letting go of an identity is fucking scary and heartbreaking. It’s easy to stay the course even when everything tells you it’s not the right fit. We often scare ourselves and remain stuck by making up stories about a reality that doesn’t exist. The future is never as scary as it seems.
I imagine there’s a percentage of newly minted entrepreneurs and VCs who keep going despite their heads, hearts, and guts telling them something isn’t right. They continue down the path because that’s what everyone expects of them. Family. Friends. Advisors. Mentors. Colleagues. Society.
No one wants to let others down or be perceived as a quitter. Myself included.
Here’s what I want you to know. It’s ok to walk away. It’s ok to change your mind. It’s ok to deeply listen to yourself. It’s ok to take a different path. It’s ok to press pause. It’s ok to question what matters most to you. It’s ok to leave a “great situation” behind. It’s ok to choose a calling over potential financial upside.
Just because you’re capable of doing something doesn’t mean it’s the right thing for you. Follow your energy and your passion. When that happens you’ll eventually become the person you are destined to become. I can’t think of anything more fulfilling and powerful than that.
Finally, I’d like to thank my wife (Eliza Blank), Holly Whitaker, Micah Baldwin, Seth Goldstein, Taylor Jacobson, Zach Verdin, Josh Klapow, Chris Sparks, Sunil Arora, Jonathan Basker, and Semil Shah for helping me see who I’m meant to be. Your support means more than you know. I appreciate you all.
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