
When entrepreneurs exit their companies, it is supposed to be a victory lap. But in reality, many find themselves in an unexpected emotional vacuum. More often than you might think, I hear variations of the same quiet confession:
“It should have been the best time of my life. But I felt lost after the exit. I lost my purpose.”
After running Wattpad for 15 years, I understand this all too well. It is like training for and running a marathon for over a decade, only to stop cold the day after the finish line. No more rhythm. No more momentum. No next mile.
Do I Miss Operating
Unsurprisingly, people often ask me:
“Do you like being a VC?”
“Do you miss operating?”
My honest answer is yes and yes
(but I get my fix without being a CEO — see below).
Being a founder and CEO was deeply challenging and also immensely rewarding. It is a role that demands a decade-long commitment to building one and only one thing. And while I loved my time as CEO, I did not feel the need to do it again. Once in a lifetime was enough. I have started three companies. A fourth would have felt repetitive.
What I missed most was not the title or the responsibility. It was the people. The team. The day-to-day collaboration with nearly 300 passionate employees when I stepped down. That sense of shared mission — of solving hard problems together — was what truly filled my cup.
Back in the Trenches in a Different Role
Now at Two Small Fish Ventures as an operating partner, I work with founders across our portfolio. I am no longer the operator inside the company, but I get to be their sounding board — helping them tackle some of the biggest challenges they face.
Let’s be honest: they call me especially when they believe I am the only one who can help them. Their words, not mine. And there have been plenty of those occasions.
That gives me the same hit of adrenaline I used to get from operating. At my core, I love solving hard problems. That part of me did not go away after my exit. I just found a new arena for it — and it is a perfect replacement.
A Playground for a Science Nerd
What people may not realize is that the deep tech VC job is drastically different from a “normal” VC job. As a deep tech VC, I am constantly stretched and go deep — technically, intellectually, and creatively. It forces me to stay sharp, push my boundaries, and reconnect with my roots as a curious, wide-eyed science nerd.
There is something magical about working with founders at the bleeding edge of innovation. I get to dive into breakthrough technologies, understand how they work, and figure out how to turn them into usable and scalable products. It feels like being a kid in a candy store — except the candy is semiconductors, control systems, power electronics, quantum, and other domains in the next frontier of computing.
How could I not love that?
Ironically, I had less time to indulge this curiosity when I was a CEO. Now I can geek out and help shape the future at the same time. It is a net positive to me.
You Do Not Have to Love It All
Of course, every job — including CEO and VC — has its less glamorous parts. Whether you are a founder or a VC, there will always be administrative tasks and responsibilities you would rather skip.
But I have learned not to resent them. As I often say:
“You do not need to love every task. You just need to be curious enough to find the interesting angles in anything.”
Those tasks are the cost of admission to being a deep tech VC. A small price to pay to do the work I love — supporting incredible entrepreneurs as they bring transformative ideas to life, and finding joy in doing so. And knowing what I know now, I do not think I would enjoy being a “normal” VC. I cannot speak for others, but for me, this is the only kind of venture work that truly energizes and fulfills me.
A New Season. A New Purpose.
So yes, being a VC brings me as much joy — and arguably even more fulfillment (and I am surprised that I am saying this) — than being a CEO. I feel incredibly lucky. And I am all in.
It feels like all my past experience has prepared me for what I do today. I often describe this phase of my life this way:
Wattpad was my regular season. TSF is my playoff hockey.
It is faster. It is grittier. The stakes feel higher. Not because I am building one company, but because I am helping many shape the future.
P.S. Go Oilers!!
Discover more from Allen's Thoughts...
Subscribe to get the latest posts sent to your email.