Looking back at when I ran my education startup (2005 to 2012), I recall a lot of emotions and feelings. I remember existential stress, since from my perspective I was building a house of cards that could collapse at any moment (I was a little bit young and dramatic). I also remember exhaustion, as I poured everything I had into this startup; progress was always shaky and turbulent. I sacrificed health and relationships along the way.
But most vividly, I recall joy and purpose in running my startup.
My startup experience was weirdly spiritual. At the time I firmly believed that God had put me on earth to build the company I was building and serve the community I was serving. Despite all the stress and exhaustion, this underlying joy brought me tremendous peace, giving me strength push myself beyond what I imagined I was capable.
My team and I celebrated an exit from my education startup in 2012. And then I became professionally aimless for the next several years.
After a wonderful 9-month sabbatical (which is documented thoroughly in this blog), I did a bunch of consulting, applied for jobs, started some new companies, and even tried worked for a big company—but nothing really every stuck and I just kept hopping around.
Home life was wonderful during this period, as I enjoyed a lot of time with my wife and now two kids. But there was a big hole gnawing inside my soul to find something to build.
Now, I am no longer wandering.
Two years ago, something happened to me that I didn’t expect would ever happen: I fell in love with venture capital.
As a means of getting a bit of income and healthcare, I joined a fund as an entrepreneur in residence, assuming I’d chill out for a few months and then continue wandering. As an EIR, I got my first taste of what it’s like to invest in founders as an institution. It was amazing.
For most of my life I viewed venture capitalists as parasites. I thought of them as slick salespeople who wiggle their way into controlling your company in exchange for dangling some money. And, there are some assholes in this industry who fit this description.
But I also met a lot of VCs who approached their craft with love—who didn’t have a goal of just screwing over founders for ownership, but rather deeply cared about helping their founders to build something great and reach their full potential.
So I started to invest. And I started to directly help founders with growth, marketing, storytelling, recruiting, and fundraising. During this time working for my founders, I began to sense an old, familiar feeling that I had not felt for years: it was joy. I re-established that spiritual connection; that I was placed on this earth to do this work.
Last May, I established Hustle Fund with two friends I’ve known for 18 years: Elizabeth Yin and Shiyan Koh. We raised $11.5M for our inaugural fund, which we’re now investing into pre-seed and seed-stage startups across North America and Southeast Asia. You can read Elizabeth’s announcement of our fund and how we help founders here. I also did a Reddit AMA that outlines my view of how VCs should partner with founders.
In the course of learning to become a VC (the learning actually never ends), I find myself coming back to a critical, final question, prior to offering a term sheet to a founder: Do I want to grow old with this person?
Early-stage venture is a long and tough path, where the deals you make often do not reach liquidity until 7-10 years later. That is a long time to spend with founders, and I simply can’t justify doing a deal into a great startup if I don’t love the founders. As critically, these founders have to love me back. I wish for our partnership to expand beyond the work, where we can invest in knowing each others’ spouses, kids, dogs, hopes, and fears.
The ‘growing old’ question should extend to any critical relationship, including the spouse you select and the co-founders you choose in your business.
With Elizabeth and Shiyan—I’m convinced I have found collaborators whom I want to grow old with. I’ve already known them for half my life, co-founded businesses with them, co-invested together, and broken bread with their families and pets. We share similar values and they love helping founders as much as I do. As a side note, I also love to troll them endlessly and can entertain myself just doing that for at least 50 years.
I’m in such a position of privilege, having landed at my last startup—a venture capital fund—which I’ll be building over the next and final 30 years of my career. ‘Blessed’ doesn’t even come close to how I feel these days.
If you’re a founder in the early stages of building a software-enabled startup, I invite you to consider Hustle Fund. Maybe you’ll want to grow old with us too, and we can create some great projects together over the next few decades.
Reach out to us: http://www.hustlefund.vc
Unrelated PS: Holy crap, first blog post in nearly 2 years! Hope to get back to more regular writing again. 🙂