Back when I was a Venture Capitalist in the early 2000’s, I remember that we lost two deals for similar reason:
The founders chose other VCs because, as they put it, we “had never been in their shoes.”
To be fair, I had some startup experience at the time - I founded a company that got washed away in the Dot Com bust. But one failed venture does not equal experience. In addition, this was Fund I at OCA (now raising Fund VI).
This hit me hard, so I knew I wanted to walk in a founder’s shoes again.
In 2011 I had a chance to re-enter the arena. I left the firm to start my own company, Shiftgig. Suddenly, I wasn’t the one asking tough questions; I was the one trying to answer them.
I was the one pitching, getting plenty of NOs, wearing many functional hats, being resource constrained, and waking up at 3 a.m. worrying about making payroll. I felt like an underdog with no customers, no product, no team…just an idea and a vision for the future.
Over 7 years, I learned a couple decades worth of lessons: partnering with co-founders, building MVPs, selling to customers, pivoting, hiring executives, blitzscaling, etc. Though we raised over $50M in venture, work life actually got busier. I am a believer of life-long learning, so while this time was stressful, I viewed it as necessary education.
Best of all, we found success: Shiftgig raised over $50 million and sold to a strategic partner in 2021.
Years later, when I became an angel investor, I had a newfound appreciation for “life in their shoes.” Now it’s my most valuable asset to founders.
Over the 7 years as an active angel investor, my approach has crystallized into a simple philosophy: I want to be the person the founder calls first, in good times and bad.
That requires a different model than traditional venture capital. For me, it is built on a few core principles:
Show Early Conviction - Every founder remembers who bet on them before anyone else. Startups can be brutal and isolating, and that early act of faith changes everything. It tells the founder, someone sees what I see and someone believes in me. From that moment on, you’re not just an investor, you’re an ally who wants their ultimate success as much as they do.
Put Founders First - The best angels know their job is to serve, not steer. Founders live closer to the problem than anyone else, and the greatest respect you can show is trusting their judgment. Putting founders first means showing up with empathy, staying founder-friendly when things get messy, and believing they have the passion, grit, and drive to build their start-up.
Always Add Value - Angels can add meaningful value through their experience. They share their playbooks, open their networks, identify patterns, and bring up roadblocks before founders even see them coming.
When I evaluate my success as an investor, I have two scoreboards. The first is simply ROI: Return on Investment. Am I making smart, risk-adjusted bets? Every investor measures this or they’ll be out of business quickly.
The second scoreboard is more meaningful to me: It’s the strength of relationships built over time. It’s a different ROI: Relationships Over Investment.
Here’s an example: A few years ago, I was the first check into Chowbus, an Asian food company started by Linxin Wen, a driven founder and underdog who immigrated to the US a few years earlier. As he later told me, meeting me “opened up a whole new window—a different world.”
In the early days, my role was more tactical. I helped with everything from introductions and negotiations to legal work and how to structure the angel and early VC rounds. For 6 years, Linxin and I spoke two or three times a week. Linxin has built an incredible company, but what I value most is our relationship.
Linxin calls me his "Dà gē", which in Chinese means ‘big brother.’
Those words mean more than any financial return. They remind me what this work is really about: proof that what we do matters, not just to the market but to the people.
Whenever I talk with aspiring or experienced Angels, I give them this advice: Add Value by spending as much time as possible with founders.
Learn their rhythms, their fears, their drive. You’ll think it’s about the product or the market—but it’s really about people. Ninety-nine percent of what you’re investing in is the founding team. The rest is just details and execution.
The best Angels aren’t just good financial analysts or have domain experience. They are great judges of character and great partners to people.
They know which ROI matters most.
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