The Accidental Mentor

An experiment in scaling mentorship for founders

Back in October, when I first announced I was launching Hyphen Capital, I had no idea what I was in for. In fact, I wasn’t even planning to announce it at all.

Backstory: After building a community of Asian-American founders over the past decade, I wanted to start a syndicate backed by the group to support new founders. I had originally written the essay with the intention of sharing internally and recruit LPs and investors from the founders circle. It was meant to be a passive effort and one where I would support occasional referrals from my network. One of our amazingly supportive members tweeted the essay to her over 100,000 followers and I was completely caught off guard. Having had a lot of experience in PR, the first lesson you learn is that you always want to have control of the narrative no matter what news gets out. I quickly wrote up a Twitter thread and LinkedIn post announcing the launch. And then it started happening…message after message, email after email, from founders, investors and people who just wanted to share their visceral reaction to the announcement with me:

“Found myself extremely inspired, even a bit tear jerked after reading your announcement for Hyphen Capital. So. Much. YES. and Thank You.”

- Justin

“I just read your announcement…and it really hit home. As an Asian American *aspiring* entrepreneur (and a fellow enneagram 7!), I also struggle with feeling like an outsider in the startup world despite having worked at venture backed companies my entire career.”

- Mei Lin

“…let me tell you, 99% of what you wrote hit me right in the feels. So much that I jumped out of bed, did my morning thing, and started composing this email. I didn't even know that term Bamboo Ceiling existed until several years ago. I thought for a long time, I wasn't getting ahead simply because of me, but after reading and hearing about so many similar experiences, maybe it was a bit of both? Since then, I've been trying to destroy that Harold (from Harold and Kumar) stereotype.”

- Tony

“I have also felt the strain of being "too whitewashed" for my family, and "too Chinese" to my friends. As a first generation Asian American (my father is an immigrant from HK and my mother is an immigrant from Taiwan), the mission behind your new fund is truly inspiring. “

- Brian

“Love and fully-support this idea; the mission resonates with me to my core.”

- Porntepp

“It was an odd feeling to see something that supports Asian American founders (as it is so rare). Really appreciate your initiative on it and for fostering generational support.” - James

“For years I've been told by various people that the bamboo ceiling didn't exist, and that I was making it all up despite direct instances as an employee and as a founder. I once had a situation where an investor assumed I was the CTO and my white co-founder as the CEO, and this I would consider more mild than other interactions I've had previously.” - Jimmy

“As a new Asian-American founder, your mission and vision really spoke to me.”

- Steven

“As a first generation, low income student, your words strongly resonated with me; I grew up in an immigrant community in Brooklyn, often helping out at my parents' small business, and have seen first-hand the difficulties our communities face in raising capital.”

- Perry

“I recently saw your article on Hyphen Capital and was previously forwarded your Bamboo Ceiling article by five different friends :) It really resonated with me and the experience growing up as an Asian American in Los Altos and even recently at Amazon when my entire reporting chain was white men all the way to Jeff Bezos.”

- Anonymous

This was only a sample of the hundreds of messages that were sent to me from around the world. The common thread was “resonance”. My words had struck a chord with people who couldn’t quite pinpoint the frustration they were feeling with their careers or their startup journeys. Whether it was inexplicably being passed over for a promotion time and again or getting rejected by investor after investor because they were unable to connect. I could sense from all of the messages that they just wanted to feel heard and needed someone who could relate and empathize. The journey of the founder is one of the most lonely paths someone could choose to take. Not having any community or mentorship can make it even more daunting.

I’ve been feeling overwhelmed by the outpouring of support, but also the cries for guidance and help. I feel guilty if I don’t respond to a message promptly, because I knew how it feels to reach out for help and receive nothing in return. In an attempt to help, I would take calls and try to coach and give advice to founders who reached out. But I have only so many hours in the day between my own startup and my family, so I knew that this was not sustainable.

I tried to think of the best way to scale my advice and guidance for as many founders as possible. That’s how I ended up here at Substack. I felt that a newsletter would be the most effective way for me to directly reach those who wanted or needed mentorship. There’s a ton of content out there about starting companies and founder experiences. I had Paul Graham’s essays back when I started my first company. There was always an essay that was relevant to something we were dealing with at the company. It’s as if he had seen this movie before several times. I am not arrogant enough to believe that I can provide any better or more valuable insight than any other founder. All I can do is share the insight and advice from my own personal experience that many founders I’ve advised over the years have found helpful to them. I hope to address questions from incorporating to whether or not to bootstrap (my first company) or raise venture capital (my current company) to what software I recommend to fundraising techniques. I won’t and don’t have all the right answers, I can only share my own personal experience and learnings. I didn’t think those mattered that much until I got the response I did to my essays about the bamboo ceiling and launching Hyphen Capital.

Someone emailed me the other day and asked for recommendations on memoirs or autobiographies of Asian-American leaders noting that Barack Obama was inspired by the stories of great black leaders like Malcolm X and James Baldwin. He named the late Tony Hsieh’s Delivering Happiness and David Chang’s brand new memoir, Eat a Peach. It struck me that I could not come up with any suggestions. I’ve read countless business memoirs from Bob Iger to Phil Knight to Steve Jobs to Andy Grove, all white males. While a lot of lessons can be gleaned from their stories, it is difficult to relate to their upbringings and backgrounds. Many of their parents were proud that their kids were starting their own businesses and some even helped financially support their dreams. On the other hand, I know many Asian-American entrepreneurs whose families practically and literally disowned them when they left their high-paying prestigious jobs to start their own companies. This cultural experience is extremely relatable for children of immigrants who sacrificed everything so their kids wouldn’t have to endure any hardships in their lives. The burden of family guilt in Eastern cultures is very real. It is important to hear perspectives from others who share your cultural values and upbringing.

You don’t have to be Asian to appreciate my advice, it’s just very much a part of my experience. I am a sum of my dichotomies. I am Asian and I am American. I am an East Coaster living in the West Coast. I have an MBA but I think I would have been just fine without it. I’ve worked in big corporate tech companies and I’ve started two companies from scratch. I bootstrapped my first company and raised venture capital for my second company. I grew my first company through SEO and free traffic and my second company relied on paid acquisition and a sales team for growth. I have experience in product, marketing, design and business development. I have been in Silicon Valley through multiple the booms and busts all the way back to 1999. I am a founder and I am an investor. My hope is that my unique exposure to both sides of many coins will create a balanced perspective that my subscribers and readers can benefit from. If I can help you to avoid the same pitfalls and mistakes that I’ve made, or inspire you to build something amazing, then it will be worth it.

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