Flying Kite

In the blink of an eye, it was the New Year.

The first time I met Brian, I almost didn’t recognize him. In his LinkedIn photo, he wore a bright, sunny smile. But the man standing before me had a beard creeping across his cheeks, a pair of heavy glasses, and an air of gloom hanging over him. When I pushed open the doors of Saluhall, the Swedish food hall, I would never have connected him with that photo if he hadn’t waved to me first.

San Francisco in January still carried a sharp chill. The New Year had just passed, people were waking from their holidays with the regret of hangovers and the pressure of calendars, ending the long Christmas break to begin another cycle of life. I told myself silently: In 2025, something has to be different.

With that mindset, I began reaching out to people on LinkedIn.

Since deciding last summer to start a new company, I had set a goal for 2025: to talk with thirty founders. I opened LinkedIn, clicked into “People You May Know.” The feed showed row after row of professionals wearing standard smiles: “People you may know in the San Francisco Bay Area.”

In this era of digital networking, it was far too easy to click “Connect.” I sent out a few requests casually, then hurried off to do other things.

Brian accepted my connection almost immediately, and at 8:35 the next morning, he sent me a message:

“Hi Xiao. Congratulations on starting RegHero—how’s it going so far?”

I clicked on his profile and studied his background: co-founder of Itoka, a company helping businesses streamline bookkeeping and taxes. Before founding Itoka, he studied finance at Jamestown University in Boston, then worked four years at a seed-stage venture capital firm, climbing from analyst to manager. Later he joined a chemistry R&D data company, and six months ago he started his own venture.

I replied: “Hi Brian, thank you! We’re currently testing a product prototype and hope to get it into use soon.”

He wrote back quickly: “Nice. Healthcare regulation is a pretty daunting topic. Are you bootstrapping right now, or looking to raise?”

“Bootstrapping for now,” I answered, “but hoping to seek VC funding this year! We don’t have much revenue yet, but once we’ve gone a bit further, I’d love to learn more about what you’re doing.”

“That’s great! We bootstrapped for a while too. Fundraising is tough, but it really helps growth. If you ever have questions—whether it’s practicing a pitch or getting introductions—I’d be happy to help. And if you run into accounting, tax, or finance issues, just ask me!”

I was genuinely glad: “Thank you so much, Brian! If you’re in San Francisco, shall we grab a coffee or do a video chat? I’d love to hear about your fundraising experience, and also talk through some of our early-stage finance and tax confusions. Last year I registered a C-corp in Delaware but later dissolved it. The law firm had issued too many shares to me and my co-founder, which made the tax burden too heavy—starting over was actually easier than cleaning it up.”

The real story behind that was of course much more tangled, but with Brian, there was no need to go into all those messy details. So we set a time: the following Wednesday morning, for coffee at Saluhall downtown, not far from his office.

For full text: https://a.co/d/018mZrMT