Would you make friends with someone who once threatened to sue you?

Shared Journey with iFly.vc

Nov 13, 2025

In my past newsletters, I’ve often focused on investment ideas, markets, founders, and lessons from building iFly.vc. This time, I want to take a pause and talk about something more fundamental: human connection.

TL;DR

Would you make friends with someone who once threatened to sue you? My reflections on emotional vs rational sides
Life-long learning and relationship building: Dunbar’s Number and Celebration of Kauffman Fellows 30-Year Anniversary
My mixed feelings towards a colleague’s departure

Being threatened with a lawsuit right after iFly.vc launched

Back in September 2016, just as iFly.vc completed its first close and subsequent SEC registration, I received a two-page, single-spaced letter from the General Counsel of a company that happened to have “iFly” in its name.

It was a classic legal threat, complete with strong language, claiming trademark infringement, and demanding that we change our name or face legal action. A few days later, their CEO reached out. Very polite, almost gentle. “Are you raising a fund? Maybe I can introduce you to potential LPs. By the way, do you really want to stick to that name?”

The carrot-and-stick approach was… impressive.

Well, not really.

I’m not a trademark lawyer, but I know well enough that the key evidence for trademark infringement is customer confusion. That company and iFly.vc are in completely separate businesses.

With my counsel’s help, we responded. The essential message was: iFly.vc is a venture capital fund. You operate in a completely different industry. There’s no evidence of confusion between our audiences.

And then, silence. They disappeared.

Fast forward nine years: the same General Counsel, who left that company some time ago, just joined a venture capital firm and added me on LinkedIn.

“Hi Han. I left the real iFLY and now doing VC thing like you. Let’s get together one of these days.“

For a moment, my emotional side wanted to say:

“The real iFly? Really? You should’ve known better. Since 9 years ago, I’ve rarely come across anyone who told me iFly.vc reminded them of your former employer. On very few occasions when that business was mentioned, the comment went “I don’t know anyone who has been there.”
“And you call yourself a VC like me? What’s your track record of investment return and founder support? Advising them to sue people and prove your worthiness?”

Of course, I didn’t say any of that. Bitterness is human, but focus is discipline.

Before I respond to him, I decide to pause, as my mind cannot help drifting to something I had just experienced: the 30th Anniversary of Kauffman Fellows.

Lifelong learning and deep connections are why I love Kauffman Fellows

Last week, I joined 400+ fellows for the Kauffman Fellows 30th Anniversary Summit in London. In addition to the summit, which featured numerous thoughtful sharing and discussion sessions, a celebration gala was held at the British Natural History Museum, an epic evening that will remain vivid in my memory.

When I applied to Kauffman Fellows and proudly joined Class 27, my goal was simple:

Lifelong learning: learn more about the known unknowns and expose myself to the unknown unknowns.
Deep connections: it’s about the depth of relationships with peers who share the same passion for learning and growing in venture capital and company building. It’s NOT about growing the number of contacts.

You can read more about why I joined Kauffman Fellows here.

Years later, those goals have been achieved yet continue to be elevated — the program continues to help me grow, and its culture of curiosity and generosity keeps delivering value far beyond expectation.

Just as I returned from London and shared my excitement about Kauffman Fellows, a friend brought up Dunbar’s Number, the theory that humans can maintain about 150 meaningful relationships. The question was: In the AI era, does that number still hold?

Technology may help us stay loosely connected to more people. But what truly matters is who we choose to spend our time with. In venture, as in life, you are ultimately defined by the circle of people you associate with, i.e., those you trust, respect, and genuinely like. These relationships compound faster than capital ever could.

My mixed feelings this week

This week, I’ve felt mixed emotions as my colleague, Martin Salomon, is about to move on to his next career chapter and join a startup based in Austin. I’ll miss collaborating with him, but I’m equally excited to see what he builds next.

Four years ago, Martin joined iFly while pursuing his part-time MBA and starting a family simultaneously. Despite the competing demands from school and home, he learned fast and made meaningful contributions across many aspects of our day-to-day work.

He raised the bar for what dedication, integrity, and intellectual curiosity look like inside a small team. His work ethic and professionalism have left an imprint on iFly’s culture that will last.

I wish Martin the best of luck with his next endeavor. The shared journey will continue, just in a different format. I look forward to continuing to have him as a friend and ally.

Conclusion

Now back to the ex-GC/now “VC” guy’s request, with my best intention to drop emotion, the real question becomes:

Do I want to engage with someone whose past judgment once clashed so sharply with my values? Would I want my portfolio companies to take money from an investor with poor judgment?

Probably not.

I’d rather focus on building with people I trust, admire, and genuinely enjoy, which is the kind of human connection worth compounding. Unless the paths are destined to cross in a positive and meaningful way at some point, I decided not to accept the meeting request in the near term, but to write up these thoughts and share them with you instead.

If this resonated, I’d love to hear your thoughts on how you manage human connection in your professional life.

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Regards,

Han