Lightspeed VC Michael Mignano on Why Apple’s Threats Influenced His Decision to Sell Anchor to Spotify, Why No FOMO in Venture is Good (AI Aside), & What NYC Founders Need to Realize

Investing in someone is primarily a business relationship. It doesn’t mean you don’t develop a personal affinity — it’s best when you do! — but creating an enduring bond transcends the question of founder:VC dynamics and is often not even directly correlated with economic outcome. Our participation in Anchor ( later acquired by Spotify) generated both a return and a friendship between us and the founders. Specifically I’ve had the chance to spend meaningful time over the years with Michael Mignano as he went from startup CEO to Executive/Angel Investor and now VC Partner at Lightspeed. Our conversations are always enjoyable, spanning tech, parenting and culture, so I decided to ask him Five Questions here.

Hunter Walk: You got to work with a number of different VCs on your cap table for Anchor. Who was the best one and why was it Homebrew? Seriously though, were there things you saw as a founder — or an angel investor in other people’s companies — that informed your own approach to venture now?

Michael Mignano: Throughout my time building Anchor, I met and pitched many, many VCs. And I think if you were to look at all of those interactions and score them on quality of the “user experience”, the majority (but not all) would probably qualify as poor UX. I don’t think this will surprise anyone. On the flipside, there were absolutely a number of investors I met with, including the ones with whom we ended up working very closely, which were phenomenal!

Ironically (or perhaps not), I believe the qualities of those investors overlap quite a bit with the qualities of great founders: speed, conviction, authenticity, respect and directness in communication, clarity of thought, human connection, empathy. And so those are the investors I’ve tried to emulate. Of course, I don’t always get it right, but I’m trying. I’ve basically tried to take my “founder brain” and just flip the goal to investing and helping, not building a company.

Again, I get it wrong sometimes and now, being on the other side, I see how high volume this job can be at times. And so I do…