What Music City Taught Me about Venture Capital

Why founders are musicians with different instruments and how coming from Nashville gave me an edge in VC

(PREFACE: It’s been a while, friends, but another friend told me to write more and I said I would and I’m a man of my word so here we are. I’m a rusty and writing these in drafts from my phone while on the go so I beg your patience and a little empathy. Speaking of empathy…)

While my grandparents moved my mother’s family to the Bay Area nearly 60 years ago and San Francisco is stuck with me now, I come with a Made-in-Florida sticker and did most of my growing in Tennessee. I called Nashville home for six years before finalizing my westward, technological transition (thank you SoFi, for hiring me), and that city is more similar to San Francisco than you think. It’s full of dreamers and entrepreneurs too. They just have guitars.

And their product is a raw piece of their heart. (Most singer-songwriters pull right from their journals.)

And the VCs there are record labels, except their A&R (artists and repertoire) departments are even bigger a-holes than most investors.

And demo day is every night you manage to book a gig, except you don’t know if the faces behind the lights include a label rep, exec, or just a smattering of your guilt-tripped friends.

I don’t know the experience first hand — my only musical qualification is that I own a ukelele — but I was that friend in the crowd 2–3 nights a week for a few years. In Nashville I was the oddball interested in tech (there’s more of a scene there now) while most of my peers were pouring their hearts out on stage or hustling almost as hard to break into music business. And a couple managed to do it: my buddy Paul Klein of LANY and my ‘brother’ Austin Fish on Taylor Swift’s management team. Others were so good you’d cry to hear their music but as in startups, Lady Luck plays your co-lead.

I, for one, was completely enamored by these unrequited paramours. They strummed and sang out their souls to a ghost-crowd of friends, stone-faced music execs, and even stonier peers — and the thing was, the best ones didn’t even care who was in the crowd. You’d have thought they were on stage at the Grammys or playing their best friend’s processional. Those songs had to come from them. They were the artists I fell for — and who briefly had me consider A&R.

So I left half of my heart in Tennessee and followed my science fiction-induced delusions of grandeur to a city where dreams are written in QWERTY instead of major/minor and eventually hacked my way into venture capital because we have artists too. And I fell for the same ones , whose work was the product of years and tears — songs they had no choice but to birth, verses torn from their most intimate journals and risked before the world.

So to me it was natural to treat them like the artists they were, with the empathy deserving of a heart laid bare. It’s just an indictment of other VCs that I was considered unique in that regard. (If you’re another VC reading this, ask for my Nashville recs; the trip will do you good.) And I named the firm for them: Cantos, after their songs (Spanish) and verses (Latin).

I guess I ended up in A&R, after all.

Views best described as cosmopolitan-to-extropian. Professional fanboy of world-positive tech @ Cantos Ventures 🛰🧬💹