On more pensive days, which have been abundant of late, I feel a sort of odd camaraderie with the late Stephen Hawking in his quixotic striving for a unified theory of gravity and quantum mechanics. Mine being a far lesser mind, the pursuit that has dogged me in ten years of investing has been a model that unifies the so-called value investing framework solidified by Benjamin Graham and tech truisms epitomized in “growth” stocks, namely FANMAG. While there are many differences between the two apparently disparate schools of thought, there are two equations they largely agree on. …

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…

I joined SoFi in early 2012 because I wanted to help fix the broken credit markets. While we built a huge business we ended up largely following the status quo. Our technology wasn’t a step-change, so it didn’t give us enough leverage to truly change anything. We were too early, mid-cycle.

Now we have a powerful new technology that can create that step-change, the leverage we need to bring transparency and accountability to credit markets. You guessed it… blockchain. …

I’m not a Core dev — I’m not an engineer at all — and I only bought my first coins around $100, but I am a cryptophile VC, Small ETH miner, and for better or worse among my larger friend group I’ve become the “Bitcoin guy”. Enough of them have asked about these forks that I figured some of you are probably also like “WTF?” So I’m publishing my synopsis here…

Bitcoin Cash (BCH), called “Bcash” by the Core/SegWit devs in an attempt to delegitimize it, is essentially Bitcoin Classic. They vehemently disagreed with the SegWit update and decided to…

I’m angry. I’m confused. Yesterday I hardly got any work done in my glassy-eyed stupor. I see now that I had been sleeping. Now I’ve been shaken awake. I’m awake.

“It’s 2016,” we said, as if we’d bent space-time to finally arrive in the future. This is 2016. The future is tomorrow. Tomorrow it will be the next day, and so goes the arrow of time. We have not arrived. This is not the end, but it is the road. That gleaming city, that distant peak, is still in the distance. Was it a mirage all along? Partly. The city…

I’ve been waiting to share something with you…

We all have passions, callings, obsessions, call them what you will, but they often lay dormant. That dormancy can be a good thing — it allows us to cultivate, refine, strategize, gain clarity — but at times it’s driven by fear, and by those who would tell you it’s impossible, that you should wait. That you should play it safe. And for four years I listened… but I also quietly laid the groundwork, building relationships, making small investments, and helping entrepreneurs and investors alike. While I waited.

Then one day something —…

A note on what follows: As I take what’s been a five-year night-job full-time I’m putting pen to pixel in an attempt to articulate my lens on early-stage investing. I call this framework my own, though in truth it’s a synthesis of counsel from wise predecessors, observation of fantastic (and not-so-fantastic) entrepreneurs, industry literature (more history than blogs), personal experience — including more mis-steps than I would like to admit — and a splash of my own techno-optimism.

This is far from a formula. It is not meant to be an absolute calculus on predicting the future (I’ll leave that…

Recently at dinner I outlined a startup I was interested in to a veteran VC. He nodded and agreed the deal sounded compelling. Then he took a few steps back and punctuated his assessment. He said, “the thing you really have to ask yourself each time you do a deal is simply this—What price glory?”

That didn’t sound simple at all — it sounded cryptic as heck! Before I could ask what in the world he meant, our companions returned from the privy and the conversation rushed headlong into the Chardonnay on the table, but the words rang in my…

Great firms pass on two deals with solid fundamentals because they had a gut feeling about the founders.

Two companies I loved. I got their mission and their products. They’d already demonstrated incredible traction with little marketing spend. They showed intense knowledge of their markets and reasonable defensibility.

Both went to partner meetings, but in the end the very partners who brought the deal in pulled the plug. In one instance (Company.ly) they found themselves wanting to replace the current CEO and knew it would be hostile. In the other (Company.io) they couldn't put a finger on it but just weren’t able to force a solid faith in the founders—but it was enough to kill the deal.

A…

A much-admired, huge round-raising entrepreneur admits he often feels insane.

He begins to doubt himself. Then he remembers that he’s an entrepreneur.

I was reviewing mock-ups of our new product the other day and thought to myself, “Have we lost our marbles? People will think this is crazy.” I almost ended development. Then it occurred to me, as an entrepreneur, if you don’t feel a little bit crazy most of the time, you’re doing something wrong. People will think our new product’s absolutely insane… or they’ll absolutely love it.*

*Quotations are my recollections.

Ian

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

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