Questions Worth Asking

That number. I hadn’t seen that number pop up on my phone in years. 12 years to be exact.  I’ve thought a lot about the conversation I had the last time that number popped up on my phone. I can still remember where I was standing, the time of day and the way the air felt on my skin as I sat on the stoop in front of my house as I answered that call. It was the fall of 2005 and we were in the final stretches of closing our first fund. Earlier that year, we’d talked to Freada Klein and Mitch Kapor about investing in the fund. Seed investing was still a new concept, but they both have a nose for what’s next and they seemed intrigued. We’d connected on a number of levels and it was looking good that they would commit. Prior to making the Continue reading "Questions Worth Asking"

OATV and

Around this time last year, Christopher Mims at the Wall Street Journal did a profile on the experiment we were running with Buried in the piece was a mention of a new fund we’d closed to continue iterating on the experiment.  That’s the only mention of the new fund.  In the proceeding months since his piece, it has become clear to me that there’s still some confusion around the relationship between OATV and Tho I’ve shared the relationship between the two in private emails and conversations, I think it’s worthwhile to unpack it a bit more publicly so we can remove any confusion about the current state of both.  OATV (O'Reilly AlphaTech Ventures) was founded in 2005 by myself, Mark Jacobsen and Tim O'Reilly. We were one of a handful of “institutional” super angel/micro VC/seed funds, which is to say that we raised Continue reading "OATV and"

Friend or Financier?

The biggest mistakes I make as a VC come when the emotions of friendship cloud the realities of being a financier. That’s an easy line to blur when your business is based on personal relationships with founders and instinctual investments. At the earliest stages, when there’s little, if any, meaningful data on which to anchor a decision, an affirmative answer to the question of “is this someone I believe in” is often all an investment decision hangs on. Working closely with, and believing in, founders often leads to deep and meaningful friendships.  I often envy the Warren Buffet types who pour over cold and sterile annual reports, company financials and stock charts looking for anomalies to explore and untapped value to unlock. There’s a structure and precision to their craft of picking. Yes, over time, they occasionally build friendships with managers they back, but those relationships begin on a bedrock Continue reading "Friend or Financier?"

What Are You For?

Today feels like the golden age of being Anti something. If my Twitter feed is any indication, there is literally no end to what people are being Anti of Anti Trump. Anti Hillary Anti Fox News. Anti CNN. Anti Bay Area. Anti New York Anti Wal Mart. Anti Juicero. Literally no end. has even been described as Anti-VC.  We aren’t anti-VC, we’re for profitability and all the freedom that comes with it. Freedom to choose how, when and if to scale. Freedom to raise, or not, from a hugely leveraged position.  We think founders who are for that too are great people to be in business with. And we think the companies they’re building on that solid foundation can make for great returns.
We’re for all of that. Being anti something pushes people and ideas away.  Being for something pulls them in.  Try it. Continue reading "What Are You For?"

The Time Thief

my Krouse Rosenthal died yesterday.

I don’t know her, but I cried when I read the dating profile she wrote for her soon to be widowed husband.

Like, big ugly cried.

I can count the number of times I’ve cried as an adult on one hand. Well maybe I’d need to borrow a few fingers, but the point is I rarely ever cry.

Maybe its because my wife is out of town and I miss the mornings with her after the kids have gone to school and the nights where we don’t even have to be talking but just being near each other is enough to put us both at ease.

Maybe it was because my son had posted a picture with his arm around his little girlfriend wishing her a happy birthday. And he still looked like a little boy. Like my little boy. And I know that won’t Continue reading "The Time Thief"

Living Above the Store

In another life I will come back as a chef with a small restaurant in a little village with less than 10 seats inside and a quaint patio outside. Word of my talents will spread far and wide and people will come from the furthest corners of the earth to sit and sample and soak in the special little space we’ll create.

Until then, I’ll watch Chef’s Table on Netflix. 

There are so many wonderful lessons for founders to take from the unique perspectives on food and business and creatively shared by the chefs the show profiles. 

For even the most talented chefs, the business of starting and running a restaurant makes launching your website in your underwear look as simple as, well, launching a website in your underwear. Their stories of sacrifice, perseverance, overcoming obscurity and rising to fame are so well crafted in the course of Continue reading "Living Above the Store"

My First Lyft Ride

Over the years I’ve used Uber 600+ times and spent 10s of thousands of dollars with them. I am neither an Uber apologist nor critic, but I did something today I’ve never done. I used Lyft. I have actively disliked Lyft since the get go. The fist bumps, the pink mustaches, the overly friendly drivers. Not my style.  The choice today was not made lightly. But it was revealing. I remember back when Google went public. There were countless and breathless debates about how there were no switching costs for anyone to move from using Google to using, say, Yahoo. No one was locked in. They could just as easily point to another search engine to find what they needed. Search was search, a commodity. Tho, at a high level that may be true (search being search) to the average user of Google at the time, Google was a Continue reading "My First Lyft Ride"