“Finishing The Work”

These days, it’s easy to start a company — and it’s hard to build one. And, we know 90% of new ventures don’t ultimately work out. We all focus on the growth and momentum, the outliers and the high-fliers, and for good reason — those outcomes end up “covering” the rest of the table. When things don’t work out, investors know it’s coming, but no one can say anything. It’s not our story to tell. And despite what we read in Medium post-mortems, there is not a uniformity of action and integrity when the founders of a failed newco wind things down. A dream passes away and across one’s mind while one signs paperwork and answers the same questions over and over again.

I wanted to highlight that, in these moments, not everyone acts out the finale of the play. Sometimes, folks can’t bear to go through the motions. In Continue reading "“Finishing The Work”"

The Story Behind My Investment In IronClad

Sometimes, picking a company to invest in is just easy. The hard part is getting in. About two years ago now, I met Jason Boehmig of IronClad during YC’s Summer 2015 batch (before Demo Day). One of my founders who was in YC singled out Jason as outstanding. Jason’s pitch was exactly what I love to hear, paraphrased: “I was an attorney (at a prestigious Valley fund). I taught myself to code. I quit my job. I founded this company to bring systems intelligence to the legal department of enterprise companies and beyond.” I had to pitch Jason to let me in and also to make a gracious consideration for me. I started to help Jason with his round immediately and got working some customers. Jason put me to work right up front but he was easy to work with. In fact, I would say he’s one of the Continue reading "The Story Behind My Investment In IronClad"

The Story Behind My Investment In WorkRamp

About a year ago, a few ex-Box friends mentioned one of their colleagues “Ted” was starting a new company. That was enough for me to swing into action. I googled around and targeted “Ted Blosser,” found we had a few close friends in common, and a few email requests later, found myself sitting in his makeshift office near Facebook HQ. In the first meeting, it was clear that Ted was driven, had a vision for the product he wanted to build, and took a sober approach to testing and refining his hypotheses as he built. We talked about general investment strategies, not related to his company, “WorkRamp“, and I liked Ted so much that I offered to start making customer introductions for the product. Generally, I like this way of getting to know a founder and product. I prefer to make introductions in advance of investing Continue reading "The Story Behind My Investment In WorkRamp"

The Story Behind My Investment In WorkRamp

About a year ago, a few ex-Box friends mentioned one of their colleagues “Ted” was starting a new company. That was enough for me to swing into action. I googled around and targeted “Ted Blosser,” found we had a few close friends in common, and a few email requests later, found myself sitting in his makeshift office near Facebook HQ. In the first meeting, it was clear that Ted was driven, had a vision for the product he wanted to build, and took a sober approach to testing and refining his hypotheses as he built. We talked about general investment strategies, not related to his company, “WorkRamp“, and I liked Ted so much that I offered to start making customer introductions for the product. Generally, I like this way of getting to know a founder and product. I prefer to make introductions in advance of investing Continue reading "The Story Behind My Investment In WorkRamp"

The Story Behind My Investment In Pillow

As I began to raise my first fund back in early 2013, I reached out to my friend Satya to see if he’d like to make a small LP investment. We met up in The Mission and I walked him through what I was trying, and he said he unfortunately couldn’t and it was related to something new he was doing with his old friend. He couldn’t participate and share more details about his new thing. It was too bad, but I understood, and was now curious what new company he’d start so I could invest! Fast-forward a few weeks, and he sent me a note right before the news about Homebrew hit. “Ah….so that’s why!” Always looking out for those around him, I began investing and Satya was kind enough to share a new deal he was working on with Homebrew. It was there that I mean Continue reading "The Story Behind My Investment In Pillow"

The Story Behind My Investment In Pillow

As I began to raise my first fund back in early 2013, I reached out to my friend Satya to see if he’d like to make a small LP investment. We met up in The Mission and I walked him through what I was trying, and he said he unfortunately couldn’t and it was related to something new he was doing with his old friend. He couldn’t participate and share more details about his new thing. It was too bad, but I understood, and was now curious what new company he’d start so I could invest! Fast-forward a few weeks, and he sent me a note right before the news about Homebrew hit. “Ah….so that’s why!” Always looking out for those around him, I began investing and Satya was kind enough to share a new deal he was working on with Homebrew. It was there that I mean Continue reading "The Story Behind My Investment In Pillow"

The Story Behind My Investment In Skysafe

Back in Q1 of 2016, when the technology sector went through a sizable (but apparently now forgotten) correction fueled by sharp hits to public tech stocks, I was happily investing into the very early-stage ecosystem, and in particular, deeper technology opportunities. It was at that time when my friend Julian introduced me to Grant Jordan, a co-founder of Skysafe. I looked up Grant’s background and read up on his work. I was 90% convinced to invest in him after a bit of online sleuthing. In the first few minutes of meeting Grant, the decision was made. Grant’s industrial expertise was off-the-charts and focused in such a way that his approach to Skysafe became, literally, a no-brainer decision. Grant had grown up as a computer tinkerer, to put it mildly, studied CS, security systems, and EE at MIT, went on to work as a core engineer at Wright Patterson Air Force Continue reading "The Story Behind My Investment In Skysafe"