Freestyle.vc

“Those of us that have been entrepreneurs know that this is a cakewalk compared to that of being an entrepreneur. That being an entrepreneur is so intense it's amazing, but it is intense, And so as a VC, the highs are not as high, but also the lows are not as l…”

“So I know if I wrote a check today, I want to make sure that that team has enough cash to make it at least 18 months, and ideally two years.”

“I'll probably lead, call it four or five investments a year”

“The history of replacing a founder at the siege stage with a new CEO, that historical performance of that experience is so poor that I can't imagine, it would have to be almost a fraud situation Situation for me to do that versus kind of replacing a founder wh…”

“I wouldn't tell the team until you have a deal.”

“I can make a short-term decision that would actually maximize shareholder value for that company, but I could Destroy my reputation doing it, and so then that, so if I look at my ultimate duty is to my LPs, so short-sightedly I can say, well, you know, I'm gon…”

“One percent of the time, I find myself out of alignment with an entrepreneur at some point in the process.”

“So last, last year we had a company go through the M&A process and we were surprised by it because we were on the page of this company being a billion dollar company. We really were. And all the investors were. And the founder had a rough experience raising ca…”