Entrepreneur, Explorer, Angel.

Sometimes all at Once.

05TH January 2017

Entrepreneur - Leadership - Operative - Platforms - Portfolio - Timeless

Man plans. And God laughs.


Beats Traffic Mac 10:1

Beats Traffic Mac 10:1

[Public Excerpt] In the decade I have been dedicated to building Vaux as a platform, I’ve come to appreciate those words – man plans, god laughs- and more each day. I’ve seen over 5,000 opportunities in the past five years, and said no to 4,987 of them rather quickly. Those that stirred my heart and soul were ones I truly believed in, and I made great plans. The Deal Gods, of course, laughed at those plans, every time. It’s humbling. And that’s why I follow and preach the diversity program with angel investing; cherry picking the “best” only adds risk on top of risk. The way to get a good deal or two in this process is to start with ten… which are filtered from a few thousand. Ask me for a password to the five year Vaux performance document that sums this all up. I’m happy to share with good people.

Here’s a good example…

When Vaux was just getting founded, I saw a company named Traffic Mac present at Mike Segal’s New York Venture Conference at the Yale Club (where he’s still going strong). I had a visceral understanding of ad-tech (such as it was back then), and I chatted up the founders. We struck a deal, I added and raised a little early money, sat on the board, saw four CEO’s come (and three go), witnessed more than a few business models thrown out, a VC round, an acquisition, and then a lot of silence and patience… until Operative (much better name) sold to Sintec for “about $200M”. Angels in that cohort of Vaux investors made ~4.75x cash return on their entire Vaux-sponsored holdings- we’ll have it all sorted by tax time..

Sometimes, with luck and hard work, man (non-gender specific) can laugh too.

When the laughter subsided and the dust settled on my five-year run, I had a long look in the mirror and concluded that a) my process of funnel, filter, and hard work actually does deliver, b) there will be thousands more core economy companies that can be improved with some tech talent, and c) I love helping select founders hone their ideas and scale to exit. Operative, however is no longer on my list of updates. A very fond Adieu.

Ask me more about Angel investing for SFO’s here.

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