Gaingels seeks to invest in the venture backed companies that embrace diversity.

Venture investor in 150+ startups. Sector agnostic but with an eye towards disruption.

In this role I parented -- with my wife -- our 2 boys, born in January 2012 and October 2013. Responsibilities included changing diapers, mashing carrots, changing diapers, singing songs, changing diapers, reading books changing diapers and reading more books. Successfully oversaw and photo-documented transition from crawling to walking. Managed library transition from board books to picture books and ultimately, chapter books. Educated both children as to importance of superheroes and kindness. Trained all direct reports to full Lego self-sufficiency. Personal development included mastering the art of speedily locating Gold Bug on every page of Richard Scarry's _Cars and Trucks and Things That Go_. While this was a full time endeavor from January 2012 to January 2019, now that my direct reports have been trained to a level of semi-self-sufficiency I've reallocated my daytime focus to working at Gaingels (see above).

One of the most fattening years of my professional life.

Created as a testing ground for a variety of passive income ideas and technologies. Interestingly, I maximized revenue by making the site look as outdated and 'homemade' as possible (hello, GeoCities!). Which is convenient, since my business partner passed away and the site is literally frozen in time. And yet... the combination of search traffic and Amazon's affiliate program continue to deliver a meaningful income. Go figure.(Update: sadly, due to technical issues the site went down on November 3, 2023. With enough effort it could be revived but without my business partner to guide the process it would be too laborious to bother. It was a good 15 year run that generated a lovely side hustle of solid cash flow.)

When I started at Meetup soon after its founding, individual Meetups had no one in charge. We directed interested parties to meet at a certain time and place... but with no one in charge. As a result, Meetups failed more often than not. Our founder, Scott Heiferman, recognized this flaw and directed us to rebuild Meetup so that every group had a self-appointed Organizer. I led the product through this massive and extremely successful transition. Next, in search of a sustainable business model, we told Meetup Organizers they would have to pay a monthly fee to use our platform. This change was... not popular. But it was the right call. I also led the product through this evolution. With two major successes under my belt, and the staff having grown from 8 to 58, it was time for me to move on.

I'd tell you, but then I'd have to... well, you know. ;-)

The other incredibly fattening year of my professional life.

I designed and executed tests for the billing systems of BellSouth... I developed a customized budgeting system for the EPA's SuperFund program in a language just one step up from COBOL... I was in hell. Then, thank god, a guy sitting across the hall in October 1994 showed me this new thing called the internet. Thanks, Jeff Gerber, wherever you are!