David Olk Email Address

Co-Founder and Board Member

Born out of frustration with the traditional cash register business, ShopKeep's iPad-based point of sale system was designed by a retailer with a noble aim: to rescue independent business owners from the nightmare of archaic POS (a.k.a. Pieces Of S**t), and replace it with something beautiful, simple and affordable. It turned out that by doing this, we were giving our fellow merchants a fighting chance against the big guys. So we kept doing it.

Starting a company is the hardest thing anyone can ever do. Primarily because you have to deal with a ton of useless hanger ons with terrible advice and VCs who can be the absolute worst: self important arrogant bros pumped out of ivy league’s schools that normally have opinions about things they know nothing about (ie, your brainchild or building a company themselves — most have never raised capital nor can operate themselves out of a paper bag). So after navigating this difficult journey a few times ourselves, we now spend our time funding early stage companies and helping them grow by telling founders the truth and providing our actual experience and networks (often from failing forward). As your company grows, among other things, we then connect you with our later stage VC friends who do not suck and will actually “be helpful”. Prior to this, co-founded ShopKeep (which exited ~$1.1b) and ran the business day to day while raising over $100m and helping to build the company into one of the larger SaaS businesses in the US. Before ShopKeep, I was Director of Mergers and Acquisitions of IAC, Barry Diller's publicly traded holding company of numerous consumer facing technology brands (Tinder, Match, Vimeo, etc). Also co-founded Voray (with Mark Gerson and Gavin Myers), a platform to help people build more authentic networks and grow their careers. We did this by ignoring the needs of field marketers who have no idea how to build community because they are incorrectly and only obsessed with demand gen (PSA: never let a marketer own community). Joined the Board of Directors for Kickstarter after advising the team and helping raise early funding rounds which built the foundation for an amazing mission. Spent the first many years of my career with PwC’s Mergers and Acquisitions team where we worked with heavily capitalized private investors and large strategics who hired us to perform commercial and financial due diligence on businesses they were buying. I have an accounting degree from Tulane and an MBA from Columbia University. I love to dive, am not as great a skier as my wife, and have run a few Triathlons as a member of the Michael J Fox Foundation's Team Fox ("run" being really generous). A Certified Public Accountant, born in Brooklyn, I no longer live in the city with my wife and two sons (FML suburbia), but regularly visit the borough that's thorough to consume large amounts of corner squares at L&Bs Spumoni Gardens.