David Sobie
Venture Advisor
David Sobie has built businesses in enterprise software, logistics, supply chain, and e-commerce at top-tier tech companies like eBay and FreeMarkets, that had a record-breaking IPO in 1999. “I’ve had a lot of opportunities as an advisor and a board member, and I tend to be pretty hands-on,” he says. As an AI Fund Venture Advisor, he wants entrepreneurs to know that “I will listen, but I’m going to tell you what I think.”
Almost 10 years ago, he planted his own flag as a founder: “It was a life goal and a career goal to be one,” starting from scratch. He was already an online retail veteran, serving as the head of marketing and business development for flash-sale site HauteLook through its acquisition by Nordstrom. Marrying HauteLook’s online customer base with Nordstrom Rack’s physical stores, he realized the opportunity in, of all things, the reverse logistics of returns. “It’s a little bit counterintuitive,” David explains. “If you make returns easy, people will shop more with you.” Why not let people take products bought online back to physical stores, without printing labels or packing boxes?
The insights that came from building the “Return to Rack” program for HauteLook are what led to founding Happy Returns. The company was founded in 2015 and ran as a venture-funded firm for six years with David as CEO. PayPal, looking for ways to improve the consumer experience, made a strategic investment in Happy Returns in 2019 and then bought the company outright in 2021.
“The single biggest challenge for founders is staying focused. The only thing that really matters is that next milestone, it's the only thing that matters.”
Happy Returns’ exit to PayPal wasn’t, however, the end of the story. Happy Returns’ growth accelerated, even as the parent payments pioneer began pivoting back toward its core business. This kicked off a yearlong process to have Happy Returns in the right place for continued success. In late 2023, PayPal divested Happy Returns to UPS.
“Having been through acquisitions twice now with Happy Returns when we sold to PayPal and then going from PayPal to UPS, what’s interesting is you hear yourself giving feedback and reacting to things,” he says. “You’ve actually learned a whole bunch along the way. You can’t read a book on it. You can’t necessarily know unless you’ve been through it.”
A resident of Los Angeles, David holds a bachelor’s degree and an MBA from the Tusk School of Business, both at Dartmouth College.
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