Woodrow
Levin

Ask most people what happens after they click "buy" on an online store and the answer is a shrug. A box shows up. Maybe it breaks. Maybe you lose the receipt. Woodrow Levin looked at that same shrug and saw a category worth building a company around.

Levin, who goes by Woody, is the founder and CEO of Extend, a San Francisco company that lets online merchants offer extended warranties and product protection through a few lines of code. He describes it in plain terms: "AppleCare for everything that's not an actual Apple product." The idea sounds simple. Turning it into a platform hundreds of brands rely on was not.

Extend launched its selling in 2019 and grew fast. In its first full year it sold roughly 300,000 protection plans, then set out to sell ten times that the following year. Behind the checkout buttons of companies like Peloton, Traeger Grills, iRobot, Harman/JBL and Backcountry sits Extend's quiet layer of coverage - a business most shoppers never notice by name.

What makes Levin unusual is not the current company so much as the road to it. He has built and sold before. BringIt, a virtual-currency casino and arcade he founded in 2009, was acquired by slot-machine giant International Game Technology in 2012. Estate Assist, a digital estate-planning service he started in 2014, was acquired by DocuSign in 2015, where Levin stayed on as head of growth. Between those chapters he even launched a multi-strategy crypto asset fund, 3.0 Capital, writing publicly about why he was chasing that market.

His background reads nothing like a template. Levin holds a law degree from Chicago-Kent College of Law and a business degree from the University of Wisconsin-Madison, and he was a Division I college hockey player before any of the startups. The common thread is not an industry. It is a willingness to start over, learn the next market, and ship again.

That resilience is something Levin talks about openly. He has appeared on Howard Lindzon's "Panic with Friends" podcast to discuss recovering from failure and the long climb toward building what he calls the "AppleCare of online retailers." In the startup world, setbacks are usually a prerequisite for anything durable, and Levin has lived that arc in public.

The turning point for Extend came in May 2021, when SoftBank's Vision Fund 2 led a $260 million Series C at a valuation above $1.6 billion. Returning backers Meritech, PayPal Ventures and GreatPoint Ventures joined, along with new investors including the insurer Nationwide. Levin's recollection of pitching SoftBank's Masayoshi Son was short and telling: "He immediately understood what we were doing."

Levin frames product protection as part of a bigger shift in how online stores operate. "Same day delivery, buy-now-pay-later, and other tools are now all part of that core e-commerce toolset," he has said. Protection, in his view, belongs in that same kit - a standard feature rather than an afterthought. And he wants to change how it feels. "We're focused on being transparent and fair with warranties," he told TechCrunch. "It's something they haven't seen before."

Beyond Extend, Levin serves on the board of directors of DraftKings, keeping a hand in the public markets while running a private, fast-growing company. The two roles reflect a founder who is comfortable operating and advising at once - building the after-checkout layer of the internet, one integration at a time.