How I Built This: 10 Years of Top Lessons

Three in the morning has a reputation among people who build things. Jamie Siminoff, who founded the doorbell camera company Ring, says a particular kind of panic shows up right on the dot: sweaty, racing, certain that everything is about to collapse (09:29). He is not alone. That hour, and the fear that comes with it, is one of the threads running through the tenth anniversary episode of How I Built This, in which host Guy Raz invited Siminoff back to listen through a decade of interviews and talk about what stuck.

The numbers behind that decade make an argument of their own. Raz has interviewed more than 600 founders since the show began (07:23), people who built companies as different as Airbnb, Dropbox, Chobani, and Kinko's. What the anniversary episode suggests, mostly by example, is that fear, failure, and rejection are not detours from a successful founding story. They are the story.

Siminoff makes this explicit early on. "I think the most important thing in that clip, which I still think is so true, is we put ourselves out of business. It's more us than anyone else," he says, reflecting on his own first appearance on the show (08:24). Fear, in his account, is not an obstacle to manage away. It is raw material. Used well, it pushes a founder forward. Used badly, it seizes a person up entirely, the way panic does at 3 a.m.

Scary Versus Dangerous

The clearest framework in the episode comes from Jim Koch, who left a stable, well paid job at Boston Consulting Group to found what became Boston Beer Company, maker of Sam Adams. Koch draws a line between things that are scary and things that are dangerous, using an analogy from his years teaching at the outdoor program Outward Bound (16:55).

"Staying at BCG was dangerous but not scary, and the risk was continuing to do something that didn't make me happy and getting to 65 and looking back and go, 'Oh my God, I wasted my life.'"

Jim Koch, founder of Boston Beer Company, speaking at [18:15].

Rappelling off a cliff feels terrifying, Koch says, but a rope rated to hold a car makes it safe. That is scary but not dangerous. Walking across a sunlit snow field on a calm afternoon feels like nothing at all, but melting snow can turn to ice, and ice can trigger an avalanche. That is dangerous but not scary (17:12). The unhappy, secure job is the snow field. It feels fine right up until it is not.

Several other stories map onto this test. Sal Khan left a lucrative finance career to found the free online education nonprofit Khan Academy, over his mother's objections (20:35). Hamdi Ulukaya, an immigrant from Turkey with no English, borrowed against a shuttered yogurt factory in upstate New York to build what became Chobani (53:33). None of these choices were safe in the ordinary sense. But staying put carried its own cost, one that simply took longer to arrive.

That cost shows up again in the obsessive, often embarrassing work of early prototyping. Justin Gold, founder of Justin's Nut Butters, made 40 different jars of peanut butter and jelly combinations in a food processor before he had a product he liked (22:55). The fashion designer Eileen Fisher showed up to her first trade show with four garments, no company name beyond her own, and so little composure that she could not answer buyers' questions (24:50). Siminoff built his own first trade show booth for Ring out of taped together cardboard boxes in the worst corner of a Las Vegas convention hall (25:40). The garage, in other words, is less a location than a permission slip, a low stakes space where a bad idea can fail quietly before it has to work in public (11:41).

Scrappiness does not end once a product exists. Sara Blakely, who founded the shapewear brand Spanx, got a buyer at Neiman Marcus to place an order after showing her a before and after demonstration in a store bathroom. But the order was not the finish line.

"Oh my gosh, that is the biggest mistake that entrepreneurs make. That is when the work begins."

Sara Blakely, founder of Spanx, speaking at [35:36].

Blakely paid friends, including people she had not spoken to since fourth grade, to buy Spanx off the shelf so the product would look like it was moving (35:45). Tom Rienks, founder of the sunscreen brand Sun Bum, ran his company out of Grand Rapids, Michigan, but routed customer calls through a Cocoa Beach, Florida post office box, instructing staff never to lie about the weather, only to call it "unbelievable" no matter which direction that cut (38:08). Mike Cesario built the water brand Liquid Death around a joke: cans that looked like cheap beer, designed to get shared on social media rather than simply bought (39:36). None of this is complicated. Most of it is just a willingness to look a little ridiculous in public.

The Fundraising Gauntlet

If there is a villain in this episode, it is the fundraising process, and the lesson is that rejection there means less than it feels like it means. Airbnb's founders pitched 20 investors in Silicon Valley in 2008 after they already had traction and press. Zero invested (45:47). Whole Foods co-founder John Mackey was turned down by a venture capitalist who told him he was "just a bunch of hippies" selling food to other hippies, missing that baby boomers were about to become the biggest consumer market in American history (45:08). Cathy Hughes, who built the radio network that became Urban One, was rejected by 32 banks while trying to raise $1 million to buy a station in the late 1970s. The 33rd banker said yes (48:20). Hughes kept pitching even after the yes, until the banker interrupted her: "Please, don't sell past the close" (48:35). The broader point, echoed by both Raz and Siminoff, is that founders who raise money easily are sometimes building something unoriginal, while the hardest pitches can belong to the ideas worth funding, because real invention rarely looks obvious to an investor meeting it for the first time (47:24).

Money does not stop being a problem once it arrives, either. The furniture brand Serena and Lily took on growth focused venture capital, then later brought in a private equity investor focused on profitability, because the company had become what Serena and Lily co-founder Lily Kanter calls a "cash incinerator," a term for a physical, inventory heavy business that burns cash fast while it scales (56:11). Raz's broader point is blunt: a small business clearing $4 million a year in sales while the founders take home $1 million in profit can be a better outcome than a much larger company that has never turned a profit (57:34).

Even a successful sale can come at a cost. Bobbi Brown stayed at her cosmetics company for 25 years after selling it to Estée Lauder, and found the final years hard as the corporation grew around her and she lost control over hiring and daily decisions (60:30). Paul Orfalea, who founded Kinko's, takes the opposite position almost forcefully.

"I never loved my business. I could enjoy it, but man, your business is an instrument to make you happy, and you own it. It doesn't own you."

Paul Orfalea, founder of Kinko's, speaking at [67:38].

Siminoff pushes back on this in real time, admitting that Ring is part of his identity in a way he is not sure is healthy (68:07). That disagreement, left unresolved, is more honest than a tidy conclusion would have been.

The episode closes on the question Raz asks nearly every guest: was it luck or skill? Zumiez founder Tom Campion credits discipline and hard work, dismissing luck almost entirely (70:02). Shopify founder Tobi Lütke credits timing almost entirely, saying his company needed the 2008 financial crisis to create the right conditions and could not have started even two years later (71:13). Dropbox founder Drew Houston splits the difference with a surfing metaphor: luck decides which wave shows up, skill decides whether a person stays on it (73:04). Raz, asked the same question about his own show, says it is mostly work, plus the luck of starting a podcast in 2013, before the format got crowded (75:40). Ten years and 600 conversations later, that answer sounds less like modesty and more like the show's actual thesis: nobody gets to pick their wave, but everyone gets to decide whether they paddle.