Tope Awotona's Advice for Bootstrapped Founders

Tope Awotona built Calendly into a service with more than twenty million users worldwide (01:13), largely without the kind of venture capital that usually fuels a unicorn. So it is worth noticing what he says about the business now, more than a decade later: it has not gotten easier. "The longer you're in business, it actually gets harder," he tells host Guy Raz, because a startup begins as the challenger with everything to gain, and ends up the incumbent with everything to defend (06:37). His response was not to coast. Last month Calendly repositioned itself from a scheduling tool into a meeting assistant platform, built around an AI feature named Callie that can read an email thread and respond with his availability like a human assistant would (03:27). He also added a new title for himself: chief product officer, on top of CEO, because in his telling, 2026 is too competitive a year for a founder to step back from the product (06:59).

That tension, between what got a business started and what keeps it alive, runs through the whole episode. Awotona spends the hour fielding calls from four founders at very different stages, and his advice keeps circling back to the same idea: figure out what is actually broken, not what you assume is broken, and fix that first.

The first caller, Dom Cotton, co-founded Newlane, a UK-made folding bike helmet that clips at the back and folds over like a Frisbee (08:03). The company did $650,000 in revenue in its first year and is approaching $1 million in its second (09:23), but margins are tight: retailers take 40 percent, and distributors take another 35 to 40 percent of what is left (11:48). Awotona's advice was not about cutting costs. He pointed out that Calendly grew without a marketing budget because the product itself created virality: every time someone used it, they introduced someone else to it. He asked Cotton whether a folded helmet could do the same thing in public.

"I can't drive that car without people asking me about it...Is there an opportunity to think about when I use this product, when it's folded, it creates this conversation." — Tope Awotona [16:14]

Cotton had already stumbled onto a version of this: 20 percent of Newlane's sales last gifting season came from people buying helmets for someone else, usually a spouse or parent worried about a cyclist's safety (15:34). Awotona's suggestion was to build that behavior into the product itself, a gift flow aimed at the person doing the worrying rather than the person riding the bike.

Before any of this, Awotona made a broader claim that is worth sitting with if a listener has no money and a half-built idea. "The barrier to building software and building technology has never been lower because of AI," he said, pointing to tools like Lovable and Replit that let anyone who can describe a problem produce a working first version of a product (05:15). He is careful to put a ceiling on the claim. A tool like this will not scale to millions of users on day one. But it can get a founder to product-market fit, and once that exists, he argues, capital tends to follow.

Keeping the Business Alive While You Are Not There

The second call came from Ivana Tay, founder of Playfield, a Vancouver company making dog-walking bags with a retractable water-bottle pocket that has gone viral on social media. The business did just over $200,000 in sales in its first full year. Tay is a solo founder, eight months pregnant, and calling to ask what systems she needs before she gives birth a month from now, during the start of her busiest quarter.

Awotona's first move was to narrow the question. He asked her to pick, if she had to choose only one priority while she was out: keeping the lights on, or nailing a major retail launch already in motion. She chose keeping the lights on. That answer, he said, pointed to the hire she needed: not a marketing person, but someone for operational excellence, someone to keep the day-to-day trains running (28:54). He drew a direct comparison to his own history at Calendly, where his second hire was a marketing person, until the product's own virality made customer service, not demand, the real bottleneck.

"It's much easier to find somebody who can make the operations run smooth than it is to find somebody who can think about brand, who can think about product." — Tope Awotona [30:59]

Raz offered Tay a second data point: Bog Bags, a beach-bag company founded by Kim Bacarella, lost tens of thousands of dollars to a manufacturing disaster, shut down entirely for two years, and came back to build a brand now doing roughly $250 million a year in sales (24:10). The point was not that every pause ends in a quarter-billion-dollar business. It was that a business put on hold does not disappear, and a founder facing a genuine life event does not have to choose between the business and the moment.

The Business That Cannot Be Copied

The most useful reframe of the hour came during the third call, from Dani Sarchell, who opened a boutique nail salon called The Nail Room in Greer, South Carolina, four months before the call and has already crossed $100,000 in gross sales (34:49). Her technique, a gel method that avoids the chemical damage of soaking off artificial tips, is good. It is also, Awotona pointed out, replicable. Other salons use the same product. What cannot be copied is how a client feels sitting in the chair.

Raz told her to think less about the manicure and more about the experience around it: a latte that changes with the season, a place for a kid to be watched, the kind of small luxury that made Alli Webb's Drybar a national blow-dry chain rather than just a good haircut. Sarchell, it turned out, already offers craft lattes, and clients tell her they look forward to the drink all day. On expansion, his advice was sequential rather than ambitious: get a bigger location and maximize revenue per store before opening a second one, then stay local, city by city, before going regional (42:25).

The final caller, Justin Kittredge, runs iSlide, a thirteen-year-old customized footwear company doing about $5.5 million a year across four channels: direct-to-consumer e-commerce, wholesale, bulk team orders, and drop-shipping through retailers like Fanatics (46:37). He wants to reach $10 million but is reluctant to cut any channel, since the mix of channels is what kept the business alive through COVID, when e-commerce spiked and wholesale collapsed, then reversed the following year. Awotona's answer drew on what he called the Apple model: the fewest products generating the most revenue (48:14). He quoted investor Naval Ravikant to make the point about focus.

"A happy man has a million wishes, but a dying man has one wish." — Tope Awotona, quoting Naval Ravikant [50:43]

He was not telling Kittredge to abandon diversification. He was suggesting a founder can keep four channels and still bet 80 percent of time and effort on the one or two that show the strongest repeat orders, rather than splitting attention evenly across all of them.

By the end of the hour, Raz asked Awotona what he would tell the version of himself who was still financing Calendly on a maxed-out 401(k) and a loan from LendingClub. His answer tied the whole episode together: "I think what I've learned 13 years in is you build a business around a customer and not a product" (53:31). First-time founders tend to fall in love with what they are making. The founders who last, in his account, fall in love with who they are making it for, because a customer, once well served, is easier to expand around than a product chasing a new type of buyer every year.