Advice Line with Tope Awotona of Calendly

Guy Raz welcomes back Tope Awotona, founder and CEO of Calendly, whose first appearance was in 2020. They revisit the origin story that Guy often cites: Tope sold alarm systems door to door, where a successful day might mean getting one customer out of 100 doors, then experimented with e-commerce and startups before building Calendly. Guy notes that Calendly now has more than 20 million users worldwide and a multibillion-dollar valuation. They also clarify Tope’s name: the pronunciation Guy used is an Americanized version chosen for efficiency, while the proper Nigerian pronunciation is different; Tope says he will respond as long as he knows someone is addressing him. Tope says his personal life has changed substantially since the earlier episode: his then-girlfriend is now his wife, and they have two children. Business has changed just as dramatically because of AI. Calendly recently repositioned itself from solely a scheduling platform toward a broader meeting-assistant platform. Its AI system, called “Cali,” can be introduced into an email thread and reply with Tope’s availability, while taking into account his preferences, the person he is meeting, and the context of the exchange. Tope says the classic Calendly scheduling experience remains central, but Cali adds the flexibility of a human assistant. He argues that building application software has become less expensive because tools such as Lovable and Replit let people describe requirements and create an initial product without millions of dollars. The hard part remains finding product-market fit; once a real problem is validated, capital and employees become easier to obtain. He also says competition gets harder as a company grows, which is why he now serves as both CEO and chief product officer and sees faster innovation as essential in 2026.

The first caller is Dominic from London, co-founder of Newlane, which makes a patented, safety-certified folding bicycle helmet. Its crown folds back into the helmet so the product becomes thin, “like a Frisbee,” and can fit into a bag. The idea came after Dominic’s co-founder was nearly hit while using a London bike-share bicycle without a helmet; Dominic had his own helmet hanging from a rucksack, prompting them to design something people could carry conveniently. The company spent six years refining the design and passing safety standards before launching in 2024. Dominic, formerly a BBC journalist and sports broadcaster, says Newlane made about $650,000 in its first year and is approaching $1 million in its second year, but profitability remains difficult because it manufactures in the UK rather than the Far East. Most sales are direct-to-consumer through Shopify and social-media advertising, though Newlane is preparing to sign a major UK and European distribution deal. The helmet sells for about £100, with an upgraded MIPS version priced around $176; retailers take roughly 40%, and distributors take another 35–40% of what remains. Dominic says paid media is increasingly expensive and distribution reduces margins. Tope asks who buys the product, and Dominic describes broad demand among London commuters and other practical, transport-oriented cyclists rather than sports cyclists. Guy says Newlane should emphasize that it is made in the UK, potentially turning local production into a premium selling point rather than immediately moving production overseas. Tope suggests two additional customer-acquisition angles: market to gift buyers, including spouses and parents who want a cyclist to wear a helmet, and position the helmet as one people will actually use because it avoids the behavioral resistance associated with bulky or inconvenient helmets. He also wonders whether the product’s unusual design can create word-of-mouth conversations, similar to the way Tope’s distinctive Defender attracts questions. Dominic says gifting already represented 20% of Newlane’s sales during the previous holiday season and agrees that both ideas deserve stronger emphasis. Guy calls the product “the Dyson of Bike Helmets,” while Tope jokingly suggests it could be attractive to investors.

Ivana, calling from Vancouver, founded Playfield, a brand of human-centric products for pet owners. Its main product, the Bailey Kit, is a sleek, modular dog-walking bag and treat pouch. It includes a built-in poop-bag dispenser, compartments for keys and cards, a leash attachment, and a hidden retractable water-bottle pocket that has helped the product go viral on social media. Ivana created it after repeatedly switching between a dog-walking bag and her everyday bag. Playfield launched in April 2024, generated just over $200,000 in its first full year, and sells primarily direct-to-consumer, with additional distribution through Chewy and independent pet boutiques. A nationwide retail launch is planned for October, but this year’s sales may be lower because Ivana is eight months pregnant with her first child. As a solo founder, Ivana still handles product design, customer service, logistics, and manufacturer relationships. She has a fulfillment center in Arizona, recently hired a social-media agency, and brought on a freelancer for the ambassador program, but almost everything still depends on her. She asks how to build systems that allow the company to operate while she gives birth and cares for the baby. Guy tells her that parenthood has been the most meaningful part of his life and cites Kim Becker-Ella of Bogg Bags, who paused her company for two years after losing $30,000–$40,000 through a manufacturing disaster, only to restart when customers began asking where the bags had gone. His point is that pausing for three or six months does not necessarily destroy a brand. Tope asks Ivana to identify the single most important priority; she chooses keeping the lights on because the retail launch is already in motion. Tope recommends hiring for operational excellence and day-to-day execution. He recalls that Calendly first hired an engineer and then a marketing employee, but when demand spread virally, marketing was not the bottleneck; customer success was, so the marketing hire pivoted. Ivana recognizes that operations have prevented her from focusing on product, brand building, and strategic partnerships. Both hosts tell her to give herself permission to slow growth, preserve the business, and return to ambitious expansion when her home and work systems are ready.

Danny, founder of The Nail Room in Greer, South Carolina, wants to end the trade-off between healthy natural nails and a beautiful, durable manicure. Instead of gluing on artificial tips and repeatedly soaking them off with acetone, her salon uses Builder Gel, a thick clear gel that strengthens the natural nail. When customers return, technicians remove the color, fill in new growth, and repaint rather than stripping the entire application. Danny opened the salon four months earlier after first learning the technique and doing nails from a room in her grandmother’s house. She had been a stay-at-home mother of three, had tried several home businesses, and was encouraged by her husband to attend nail school. Demand quickly forced her to close her books at the home studio and consider a larger salon. The Nail Room has six technicians, is extremely booked, and has already reached $100,000 in sales. Danny personally sees only six clients a week so she can spend time with her children, while a manager and assistant help run the business. Her ambition is to build a national concept comparable to Drybar, but she is unsure whether expansion is right for her family and marriage. Guy points to Drybar founder Alli Webb and encourages Danny to think beyond the Builder Gel technique, which competitors can copy. He argues that the differentiator should be the customer experience: the way clients feel while they are there, potentially through champagne, espresso, child care, or other memorable services. Danny says The Nail Room already offers seasonal craft lattes, and customers tell her they look forward to them. Tope agrees that experience is the crucial advantage because a technique can be replicated but a feeling is harder to copy. He also advises maximizing revenue from the existing location before opening several stores. Guy suggests first expanding within the local market, perhaps to downtown Greenville, then considering Charlotte, and recommends operating the second location for a year before adding a third. Tope emphasizes that expansion is a personal choice involving sacrifices, not merely a business calculation.

Justin Kittrick of Boston runs iSlide, a premium customized footwear company selling slide sandals, slippers, and socks. The slides can be customized one pair at a time with logos or designs, including NBA, MLB, NHL, college, local team, corporate, and brand marks. iSlide has been operating for 13 years and generates about $5.5 million in annual sales. It sells through four main channels: its own e-commerce site, traditional wholesale to retailers and other e-commerce companies, bulk orders directly to teams and organizations, and drop-shipping partnerships in which companies such as Fanatics display many designs while iSlide prints and ships each order. Justin says the company has grown in 12 of its 13 years but has focused on profit in recent years. Now he wants to return to higher growth and reach $10 million, but is reluctant to abandon channels because different channels performed differently during COVID. E-commerce and drop shipping surged when wholesale and brick-and-mortar were weak, while other channels recovered later. Tope recommends using an Apple-like model: maintain the fewest products and activities capable of generating the most revenue, and seek leverage through focus. He asks which parts have the strongest repeat-order, revenue, and personal-interest metrics. Justin says he especially likes licensed products and direct team sales, because teams can now offer athletes a complete branded look from head to toe rather than only branded hats and jerseys. Tope argues that moving from $5 million to $10 million will probably require trade-offs and suggests acting as though the business has one overriding goal. Guy adds that iSlide need not eliminate every channel, but should pursue larger, more efficient partnerships rather than many small orders. Justin says the company is looking for more partners with consistent daily sales and is exploring AI to help sales representatives conduct more outreach and manage communications. Tope agrees that AI could allow the existing sales team to do substantially more, but the core recommendation is to place roughly 80% of time and effort behind one or two strongest channels while deprioritizing the rest, rather than allowing diversification to prevent meaningful scale.

Before Tope leaves, Guy asks what advice he would give his younger self—the founder who emptied his savings and 401(k), borrowed at high interest, maxed out credit cards, and worked with a developer in Ukraine to build Calendly. Tope’s answer is that he now builds a business around a customer rather than around a product. He says first-time entrepreneurs often think product-first, but his current approach begins with understanding and serving a particular customer. Once a company has acquired that customer, served them well, and created a brand for them, it is easier to expand with the same customer type than to branch immediately into entirely different customers. Tope says a successful company eventually needs both customer expansion and broader reach, but customer-first thinking is what now guides Calendly’s product expansion. The episode closes with Guy thanking Tope and reminding listeners to hear the original 2020 Calendly episode. A clip from that episode recounts Tope’s early financial commitment: building the prototype was expected to cost slightly more than $200,000, so he emptied his 401(k), used his savings, borrowed through LendingClub at a very high interest rate, and maxed out his credit cards even though the product did not yet have a name. Guy also announces that this is the final Advice Line episode. The show’s closing credits thank the callers and returning guests, and Guy directs listeners to his free newsletter at guyraz.com and Substack. The transcript also includes a promotional break for Phoebe Judge’s Criminal live tour, which is separate from the business advice conversation.