Tope Awotona
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How I Built This with Guy Raz · Advice Line with Tope Awotona of Calendly
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Should a Full Nail Salon Open a Second Location?
Tope Awotona tells Danny, who owns The Nail Room, not to open a second location yet. The salon is already full, so the next move is a bigger space and more revenue from each store. Maximize that before thinking about a second store.
How large the company should become is a personal decision. Growth has a cost. Awotona does not see his friends as often as he would like, and he is not always a great cousin or brother. The financial rewards of Calendly have also let him help many people, which he is proud of. Once the first store is running well, stay local for a year, starting in downtown Greenville, and only later consider a farther city such as Charlotte.
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Why Did Calendly's Marketer Become Customer Success?
Tope Awotona's first employee at Calendly was an engineer. The next hire was a marketer, brought in to grow the top line and increase demand. Virality in the product took off so much that marketing was not the bottleneck. Serving the customers already coming in was, so that marketer quickly became a customer success person.
A founder can keep a list of functions to scale next. What shows up instead is something clearly broken, and that break makes the next thing to automate obvious. For Ivana, who makes Playfield's dog-walking gear and is about to have her first child, that broken piece is operations. Automating it would free her to spend her energy on the product and on revenue.
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Who Should a Bike Helmet Brand Market to?
Tope Awotona tells Dominic, who makes the Newlane folding bike helmet, to market to the person who gets the rider to wear a helmet, not only to the cyclist. Awotona bought his own helmet because his wife insisted, then wore it so his kids would wear theirs. A gift path on the site would let that buyer purchase the helmet for someone else.
The harder objection may be behavior. People buy helmets and do not use them, or they never buy one because a helmet is a pain. The pitch can move up a level: this is the helmet a person will actually use. Dominic says that in the last gifting season, 20% of sales were bought by one person for another.
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Should a Hardware Startup Manufacture at Home or Overseas?
Guy Raz tells Dominic, who makes the Newlane folding bike helmet in the United Kingdom, to pick one path: push the made-in-the-UK label as a premium, or manufacture abroad and cut costs. The website does not make that origin obvious. The origin is a premium on a high-quality product, and the manufacturers are probably highly skilled, so for now Raz would lean into the label.
Dominic says gross margins are healthy. The helmet sells for £100, with a higher-priced version. A retailer takes 40%, and a distributor takes about 35% to 40% of what is left. Moving the tools to a factory in the Far East would be expensive, and the geopolitical picture makes that move harder. The MIPS version adds a s
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What Is Calendly's AI Assistant Kali?
Tope Awotona says Calendly's AI assistant is Kali. The company has repositioned from a scheduling platform to a meeting assistant platform. Online scheduling is still a large part of the business and will stay that way for a long time, because it serves a real purpose. Kali sits on top of that, with several skills, and one of them is scheduling.
A person can add Kali to an email thread. If someone writes to set up coffee, Kali replies like a human assistant with that person's availability. It knows the preferences, who the meeting is with, and which times to offer. The classic scheduling product remains. The new layer is an AI system meant to be as flexible as a person.
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Why Build Calendly Around the Customer?
Tope Awotona says the lesson 13 years into Calendly is to build a business around a customer and not a product, and he calls that shift maybe the biggest thing he thinks about differently 13 years on. First-time entrepreneurs who are still learning have a tendency to think product first. Customer first is the view now, and it is what guides the company while the product expands.
Once a customer is acquired, served really well, and given a brand, it is a lot easier to expand with that existing customer type than it is to go try to expand the different types of customers served. Ultimately, over time, a company needs to do both.
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How Should a Small Brand Pick Which Sales Channel to Focus on?
Tope Awotona says a small brand should pick one or two sales channels and put 80% of the founder's time there, while still keeping some diversification. The chief executive should spend no time on the channels that are set aside.
Going from $5 million to $10 million in revenue will probably force trade-offs. What carried a business from zero to one differs from what carried it from one to $5 million. Awotona quotes Naval Ravikant, whom he calls a philosopher from Angel's List: a happy man has a million wishes, but a dying man has one wish, which is to live. Justin's company is not dying. It is doing well and has been around for 13 years. Treating the move from five to $10 million as that on
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What Is Builder Gel at the Nail Room?
Danny, who owns The Nail Room in Greer, South Carolina, says builder gel is a clear, thick gel applied to the natural nail so the nail gets stronger. Color goes on over the gel. When a client comes back, the color comes off, the new growth is filled in, and the nails are painted again. The gel never has to be soaked off.
Most salons glue on artificial tips, then soak those tips off in acetone, which keeps thinning and damaging the nail. The Nail Room opened four months ago, and gross sales just hit $100,000. Danny had been a stay-at-home mom for five years and has three little ones. She did her own nails at home, went to nail school after her husband encouraged her, and worked out of a room
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Should a Founder Pause Growth for a New Baby?
Guy Raz tells Ivana, founder of Playfield, that an ambitious founder may need to put the brakes on for a couple of months. Her baby is due in the quarter before Christmas, so that Christmas quarter might not be the one she wants, and next year is the time to ramp up once home systems are in place. The business can still succeed because she is motivated to make it grow.
Tope Awotona says keeping the business afloat is the most important thing. If the business stays afloat, there is another day to fight. The person to hire should bring operational excellence, because a lot happens day to day and the trains need to keep running.
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Can Founders Ship Software Without Much Money?
Tope Awotona says founders can still launch application software without a lot of money. A frontier lab needs billions of dollars. Application software is a different category. The barrier to building software and technology has never been lower because of AI.
Anyone who can write and articulate requirements can pick tools like Lovable and Replit and create a product. The first version will not scale to millions of users on day one. It can still get out without a lot of money. The most critical step is product market fit: creating something that solves a real problem for people. Once that validation is in hand, capital to scale the product and recruit people becomes available.