Calendly: Tope Awotona

Calendly: Tope Awotona

After emigrating from Nigeria to the US to attend college, Tope Awotona worked as a door-to-door salesman and eventually set out to become a tech entrepreneur. He launched a series of e-commerce businesses that quickly fizzled when he realized he had no passion for them. But then he landed on an idea he was truly excited about: designing software that would minimize the hassle and headache of scheduling meetings. In 2013, he cashed in his 401k and went into debt to build Calendly, a scheduling service expected to make about $60 million this year.

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Episoder(809)

Advice Line with Bill Creelman of Spindrift

Advice Line with Bill Creelman of Spindrift

Bill Creelman, CEO and founder of Spindrift, joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Bill and Guy talk about the importance of solving one problem...

27 Nov 202548min

Hydro Flask: Travis Rosbach. How a thirsty surfer changed the water bottle industry

Hydro Flask: Travis Rosbach. How a thirsty surfer changed the water bottle industry

What if the idea that changes your life… starts with something as ordinary as being thirsty?In 2007, Travis Rosbach walked into a sporting goods store looking for a water bottle—and stumbled onto a pr...

24 Nov 20251h 4min

Advice Line with Anthony Casalena of Squarespace

Advice Line with Anthony Casalena of Squarespace

Squarespace founder Anthony Casalena joins Guy on the Advice Line, where they answer questions from three early-stage entrepreneurs. Plus, Anthony shares how Squarespace is leveraging AI to help peopl...

20 Nov 202548min

Gymshark: Ben Francis.  From pizza delivery to billion-dollar fitness brand.

Gymshark: Ben Francis. From pizza delivery to billion-dollar fitness brand.

At 19, Ben Francis was lifting weights during the day and delivering pizza at night. He didn’t have money. He didn’t have fashion experience. He didn’t even know how to sew. What he did have was a fro...

17 Nov 20251h 16min

Advice Line with Chet Pipkin of Belkin International

Advice Line with Chet Pipkin of Belkin International

Chet Pipkin, former CEO and founder of the electronic goods company Belkin International, joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Chet and Guy dril...

13 Nov 202547min

Backroads: Tom Hale. How a desk worker became a trailblazer in active travel

Backroads: Tom Hale. How a desk worker became a trailblazer in active travel

In his 20’s, working an office job he hated, Tom woke up in the middle of the night with a wild idea: why not take people on bike trips? No playbook. No investors. Just a sense that he could make a li...

10 Nov 202550min

Advice Line with Tariq Farid of Edible Arrangements

Advice Line with Tariq Farid of Edible Arrangements

Tariq Farid the founder of Edible Arrangements joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Tariq updates Guy on how he’s pivoting into a new industry w...

6 Nov 202550min

Babylist: Natalie Gordon. How a new mom used nap time to build a $500M business.

Babylist: Natalie Gordon. How a new mom used nap time to build a $500M business.

In 2010, software engineer Natalie Gordon was pregnant– and fed up with the overwhelming baby aisles in big box stores. So she quit her computer job to code the registry she wished existed. No pink-a...

3 Nov 20251h 7min

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