What’s it like to raise 7 funding rounds in 7 years? We’re speaking with Jack Tang from Urban, a website that allows you to book wellness treatments at your home or work.

In this episode, Jack and I talk about investors that ‘simply don’t get it’, Jack shares the wellness rituals that help him manage extreme stress, and we discuss what it was really like to make cuts at the start of the global pandemic. We also talk about ways you can build trust in a growing team.

Key links:

Urban website: https://urban.co/en-gb/

Open job positions: https://apply.workable.com/urban/

Jack Tang profile: https://www.linkedin.com/in/jackcktang/

Key timestamps:

[03:14] What was it like to find product-market fit?

[10:25] What's your best story about clueless investors?

[13:29] What was different about your Series B?

[17:42] What are your routines to avoid stress?

[21:24] What was it like to restructure the team?

[27:46] How do you build trust?

[37:34] What's the future for Urban?

Got feedback? Email us on [email protected]. And don't forget to hit follow/subscribe so you don't miss out on new episodes.

What's it like to go from 50 to 100 employees? Meet Chris Edson, CEO of Second Nature, an online weight loss plan that helps people make healthy lifestyle changes.

In this episode, Chris explains why reaching 100 employees feels like 'going through startup puberty', what made his $10M Series A easier than his seed round, and how brutal honesty won over an experienced US investor. We also talk frankly about why it's difficult for founders that love building to step out of daily operations.

Key links:

Second Nature website: https://www.secondnature.io/

Open job positions: https://apply.workable.com/secondnature/

Chris Edson profile: https://www.linkedin.com/in/chris-edson/

Key timestamps:

[01:48] Tell us the story of Second Nature.

[06:50] What's it like to go from a 50- to 100-person company?

[15:57] How much did you prepare for your pitches and how much was your success down to this preparation?

[20:56] How did your Series A compare to your seed round?

[32:29] What mistakes have you made along the way and what did you learn from them?

[36:29] What advice would you give to someone pushing back against the CEO?

[43:27] What's your favourite part of your leadership meeting?

[44:32] What's something challenging about being a CEO that you've never told anyone before?

A very big thank you (in no particular order) to Megan Kiely, Lorena Morais, Tamzin Foster, Vladimir Banovcanin, Fred Destin, Harry Stebbings, Rory Stirling, Sitar Teli, Matt Lerner, Tom Wakeling, Mike Gibbs, Carlo Bellini, and of course, Chris Edson for making this first episode happen.

Got feedback? Email us on [email protected]. And don't forget to hit follow/subscribe so you don't miss out on new episodes.

Hello world! This is Dave Bailey and I’m the writer of the Founder Coach blog, which is now read by millions of entrepreneurs each year. If you’ve read any of my essays, you know I’m very open about the mistakes that I made when founding and building three venture-backed tech businesses.

So I’m on a mission to share the stories of other CEOs that are also willing to be open about the harsh realities of raising venture capital, growing a team, and the mistakes that they’ve made—or are making right now.

We’ll be focusing on CEOs that have raised their Series A. Why Series A? Well, there are many thousands of entrepreneurs that want to raise a Series A, and if you’re one of them, you’ll learn what it actually takes to raise growth capital from people that just did it.

And if you’ve already raised a growth round and you’re scaling your business, you’ll hear from others facing the same problems that you’re facing—and maybe a few problems that are just around the corner. And for sure, some of these conversations are going to hit home.

If you’re into entrepreneurship, the Series A companies I’m speaking with are fascinating to learn about. After all, there are millions of ideas, but only a small number have the chance to really scale.

So join me and listen in on powerful conversations with scale-up CEOs where they talk about things they may have never talked about before.

Hit subscribe . . . the journey begins next week.