What It’s Like to Go From 50 to 100 Employees | Chris Edson, CEO Second Nature (Series A)

What It’s Like to Go From 50 to 100 Employees | Chris Edson, CEO Second Nature (Series A)

Author: Dave Bailey November 18, 2020 Duration: 48:52

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 podcast@foundercoach.co. And don't forget to hit follow/subscribe so you don't miss out on new episodes.



Behind the polished success stories and press releases, there's a messier, more human reality to building a company. The Founder Coach Podcast pulls back the curtain on that process. Hosted by Dave Bailey, a top CEO coach whose writing reaches millions of founders annually, these conversations get into the granular, often unspoken challenges that tech leaders face after the initial excitement fades. You’ll hear scale-up CEOs speak candidly, not about their victories, but about the difficult decisions, the personal doubts, and the operational grit involved in steering a growing business. Each episode feels like a private coaching session, focusing on pivotal moments like navigating the complexities that follow a Series A round-figuring out how to scale a team effectively, managing the relentless pressure of the board, and maintaining a clear vision amidst daily fires. This isn't about abstract theory; it's a series of raw, practical dialogues that reveal what the title of CEO actually demands day-to-day. For any entrepreneur or business leader who wants to learn from the real experiences of their peers, this podcast offers a rare and invaluable perspective. Dave facilitates a space where his guests can share the unvarnished truth, making each discussion a resource for anyone on the demanding path of leadership.
Author: Language: English Episodes: 22

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