How The Role of CEO Changes You | Charles Wells, CEO of HelloSelf (Series A)

How The Role of CEO Changes You | Charles Wells, CEO of HelloSelf (Series A)

Author: Dave Bailey May 19, 2021 Duration: 35:51

How does the role of CEO force you to change? Meet Charles Wells, CEO of HelloSelf—a company with a mission to help everyone practically work on self-improvement. 

In this episode, Charles shares his company's amazing origin story, we discuss the transition from manager to leader, and the challenge of giving up areas of the business.

We also discuss shadow cultures and how to avoid letting the external mission corrode the internal one.


Key links:

HelloSelf website: https://www.helloself.com/

Charles' profile: https://www.linkedin.com/in/charlesjwells/


Key timestamps:

[01:17] Did I get the problem statement correct?

[03:17] What were some  preconceptions you had about raising money ?

[09:41] What's different about HelloSelf's approach?

[16:14] How did you decide on which problem to solve?

[19:33] What's difficult about being a CEO that we don't talk enough about?

[21:56] What skills did you have to learn to transition from manager to leader?

[26:07] The danger of shadow culture

[29:56] Did you hand over problems too early, too late or about right?

[30:45] Quick-fire round (new!)

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

The Founder Coach Podcast
Podcast Episodes
Why Communication is Critical To Scale | Ed Klinger, CEO of Flock [not-audio_url] [/not-audio_url]

Duration: 36:51
How can scale-ups maintain good communication as they scale? My guest, Ed Leon Klinger, is the CEO of Flock—a company that uses data to provide usage-based insurance for drones, cars and vans. In this episode, Ed explain…
Why Jewellery Needs a New Model | Ilana Lever, CEO of Motley [not-audio_url] [/not-audio_url]

Duration: 47:26
Why have traditional marketplace models failed in the jewellery sector? My guest, Ilana Lever, is the CEO of Motley—a company that enables jewellery designers to bring their designs to market at scale. In this episode, I…
When to Step Back as CEO | James Routledge, Founder of Sanctus [not-audio_url] [/not-audio_url]

Duration: 44:16
What would make a founder give up their role as CEO? My guest, James Routledge, is the founder of Sanctus—a company that offers coaching services to businesses to support employee mental health. In this episode, James wa…