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The Founder Coach Podcast

The Founder Coach Podcast

By Dave Bailey
Dave Bailey gets up close and personal with scale-up tech CEOs so you can hear the unvarnished truth about growing a business. Dave is one of Europe's top CEO coaches and his blog, The Founder Coach, is read by millions of entrepreneurs each year. Now, Dave's on a mission to help other CEOs share their stories about what it really means to be CEO.

Listen in as Dave discusses what happens after you raise a Series A—growing the team, managing the board, and the challenges that keep founders up at night. Hit subscribe and get ready for some powerful conversations.
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Currently playing episode

What It Means to Put People First | Ben Stephenson, CEO of Impala (Series B)

The Founder Coach Podcast

What It Means to Put People First | Ben Stephenson, CEO of Impala (Series B)

The Founder Coach Podcast

Special Edition: Why Vulnerability is a CEO Super-Power | 10th Episode Celebration
In this special edition to mark the 10th episode of the Founder Coach Podcast, I unpack the most powerful moments on the show this far—moments that demonstrate and celebrate the power of vulnerable leadership. As well as sharing practical takeaways on topics like building a culture of resilience and challenge, managing stress, and stepping out of the details, I'll leave with you with some powerful questions that help you integrate these ideas in your role as a leader. I hope you enjoy listening to this episode as much as I enjoyed creating it. Key Timestamps: [01:21] Chris Edson, CEO Second Nature, on stepping out of the details [05:11] Paul Ford, CEO Acin, on building resilience [09:28] Jacob Waern, CEO EduMe, on showing vulnerability as a leader [13:00] Jack Tang, CEO Urban, on routines for stress management [16:01] Anastasia Leng, CEO CreativeX, on encouraging challenge from your team [21:01] Ben Stephenson, CEO Impala, on having tough conversations with leaders [25:27] Rebecca Kelly, CEO VenueScanner, on hiring a Chief of Staff [29:30] Will Read, CEO Sideways 6, on the importance of self-compassion A big thank you to all the CEOs that have taken part and supported our mission—to share unvarnished stories about the emotional realities of leading high-growth tech startups. You're not alone.
March 31, 2021
Why Being a Peacetime CEO Isn't Easy | Will Read, CEO of Sideways 6 (Scale-up)
How easy is it to transition from 'wartime' to 'peacetime' as a CEO? Meet Will Read, CEO of Sideways 6—a company that helps companies capture big ideas from their employees. In this episode, Will shares his capital-efficient approach to growth, we discuss the anxiety that comes with the CEO role, and explain why it's important to celebrate wins with your team. We also unpack the transition from 'wartime' to 'peacetime' CEO—and why it's not as easy as you may think. Key links: Sideways 6 website: Will Read's profile: Key timestamps: [02:58] How did you adapt Sideway 6 as you scaled? [05:49] Capital efficiency: How much did you raise? [09:12] How did you reposition the business after Covid? [11:24] Which of the experiments didn't work and which messaging has ended up working out for you? [13:56] How is your corporate podcast coming along? [16:21] Peacetime vs. wartime CEO [19:30] The anxiety of strategy [22:54] How do you exercise self-compassion as CEO? [26:41] Celebrating your teams wins Got feedback? Email us on And don't forget to hit follow/subscribe so you don't miss out on new episodes.
March 17, 2021
How Do You Encourage New Behaviours | Luke Fisher, CEO of Mo (Series A)
How do you encourage new behaviours? Meet Luke Fisher, CEO of Mo, SaaS software that allows teams and companies to share their wins and encourage new behaviours.  In this episode, Luke Fisher explains how he 'dog-foods' his own product to celebrate wins in his team, how he adapted his fundraising approach during COVID, and how the North Star Metric framework links to OKRs. We also talk about the often conflicting needs of end-users and the economic buyer. Key links: Mo website: Luke Fisher profile: Key timestamps: [00:41] What was the context at WorldPay before you started the business? [04:12] How does Mo work? [08:15] Do you use the platform at your company? [10:52] What did you have to do to adapt to remote pitches during COVID? [14:06] What are the specific benchmarks that drive stress in your company? [16:00] How do you implement the North Star Metric framework? [18:00] How do align pricing with customer value? [21:00] How would Mo work in small teams? [25:00] How do you align a team when there's uncertainty? Thanks to Jason and Merlin for their great input. Got feedback? Email us at And don't forget to hit follow/subscribe so you don't miss out on new episodes.
March 2, 2021
Why Every Founder Needs a Chief of Staff | Rebecca Kelly, CEO of VenueScanner (Series Seed)
What's it like to see revenues drop 95%? Meet Rebecca Kelly, CEO of VenueScanner—a marketplace that connects event organisers with their ideal venue. In this episode, Rebecca shares her insights on marketplace business models, tells the story of how Covid dramatically impacted her business, and how she reinvented an events marketplace to stay relevant—even when there are no events happening. She also explains how to think about the Chief of Staff role—a must-listen for every CEO interested in recruiting one. Key links: VenueScanner website: Rebecca Kelly profile: Key timestamps: [03:51] What were some assumptions about the events space that turned out to be false? [07:18] How can you tell whether to push commissions or subscriptions? [12:07] Why did you decide to hire a Chief of Staff? [20:54] How did Covid affect your business? [27:02] What does it take to build good relationships with investors? [28:37] How have you reinvented your business model in light of the pandemic? Thanks to Guy and Angus for their great input. Got feedback? Email us on And don't forget to hit follow/subscribe so you don't miss out on new episodes.
February 16, 2021
What It Means to Put People First | Ben Stephenson, CEO of Impala (Series B)
What does it mean to put 'People First' in a fast-growing company? Meet Ben Stephenson, CEO of Impala—a company building a suite of travel APIs that make building travel tech a lot easier. In this episode, Ben Stephenson explains how he went from Seed to Series B in six months, how the pandemic affected their travel-focused business, and why hiring a head of people made a huge difference in building a remote-first culture. We also discuss the importance of inviting your leaders to the conversation.  Key links: Impala website: Ben Stephenson profile: Key timestamps: [01:47] What happened in TechStars? [07:07] How did you approach your Series A? [08:52] How did you raise Series A in less than a month? [10:37] How did you raise a Series B 6 months later? [14:47] What happens when you get a global pandemic in travel? [16:48] How do you shape culture in a remote environment? [23:51] Why do you use external search firms [25:51] What has been one of your most significant learnings as a CEO? [30:58] What can we expect from Impala in the next few months? Thanks to Jens, Jean and Julian (all the Js) for their great input. Got feedback? Email us on And don't forget to hit follow/subscribe so you don't miss out on new episodes.
February 3, 2021
How to Encourage Constructive Dissent | Anastasia Leng, CEO of CreativeX (Series A)
How do you get your team to speak up to the CEO? Meet Anastasia Leng, CEO of CreativeX—a Series A SaaS company that helps B2C brands understand the performance of image and video content. In this episode, Anastasia explains how she got term sheets for a company with no name, unpacks the founder-investor partnership, and explains why high-standards are a perk. We also discuss 'Devil's Avocado' (a term borrowed from Sarah Wood), and other ways to encourage constructive dissent. Key links: CreativeX website: Open job positions: Anastasia Leng profile: Dave's essay on wise interventions: Key timestamps: [01:01] What's it like to be back in the office (alone)? [05:50] How do you collect data on being 'on-brand'? [08:20] Tell us about your Series A raise. [12:09] How did you go from agency to SaaS? [23:21] What's it like to lead a team of 35 employees? [27:01] How did you define your company's values? [31:21] What are the challenges of having a culture of constructive dissent? [33:13] How do you encourage people to speak up? Thanks to Alex Dunsdon and John Griffin for their great input. Got feedback? Email us on And don't forget to hit follow/subscribe so you don't miss out on new episodes.
January 20, 2021
What It Means To Leave Your Comfort Zone | Jacob Waern, CEO of EduMe (Series A)
What does it mean to leave your comfort zone as a CEO? Meet Jacob Waern, CEO of EduMe (Series A), a mobile-based training tool that gives desk-less workforces the knowledge they need to succeed. In this episode, Jacob talks about his experience reducing his team by 90%, explains how he raised while sick with suspected Coronavirus, and we discuss what it takes to build a strong leadership team. We also look at the tension between empowering processes and empowering people. Key links: EduMe website: Open job positions: Jacob Waern profile: Key timestamps: [01:23] What's the story EduMe? [03:02] What are common misconceptions about pivots? [07:43] What was it like to fire 90% of the company? [13:37] When did you decide to build a category? [17:00] What was it like to raise during Covid [22:57] How did you build a relationship with a Valley investor? [32:24] What system can result in a strong leadership team? [37:37] What's it like to realise the company can grow faster than its individuals? [42:41] Vulnerability vs. over-sharing Thanks to Andreas Schörling, Anders Nilsson and Pietro Bezza for their great input. Got feedback? Email us on And don't forget to hit follow/subscribe so you don't miss out on new episodes.
December 16, 2020
What It Means to Speak VC | Paul Ford, CEO of Acin (Series A)
How many languages do founders need to learn? Meet Paul Ford, CEO of Acin, a SaaS tool that helps banks manage their operational risk. In this episode, Paul and I discuss why raising money is like learning a new language, Paul shares how the army helped him become more resilient, and we talk about what it was like to step down as CEO of his previous company. We also explore how to find topics that resonate with end users. Key links: Acin website: Open job positions: Paul Ford profile: Key timestamps: [02:03] How did the army help you stay resilient? [12:42] Why did you step down from your previous company? [16:20] Why did you decide to raise a Series A now? [20:20] What was it like to raise VC having worked in a bank? [26:18] What are some of the things that you still struggle with as a CEO? [37:08] Dave describes the messaging matrix Thanks to Simon Ball and Rocket for their great input. Got feedback? Email us on And don't forget to hit follow/subscribe so you don't miss out on new episodes.
December 2, 2020
What It's Like to Raise 7 Rounds in 7 Years | Jack Tang CEO of Urban (Series B)
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: Open job positions: Jack Tang profile: 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 And don't forget to hit follow/subscribe so you don't miss out on new episodes.
November 25, 2020
What It’s Like to Go From 50 to 100 Employees | Chris Edson, CEO Second Nature (Series A)
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: Open job positions: Chris Edson profile: 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 And don't forget to hit follow/subscribe so you don't miss out on new episodes.
November 18, 2020
Introducing The Founder Coach Podcast
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.
November 9, 2020