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.
Why Communication is Critical To Scale | Ed Klinger, CEO of Flock
36:51How 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 explains why he likes to transcribe fundraising meetings to hunt for learnings, he shares why he's grateful that his board let him fail, and we unpack the broad challenge of communication as you scale the team. Key links: Flock website: https://flockcover.com Ed Leon Klinger profile: https://www.linkedin.com/in/edleonklinger/ Dave Bailey profile: https://www.linkedin.com/in/davesuperman/ Timestamps: [01:18] When did you expand from drones to automotive? [05:48] What unique approaches helped you close your Series B? [12:15] How did you choose your Series B investor, Social Capital? [17:30] How has pivoting the business shaped you as a leader? [21:56] What assumptions about enterprise SaaS turned out to be false? [29:41] What are ways to influence culture aside from communicating it? [34:59] What books do you recommend for founders? Got feedback? Email us at firstname.lastname@example.org. And don't forget to hit follow/subscribe so you don't miss out on new episodes.
What It's Like to Be Always on Show | Raoul Fraser, CEO of Lovat Parks
38:35As a founder you're always on show. My guest, Raoul Fraser, is the CEO of Lovat Parks—a scale-up building residential and holiday caravan parks across the UK. In this episode, Raoul walks us through his vision for the caravan park industry, he explains the challenges of having physical locations, and we discuss the difficulty of feeling like you're always on show to your team—something every leader can relate to. Key links: Lovat Parks website: https://lovatparks.com/ Raoul Fraser profile: https://www.linkedin.com/in/raoul-fraser/ Dave Bailey profile: https://www.linkedin.com/in/davesuperman/ [00:53] How did you end up building holiday parks? [04:24] What is your vision for Lovat Parks? [07:55] What challenges come with having physical locations? [10:28] Why are customer reviews so important? [15:14] What practices haven't scaled? [19:01] How do you get honest feedback from the team? [20:22] How do you approach building your network? [23:29] How much responsibility should founders take for mistakes? [27:41] What are the challenges to finding balance as CEO? [32:37] How to meditate without sitting still Got feedback? Email us at email@example.com. And don't forget to hit follow/subscribe so you don't miss out on new episodes.
Why Jewellery Needs a New Model | Ilana Lever, CEO of Motley
47:26Why 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, Ilana walks us through Motley’s business model, she explains what stopped her letting go of the details sooner, and we discuss challenges and learnings from fundraising four times. Key links: Motley website: https://www.motley-london.com/ Ilana Lever profile: https://www.linkedin.com/in/ilana-lever-07551138/ Dave Bailey profile: https://www.linkedin.com/in/davesuperman/ Key timestamps: [01:01] What does Motley do? [05:49] Where are you on your journey to product market fit? [12:49] So you're getting married... [15:18] What stopped you letting go of the details sooner? [18:44] The challenge of fundraising [21:35] How does Motley contribute to reducing global warning? [30:12] How might investors avoid bias? [33:34] What's your biggest fundraising hack? [39:55] Quickfire questions Thanks to Aron Gelbard for help researching the episode. Got feedback? Email us at firstname.lastname@example.org. And don't forget to hit follow/subscribe so you don't miss out on new episodes.
When to Step Back as CEO | James Routledge, Founder of Sanctus
44:16What 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 walks us through his decision to step back from the CEO role, he explains why he decided not to hire a COO, and we discuss how ego can lead us to unhappiness. This is genuinely one of my favourite episodes, and a must-listen if you’re a CEO scaling your business. Key links: Sanctus website: https://sanctus.io/ James Routledge profile: https://www.linkedin.com/in/jdroutledge1/ Dave Bailey profile: https://www.linkedin.com/in/davesuperman/ Key timestamps: [02:29] How does it feel to see Sanctus scale? [06:21] What techniques helped you develop self-awareness? [09:24] What need does Sanctus address? [13:36] Why did you step down as CEO? [21:40] How to you separate the roles of CEO and founder? [26:45] Why are VC-backed founders less likely to consider their own fulfilment? [33:55] Why did you choose not to hire a COO? [36:41] The gap in strategy and leadership in tech [39:49] Quickfire questions Thanks to Nabil and George for help researching the episode. Strategy is a core role of a scale-up CEO and key to a company's success. Yet many CEOs don't dedicate enough time and resource to it. If you'd like my help in clarifying your vision and strategy, apply for my Clarity Program. Got feedback? Email us at email@example.com. And don't forget to hit follow/subscribe so you don't miss out on new episodes.
Why an Inspiring Mission is Everything | Simon Mellin, CEO of The Modern Milkman (Series A)
28:41How much plastic do you consume? Meet Simon Mellin, CEO of The Modern Milkman a company that delivers plastic-free milk and groceries to your door. In this episode, Simon talks about how a milk cart became venture-backed, we discuss his journey to Series B, and the importance of hiring when building a low-ego culture. Key links: The Modern Milkman website: https://themodernmilkman.co.uk/ Simon Mellin profile: https://www.linkedin.com/in/simonmellin/ Key timestamps: [00:44] How did a milk cart become a venture-backed business? [05:31] What's going on in groceries right now? [10:44] What's it like to be based in Lancashire? [12:29] What's your management philosophy? [13:54] What's happened as you've scaled? [16:18] What's the value of an inspiring mission? [18:20] How are you thinking about market expansion? [20:53] Where do you find yourself spending your time? [23:22] Quickfire questions Got feedback? Email us at firstname.lastname@example.org. And don't forget to hit follow/subscribe so you don't miss out on new episodes.
Why You Need To Train Your Workforce | Rajeeb Dey, CEO of Learnerbly (Series A)
33:44Why do you need to train your workforce? Meet Rajeeb Dey, CEO of Learnerbly—a company that helps businesses train their employees. In this episode, Rajeeb shares how he dealt with a life-threatening back issue as CEO, we discuss the hard decisions that come with internalisation and talk about how the training space is changing. Key links: Learnerbly website: https://www.learnerbly.com/ Rajeeb Dey profile: https://www.linkedin.com/in/rajeebdey/ Key timestamps: [01:13] Why did you start Learnerbly? [04:22] Who are Learnerbly's customers? [07:22] How do you encourage employees to seek training? [10:51] What growing pains have you experienced? [13:49] What was it like to have a serious back injury as CEO? [20:12] What issues do you face as you internationalist? [22:47] How do you manage your time? [24:56] How do train as a CEO? [26:37] Quickfire questions Thanks to Will and Toby for their great input. Got feedback? Email us at email@example.com. And don't forget to hit follow/subscribe so you don't miss out on new episodes.
How to Identify High Performance | Alex Young, CEO of Virti (Series A)
40:06How do you identify high performers in your recruiting? Meet Alex Young, CEO of Virti—a company that creates immersive training experiences using VR that replicate the stress and emotion of clinical practice and beyond. In this episode, Alex talks us through his Series A fundraise, we discuss the surprising applications of VR and immersive training, and he shares some of his recruiting tactics. We also discuss the challenges Alex overcame when building his online brand. Key links: Virti website: https://virti.com/ Alex Young profile: https://www.linkedin.com/in/alexander-f-young/ Dave Bailey profile: https://www.linkedin.com/in/davesuperman/ Key timestamps: [01:35] The background and the round [03:46] Fundraising while remote [08:41] Preparing for fundraising [13:32] Using VR to create stressors in training [16:22] Applications of VR training [19:56] CEO struggles [21:50] Approach to recruiting [29:11] Self-development as CEO [32:08] Growing as a thought leader [34:33] Quickfire questions Got feedback? Email us on firstname.lastname@example.org. And don't forget to hit follow/subscribe so you don't miss out on new episodes.
How to Stay Resilient in a Scale-Up | Joe Cripps, CEO of Trail (Series A)
29:23How have you dealt with the ups and downs of Covid-19? Meet Joe Cripps, CEO of Trail, a company that helps multi-site operators in hospitality and leisure to manage their daily tasks. In this episode, Joe shares his experience of the hospitality crisis, he shares learnings from running a remote-first company, and we talk about the mental health challenges many of us have faced during the pandemic. Key links: Trail website: https://trailapp.com/ Joe Cripps profile: https://www.linkedin.com/in/joecripps/ Dave Bailey profile: https://www.linkedin.com/in/davesuperman/ Dave's one-on-one guide: https://bit.ly/dave-one-on-ones Key timestamps: [00:56] How did you get the idea for Trail? [04:10] What was it like when COVID hit? [08:52] How do you think about the sales process as you come out of COVID? [11:46] How did you come up with your core messaging? [14:32] How do you support the team on the emotional side of Covid? [17:28] What have you learned about remote-first work? [19:42] How have you integrated business culture in slack? [21:35] What are the unique challenges for leaders of remote teams? [22:41] What are the unique challenges for leaders of remote teams? [24:39] Quickfire Questions A shout out to co-founder Wil—miss you and let's catch up soon! Got feedback? Email us on email@example.com. And don't forget to hit follow/subscribe so you don't miss out on new episodes.
Why and How to Grow Inorganically | Aron Gelbard, CEO of Bloom & Wild (Series D)
31:42Why and how do you grow a company through acquisitions? Meet Aron Gelbard, CEO of Bloom & Wild—a company which sends you flowers through your letterbox. In this episode, Aron talks about applying AI to the flowers industry, raising from a US VC without a US presence, and the opportunities and challenges of growing through acquisitions. Aron also shares how he came to lead the Thoughtful Marketing trend. Key links: Bloom & Wild website: https://www.bloomandwild.com/ Aron Gelbard profile: https://www.linkedin.com/in/aron-gelbard-a075a11/ Dave Bailey profile: https://www.linkedin.com/in/davesuperman/ Key timestamps: [36:25] How can you apply AI in the flower business? [06:38] What led you to start acquiring companies? [10:51] What challenges have you faced after acquiring Bloomon? [13:42] What have you learned about hiring senior leaders? [15:50] How did you come to lead the Thoughtful Marketing trend? [22:17] What are the challenges you're facing now? [24:56] How has your role developed over time? [27:43] Quickfire questions Thanks to Camilla Dolan from Eka Ventures for her input! Got feedback? Email us on firstname.lastname@example.org. And don't forget to hit follow/subscribe so you don't miss new episodes.
What It Takes To Build a Diverse Company | Maya Pindeus, CEO of Humanising Autonomy (Seed)
24:27What does it take to build a truly diverse company from Day One? Today's guest is Maya Pindeus, CEO of Humanising Autonomy which is a company that uses AI and computer vision to predict human behaviour. In this episode, Maya walks us through how she built a thought leadership position as an AI startup, how she prioritised diversity from the start, and the challenges of a listening culture. She also shares an interesting approach to brainstorming at scale. Key links: Humanising Autonomy website: https://www.humanisingautonomy.com/ Maya Pindeus LinkedIn: https://www.linkedin.com/in/mayapindeus/ Key timestamps: [01:00] How do you predict human behaviours? [03:35] How did you come up with the idea? [06:01] Where do you see most traction? [07:25] How did you become a thought leader? [10:48] How has scaling been challenging? [11:24] What's more difficult than you expected about championing diversity? [16:02] How do brainstorm as a company? [17:29] How do you stay proactive? [19:01] What are the challenges in building a listening culture? [20:29] Quick-fire questions Got feedback? Email us on email@example.com. And don't forget to hit follow/subscribe so you don't miss out on new episodes.