Episodes

  • 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 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 [email protected]. And don't forget to hit follow/subscribe so you don't miss out on new episodes.

  • As 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 protected]. And don't forget to hit follow/subscribe so you don't miss out on new episodes.

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  • 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, 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 [email protected]. And don't forget to hit follow/subscribe so you don't miss out on new episodes.

  • 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 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 protected]. And don't forget to hit follow/subscribe so you don't miss out on new episodes.

  • How 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 [email protected]. And don't forget to hit follow/subscribe so you don't miss out on new episodes.

  • Why 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 protected]. And don't forget to hit follow/subscribe so you don't miss out on new episodes.

  • How 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 [email protected]. And don't forget to hit follow/subscribe so you don't miss out on new episodes.

  • How 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 protected]. And don't forget to hit follow/subscribe so you don't miss out on new episodes.

  • What 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 protected]. And don't forget to hit follow/subscribe so you don't miss out on new episodes.

  • How do you set realistic standards for your team? Meet Gren Paull, CEO of Lilli—a company that helps vulnerable people live independently and safely, using smart in-home sensors.

    In this episode, Gren shares how he took over as CEO, the differences between the COO and CEO role, and his approach to setting standards for the team.

    We also discuss the value of a Head of People, even during the early stages.

    Key links:

    Lilli website: https://www.intelligentlilli.com/

    Gren Paull profile: https://www.linkedin.com/in/gren-paull-a89a541

    Key timestamps:

    [01:02] What's Lilly's backstory?

    [02:06] What limitations have you seen in founders as they scale?

    [03:45] How did you come to be CEO of Lilly?

    [09:24] What's the difference between the COO and CEO role?

    [10:50] How would you describe a high performing team?

    [11:34] Do you set realistic standards for your team?

    [15:26] What's the value of a Head of People?

    [17:12] What are the challenges you face in developing as a CEO?

    [18:35] How do you manage the pressure of the role?

    [21:50] Why is scaling like driving a car?

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

  • 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 [email protected] And don't forget to hit follow/subscribe so you don't miss out on new episodes.

  • 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.

  • 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: https://www.sideways6.com/careers

    Will Read's profile: https://www.linkedin.com/in/wread/

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

  • 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: https://mo.work/

    Luke Fisher profile: https://www.linkedin.com/in/lsfisher/

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

  • 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: https://www.venuescanner.com/

    Rebecca Kelly profile: https://www.linkedin.com/in/rebecca-kelly-5928054b/

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

  • 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: https://impala.travel/

    Ben Stephenson profile: https://www.linkedin.com/in/ben-stephenson-13032b33/

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

  • 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: https://www.creativex.com/

    Open job positions: https://creativex.freshteam.com/jobs

    Anastasia Leng profile: https://www.linkedin.com/in/aleng/

    Dave's essay on wise interventions: http://bit.ly/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 [email protected]. And don't forget to hit follow/subscribe so you don't miss out on new episodes.

  • 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: https://edume.com/

    Open job positions: https://edume.com/join-us

    Jacob Waern profile: https://www.linkedin.com/in/jacob-waern-a13165/

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

  • 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: https://acin.com/

    Open job positions: https://acin.com/company/careers/

    Paul Ford profile: https://www.linkedin.com/in/paul-ford-56b509/

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

  • 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.