The Startup CEO Show

If you want to connect with other CEOs who are grappling with co-founder conflict, come join Limitless.ceoI’ve known Yoseph West, the Co-founder and CEO of Relay, for years, and in this episode of The Startup CEO Show, we finally get to unpack his story. Yoseph has quietly built one of the fastest-growing fintech companies in North America, serving thousands of small businesses while staying true to his principles.We talk about how he went from the early days at Hubdoc to leading a 200-person company, what it takes to earn trust in a regulated space, and how he’s learned to lead with intensity without burning out. Yoseph opens up about his personal growth journey, from hands-on founder to strategic CEO, and how coaching, emotional intelligence, and discipline have shaped him along the way.This is one of those conversations that reminds you what real leadership looks like: clarity, humility, and long-term focus. If you’re building something ambitious and trying to grow as fast as your company, this one’s for you.Yoseph West relayfi.comConnect with me:My website: https://limitless.ceo/Linkedin:https://www.linkedin.com/in/themarkmacleod/Instagram: https://www.instagram.com/markmacleodcoach/Subscribe to Mark MacLeod for The Startup CEO Show Podcast, actionable insights, coaching, and strategy for CEOS.https://www.youtube.com/@MarkMacLeod-CEOCoach?sub_confirmation=1

If you want to connect with other CEOs who are grappling with co-founder conflict, come join Limitless.ceoWhy do 65% of startups fail?It’s not a lack of funding. It’s not product-market fit. Matt Jones, psychologist, coach, and author of The Co-Founder Effect, says the number one killer of startups is co-founder conflict.In this episode of The Startup CEO Show, I sit down with Matt to unpack why co-founder relationships make or break companies and what founders can do to prevent disaster. We explore the hidden reasons co-founders clash, why alignment and values matter more than strategy or capital, and the practical frameworks Matt uses to save partnerships before they implode.Whether you’re choosing a co-founder, scaling through Series B, or already feeling the strain, you’ll learn how to protect your partnership and your company’s future.Dr. Matthew Jones-Book The Cofounder Effect: How to Diagnose, Fix, and Scale Healthy Communication for Startup SuccessConnect with me:My website: https://limitless.ceo/Linkedin:https://www.linkedin.com/in/themarkmacleod/Instagram: https://www.instagram.com/markmacleodcoach/Subscribe to Mark MacLeod for The Startup CEO Show Podcast, actionable insights, coaching, and strategy for CEOS.https://www.youtube.com/@MarkMacLeod-CEOCoach?sub_confirmation=1

Want to unlock your limit as CEO? Come join us:https://limitless.ceo/What happens when 41% of all VC dollars flow to just 10 companies?In this episode of The Startup CEO Show, I sit down with my friend and serial founder/investor Amar Varma (Mantle, Xtreme Labs, Pivotal) to unpack the new power law era of venture capital, the rise of AI, and what it all means for startup founders today.We talk about how AI is reshaping startup costs, why some founders are skipping entire funding rounds, and how the next wave of alumni networks could rival the PayPal Mafia. We also dive into what happens when incumbents get disrupted and why the very idea of a moat is being redefined in real time.This was one of those conversations where I walked away both excited and uneasy about the future of tech startups, VC trends, and entrepreneurship. I think you will too.Amar VarmaConnect with me:My website: https://limitless.ceo/Linkedin:https://www.linkedin.com/in/themarkmacleod/Instagram: https://www.instagram.com/markmacleodcoach/ If you’re building, raising, or investing, you don’t want to miss this one.Subscribe to Mark MacLeod for The Startup CEO Show Podcast, actionable insights, coaching, and strategy for CEOS.https://www.youtube.com/@MarkMacLeod-CEOCoach?sub_confirmation=1

In this illuminating episode of the Startup CEO Show, host Mark MacLeod dives deep into the habits and traits of some of the world's most successful tech leaders. Drawing from his extensive research and experience coaching CEOs, MacLeod explores what sets apart founders who continue to scale and innovate year after year. He examines 11 companies with a collective market cap of $6.4 trillion, including giants like Airbnb, Meta, and Shopify, to uncover the secrets behind their limitless growth.MacLeod breaks down the personal habits and leadership traits of CEOs like Brian Chesky, Melanie Perkins, and Tobi Lütke, revealing surprising insights about their routines, decision-making processes, and management styles. From prioritizing sleep and mindfulness to fostering customer empathy and making bold bets, these leaders share common threads that contribute to their ongoing success. The episode challenges conventional notions of hustle culture, highlighting how many top CEOs actually prioritize work-life balance, continuous learning, and self-reflection.Don't miss out on these invaluable lessons from the tech world's most enduring visionaries. Tune in now and unlock your potential for limitless growth.LIMITLESS CEO: https://limitless.ceo/Slides: https://pitch.com/v/limitless-leadership-why-some-ceos-never-stop-growing-69v8ynConnect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Contact Mark: https://markmacleod.me/Subscribe to Mark MacLeod for The Startup CEO Show Podcast, actionable insights, coaching, and strategy for CEOS.https://www.youtube.com/@MarkMacLeod-CEOCoach?sub_confirmation=1

In this insightful episode of the Startup CEO Show, host Mark McLeod sits down with Marie Chevrier Schwartz, former founder and CEO of Sampler, to discuss the challenging journey of entrepreneurship and the importance of community in the startup ecosystem. Marie openly shares her experience of Sampler's bankruptcy, offering valuable lessons on losing product-market fit and the need for founders to separate their identity from their business. She emphasizes the importance of being prepared for market shifts and understanding the type of company you're building. The conversation takes an inspiring turn as Marie discusses her transition to leading Tech2, Canada's largest tech community, where she now focuses on supporting and connecting entrepreneurs across the country. Listeners will gain a unique perspective on failure, resilience, and the power of authenticity in the startup world. Whether you're a seasoned entrepreneur or just starting out, this episode offers crucial insights into navigating the ups and downs of building a company and the vital role of community support. Tune in to hear Marie's candid reflections and learn how to approach entrepreneurship with a healthier mindset.Marie Chevrier Schwartz02:29 From Montreal to Entrepreneurship06:31 When Ventures Fail: Sampler's Story15:34 Rebirth of a Business Idea17:55 Bouncing Back from Bankruptcy02:29 From Montreal to Entrepreneurship06:31 When Ventures Fail: Sampler's Story15:34 Rebirth of a Business Idea17:55 Bouncing Back from Bankruptcy------------------------------------------------------------------------------Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Contact Mark: https://markmacleod.me/Subscribe to Mark MacLeod for The Startup CEO Show Podcast, actionable insights, coaching, and strategy for CEOS.https://www.youtube.com/@MarkMacLeod-CEOCoach?sub_confirmation=1

In this episode of the Startup CEO Show, host Mark MacLeod sits down with Tanya Papanikalov, founder of Rainbo, a leading functional mushroom brand. Tanya shares her fascinating journey from holistic nutritionist to successful entrepreneur, detailing how her personal healing experiences led her to create Rainbo. The conversation delves deep into the world of medicinal mushrooms, exploring their myriad health benefits and Tanya's mission to educate consumers about these powerful natural remedies. Listeners will gain valuable insights into the challenges of building a direct-to-consumer business, expanding into major retail channels like Whole Foods, and balancing entrepreneurship with spiritual practices. Tanya's unique background in mind-body medicine and Kundalini yoga adds a compelling dimension to the discussion, offering listeners a fresh perspective on integrating mindfulness and spirituality into business leadership. Whether you're an aspiring entrepreneur, health enthusiast, or simply curious about the intersection of business and wellness, this episode offers a wealth of knowledge and inspiration. Tune in to discover how Tanya's journey can inform your own path to success and well-being.Tonya Papanikolov00:01:04 Meet Rainbow's Mushroom Maven00:03:57 Full Moon Guru Wisdom00:12:14 Mushroom Magic in Every Product00:16:11 Western Approach to Eastern Wisdom00:18:21 Mushrooms 101: Beginner's Guide00:30:50 Power Couple Behind Rainbow00:39:20 Standing Out in Mushroom Market00:48:18 Kundalini Culture in Company00:58:39 Midlife Kundalini AwakeningSince 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Contact Mark: https://markmacleod.me/Subscribe to Mark MacLeod for The Startup CEO Show Podcast, actionable insights, coaching, and strategy for CEOS.https://www.youtube.com/@MarkMacLeod-CEOCoach?sub_confirmation=1

In this insightful episode of the Startup CEO Show, host Mark MacLeod sits down with Nick Mehta, co-founder and CEO of Gainsight, to explore the journey of building a category-defining company. Mehta shares how Gainsight played a pivotal role in creating the customer success profession and job category, transforming how businesses approach customer retention in the SaaS world. The conversation delves into Gainsight's funding history, with Mehta offering valuable perspectives on navigating relationships with top-tier venture capital firms and aligning expectations. He provides a candid look at the challenges of scaling a startup while maintaining a strong company culture, discussing Gainsight's core values and how they've shaped the organization's growth. Mehta also opens up about personal growth and the evolving priorities of a long-term CEO, offering wisdom on balancing professional ambition with personal fulfillment. This episode is a must-listen for founders, aspiring entrepreneurs, and anyone interested in the human side of building a successful tech company.Nick Mehta00:53 Gainsight's Guru: Meet Nick Mehta02:14 Taylor Swift: Nick's Unexpected Muse05:01 The Many Faces of Nick13:29 Nick's Literary Legacy: Five Books17:48 Keeping Customer Focus at Scale24:16 Glassdoor Glory: Gainsight's Triumph28:44 Five Pillars: Gainsight's Core Values38:22 Ganesh's Wisdom: Letting Go46:28 Wrapping Up: Kudos to NickSince 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Contact Mark: https://markmacleod.me/

Mark MacLeod sits down with fitness coach Greg Newlands to explore the critical importance of health and wellness for high-performing entrepreneurs. As a coach to successful business leaders, Greg shares his expertise on how CEOs can optimize their physical and mental performance through strategic fitness and nutrition practices. The conversation dives deep into the four key pillars Greg focuses on with clients: daily step count, weigh-ins, calorie tracking, and protein intake. Greg emphasizes the power of resistance training for maintaining muscle mass and a high metabolism as we age, allowing entrepreneurs to sustain energy and productivity. The episode also covers practical tips for creating boundaries and implementing strategic breaks throughout the workday to avoid burnout. Greg provides actionable advice on nutrition, recommending whole foods and explaining the roles of protein, carbs, and fats in achieving peak performance. Whether you're a startup founder looking to boost your energy or an executive aiming to optimize your health, this episode offers valuable insights to help you perform at your best. Tune in to learn how treating yourself like a "high-performance Formula One car" can transform your business and life.00:53 Health: The CEO's Secret Weapon05:23 Comeback Kings: Fitness Redemption Stories09:37 Sleep: The Sacrificial Startup Lamb16:59 Burnout: Recognizing the Warning Signs20:59 KPIs for Your Body33:05 Urgency vs. Boundaries: Finding Balance38:16 Outsourcing Meals: Fueling Success Effortlessly48:50 Sobering Up: Energy and Productivity Boost56:13 Startup CEO Show: Until Next TimeSince 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Contact Mark: https://markmacleod.me/

Mark MacLeod's Startup CEO Show brings us an enlightening conversation with Alina Vandenberghe, the dynamic co-founder and co-CEO of Chili Piper. This episode offers a deep dive into the unique challenges and opportunities of co-leading a company with your spouse, as Alina candidly discusses her partnership with her husband and co-CEO. The discussion sheds light on their fluid approach to dividing responsibilities and how they've managed to create a flat organizational structure despite having 150 employees across 38 countries.Alina shares invaluable insights on hiring for values, detailing how they assess candidates not just for skills but for alignment with company culture. The conversation takes an interesting turn as Alina reflects on her background growing up in communist Romania and how it shaped her entrepreneurial journey, instilling in her a unique perspective on resource management and customer motivations. This episode is packed with practical advice on building a strong company culture, leveraging personal branding for business growth, and adapting to the rapidly changing tech landscape.Don't miss this opportunity to learn from one of tech's most innovative and authentic leaders.Timestamps: 01:06 Meet Alina: Chili Piper's Spicy CEO03:26 Chili Piper: Spicing Up Sales Software06:11 Raw and Real: Alina's Authentic Approach10:16 Social Media: The Pipeline Powerhouse12:20 Speaking Up: Time Well Invested16:42 Dividing and Conquering CEO Duties19:42 Remote Work: Born from Wanderlust29:48 Bootstrapping to Millions: Chili Piper's Journey35:48 AI: Blessing or Terminator Scenario?43:00 Corporate Wisdom in Startup Land48:07 Inspiring Women: Alina's Ripple EffectSince 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, Mark MacLeod sits down with Mark Bordo, co-founder and CEO of Vetster, to explore the world of pet telemedicine and marketplace businesses. Bordo shares the origin story of Vetster, born from a personal need and launched just before the COVID-19 pandemic. He discusses how the company quickly scaled across North America, balancing supply and demand in the veterinary marketplace.Bordo offers valuable insights into building and growing a successful marketplace business, emphasizing the importance of data-driven decision-making and continuous optimization. He also touches on the challenges of regulatory environments in different states and provinces, and how Vetster navigates these complexities. The conversation delves into Bordo's 25-year journey as an entrepreneur, highlighting lessons learned and strategies for personal growth that have enabled him to stay ahead of his rapidly expanding businesses. From the intricacies of customer acquisition to the evolution of marketing strategies in the age of AI, this episode is packed with practical advice for aspiring and seasoned entrepreneurs alike. Tune in to gain valuable knowledge on building and scaling a marketplace business in today's dynamic digital landscape.-------------------------------------Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Contact Mark: https://markmacleod.me/