Want to unlock your limit as CEO? Come join us:

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In this episode, I sit down with Benjamin Alarie, co-founder and CEO of Blue J, to explore one of the most fascinating founder journeys I’ve ever encountered. Imagine simultaneously being a tenured law professor and a venture-backed CEO, while reinventing one of the most painful and universal professional workflows: tax research. Ben shares how Blue J evolved from an academic insight into a hyper-growth AI platform transforming how tax professionals, enterprises, and advisors find answers in seconds instead of hours.

We dive deep into the origin story of Blue J, including how a walk down Charles Street in Toronto inspired the name, how Ben threaded the needle between academic life and startup life, and how large language models completely reshaped the company’s trajectory. Ben also breaks down the realities of selling into a concentrated enterprise market, navigating the economics of professional services, and scaling from idea to 300%+ year-over-year growth.

Whether you’re a founder, an operator, or a curious learner, this conversation is packed with insights on identity, reinvention, enterprise sales, AI transformation, and the emotional journey of becoming a venture-backed CEO.

Benjamin Alarie

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Join a community of ambitious CEOs who are looking to build market-leading companies without sacrificing health and happiness. Check out

https://limitless.ceo/

What does it take to survive, then thrive, as a public e-commerce CEO? In this episode of Start Up CEO, I sit down with Ghassan Halazon, co-founder and CEO of Emerge Commerce, who has spent 15-plus years buying, building, and turning around brands that together have generated more than one billion dollars in GMV.

We go deep on the shift from a wide roll-up to a focused portfolio in grocery and golf, the reality of timing acquisitions during the pandemic, and how Ghassan led a dramatic debt reduction while getting back to profitable growth. He shares how to handle competitor outreach, how to think about LTV to CAC, and what public market life actually feels like when the cycle turns.

If you are scaling an e-commerce company or considering acquisitions, this is a playbook on focus, discipline, and resilience.

Ghassan Halazon

If you want to connect with other CEOs who are grappling with co-founder conflict, come join Limitless.ceo

I’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.com

Connect 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.

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If you want to connect with other CEOs who are grappling with co-founder conflict, come join Limitless.ceo

Why 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 Success

Connect 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.

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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 Varma

Connect 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.

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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-69v8yn

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Contact Mark: https://markmacleod.me/

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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 Schwartz

02:29 From Montreal to Entrepreneurship

06:31 When Ventures Fail: Sampler's Story

15:34 Rebirth of a Business Idea

17:55 Bouncing Back from Bankruptcy

02:29 From Montreal to Entrepreneurship

06:31 When Ventures Fail: Sampler's Story

15:34 Rebirth of a Business Idea

17:55 Bouncing Back from Bankruptcy

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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 Papanikolov

00:01:04 Meet Rainbow's Mushroom Maven

00:03:57 Full Moon Guru Wisdom

00:12:14 Mushroom Magic in Every Product

00:16:11 Western Approach to Eastern Wisdom

00:18:21 Mushrooms 101: Beginner's Guide

00:30:50 Power Couple Behind Rainbow

00:39:20 Standing Out in Mushroom Market

00:48:18 Kundalini Culture in Company

00:58:39 Midlife Kundalini Awakening

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 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 Mehta

00:53 Gainsight's Guru: Meet Nick Mehta

02:14 Taylor Swift: Nick's Unexpected Muse

05:01 The Many Faces of Nick

13:29 Nick's Literary Legacy: Five Books

17:48 Keeping Customer Focus at Scale

24:16 Glassdoor Glory: Gainsight's Triumph

28:44 Five Pillars: Gainsight's Core Values

38:22 Ganesh's Wisdom: Letting Go

46:28 Wrapping Up: Kudos to Nick

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/

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 Weapon

05:23 Comeback Kings: Fitness Redemption Stories

09:37 Sleep: The Sacrificial Startup Lamb

16:59 Burnout: Recognizing the Warning Signs

20:59 KPIs for Your Body

33:05 Urgency vs. Boundaries: Finding Balance

38:16 Outsourcing Meals: Fueling Success Effortlessly

48:50 Sobering Up: Energy and Productivity Boost

56:13 Startup CEO Show: Until Next Time

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/