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/

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 CEO

03:26 Chili Piper: Spicing Up Sales Software

06:11 Raw and Real: Alina's Authentic Approach

10:16 Social Media: The Pipeline Powerhouse

12:20 Speaking Up: Time Well Invested

16:42 Dividing and Conquering CEO Duties

19:42 Remote Work: Born from Wanderlust

29:48 Bootstrapping to Millions: Chili Piper's Journey

35:48 AI: Blessing or Terminator Scenario?

43:00 Corporate Wisdom in Startup Land

48:07 Inspiring Women: Alina's Ripple Effect

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/

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.

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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/

In this episode of the Startup CEO Show, Mark MacLeod sits down with Christine Song, a multi-time Chief People Officer with extensive experience in both established corporations and high-growth startups. They dive deep into the critical role of people and HR in scaling successful companies. Christine shares her journey from corporate HR to becoming a strategic partner for startup CEOs, offering a wealth of knowledge on building high-performance cultures, giving direct feedback, and balancing employee growth with business objectives.

The conversation explores how HR has evolved from a back-office function to a key strategic role, especially in the wake of COVID-19. Christine emphasizes the importance of HR leaders earning their seat at the executive table by tying initiatives to business outcomes and being willing to have difficult conversations. She also discusses the challenges of scaling company culture, the need for honest communication about work expectations, and the value of investing in high-potential employees. Mark and Christine debate the merits of pushing people out of their comfort zones versus prioritizing employee happiness, offering valuable insights for leaders grappling with these tradeoffs.

Listeners will gain practical advice on improving company communication, implementing effective coaching and talent development programs, and creating a culture of feedback and continuous improvement. The episode concludes with Christine introducing her new venture, Five to Nine Society, an exclusive network for elite operators and founders. Don't miss out on this compelling discussion - tune in now to elevate your leadership and people management skills!

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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/

In this insightful episode of the Startup CEO Show, host Mark MacLeod sits down with Darrell Heaps, co-founder and CEO of Q4 Inc., to explore the fascinating 18-year journey of building a successful investor relations platform.

Heaps shares his experiences navigating different stages of growth, from bootstrapping to venture funding, going public, and ultimately becoming private equity-backed. He offers valuable advice on avoiding burnout as a long-term CEO, emphasizing the importance of setting challenging goals and constantly evolving. Heaps discusses how he's grown as a leader, including learning to delegate effectively and leverage diverse personality types on his executive team.

He provides an inside look at the realities of taking a company public, including the challenges of managing stock price fluctuations and balancing investor relations with day-to-day operations. For founders considering an IPO, Heaps offers candid insights on the pros and cons, as well as key considerations around timing and scale. Tune in to gain wisdom from Heaps' nearly two decades of experience leading Q4 through multiple phases of growth and funding.

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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/

In this episode of the Startup CEO Show, host Mark MacLeod sits down with Casey Woo, founder of Operators Guild and Fog Ventures, to explore the evolving landscape of executive roles in the tech industry. Woo, a former military officer and six-time CFO, shares his unique perspective on how AI is reshaping the business world and creating new opportunities for multidisciplinary leaders he calls "scalers."

The conversation delves into the changing nature of the CFO role, with Woo arguing that modern CFOs are becoming "mini CEOs" who need to be strategic partners rather than just number crunchers. He discusses how AI is making specialists vulnerable while elevating the importance of generalists who can synthesize information across disciplines. Woo introduces the concept of "scalers" - versatile executives who don't code or sell, but excel at solving complex business problems and leveraging AI for insights.

Listeners will gain valuable insights into the future of executive leadership, the impact of AI on various roles, and the growing importance of business intelligence. Woo also shares details about Operators Guild, a community he founded for non-technical executives in tech startups. Tune in to learn how you can position yourself for success in this rapidly changing 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/

In this captivating episode of the Startup CEO Show, host Mark MacLeod sits down with Rand Fishkin, co-founder and CEO of SparkToro, for a candid conversation about entrepreneurship, venture capital, and building successful businesses. Rand, best known for founding Moz and his influential role in the SEO industry, shares invaluable insights from his journey as a founder and thought leader.

The discussion delves into the pros and cons of building a personal brand as a CEO, with Rand reflecting on how his own high profile impacted Moz both positively and negatively. He offers a refreshing perspective on the venture capital world, discussing why he now advocates for alternative funding models that prioritize sustainable growth over hypergrowth. Rand also provides a fascinating look at his current ventures, including SparkToro and Snackbar Studio, explaining how he's applying lessons learned from Moz to build more balanced, founder-friendly companies.

This episode is a must-listen for entrepreneurs, marketers, and anyone interested in the realities of building and scaling startups in today's competitive landscape. Tune in to gain actionable advice from one of tech's most respected voices and learn why sometimes the path less traveled leads to greater success and fulfillment.

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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/

In this insightful episode of the Startup CEO Show, host Mark MacLeod sits down with Eli Portnoy, a serial entrepreneur with two successful exits under his belt. Portnoy shares his journey from his first venture to his current role as co-founder and CEO of BackEngine, offering a masterclass in navigating acquisitions and building thriving startups. The conversation delves into the psychological aspects of selling a company, the importance of building relationships with potential acquirers, and the challenges of transitioning from founder to employee post-acquisition.

Portnoy's candid reflections on his experiences provide valuable lessons for aspiring entrepreneurs, emphasizing the rarity of acquisition opportunities and the need to carefully consider one's motivations when faced with an offer. The episode also explores Portnoy's current venture, Back Engine, which leverages AI to help companies maintain a strong connection with their customers as they scale. Listeners will gain actionable insights on fundraising, exits, and the evolving landscape of startup leadership in the age of AI.

Tune in to learn from Portnoy's successes and challenges, and discover how to build a company with long-term vision while remaining open to transformative opportunities.

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/