In this milestone 50th episode of The Startup CEO Show, host Mark MacLeod reflects on 25 key lessons from his 25 years in the startup world. Drawing from his extensive experience as a CFO, venture capitalist, and advisor, Mark shares invaluable insights on timing, market dynamics, fundraising, and leadership.

He emphasizes how timing and luck play a crucial role in startup success, citing examples like Tungle's fortunate Series A raise just before the 2008 financial crisis. MacLeod also delves into the challenges of operating in hot markets, the potential of disrupting established industries, and the pitfalls of poor market selection. He shares candid thoughts on the venture capital industry, board dynamics, and the importance of founder self-awareness.

Throughout the episode, Mark peppers in anecdotes from his work with successful companies like Shopify, providing listeners with a rich tapestry of startup wisdom.

Tune in to gain insights that could shape your entrepreneurial journey and potentially save you from costly mistakes.

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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/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

The Startup CEO Show takes a deep dive into the world of conscious entrepreneurship in this enlightening episode featuring Shrad Rao, the visionary former CEO of Wagepoint. Host Mark MacLeod guides listeners through a fascinating discussion that bridges Eastern spirituality with Western business acumen. Rao, fresh from stepping down after over a decade at the helm of Wagepoint, shares his journey of building a successful tech company while maintaining a strong spiritual foundation.

The episode explores the emotional landscape of transitioning out of a long-held CEO position, with Rao candidly discussing the mix of exhilaration and grief he experienced. He reveals his unique approach to leadership, emphasizing the importance of caring deeply for employees and creating a culture of experimentation and growth. Rao's insights into conducting personal "culture calls" with potential hires and his philosophy on parting ways with employees compassionately offer valuable lessons for leaders at all levels.

MacLeod and Rao delve into the power of intuition in business decision-making, discussing how to balance analytical thinking with gut instincts. The conversation takes an introspective turn as both share their experiences with Eastern spiritual practices and how these inform their leadership styles. Rao's perspective on the intersection of creativity and technology, inspired by figures like Steve Jobs and Warren Buffett, provides a fresh take on innovation in the tech industry.

This episode is a must-listen for entrepreneurs and leaders seeking to infuse their business practices with mindfulness and compassion while driving success.

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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/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, Mark MacLeod engages in a deep and insightful conversation with Alison Taylor, co-founder and co-CEO of Jane App, a leading practice management and scheduling platform for healthcare clinics. Alison shares the remarkable journey of building Jane from a solution for her own healthcare practice to a thriving company with 600 employees and a global user base. Alison's unique perspective on growth, prioritizing customer and team satisfaction over rapid expansion at all costs, provides a refreshing alternative to the typical startup narrative.

The conversation delves into the intricacies of maintaining a successful co-founder relationship, with Alison and her partner Trevor sharing the CEO role. She emphasizes the importance of values alignment and having a shared vision for the company's future. Alison also provides valuable insights into the advantages and challenges of building a tech company in Canada, advocating for the strength of the Canadian startup ecosystem and the importance of contributing to its growth.

One of the most compelling aspects of the conversation is Alison's candid discussion of balancing the demands of running a fast-growing company with personal life. As a solo parent to three teenagers, she offers a unique perspective on the challenges faced by working parents, particularly women, in leadership roles. Alison provides thought-provoking insights into gender roles in the workplace and at home, emphasizing the need for true equality in both spheres.

Don't miss this opportunity to learn from one of Canada's most successful tech entrepreneurs - tune in to the Startup CEO Show with Mark McLeod and gain invaluable insights that could shape your own entrepreneurial journey.

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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/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, host Mark MacLeod sits down with David Cancel, a five-time founder and tech industry veteran, to explore the secrets behind building successful startups.

David shares invaluable insights from his experiences founding companies like Performable and Drift, as well as his pivotal role at HubSpot. The conversation delves into David's decision to sell Performable to HubSpot, a move that transformed both companies. David reveals how he rebuilt HubSpot's engineering team from the ground up while simultaneously scaling the business towards an IPO - a feat he likens to "changing a plane engine mid-flight." Listeners will gain a rare glimpse into the strategic thinking and bold decision-making that propelled HubSpot to its current $36 billion valuation.

The episode also covers David's journey with Drift, exploring how he identified a massive opportunity in conversational marketing and built one of the fastest-growing SaaS companies in history. David offers candid reflections on work-life balance, the challenges of entrepreneurship, and the importance of continuous learning.

Don't miss out on these hard-earned lessons from one of tech's most accomplished leaders - tune in now!

The latest episode of the Startup CEO Show features an enlightening conversation with Nick Franklin, the visionary behind ChartMogul, a leading subscription analytics platform. Mark McLeod explores ChartMogul's evolution from a niche product to a comprehensive platform for B2B SaaS companies. Nick shares fascinating insights into the state of SaaS metrics, revealing that while core metrics like MRR and churn remain crucial, the rise of AI and metered billing is reshaping the landscape.

The discussion touches on ChartMogul's unique position as a barometer for the SaaS industry, offering listeners a rare glimpse into industry-wide trends and benchmarks. Nick's journey from an illustration background to becoming a successful tech CEO is both inspiring and instructive, highlighting the importance of adaptability and continuous learning in the startup world.

The episode also dives into the challenges of remote work, with ChartMogul embracing a distributed model long before it became mainstream. Listeners will appreciate Nick's candid reflections on the pros and cons of venture funding, and his decision to prioritize profitability over rapid, unsustainable growth. Don't miss this opportunity to learn from one of the industry's most experienced and thoughtful leaders.

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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/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Contact Mark: https://markmacleod.me/

In this captivating episode of the Startup CEO Show, host Mark MacLeod sits down with Mike Serbinis, a prolific tech entrepreneur with over $1 billion in exits under his belt. Mike shares his incredible journey from engineer to CEO, including competing against Amazon with his e-reader company Kobo and his current venture League, a healthcare technology platform with over 20 million users.

Dive into Mike's experiences in Silicon Valley, his approach to building and scaling companies, and how he's tackled immense challenges in the healthcare industry. Mike discusses the importance of going for "gold" in business, likening it to the Olympics where only the top performers are remembered. He also reveals his strategies for maintaining work-life balance while pursuing ambitious goals, including his weekly "Week Ahead" memos that have become a cornerstone of his leadership style.

Tune in now to learn from one of tech's most successful founders and gain actionable insights to apply to your own entrepreneurial journey.

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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/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

This episode of the Startup CEO Show delves deep into the world of sustainable business practices and corporate responsibility with Stuart Lombard, the visionary behind Ecobee. Mark MacLeod guides the conversation through Lombard's philosophy on building a company that not only succeeds financially but also makes a positive impact on the world.

Lombard shares compelling examples of how Ecobee integrated sustainability into its core business model, from reducing packaging and optimizing shipping methods to negotiating better payment terms with suppliers. He explains how these practices not only reduced the company's environmental footprint but also improved its bottom line, challenging the notion that sustainability always comes at a cost.

The discussion also touches on Ecobee's innovative "donate your data to science" program, which allowed the company to contribute to groundbreaking research in energy efficiency and senior care. Lombard's insights demonstrate how corporations can act as responsible citizens in their communities while driving innovation and growth.

Don't miss this inspiring conversation that will change the way you think about business and sustainability.

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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/

Connect on X/Twitter: https://twitter.com/markmacleod_

Contact Mark: https://markmacleod.me/

Welcome to another episode of The Startup CEO Show!

This week, we have a special video edition featuring Joel Gascoigne, founder and CEO of Buffer, known for its revolutionary approach to transparency and remote work. Our host, Mark MacLeod, dives deep with Joel into the intricacies of managing a startup during times of growth and decline, the strategic changes that Buffer has embarked on, and the personal journey of leadership.

Joel shares his unique experience of managing 12 direct reports and transitioning to an asynchronous communication model to foster deep work and reduce meeting overload. He reflects on overcoming challenges, such as plateauing growth and navigating the pandemic's impacts with a renewed focus on supporting entrepreneurs and small businesses. We also explore the dynamics of co-founder relationships, raising and managing investor expectations, and Buffer’s return to a bootstrap model after a strategic VC buyout.

Joel's insights into the long-term strategic vision, maintaining company culture, and embracing transparency offer invaluable lessons for startup CEOs and leaders striving to sustain growth while preserving core values. Plus, we touch on how fatherhood has influenced Joel's productivity and work-life balance.

Tune in to glean actionable strategies for managing your startup more effectively and authentically.

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

Stay updated on X: https://x.com/markmacleod_

Get in touch with Mark: https://markmacleod.me/