The Startup CEO Show Mark MacLeod

Seeking valuable insights on startup success and leadership strategies for CEOs?
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In this episode of The Startup CEO Show, host Mark MacLeod engages in a thought-provoking dialogue with Michael Litt, the innovative CEO of Vidyard and investor at Garage Capital. Discover the secrets behind transforming startups into scale-ups, insights of being part of Y Combinator in Silicon Valley, and navigating the ever-evolving tech landscape.
Explore Michael's perspective on staying innovative and energized, the nexus between investing and entrepreneurship, and the pivotal role of bleeding-edge technology in shaping the future of businesses.
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Key highlights:
04:15 The Genesis of Vidyard and Entrepreneurial Journey
08:30 Unleashing the Potential of AI in B2B Commerce
12:45 Crafting Sustainable Growth Strategies
18:20 Revolutionizing Customer Interactions with AI Avatars
24:10 Building a Strong Executive Leadership Team
30:50 Leveraging AI for Enhanced Customer Outreach
37:30 The Impact of University of Waterloo on Startup Ecosystem
42:15 Founder CEO vs. Professional CEO Insights
48:40 Navigating the Startup Landscape and Building 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/

Seeking the best startup and leadership advice tailored for CEOs?
SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/
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Are you curious about the journey of raising over $400 million in capital and navigating the path from startup to IPO? Tune in for this enlightening conversation!
In this episode, host Mark MacLeod delves deep with Jack Newton, the co-founder and CEO of Clio, to explore the multi-faceted aspects of leading a legal tech company. Jack shares the inspiring story of Clio's origin, the pivotal moments in their fundraising journey, and the strategic decisions that led them to become a market leader.
Discover insights into how Jack and his co-founder Ryan balanced their roles, the crucial importance of continuous learning, and how surrounding oneself with experienced team members can propel a company forward.
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Key moments:
04:15 The Origin Story of Clio
08:30 Importance of Product and Technology Expertise
11:45 Securing First Institutional Angel Funding
19:20 Growth Stage Power Dynamics
25:50 Transitioning from Venture to Private Equity
33:05 Choosing the Right Partners for Growth
40:50 Vertical SaaS and Customer Retention
46:30 Preparing for an IPO and Future Growth
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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/

Are you seeking invaluable tips on becoming a successful startup CEO?
SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/
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In this episode, Mark MacLeod gets into an engaging discussion with Hiten Shah, the co-founder and CEO of Nira, exploring the myriad facets of leading and funding a startup. Hiten shares his experiences and philosophies, ranging from the necessity of aligning product development with customer feedback to the intricacies of venture capital and self-funding.
Discover the profound insights on venture capital investment, the vital importance of investor-founder alignment, and Hiten's unique approach to product innovation and company culture. This episode is perfect for aspiring entrepreneurs and seasoned executives alike, who are eager to learn from someone who has walked the challenging path of startup success.
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Key moments:
05:10 How to Build a Startup from Scratch
11:20 Advantages of Self-funding versus VC
14:45 The role of Investors
19:30 Strategies for Handling Risk and Investors
29:10 Remote Work and its Impact on Company Culture
32:40 Discussion on Customer Obsession
37:50 Challenges of raising money and the timing of investment pitches.
42:05 Understanding and Leveraging Investor Expectations.
47:00 Accountability in Remote Work and Transparency in Business.
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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/

Looking for the best Startup CEO insights?
SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/
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In this episode, Mark MacLeod sits with Stephany Lapierre, the founder and CEO of Tealbook, as she recounts her journey from a background in consulting to becoming a trailblazing female founder in the tech industry.
They explore the evolution of Tealbook, emphasizing the importance of using feedback to drive decisions, the challenges of scaling technology, and the unique difficulties she faced as a solo female founder. The conversation also delves into the crucial support systems for women-led technology companies and the importance of community in fostering startup growth. This episode is a must-listen for anyone interested in the highs and lows of startup leadership, especially from the perspective of a resilient entrepreneur working to bridge gender gaps in the tech industry.
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Key moments:
00:00 Introduction to Stephany Lapierre and Tealbook.
04:15 Discussing the transition from consulting to tech startup.
09:22 The role of feedback in decision making.
12:37 Challenges in scaling and technology development.
17:45 The support from Fresh Founders and Stand Up Ventures.
22:30 Gender challenges in the startup ecosystem.
27:00 Insights into hiring and building a company culture.
31:55 How the COVID-19 pandemic influenced business operations.
38:10 Navigating underfunding and technology scalability.
43:03 The importance of staying informed and understanding technology.
48:15 Final thoughts on leadership and future aspirations.
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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/

Looking for the best Startup CEO Insights?
SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/
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In this episode, we’re joined by former Dribbble CEO, Zack Onisko, who shares his insightful experiences from leading one of the few remaining independently owned social networks designed specifically for designers.
Zack and host Mark MacLeod discuss his decision to step down, reflecting on a period of significant profitability and growth at Dribbble, achieved without the backing of venture capital. Making major career transitions, the impact of leadership on company culture, and the importance of aligning personal values with professional endeavors are some of the key topics of this episode. Join us for a compelling conversation that unveils the nuances of steering a tech enterprise through evolving landscapes and personal growth.
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Key moments:
00:00 Leaving Dribbble due to personal pursuits.
05:42 Silicon Valley raised CEO reflects on growth.
06:48 Talking to investors, company grew, profitable results.
10:11 Technology has shifted startup landscape, lowering expenses.
13:54 Email crucial for user acquisition and revenue.
18:00 Transition from investment banker to coach amidst COVID.
20:58 Transition from employee to successful entrepreneur for freedom.
24:27 Self-driven urgency led to company's success.
28:01 Learning from Andrew's entrepreneurial and investment approach.
30:29 Transitioned from startup operator to capital management.
36:43 Reinvesting profits to fuel company growth and acquisitions.
40:52 Shifted managerial style, focused on building trust.
42:10 Remote work offers efficiency and productivity benefits.
46:58 Found your insights helpful, want to explore further.
50:28 Joining Dribbble was a dream come true, looking to pursuit new ones
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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/

Want to receive the best Startup CEO Insights?
SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/
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In this episode of the Startup CEO Show, explore the power of long-term vision and work-life integration with our host Mark MacLeod and the inspiring Erin Bury, co-founder and CEO of the innovative estate planning platform, Willful.
Tune in as Erin sheds light on rejecting hustle culture, creating ease for families with online wills, and steering a startup alongside her spouse. Discover how Willful is simplifying end-of-life planning and Erin's unique approach to leading a consumer brand and fostering a startup that values both profitability and a balanced lifestyle.
Make sure to like, share, comment, and subscribe to stay updated with more fascinating episodes like this one from the Startup CEO Show!
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⏰Timestamps:
02:20 - 05:49: Rejecting "Hustle Porn" for Work-Life Balance
05:50 - 08:33: Willful's Origins and Market Disruption
08:34 - 12:05: Overcoming Investor Doubts
12:06 - 15:40: The Joys and Juggles of a Spouse-Run Startup
15:41 - 18:15: Erin's CEO Strategy: Hiring, Vision, and Financial Stability
18:16 - 22:10: Personal Time Management
22:11 - 26:00: The Willful Couple's Work-Life Blend
26:01 - 29:35: Startup Ecosystem as a Consumer Brand
29:36 - 33:08: The Canadian Startup Scene
33:09 - 36:45: Fostering a Sustainable Business
36:46 - 40:25: Young Parents and Elderly Individuals
40:26 - 43:10: Strategic Partnerships and Marketing in Estate Planning
43:11 - 46:55: Life, Legacy, and Running a Startup
46:56 - 50:26: The "Unicorn" Potential
50:27 - 55:00: Intentional Living and the Reality of Entrepreneurship
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Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/
Connect on X/Twitter: https://twitter.com/markmacleod_
Contact Mark: https://markmacleod.me/