Seeking the best startup and leadership advice tailored for CEOs?SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/ ----------------------------------------------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. -------------------------Key moments: 04:15 The Origin Story of Clio08:30 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-----------------------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/----------------------------------------------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.-------------------------Key moments:05:10 How to Build a Startup from Scratch11:20 Advantages of Self-funding versus VC14:45 The role of Investors19:30 Strategies for Handling Risk and Investors29:10 Remote Work and its Impact on Company Culture32:40 Discussion on Customer Obsession37:50 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.----------------------------------------------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/----------------------------------------------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.-------------------------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.----------------------------------------------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/

Former Dribbble CEO Zack Onisko discusses leading a profitable social network without VC. Key topics: leaving for personal growth, Silicon Valley growth reflections, email for acquisition, transition to coaching, and self-driven success.

Want to receive the best Startup CEO Insights? SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/ ------------------------------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!-----------------------------------------⏰Timestamps: 02:20 - 05:49: Rejecting "Hustle Porn" for Work-Life Balance05:50 - 08:33: Willful's Origins and Market Disruption08:34 - 12:05: Overcoming Investor Doubts 12:06 - 15:40: The Joys and Juggles of a Spouse-Run Startup15:41 - 18:15: Erin's CEO Strategy: Hiring, Vision, and Financial Stability 18:16 - 22:10: Personal Time Management22:11 - 26:00: The Willful Couple's Work-Life Blend 26:01 - 29:35: Startup Ecosystem as a Consumer Brand29:36 - 33:08: The Canadian Startup Scene33:09 - 36:45: Fostering a Sustainable Business36:46 - 40:25: Young Parents and Elderly Individuals40:26 - 43:10: Strategic Partnerships and Marketing in Estate Planning43:11 - 46:55: Life, Legacy, and Running a Startup46:56 - 50:26: The "Unicorn" Potential50:27 - 55:00: Intentional Living and the Reality of Entrepreneurship---------------------------------------------------------------------------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, join Mark MacLeod and Elizabeth Caley for an insightful discussion with Elizabeth Caley, co-founder and CEO of Poppy. Learn how Poppy is revolutionizing indoor air quality with cutting-edge technology and bold leadership.Gain strategic insights as Elizabeth shares her journey from corporate to startup life, navigating product development, and embracing the chaos of entrepreneurship. Discover the power of clear communication, remote work culture hacks, and the magic of co-founder synergy.Don't forget to like, share, comment and subscribe for more insightful episodes like this!-----------------------------------------⏰Timestamps: 04:33 - 07:01: How the Pandemics Shifted Businessess07:01 - 11:11: Strategic Moves: Meta.com Acquisition11:11 - 14:54: Startup Success: Pandemic Agility14:54 - 18:55: Energy Efficiency: HVAC Optimization20:06 - 25:20: Seamless Transition to Remote Work25:20 - 28:01: Collaboration & Resilience28:01 - 31:50: CEO's Time Management: Maximizing Availability31:50 - 36:24: Inclusive Leadership: Empowering Sales38:06 - 42:34: Embracing Change: COO to CEO42:34 - 45:24: Career Evolution: Shedding Norms45:24 - 49:02: Diverse Journey: Consulting to Product Leadership---------------------------------------------------------------------------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, join us as Mark MacLeod welcomes special guest Amar Varma, co-founder and CEO of Mantle, for a captivating discussion. Discover how Mantle is revolutionizing private asset tracking through innovative AI integration and fresh approaches. Gain strategic insights from Amar as he explores market opportunities for startups and the transition to an enterprise-driven model. Explore the complexities of investment strategy and the transformative potential of AI, all while delving into Amar's invaluable firsthand experiences in the startup world.Don't forget to subscribe for more insights on how to become a successfull startup CEO!-----------------------Key moments:00:00 - 04:39 Reimagining market with fresh approach and AI.04:39 - 08:23 A dominant player in finance.08:23 - 13:03 Becoming investor after previous experiences with no regrets.13:03 - 16:25 Invest wisely, be mindful about timing and luck.16:25 - 20:26 Embracing feedback, self-awareness, and professional growth.20:26 - 23:54 Understanding my process and transparent communication23:54 - 26:46 Identify winners by DNA and winning consciousness.26:46 - 29:29:Obsessive people find success in various domains.32:00 - 37:14: Considering alignment before investing in overpriced companies. 37:14 - 41:05: AI progress with potential misuse concerning.41:05 - 43:11: Founder-led company going public. ------------------------------------------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 The Startup CEO Show with Mark MacLeod. In this episode we are diving into a truly enlightening conversation with none other than Chris Savage, the co-founder and CEO of Wistia.This time, we unpack the deeply rooted values that have shaped Chris's company, emphasizing the importance of genuine connections, personal growth, and integrity in leadership.We also explore into the importance of personal branding in today's social media landscape, with Chris explaining why CEOs should be building genuine profiles that resonate with their community. So grab your favorite beverage and enjoy this in-depth episode. Don't forget to subscribe to learn the best advice from the best startup CEOs.------------------------------------------------------Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Connect on X/Twitter: https://twitter.com/markmacleod_Contact Mark: https://markmacleod.me/

Welcome back to the Startup CEO Show with Mark MacLeod. In this episode, we dive deep with Jason Smith, CEO of Klue, into the gritty details of building and leading a tech company in the Competitive Enablement space. Connect with his story as we unravel the nuanced strategies of convincing C-suite executives of your product's value, the science of proving ROI through innovative attribution models, and the brave new world of AI's integration in business operations.Whether you're a startup CEO, a product marketer, or just someone passionate about the intersection of technology, leadership, and growth, this is an episode packed with wisdom you won't want to miss. So plug in and get ready to take notes - this is Startup CEO Show.---------------------Key moments:00:00 - 04:21 How AI is facilitating the transition from raw intel to insight.04:22 - 08:48 Networking and promoting innovative thinkers for change.08:50 - 14:01 In a world with competitive radar, investors see potential.15:35 - 19:01 Comparing sellers' adoption of clue for sales.19:21 - 22:00 Focusing on building culture and customer satisfaction.22:08 - 24:40 Productivity at home, missing human connection.24:43 - 29:50 Leaders learn from mistakes, delegate for growth.30:00 - 33:01 Experience navigating VC world during COVID challenges.33:10 - 36:10 Harnessing competitor data, leveraging AI for insight.36:14 - 38:01 Platform insight still needed for specific competitive edge.41:11 - 45:01 CEO key advices on managing and growing a SaaS company45:02 - 48:15 Balancing work and family life with focus.------------------------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 the Startup CEO Show, where we dive deep into the heart of startup leadership and growth. In this episode, join our host Mark MacLeod as he engages on a thrilling conversation with Notch's CEO, Jordan Huck, regarding the critical decisions and pivots that shape a startup's journey.We will explore the dynamic world startup leaders navigate daily and take a closer look at the challenges faced by companies as they brave new markets. We'll also focus on the relevance of sales and venture capital savvy in the Canadian startup scene.From discussing the emotional rollercoaster of passionate leadership to the cutthroat venture capital markets, we tackle the nuances of growth, value alignment, and the crucial need for personal growth outside one's comfort zone. Get ready to aprehend valuable lessons from a resilient startup CEO! And don't forget to subscribe for more insightful episodes like this.----------Chapters:00:00 - 8:50 How to face challenging times while building a startup09:00 - 18:00 Honest journey, relationship building, finance automation.18:33 - 30:00 Adaptation is vital for business survival.30:09 - 45:00 Raising venture capital fuels growth.46:20 - 48:00 Challenges drive success, belief in ethical leadership.-----------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/