The Startup CEO Show Mark MacLeod

Are you seeking invaluable tips on becoming a successful startup CEO?
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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/

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!
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⏰Timestamps:
04:33 - 07:01: How the Pandemics Shifted Businessess
07:01 - 11:11: Strategic Moves: Meta.com Acquisition
11:11 - 14:54: Startup Success: Pandemic Agility
14:54 - 18:55: Energy Efficiency: HVAC Optimization
20:06 - 25:20: Seamless Transition to Remote Work
25:20 - 28:01: Collaboration & Resilience
28:01 - 31:50: CEO's Time Management: Maximizing Availability
31:50 - 36:24: Inclusive Leadership: Empowering Sales
38:06 - 42:34: Embracing Change: COO to CEO
42:34 - 45:24: Career Evolution: Shedding Norms
45:24 - 49:02: Diverse Journey: Consulting to Product Leadership
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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/

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!
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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 communication
23:54 - 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.
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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/