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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/