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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.

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Contact Mark: https://markmacleod.me/