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Mark Macleod: Ex-Shopify CFO: The Exit Strategy Every Founder Should Hear
What does it really take to sell your company for life-changing money?
In this episode of THE EXIT, I sit down with Mark Macleod — former CFO of Shopify and FreshBooks, founder of SurePath Capital, and the coach behind over $1B in successful exits — to uncover the real truth behind the startup exit process.
We talk about:
- The biggest mistakes founders make during an exit
- The psychology of selling your company (and what comes after)
- Why most earn-outs are traps
- How Marc built his post-exit life around mindfulness, purpose, and founder performance
- Tactical advice on aligning with acquirers and investment bankers
- Why your physical and mental health are the #1 growth tools as a founder
If you're building, scaling, or selling a venture-backed startup, this is the episode you can't afford to miss.
Subscribe for more real conversations with world-class founders, investors, and M&A experts.
Timestamps
00:00 Introduction of Mark Macleod
01:00 Mark's Background in Venture-Backed Startups
02:15 Yahoo Purchasing Facebook?
04:30 What Makes for a Successful Acquisition?
06:24 Why I Avoid Earnouts
07:55 Psychological Aspects of Selling a Company
09:55 Founder Burnout and Recovery Time
12:36 Importance of Being Present
13:20 Fitness and Mental Health for CEOs
20:00 The Role of Coaching in Startups
21:34 Operational Experience in Coaching
26:20 Two Things You Need to Succeed in Business
29:04 What Founders Get Wrong Pre-Exit
32:30 Should Founders Work With I-Bankers and When?
41:28 Avoiding Exit Landmines
48:24 Coaching and Providing Tough Feedback
49:44 Creating a Massive Business You Never Want to Exit
🔗 Follow the Guests & HostsTHE EXIT GROUP® – https://www.theexit.group
Instagram – http://www.instagram.com/theexit.group
Mark Macleod – https://www.linkedin.com/in/themarkmacleod/
Adrian Salamunovic – https://www.linkedin.com/in/adriansalamunovic/
#startup #founderlife #exitstrategy #venturecapital #marcmacleod #adriansalamunovic #theexitpodcast #shopify #freshbooks #burnout #startupcoach #founderhealth #startupmistakes #mna #founderexit
View all episodes
By Adrian SalamunovicWhat does it really take to sell your company for life-changing money?
In this episode of THE EXIT, I sit down with Mark Macleod — former CFO of Shopify and FreshBooks, founder of SurePath Capital, and the coach behind over $1B in successful exits — to uncover the real truth behind the startup exit process.
We talk about:
- The biggest mistakes founders make during an exit
- The psychology of selling your company (and what comes after)
- Why most earn-outs are traps
- How Marc built his post-exit life around mindfulness, purpose, and founder performance
- Tactical advice on aligning with acquirers and investment bankers
- Why your physical and mental health are the #1 growth tools as a founder
If you're building, scaling, or selling a venture-backed startup, this is the episode you can't afford to miss.
Subscribe for more real conversations with world-class founders, investors, and M&A experts.
Timestamps
00:00 Introduction of Mark Macleod
01:00 Mark's Background in Venture-Backed Startups
02:15 Yahoo Purchasing Facebook?
04:30 What Makes for a Successful Acquisition?
06:24 Why I Avoid Earnouts
07:55 Psychological Aspects of Selling a Company
09:55 Founder Burnout and Recovery Time
12:36 Importance of Being Present
13:20 Fitness and Mental Health for CEOs
20:00 The Role of Coaching in Startups
21:34 Operational Experience in Coaching
26:20 Two Things You Need to Succeed in Business
29:04 What Founders Get Wrong Pre-Exit
32:30 Should Founders Work With I-Bankers and When?
41:28 Avoiding Exit Landmines
48:24 Coaching and Providing Tough Feedback
49:44 Creating a Massive Business You Never Want to Exit
🔗 Follow the Guests & HostsTHE EXIT GROUP® – https://www.theexit.group
Instagram – http://www.instagram.com/theexit.group
Mark Macleod – https://www.linkedin.com/in/themarkmacleod/
Adrian Salamunovic – https://www.linkedin.com/in/adriansalamunovic/
#startup #founderlife #exitstrategy #venturecapital #marcmacleod #adriansalamunovic #theexitpodcast #shopify #freshbooks #burnout #startupcoach #founderhealth #startupmistakes #mna #founderexit