Mark MacLeod on AI, Leadership & Redefining Success

Meet Mark MacLeod, since 1999, Mark MacLeod has been funding, growing and exiting high growth software companies as either a CFO, VC, investment banker or CEO coach.

Mark served as CFO for many companies including Shopify and FreshBooks. He was a General Partner at Real Ventures, Canada’s largest seed stage venture fund. In addition, he founded SurePath Capital Partners, the leading investment bank focused on SMB software companies.

Mark coaches the CEOs of high growth software companies, helping them lead all the way to a massive exit without burning out and is the host of The Startup CEO Show podcast.

Ahead of his Turing Fest 2025 talk, Mark MacLeod sat down with us to talk AI, ethics and why working 8 hours a day is a bad idea.

1. What new technology do you believe will have the biggest impact on the product development, marketing or tech world in the next 12 to 24 months?

This answer will be shocking: AI. 🙂

I coach a few marketing tech CEOs. The big change I am seeing is experts creating AI agents to scale their impact. Some of the people speaking at Turing Fest may soon have agents. I have one!

2. Reflecting on your experience, what major challenges do you anticipate product/growth/tech will face in the coming years? How do you think leaders should be preparing themselves and their teams to tackle these challenges?

AI is an arms race. OpenAI just raised $40B. There will be “have”s and “have not”s.

Companies will have to disrupt themselves or be disrupted.

3. Considering recent advancements in AI, what are yourl thoughts on the ethical implications? From your perspective, what are the critical ethical challenges that need to be addressed as AI becomes more widespread?

Ethics? Hmmm.. Big thing for me is knowing when I am interacting with AI and AI content or not.

My big concern is that AI is going to make harder for people starting their career to get jobs.

4. From your own experience, how do you see the continuing evolution of remote work and its technologies impacting your own work-life balance?

The CEOs I speak with want staff in office. Staff like remote. It’s a stand off. I expect a lot more companies to mandate in-office.

I am interpreting this as personal sustainability.

Chronic stress is rampant. My big hope is that AI will enable people to automate and delegate a lot more..

6. If you could implement changes to the way people work based on your own routines and practices, what specific adjustments would you make to improve productivity or well-being?

People need boundaries. Every other create on this planet exists in harmony with nature. Humans think we are above it. We are not.

Your brain is not meant to do 8 hours of meetings in a row.

Health is the foundation of your performance and the key to a happy life.

Mark MarcLeod’s Turing Fest talk:** Limitless Leadership: How Top Leaders Keep Growing No Matter the Scale

Why do some leaders hit a wall while others keep going forever? What separates them? What habits, techniques & tools do limitless leaders have? Mark MacLeod coaches some of the most ambitious founders on the planet.
In this talk he shares his insights on how to become a limitless leader.