🏠 Is Canada’s dream of home ownership officially dead?

In this episode of the Profit or Pivot Podcast, I sit down with Mark Freedman, entrepreneur, investor, and former Head of Product who helped lead a startup to a $100M+ exit, to talk about building and scaling businesses, product leadership, and why real estate in Canada and other major cities is becoming increasingly out of reach.

Mark shares how he helped grow a SaaS company from $600K ARR to over $10M and what those lessons taught him about value creation, conviction, and execution. Now, as a partner at Stonefield Capital, he turns that same discipline toward real estate lending and investing, and offers an unfiltered take on Canada’s housing market.

We discuss:

• Why owning a home in Canada may soon be impossible for most
• The real cause of the housing affordability crisis
• Lessons from scaling a business to a $100M exit
• Why conviction and discipline matter in every market, housing or tech
• Why most startups underprice their products (and how to fix it)
• The art of letting go of bad customers

Whether you’re a founder, product leader, or investor, Mark’s journey is packed with lessons about growth, conviction, and building lasting businesses, and it’s a must-watch for anyone who cares about building wealth, investing smart, and understanding the future of real estate in Canada.

About Mark Freedman

Mark is a seasoned technology and financial services professional/entrepreneur with a track record of driving rapid growth and operational scale. Most recently, he helped grow Mortgage Automator from a 12-person, $500K revenue startup into a 65-person, $10M ARR company, culminating in a nine-figure acquisition within four years.

Before that, Mark held diverse roles across sports engineering, higher education, and financial services, as well as a brief period in consulting. He now serves as Managing Partner at Stonefield Capital, a private lending firm based in Canada, where he has helped grow assets under management by over 30% year-over-year, currently surpassing $50M.

A lifelong technologist and father of two, Mark is passionate about community building, mentorship, and leveraging technology to streamline traditional finance operations.

Connect with Mark

LinkedIn

Email: ✉️ [email protected]