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Investing: Hard Lessons From a Collapsing Portfolio - Forge Contractor Podcast
In this episode of Forge, Josh and Kenton dive into a deeply personal story from Kenton’s early years in business. In his twenties, Kenton was heavily involved in real estate investing, building momentum with multiple properties, partnerships, and ambitious development projects.
It was a time marked by optimism, energy, and the feeling that anything was possible. Deals were working, banks were lending, and every step forward seemed to open another opportunity.
But life has a way of testing even the most confident seasons.
Within a short period of time, several major events collided. A large development project in northern Alberta fell apart at the last moment. Seven rental units over half of his portfolio, suddenly became vacant at the same time.
At home, Kenton and his wife were navigating the emotional weight of losing two grandparents within weeks of each other while also expecting their first child. What had once felt like unstoppable momentum quickly turned into overwhelming pressure.
Faced with that perfect storm, panic set in. Instead of leaning on his partners and the relationships he had built, Kenton made decisions in isolation, fire-selling properties and stepping away from opportunities that, in hindsight, could have changed the trajectory of his life.
The lesson wasn’t just about business strategy. It was about pride, communication, and the weight leaders sometimes place on their own shoulders.
Throughout the conversation, Josh and Kenton reflect on the tension many entrepreneurs experience: the instinct to shoulder responsibility alone versus the humility required to ask for help. They explore how assumptions about what others are willing or able to do can quietly shape the decisions we make in moments of stress.
They also discuss how failure affects different personalities. For someone used to succeeding, a major setback can cut deeper and take longer to recover from. The optimism and confidence that fuel early success can also make failure feel like a defining moment rather than simply part of the journey.
This episode is not about dwelling on the past, but about understanding how pivotal moments shape the way we lead, take risks, and build trust moving forward. It’s a conversation about leadership under pressure, the importance of honest dialogue with partners, and the long process of rebuilding confidence after a major setback.
Original theme music composed and performed by: Ben Smith
Produced by: Seth Steward Productions
Co produced by: Kalen Wookey
Website: https://forgealliance.ca/
Instagram: https://www.instagram.com/forgecontractoralliance
Facebook: https://www.facebook.com/profile.php?id=61575541841797
X https://x.com/forge_ca
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By Forge Contractor AllianceIn this episode of Forge, Josh and Kenton dive into a deeply personal story from Kenton’s early years in business. In his twenties, Kenton was heavily involved in real estate investing, building momentum with multiple properties, partnerships, and ambitious development projects.
It was a time marked by optimism, energy, and the feeling that anything was possible. Deals were working, banks were lending, and every step forward seemed to open another opportunity.
But life has a way of testing even the most confident seasons.
Within a short period of time, several major events collided. A large development project in northern Alberta fell apart at the last moment. Seven rental units over half of his portfolio, suddenly became vacant at the same time.
At home, Kenton and his wife were navigating the emotional weight of losing two grandparents within weeks of each other while also expecting their first child. What had once felt like unstoppable momentum quickly turned into overwhelming pressure.
Faced with that perfect storm, panic set in. Instead of leaning on his partners and the relationships he had built, Kenton made decisions in isolation, fire-selling properties and stepping away from opportunities that, in hindsight, could have changed the trajectory of his life.
The lesson wasn’t just about business strategy. It was about pride, communication, and the weight leaders sometimes place on their own shoulders.
Throughout the conversation, Josh and Kenton reflect on the tension many entrepreneurs experience: the instinct to shoulder responsibility alone versus the humility required to ask for help. They explore how assumptions about what others are willing or able to do can quietly shape the decisions we make in moments of stress.
They also discuss how failure affects different personalities. For someone used to succeeding, a major setback can cut deeper and take longer to recover from. The optimism and confidence that fuel early success can also make failure feel like a defining moment rather than simply part of the journey.
This episode is not about dwelling on the past, but about understanding how pivotal moments shape the way we lead, take risks, and build trust moving forward. It’s a conversation about leadership under pressure, the importance of honest dialogue with partners, and the long process of rebuilding confidence after a major setback.
Original theme music composed and performed by: Ben Smith
Produced by: Seth Steward Productions
Co produced by: Kalen Wookey
Website: https://forgealliance.ca/
Instagram: https://www.instagram.com/forgecontractoralliance
Facebook: https://www.facebook.com/profile.php?id=61575541841797
X https://x.com/forge_ca