What if the person who pulled you out of the wrong room turned out to be the right partner for the next 25 years?

In this episode, Jason Henneberry, founder of Dependency Design and senior partner in a national Canadian mortgage brokerage with over 600 professionals, shares the story of a career that has spanned market peaks, a near-bankruptcy in 2008, a dramatic rebuild, and a bold acquisition spree that captured 2% of the Canadian mortgage market in 12 months.

At the center of it all is a man who walked into a bank branch, pulled a young Jason out of the corporate world, and said: come do mortgages with me. That was 2003. They still work together today.

[00:03:30] What He Does and Who He Serves

Senior partner in a national Canadian mortgage brokerage with over 600 agents
Runs a coaching platform and SaaS tools for the mortgage industry
Tests ideas externally before bringing them in-house; it proves demand and pays for development

[00:07:00] What Inspires Him: The Creative Process

Loves coming up with new ideas and testing them in the market
Protects the core business while running two or three experiments at a time
Goes deep on whatever works and drops the rest

[00:11:30] Client Impact: Helping Mortgage Brokers See the Full Picture

Coaches mortgage professionals on advanced financial strategies most brokers never explore
Helps brokers connect mortgages to tax, wealth, and estate planning
Watches clients implement and grow without being involved in the transactions

[00:13:30] The Relationship That Changed Everything: His First Mentor

Was working in a bank branch when a gentleman pulled him out and said: come do mortgages with me
That was 2003; they have worked together every year since
The mentor now sits as chairman of the board of the company they built together
Nearly 25 years later that one moment still underpins everything Jason has built

[00:15:00] The 2008 Collapse: Everything Came Apart

Ran 300 homeowner seminars and put 20,000 people through the program in 2006 and 2007
Wrote a 12-month marketing check in August 2008; the market collapsed on September 14th
Had to sell everything including a house with an ocean view
Reset from zero with three young kids and no runway

[00:18:00] The Capital Markets Mentor Who Rebuilt Everything

Around 2016 met someone deeply experienced in raising capital
That relationship led to the formation of Tango and a major capital raise
Used the capital to acquire brokerages across the country
Captured roughly 2% of the Canadian mortgage market in 12 months

[00:20:00] The Leadership Lesson from All Three Mentors

All three mentors had different skill sets but shared one principle
Point good people in the right direction and get out of their way
People with the right skills and direction will always exceed what you could do alone

[00:21:30] Dependency Design: The Book and the Mission

Wrote a free 15-minute PDF called Dependency Design, available at dependencydesign.com
Explores why founders build businesses that feel like freedom but end up like traps
Helps leaders see where responsibility has quietly settled and how to rise above it

KEY QUOTES

"When you let good people apply their skills with a little bit of direction, they can do things that far exceed anything you could possibly imagine doing for yourself." - Jason Henneberry

"No one wakes up and says I want to be a mortgage broker. My first choice didn't work out, so I did this instead." - Jason Henneberry

CONNECT WITH JASON HENNEBERRY

Website: https://dependencydesign.com

LinkedIn: https://www.linkedin.com/in/jasonhenneberry

Facebook: https://www.facebook.com/henneberryjason

Thanks for tuning in!

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