From Bank Employee to Mortgage Brokerage CEO: Building a 60-Person Team

How Three Brothers Built and Sold Truebill for $1.275 Billion

In this episode, I sit down with Yaya Mokhtarzada, one of three brothers who co-founded Truebill and sold it to Rocket Companies for over a billion dollars. Yaya shares the rollercoaster journey from bootstrapping in a basement to hitting $100M in revenue, including the manual work that got them started and the paid acquisition strategy that scaled them to unicorn status.

From Free Coaching to $700 Per Session: My 13-Year Journey

Michelle Tasco built a $550,000/year one-on-one financial coaching business over 13 years, starting from $8,000 in year one. This is the story of how she went from $68,000 in credit card debt to charging $700 per session, working only 18-23 hours per week. No courses, no group programs, just consistent growth through referrals, local SEO, and mastering the discovery call. She shares her exact five-step coaching process, pricing evolution, marketing strategies, and why the world needs more coaches willing to stick around long enough to succeed.

How I Built an 8-Figure Health Apparel Brand From Scratch

Arthur Menard built three successful businesses before turning 30: an automated online education platform still running a decade later, a door-to-door SaaS company for French bakeries, and now Lambs, an 8-figure health apparel brand. This is the story of how a podcast listener became a guest, how walking around CES in underwear created breakthrough exposure, and how focusing on conversion rates before spending on ads built a company serving tens of thousands of customers worldwide.

Building Voices.com: From $15,000 Studio to Nasdaq Dreams

David Ciccarelli and his wife Stephanie built Voices.com from a newspaper ad and a $15,000 loan into a 130-person marketplace connecting over 2 million voice talent with clients worldwide. This is the story of bootstrapping through 10,000 cold calls, betting $30,000 on a domain name they couldn't afford, surviving as a husband-and-wife founding team, and raising $18 million from Morgan Stanley to chase a Nasdaq IPO. It's a masterclass in marketplace dynamics, strategic financing, and building a Canadian tech success story.

From Bank Employee to Mortgage Brokerage CEO: Building a 60-Person Team

Teddy Keres built one of Montreal's most successful mortgage brokerages by mastering the art of relationship-driven sales and strategic scaling. This article chronicles his journey from hockey player to peak-performing mortgage specialist at Bank of Montreal (closing 500 deals annually), then to founder of Group Orbis, a 60-person brokerage. We explore his client acquisition strategies, his personal real estate investing philosophy focused on student housing near McGill University, the mechanics of transitioning from employee to entrepreneur, and his perspective on the future of mortgage lending including decentralized finance. Packed with actionable insights on financing properties, building service businesses, and scaling through people.