Dominic Rubino, a serial entrepreneur and business coach, shares his thrilling journey from a failed Christmas light business to selling CanadaPharmacy for $120M. He emphasizes the importance of embracing failure and using it as a stepping stone to success. The conversation dives into the value of relationships and networking in entrepreneurship, revealing how true fulfillment often outweighs profit. Rubino highlights that entrepreneurship is non-linear, focusing on systems and the willingness to adapt. He inspires listeners to connect and explore their passions.
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question_answer ANECDOTE
First Sale Sparked Entrepreneurial Drive
Dominic's first sale was selling licorice at school for charity and he sold every box without realizing how hard it was.
That early success taught him he liked selling and creating from nothing despite not knowing the process.
question_answer ANECDOTE
Failed Christmas Lights Business
In high school Dominic started a Christmas light installation business that failed hard and barely made money.
The failure still taught him he enjoyed building businesses and doing the work.
question_answer ANECDOTE
College Pool Business Paid Lessons
Dominic cleaned and sold pool services while in college, turning casual offers into paid accounts and spending the earnings quickly.
That messy early revenue confirmed product-market fit even if the money disappeared fast.
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Dominic Rubino is a serial entrepreneur, business coach, podcast host, and self-proclaimed terrible fly fisherman. From starting a Christmas light installation company in high school to building and selling CanadaPharmacy for $120M, Dominic has seen—and done—it all. Through his popular podcasts, Cabinet Maker Profit System and Profit Tool Belt, he shares practical tips for trades and business owners, focusing on real systems, mindset, and relationships over theory.
On this episode we talk about:
Dominic’s journey from failed Christmas light business to multi-million dollar exits and coaching
Lessons from building businesses in trades, e-commerce, pharma, vending, and coaching
Why failing fast, trying new things, and “not knowing any better” is a superpower in entrepreneurship
The critical role of relationships and purposeful networking in unlocking both fulfillment and profit
The underrated businesses and moments where meaning—not just money—made the difference
Top 3 Takeaways
1. Embrace failure early and often—each “hard fail” is a data point that shapes future success and shows what you truly enjoy. 2. Your relationships and ability to connect others at scale can be a bigger asset than any single skill or product. 3. Entrepreneurship isn’t linear—use systems, stay humble, and don’t be afraid to reinvent or shed what’s not working.
Notable Quotes
“My job is to get my head kicked in and stand up again—like that was supposed to happen.”
“Follow the numbers in your business, but also follow what makes you want to get up and do it again.”
“I don’t monetize the podcast—it’s really just there to meet people and build great relationships.”
Travis Makes Money 