Most business content celebrates the exit but rarely talks about the decades of discipline it took to earn it.
In this episode of Built The Hard Way, Josh sits down with entrepreneur and former CoolToday founder Jaime DiDomenico to unpack one of the most methodical business-building stories you'll hear. Jamie didn't start with investors, a groundbreaking idea, or a shortcut. He started earning $4 an hour stocking HVAC technician bins while putting himself through college, believing his future would be in corporate accounting.
Instead, he found opportunity in the skilled trades.
After nearly two decades climbing from warehouse employee to executive, Jaime took the biggest risk of his career by purchasing a struggling HVAC company that was losing money every year. Rather than chasing quick wins, he built a 15-year strategic plan, established clear company values, invested in culture, and committed to long-term execution over short-term growth.
Fifteen years later, that failing business had grown from $1.7 million in annual revenue to nearly $39 million, ultimately becoming part of one of the largest home service organizations in the country.
Throughout the conversation, Jamie shares why entrepreneurship demands discipline more than brilliance, why company culture isn't optional, how strategic planning creates freedom, and why building a business that's valuable to others requires thinking decades ahead instead of quarter to quarter.
Whether you're running a home service business, leading a growing company, or dreaming of one day selling what you've built, this conversation offers practical lessons from someone who truly built it the hard way.
Connect with Joshua Pies
👉LinkedIn: https://www.linkedin.com/in/joshuapies/
Connect with Jaime DiDomenico
👉LinkedIn: https://www.linkedin.com/in/jaime-didomenico-819147b/
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https://c47films.com/about/bu-business-podcast-network/built-the-hard-way/
00:00 Introduction to Entrepreneurship Mindset
03:02 Journey from HVAC to Entrepreneurship
06:02 The Transition to Business Ownership
09:09 Strategic Planning and Growth
12:00 Selling to Wrench Group
14:56 Navigating Challenges and Market Changes
18:08 The Importance of Service in Business
21:02 The Value of Trades and Education
23:59 Embracing Technology and AI in Business
26:47 Transformational Phases in Entrepreneurship
30:32 Community Engagement and Philanthropy
32:36 Curating Company Culture
36:16 Learning Through Experience
39:40 The Reality of Entrepreneurship
42:44 The Secret Sauce of Success
46:33 Books and Resources for Entrepreneurs
53:48 The Call to Action for Community Involvement
🔔Follow Built the Hard Way on Apple Podcasts, Spotify, Amazon Music, iHeartradio, Deezer and etc., for honest conversations with founders, operators, and builders who know success is never as simple as it looks online.
Because behind every great business is a story nobody talks about enough: what it cost to build it.
#BuildTheHardWay #Entrepreneurship #BusinessGrowth #BusinessExit #HVAC
