Ep 42: Mindsets for Growth with Alyssa Rogers

Breaking Through Barriers: Building a Generational Business, Embracing Mindset, and Marketing That Sticks

What does it really take to grow a generational business in today’s world? In this post, I dive into a candid discussion I had with Alyssa Rogers, co-owner of Rogers Heating & Cooling, about the real (and sometimes messy) business of scaling from local operation to bold aspirations of $100 million in revenue. We explore the importance of mindset, the value of being “in the right room,” building the right team, and real-world marketing that goes beyond the shiny promise of digital ads. Whether you’re leading a family business, chasing big dreams, or looking for practical marketing tactics, this article shares insights you can actually use, straight from entrepreneurs in the trenches.

Embracing the Generational Legacy

Hey everyone, Bryan here. If you know me, you know I love having conversations with business owners, especially those building something that lasts beyond the next quarter. When I sat down with Alyssa Rogers of Rogers Heating & Cooling, we didn’t just chat about HVAC units and business plans. We dug deep into what it’s like to step into a family business, make it your own, and stare down the intimidating goal of scaling to $100 million.

Alyssa’s story begins in South Boston, Virginia, a small town with big dreams. She shared how her husband Joey literally grew up in the business, starting out as his dad’s right-hand-helper and eventually taking over, rebranding, and, most importantly, deciding together to go for real, lasting growth.

The Power of Mindset - How “The Room” Changes Everything

One of the most powerful moments in our conversation was Alyssa’s “aha” at a conference in 2021. Sitting in a room surrounded by much larger companies, she and Joey realized that the ceiling they’d set for themselves was just that, a limit in their own minds. Suddenly, $10 million wasn’t the finish line; it was just the starting point.

Surrounding yourself with people who are already where you want to go, or at least thinking even bigger, is transformative. For those listening: if you’re feeling stuck, maybe it’s time to find a new “room.” Alyssa and Joey found new mentors, new best-practice groups, and their belief in what was possible multiplied overnight. You can do the same.

Building a Team That Buys In

Scaling isn’t about micromanagement, it’s about building a team that sees the vision and grows with it. Alyssa talked a lot about being transparent with the team, sharing not just the company’s goals, but also asking employees about their own dreams: personal, professional, financial. Turns out, most people have never even been asked what they really want. Helping team members grow, not just as workers but as people, creates the kind of company culture where everyone is invested.

And yes, it’s still a work-in-progress! But as Alyssa put it: “It just takes commitment and putting your head down and getting to work.” The entrepreneurial journey is messy, and sometimes people will leave, that’s okay. Focus on those ready to rise with you.

Marketing: Getting Real and Grassroots

Throwing money at fancy campaigns doesn’t always move the needle. I asked Alyssa about what’s actually working in her rural market. Her answer: authenticity. Get out in your community. Sponsor events. Partner with local organizations. Don’t hide behind a logo, but also don’t hog all the spotlight. Shine it on your team.

One funny flop she shared was trying a big “Black Friday” flyer drop on local cars. Turns out, nobody thinks about their HVAC system while holiday shopping. Big lesson: experiment, but always measure and adjust.

Authority and Giving Back: The Power of Podcasting

Alyssa’s other ace? Her community podcast, “Hello, Hello.” What started as a brand play is now a platform for sharing stories, spotlighting other local businesses, and giving leaders a voice. It’s not about monetizing each guest, it’s about giving, connecting, and building local authority. Content like this keeps your business top of mind and positions you as a true community partner.

Define Your Own Success

Not everyone wants to build a $100 million platform, and that’s okay. Maybe your goal is a profitable million-dollar business and more time with your family. Own it.

But if you’re ready to break your own limits, find your room, tell your story, and put in the work, you’ll be amazed where you end up. Let’s keep building, together.

Thanks again to our amazing guest Alyssa and make sure to listen to the full podcast episode here!