In a captivating and insight-packed panel hosted by Spyglass Realty’s John McCarthy, two of the real estate industry’s most respected names, Tim Heyl and Gary Ashton. opened up about their entrepreneurial journeys.
From humble beginnings to founding nationally recognized companies, Tim and Gary prove that there’s no single path to success in real estate, but there are invaluable lessons along the way. Whether you’re just starting out or scaling a team, this conversation offers real talk, tangible strategies, and refreshing honesty about what it really takes to make it in this business.
Table of Contents
Tim Heyl’s Journey in Real Estate
Tim Heyl, an Austin native, didn’t set out to be a real estate mogul, he fell into it after struggling to find a job during the 2009 financial crisis. What started as a temporary gig quickly became a lifelong calling.
Armed with a finance degree and no connections to homebuyers, Tim started cold-calling homeowners in the outskirts of Austin, Leander, Cedar Park, Kyle, and Buda. After a few hundred calls, he landed a listing for not one, but three homes. That first taste of success sparked something: the realization that if you make the calls and stay consistent, real
From 2010 to 2012, Tim made 1,000 calls a day without missing a weekday. His focus? Listings only, no buyer leads, no distractions. That laser focus paid off, and before long, he was dominating the Austin market.
But success didn’t come without setbacks. In 2012, his entire team walked out. Instead of collapsing, Tim took it as a wake-up call. He rebuilt differently. He learned to lead, delegate, and, most importantly, to build a business where others could thrive, too. That led to Homeward, a groundbreaking company providing financial flexibility to buyers and sellers through innovative products like the Buy Before You Sell program and Cash Offers.
Gary Ashton’s Unique Path to Real Estate
Gary Ashton’s journey couldn’t have been more different. Born in England, Gary was a professional drummer who once opened for Tears for Fears. After his band fell apart and he sold a family-owned motel, he made his way to Nashville, partly for music, partly for real estate investments.
Once there, he realized Nashville wasn’t short on talented musicians… and his real estate license might be the better career move. He used his background in advertising to generate early leads through online marketing, learning HTML and user behavior in the early days of the internet. By 2001, Gary bought the domain GaryAshton.com and began a journey that would eventually lead to building the number one RE/MAX team in the world.
Gary was one of the first agents in Nashville to use PPC (Pay Per Click) advertising. His sharp focus on lead generation helped him secure high-value partnerships like Nashville.com and Zillow Flex. He embraced SEO, created an overseas ISA team, and wasn’t afraid to reinvest aggressively in systems and tools. His success wasn’t just because of talent, it was also his willingness to bet big and surround himself with the right people.
Building and Scaling a Real Estate Business
While their origins differ, Tim and Gary share one thing in common: an unwavering commitment to growth through systems and people.
- Tim built his early business on outbound prospecting, then transitioned to hiring, training, and empowering team members. He moved from “I do it” to “we do it” to “they do it”, eventually reaching a level where others ran the day-to-day, and he could innovate.
- Gary scaled by owning his lead gen, investing early in technology, and building a team with specialized roles. His team operates like a machine, with licensed ISAs, backend support from virtual assistants, and clear responsibilities.
Both agreed that your business will only grow as fast as the people you trust to help you grow it.
Embracing Risk, Staying Focused
Gary has a simple philosophy: spend big, stay focused, and make it work. From investing in exclusive zip codes to becoming a Flex Partner with Zillow, he’s never been afraid to go all in. He shared how working closely with skilled partners, including business partner Scott Hull and operations guru Deborah Beagl, helped him stay in his lane and let experts shine.
Tim shared a similar mindset. After years of working 80-hour weeks, he started multiple businesses — some of which were distractions more than opportunities. He later realized that the same focus that built his first success needed to guide the next chapter. That’s when he founded Homeward, and found clarity by solving a real pain point for sellers and buyers using capital as leverage.
Advice for Agents Ready to Scale
Tim and Gary’s journeys show us that real estate isn’t just about transactions; it’s about entrepreneurship, leadership, and evolution.
✅ Focus beats everything. Stay laser-sharp on what moves the business.
✅ Surround yourself with the right people. The wrong hire can stall your growth; the right one can triple it.
✅ Embrace hard times. Growth comes from challenge, not comfort.
✅ Don’t be afraid to go big. Whether it’s a tech investment, a new lead platform, or a new market, commit and make it work.
✅ Be willing to reinvent. What worked in 2020 may not work in 2025.
From cold calls to capital-backed innovation, from a music dream in Nashville to a data-driven lead machine, these are the stories that fuel the next generation of industry leaders.
If you’re building your own real estate business, take a page out of their playbooks: stay focused, stay resilient, and surround yourself with people who elevate you.
Want to Learn More? Watch the Full Panel Conversation
In this must-see panel, Tim Heyl and Gary Ashton share:
- How they each got their start in real estate, from cold calls to music tours.
- The steps they took to scale from solo agents to industry leaders
- Why hiring the right people can make or break your business
- How to turn failure and setbacks into future growth
- The tech, systems, and mindset shifts that took their businesses to the next level
Don’t miss the full conversation if you’re ready to grow smarter, lead better, and build a real estate business that lasts. Watch the full episode now and get inspired to level up your journey!
Big thanks to Tim Heyl and Gary Ashton for their transparency, wisdom, and willingness to share what it really takes to build a real estate empire.
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