Chasing and Achieving Big Dreams While Building Potent Ongoing Wealth with Austin Hair
with Austin Hair
Austin Hair traded a career in professional wakeboarding for one in real estate, building an Airbnb empire and buy-and-hold portfolio that generates ongoing wealth while still allowing him to chase big dreams. In this episode of The REI Agent Podcast, Austin shares how house hacking, short-term rentals, and strategic delegation helped him create a life where passion and profit go hand in hand. His story answers a question most people are afraid to ask: can you actually have both?
How did you transition from wakeboarding to real estate?
Austin’s journey into real estate started unconventionally—as a professional wakeboarder, he lived a lifestyle that most people dream about. He was getting paid to do something he loved, traveling, competing, experiencing the freedom that comes with doing what you’re passionate about. But he also saw the ceiling. Professional athletes have a short window. Injuries happen. Sponsorships dry up. There’s no equity buildup, no asset creation, no path to financial security beyond the next contract.
So Austin faced a choice: keep chasing the dream and hope it never ended, or build something that would sustain him beyond the career window. He chose the latter, but smartly. He didn’t abandon the thing he loved. He built a business that would fund the freedom to pursue what mattered to him.
His first move into real estate was house hacking—buying a property with multiple units (or a single-family with an ADU), living in one unit, and renting out the others. This strategy is genius for someone in his position because it solves the biggest problem: housing cost. His rent disappeared. Suddenly, a career that didn’t pay enough to live in an expensive market became viable. He was learning property management, cash flow, tenant relations, and renovation—all while living essentially for free.
House hacking isn’t about getting rich. It’s about lowering your survival costs while building foundational knowledge. Austin used that knowledge as a springboard. Once he understood how to manage a property and optimize cash flow, he could scale.
How did you build your Airbnb empire?
After house hacking, Austin recognized something that most long-term rental investors miss: Airbnb properties can generate 2-3x more revenue than traditional long-term leases. A property that would rent for $2,000/month long-term might generate $5,000-$7,000/month through short-term rentals. The tradeoff is management complexity—more turnovers, more guest interaction, more potential issues.
Austin saw the opportunity and decided to solve the complexity problem through systems and delegation. He didn’t try to manage Airbnbs himself (which would be insane). Instead, he built the backend: sourcing properties with strong Airbnb potential (location, layout, appeal), buying them under market value, and then contracting out the day-to-day operations to property managers who specialize in Airbnbs.
His approach to scaling was methodical. After the first property, he analyzed what worked: which neighborhoods attracted guests, which amenities justified premium pricing, what guest experience elements drove better reviews (and therefore bookings). Then he replicated that system with the next property. By the time he had 3-4 properties running, the system was working so well that adding new properties was just running the playbook again.
The reinvestment piece is critical. He didn’t cash flow the Airbnbs and spend the money. He reinvested profits into down payments for new properties. This compounds. If one property generates $2,000/month in profit, after a year that’s $24K toward another down payment. After three years, the cumulative profit from all three properties funds the fourth property. This is how you scale from one to many without needing a six-figure income to start.
The other operational lever Austin pulled is pricing optimization. Short-term rentals aren’t rented at a fixed price. You can adjust daily rates based on demand, season, local events, and occupancy trends. Austin uses data on booking patterns to optimize: raise prices during high-demand periods (weekends, holidays, local events), drop prices strategically during slow periods to maintain occupancy rather than sit empty. This maximizes revenue without requiring more properties.
What role does delegation play in your success?
Here’s where Austin’s success gets interesting. He understood something early that many investors never learn: trying to be the agent, the investor, the property manager, and the handyman is a recipe for mediocrity at all of them and burnout.
He made the decision to know his lane and delegate everything else. His lane is deal sourcing and strategy—finding good properties, negotiating under market, structuring the acquisition. Everything else—property management, maintenance, guest communication, tenant screening—he hired out. This seems expensive until you realize that a property manager costs $400-600/month but generates $5,000+ in revenue. It’s not a cost, it’s leverage.
This shift from doing to leading is the difference between building a job and building a business. When you’re doing everything, you’ve created a job that pays well but consumes your time. You can’t take vacation without the business breaking. You’re the bottleneck. When you delegate, the business runs whether you’re there or not. That’s when you can actually scale.
Austin’s delegation strategy also freed him to focus on what he enjoys. Some investors love the day-to-day operations. Austin loves the strategy and sourcing. He focuses on that and pays others to do the rest. That’s not lazy—that’s smart leverage.
How do you balance buy-and-hold with short-term rentals?
Austin runs two parallel strategies: Airbnbs for cash flow and traditional buy-and-holds for wealth building. They serve different purposes and they feed each other.
Airbnbs are the cash flow engine. They generate significant monthly revenue that can be reinvested or taken as income. They’re more hands-off than you’d think (with a good property manager), but they’re still more management-intensive than a traditional lease. The downside is that the cash flow is contingent on continued management. If you stop actively managing or optimizing the property, bookings drop and cash flow dries up.
Buy-and-holds are different. You find a property, rent it long-term, and let it generate steady income while appreciation builds equity. A $300K property with a $240K mortgage generating $300/month in positive cash flow is also appreciating (hopefully) 3-4% annually. That’s $9K-$12K in appreciation per year, plus $3,600 in cash flow. The cash flow alone isn’t impressive, but the equity buildup is substantial. Over 10 years, that’s $100K+ in appreciation plus mortgage principal paydown plus cash flow.
The tension between them is real: Airbnbs pay you now, buy-and-holds pay you later. Austin solved this by using Airbnb cash flow to fund buy-and-hold acquisitions. The Airbnbs generate income that covers down payments and closing costs on the buy-and-holds. The buy-and-holds build equity that secures his long-term wealth. Together, they create a portfolio that pays him today and pays him forever.
Diversification also hedges risk. If short-term rental markets change (regulations, competition, decreased tourism), his buy-and-hold properties still generate income. If the long-term rental market softens, the Airbnbs can still produce strong cash flow. Most investors get all-in on one strategy. Austin diversified.
What advice do you have for agents who want to start investing?
Austin’s advice is radical in its simplicity: stop overthinking and start with what you have. Most agents have income, access to capital, and know real estate. They should use those advantages.
House hacking is his recommended first step. Here’s why: it’s the fastest path to zero housing cost (your biggest expense), it teaches you property management at scale, it generates cash flow, and it sets you up for the next deals. An agent making $60K-$80K income can house hack, eliminate their $1,500-$2,000 housing cost, and suddenly have $18K-$24K annual cash flow that can fund additional investments. Within 2-3 years, you’re not just making agent income—you’re making agent income plus investment returns.
The other piece of advice is to find partners and explore syndications. Not every investor has $50K-$100K for a down payment on a rental property. Syndications allow you to invest $5K-$25K as a passive partner in larger deals. This gives diversification and access to deals you couldn’t do alone. Many successful investors started with syndications, built capital, and then moved to direct property ownership.
The biggest mistake Austin sees agents make is waiting for the perfect deal. They research endlessly, wait for the perfect market conditions, try to time the bottom. Meanwhile, they’re not building anything. A good deal that you execute today is better than a perfect deal you might find someday. The people who are wealthy in real estate aren’t the ones who found perfect deals. They’re the ones who made imperfect decisions, learned, adjusted, and built momentum.
About Austin Hair
Austin Hair is a real estate investor and former professional wakeboarder who built a thriving Airbnb empire and buy-and-hold portfolio by combining passion with strategic investing. His journey from extreme sports to real estate demonstrates that chasing big dreams and building lasting wealth aren’t mutually exclusive.
Connect with Austin Hair:
Listen to The REI Agent Podcast
The REI Agent Podcast interviews agents and investors who’ve found the balance between professional success and personal fulfillment. New episodes weekly.
Never Miss an Episode
Get the weekly digest with episode summaries, key takeaways, and investing insights — delivered every Friday.
Free REI Agent Playbook
Why producing agents have an unfair advantage as investors — and how to use it.