Why Most Real Estate Agents Fail (And How to Avoid It) w/ Steve Rupp

03/16/25 • 43 min

Real Estate Makes us Drink & The Success Happy Hour

In this episode of Real Estate Makes Us Drink, Brian and Brad welcome Steve Rupp, former top-producing real estate agent turned business coach. We’re talking about burnout, career transitions, and the secret to predictable success—with a little tequila and marathon training talk thrown in.

Thinking of leaving real estate or leveling up your business? Steve breaks down:

✅ Why agents burn out—and how to avoid it

✅ The power of systems & strategy for long-term success

✅ Why action beats perfection every time

✅ How to stop caring what others think and just WIN

If you're in real estate, entrepreneurship, or just chasing big goals, this episode is for you. So grab a drink and get ready for some real talk, real laughs, and real estate insights. Cheers!

Like, subscribe, and drop a comment below—what’s your biggest business challenge? Cheers!

#RealEstatePodcast #EntrepreneurMindset #BusinessSuccess #Coaching #TequilaTalk

Schedule a consultation with Brian or Brad https://calendly.com/therealtorindy

Thinking of leaving real estate or leveling up your business? Steve breaks down:

✅ Why agents burn out—and how to avoid it

✅ The power of systems & strategy for long-term success

✅ Why action beats perfection every time

✅ How to stop caring what others think and just WIN

If you're in real estate, entrepreneurship, or just chasing big goals, this episode is for you. So grab a drink and get ready for some real talk, real laughs, and real estate insights. Cheers!

Like, subscribe, and drop a comment below—what’s your biggest business challenge? Cheers!

#RealEstatePodcast #EntrepreneurMindset #BusinessSuccess #Coaching #TequilaTalk

Schedule a consultation with Brian or Brad https://calendly.com/therealtorindy

Previous Episode

Learning from Failing & Property Management Insights | Real Estate Business Tips. Ep 71

Learning from Failing & Property Management Insights | Real Estate Business Tips

Join us on Real Estate Makes Us Drink as we chat with Brayden Sammons, co-owner of Property Partners Indiana. Brayden shares his journey into property management and the real estate industry. In this episode, we dive deep into the challenges and rewards of property management, the importance of tenant management, and how property owners can succeed in the business. Whether you're an aspiring property manager, real estate agent, or investor, this video offers valuable insights to grow your real estate career. Don’t miss out on these expert tips and real estate advice! Cheers!

management business.

How Braden got started in property management

The biggest challenges in the industry

Key tips for managing rental properties

How real estate agents can work effectively with property managers

The role of a real estate team in property management

Whether you're an investor, real estate agent, or aspiring property manager, this episode is packed with valuable insights to help you succeed in real estate.

Subscribe for more real estate insights! Don't forget to like, comment, and share if you found this helpful!

In this episode of Real Estate Makes Us Drink, we sit down with Brayden Sammons, co-owner of Property Partners Indiana, to explore his entrepreneurial journey from launching a unique ice cream shop to thriving in real estate and property management.

Brayden shares how he started Campus Craves in Bloomington, Indiana, the challenges of running a business during COVID-19, and what led him to transition into real estate investing and rental property management. We dive into the importance of experience over formal education, how referrals drive success in property management, and what it takes to build a business from the ground up.

If you're an aspiring real estate investor, a small business owner, or just love a great entrepreneurial success story, this episode is for you!

Schedule a consultation with Brian or Brad https://calendly.com/therealtorindy

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Keywords:

Learning from Failing, Property Management Insights, Real Estate Business Tips, Real Estate Team, property management business, property management, Real Estate Makes Us Drink, Real Estate Marketing, home selling tips, real estate branding, real estate clients, real estate market analysis, property ownership, Real Estate Marketing Ideas, real estate market trends, real estate leads, property management companies, Real Estate Investing, real estate digital marketing

Hashtag: #RealEstate #PropertyManagement #RealEstateInvesting #MortgageIndustry #HomeBuying #RealEstatePodcast #RealEstateBusiness #RentalProperty #RealEstateSuccess #RealEstateMarketing

Next Episode

Making Insurance Suck Less | Truth About Insurance, Real Estate, & Rising Costs

Making Insurance Suck Less | Truth About Insurance, Real Estate, & Rising Costs Ep. 73 | Real Estate Makes Us Drink

In this episode of Real Estate Makes Us Drink, hosts Brian Quinlan and Brad Niccum are joined by J.C. Wogomon, founder of Catalyst Insurance Group, for an in-depth discussion on the intersection of real estate and insurance. They explore insurance industry trends in 2025, cash buyers, the evolving insurance claims culture, and how insurance impacts real estate decisions.

Key Topics Covered:

✅ The role of insurance in the real estate market and its growing importance

✅ Trends shaping homeowners insurance in 2025

✅ Real estate marketing strategies for success in 2025

✅ The increasing role of cash buyers in real estate deals

✅ How real estate risk management helps protect investments

✅ The importance of building relationships in real estate marketing

✅ Why community business efforts are crucial for real estate success

✅ Lowering home insurance rates and its effect on buyers and sellers

Whether you're a realtor, insurance professional, or an investor, this episode will provide you with valuable insights to stay ahead in a rapidly changing market.

Subscribe for more insights into the world of real estate and insurance.

Like, comment, and share to help others stay informed!

Schedule a consultation with Brian or Brad: https://calendly.com/therealtorindy ========================================== ✅ Stay Connected With Us: Facebook: / brian.quinlan.7 Contact: [email protected]