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The Indy Investor Speakeasy

The Indy Investor Speakeasy

Hosted by Brooks Rothschild

BusinessInvestingInterviews guests

Episodes

31

Latest episode

Jan 2025

Language

EN-US

About the show

Welcome to "The Indy Investor Speakeasy," the go-to podcast for the scoop on the Indianapolis real estate market and beyond. Your hosts, Brooks, Nick, and Randy, invite you into their cozy corner of the internet, where the conversation flows as smoothly as the bourbon. Each episode, we pour a glass and pour over the latest trends and strategies in real estate investing, offering up a blend of local expertise and national perspectives. Whether you're an experienced investor eyeing the vibrant Indianapolis scene or a newcomer eager to learn the ropes, our relaxed, speakeasy-style chats will serve you the knowledge you need, neat or on the rocks. We'll bring in seasoned investors from around the country to share what's working for them, shining a light on the diverse ways to succeed in this dynamic field. Our candid discussions cut through the complexity of investing to give you straightforward advice and insider insights, all while enjoying a good bourbon. So, pull up a chair and join us at "The Indy Investor Speakeasy," where the wisdom of real estate meets the warmth of Southern hospitality—right here in the heart of Indianapolis. Subscribe and tune in to raise a glass and your real estate game.

Listen to episodes

31 recent
January 2, 202546 min

The Indy Investor Speakeasy LIVE with Kenny Hall

We will be talking all things Property Management today with Kenny Hall.

December 31, 202456 min

Self Storage, AirBnBs, and more with Paul Beets!

Come have a drink with us and ask Paul your questions on investing!

December 30, 20241 hr 9 min

10/31 Live Show

Come join us for a drink and talk real estate!

December 26, 202438 min

The Indy Investor Speakeasy Live! 10/17

Come join us for a drink and talk real estate!

December 24, 20241 hr 3 min

The Indy Investor Speakeasy Live!

Come have a drink with us and talk real estate!

December 23, 202449 min

Talking Rates with Jared Shore from Mamba Mortgage

December 6, 202458 min

8/10 Live Show: Banter, Bourbon, and Inside Tips

Join our special dual live stream on YouTube and Instagram as we engage in lively discussions on various aspects of real estate investment. From nostalgic chats about fall breaks and bourbon preferences to in-depth insights into HELOCs, home improvement loans, and navigating private money and seller financing, this episode covers it all. Discover strategies for analyzing property values, assessing real estate deals, and understanding the differences between wholesale and wholetail investments. Learn about securing free roofs, mitigating capital expenditures, and getting insurance discounts. Whether you're a seasoned investor or just getting started, tune in for valuable tips, expert advice, and interactive Q&A sessions. Don't miss out on optimizing your property investment strategy! 00:00 Going Live on YouTube and Instagram 00:47 Fall Break and Nostalgia 01:24 Technical Difficulties and Winging It 02:32 Upcoming Content and Bourbon Talk 06:36 Wedding Venues and Bookings 10:58 Real Estate Analysis and Market Insights 23:13 Analyzing Property Competency 23:48 Evaluating Market Listings 25:26 Calculating ARV and Costs 30:19 Negotiation Strategies 40:35 Seller Financing Insights 51:24 Insurance and Maintenance Tips 58:01 Concluding Thoughts and Future Plans

October 8, 202453 min

Exploring Real Estate Investing with Andrew Owlett

Join us as we catch up with Andrew Owlett, a real estate investor with a fascinating journey from his first property purchase in 2015 to his ambitious plan to develop a boutique wellness resort in Virginia. In this episode, Andrew shares his insights on managing short and long-term rentals, his evolving approach to outsourcing tasks, and the challenges and rewards of venturing into the hospitality industry. He also discusses the importance of networking, learning from mentors, and adapting to new opportunities in the real estate market. Don't miss this engaging conversation full of valuable lessons and entrepreneurial spirit! 00:00 Reconnecting After Years 00:52 The Speakeasy Studio 01:49 Real Estate Realities 02:02 Robbery Stories 03:17 Life in Maryland 05:58 Starting in Real Estate 07:33 Scaling Up and Outsourcing 20:42 Short-Term Rental Success 27:13 Dreaming of a Boutique Wellness Resort 28:16 Acquiring the Perfect Land 28:52 Designing the Unique Experience 29:52 Financial Planning and Challenges 31:18 Understanding Valuation and Market Trends 35:12 Marketing Strategies and Future Plans 35:39 Seeking Partnerships and Overcoming Insecurities 41:35 Networking and Sharing Knowledge 48:11 Final Thoughts and Future Collaborations Connect with Andrew: https://www.instagram.com/andrewowlett/

September 16, 202454 min

Understanding Wholesaling Real Estate: Ethics, Strategies, and Real-Life Insights

In this episode of The Indy Investor Speakeasy, hosts Max Brooks and Randy dive into the nuances of wholesaling real estate with a detailed discussion on ethical concerns, business structures, and strategies to minimize risks. They share insights on how to break into the wholesaling business, the importance of transparency, and dealing with motivated sellers. The episode also covers the benefits and challenges of wholetailing, managing cold calling, developing strong lead qualification processes, and leveraging relationships with investors. Expect real-life examples that illustrate common pitfalls and successful approaches in the wholesaling industry.00:00 Introduction and Episode Overview 01:31 Understanding Wholesaling Ethics 03:59 Wholesaling vs. Wholetailing 05:49 Cold Calling and Lead Management 08:44 Challenges and Strategies in Wholesaling 21:03 Reputation and Ethical Practices 28:23 The Challenges of Showing Occupied Properties 29:43 Dealing with Neighborhood Confusion 30:52 The Ethics of Wholesaling 34:16 Financial Considerations for Wholesaling 35:08 Long-Term Rentals vs. Wholesaling 43:45 The Appeal of Development Projects 46:44 Analyzing Potential Deals 51:47 Concluding Thoughts and Future Plans

September 4, 202459 min

Wholesaling Insights and Market Trends with Tyler, Brooks and Randy

In this kickoff episode of The Indy Investor Speakeasy live stream, hosts dive deep into the world of real estate investing with a focus on wholesaling. They engage in a freestyle discussion, addressing questions related to acquiring properties, lead quality, and market conditions. They explore the roles of cold calling, the current seller and buyer dynamics, and the practicality of flipping versus wholesaling. Towards the end, they also touch on the importance of networking in the real estate community, share personal experiences, and discuss the evolving nature of buyer's and seller's agent commissions amid new regulations. Get valuable insights and tips from experienced investors and learn more about structuring your real estate business effectively. 00:00 Introduction to the Indy Investor Speakeasy Live Stream 01:17 Discussing Wholesaling and Market Updates 02:26 Lead Generation and Marketing Strategies 06:17 Challenges and Strategies in Real Estate Investing 10:30 Partnership Dynamics and Business Operations 22:47 Market Trends and Investor Insights 31:25 Navigating New Real Estate Negotiations 32:01 Challenges with Broker Compensation Forms 32:43 Transitioning Listing Agreements 34:12 Competitive Market Dynamics 38:28 Agent Networking and Collaboration 40:28 The Importance of Real Estate Meetups 42:25 Personal Experiences in Real Estate 46:11 Community and Networking in Indianapolis 57:30 Upcoming Podcast Guests and Topics

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