The Retiring Real Estate Investor

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Latest episode

Oct 2025

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About the show

Brandon Bruckman, from Insight Investment Advisers, talks to Real Estate investors about deferring taxes, earning passive income, understanding 1031 exchanges, Delaware Statutory Trusts, and more.

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58 recent

October 7, 202546 min

57: Ben and Eric Nelson - Wild Oak Capital

SummaryIn this episode of the Retiring Real Estate Investor podcast, host Brandon Bruckman engages with Eric and Ben from Wild Oak Capital to explore the intersection of real estate investing and lifestyle choices. They share their personal journeys into real estate, the importance of mentorship, and the necessity of taking action. The conversation delves into market insights, particularly focusing on Tulsa as a promising investment location, and discusses the dynamics of team collaboration in real estate. Additionally, they touch on the lifestyle changes that come with remote work and living abroad, emphasizing the importance of balancing work and personal life.TakeawaysReal estate offers various pathways to financial success.Mentorship is crucial for navigating the real estate landscape.Taking action is essential; education alone isn't enough.Transitioning from single-family to syndication can be challenging but rewarding.Understanding market dynamics and having a reliable team is key.Establishing a clear buy box helps in identifying good deals.Current market conditions present unique opportunities for investors.Tulsa is an underrated market with strong growth potential.Lifestyle choices can significantly impact personal happiness and productivity.Protecting your time and calendar is vital for achieving work-life balance.Chapters00:00Introduction to Real Estate and Lifestyle02:32Personal Journeys into Real Estate05:14The Importance of Mentorship08:20Taking Action in Real Estate11:01Transitioning to Syndication13:54Market Insights and Team Dynamics16:59Understanding Buy Boxes and Deal Criteria19:53Current Market Conditions and Opportunities22:45Exploring Tulsa as a Market25:45Lifestyle Choices and Living Abroad28:41Balancing Work and Life31:22Final Thoughts and ConnectionsSocial Links:Podcast: The Retiring Real Estate InvestorFollow us on Instagram: @InvestWithInsightFollow us on Facebook: @InvestWithInsightFollow Brandon on Linkedin: @BrandonBruckmanJoin the Facebook group: Invest with InsightListen on Spotify: The Retiring Real Estate InvestorListen on Apple: The Retiring Real Estate InvestorIf you're looking to learn more about DSTs, 1031 exchanges and passive investing, visit www.investwithinsight.comThe firm is a registered investment adviser with the states of KS, MO, WI, CA, AZ, TX, LA, and may only transact business with residents of those states, or residents of other states where otherwise legally permitted subject to exemption or exclusion from registration requirements.

September 22, 202541 min

56: Dwight Dunton and Ryan Conoboy - Bonaventure

In this episode, Brandon Bruckman hosts Dwight Dunton, Founder and CEO, and Ryan Conroy, VP of Capital Markets, from Bonaventure, a multifamily investment firm. They discuss the evolution of Bonaventure, its unique market strategies, and the importance of vertical integration in real estate. The conversation delves into the role of debt as an asset, current market dynamics, and the challenges faced in financing. They also explore the differences between DST and 721 UpREIT structures, emphasizing the need for better alignment of interests in real estate investments. The episode concludes with a focus on future innovations in the industry.TakeawaysBonaventure manages approximately $2.75 billion in assets.The firm was founded out of necessity to manage family investments.Vertical integration is key to ensuring quality and returns.Debt is viewed as a strategic tool to minimize downside risk.Current market conditions present both challenges and opportunities.Long-term investment strategies are preferred to avoid tax leakage.The financing environment is becoming more challenging for sponsors.DST structures often misalign interests between sponsors and investors.Innovations in real estate investment are necessary for growth.The industry needs to focus on better alignment and transparency. Chapters00:00 Introduction to Bonaventure and Its Founders02:43 The Evolution of Bonaventure and Its Market Strategy05:36 Understanding Vertical Integration in Real Estate08:22 The Role of Debt as an Asset11:10 Current Market Dynamics in Multifamily Real Estate13:49 Navigating Opportunities Amidst Market Disruption16:38 The Importance of Long-Term Investment Strategies19:24 The Challenges of the Current Financing Environment22:22 Comparing DST and 721 UpREIT Structures25:19 The Need for Better Alignment in Real Estate Investments27:53 Future Innovations in Real Estate Investment StrategiesSocial Links:Podcast: The Retiring Real Estate InvestorFollow us on Instagram: @InvestWithInsightFollow us on Facebook: @InvestWithInsightFollow Brandon on Linkedin: @BrandonBruckmanJoin the Facebook group: Invest with InsightListen on Spotify: The Retiring Real Estate InvestorListen on Apple: The Retiring Real Estate InvestorIf you're looking to learn more about DSTs, 1031 exchanges and passive investing, visit www.investwithinsight.comThe firm is a registered investment adviser with the states of KS, MO, WI, CA, AZ, TX, LA, and may only transact business with residents of those states, or residents of other states where otherwise legally permitted subject to exemption or exclusion from registration requirements.

September 2, 202547 min

55: Joel Miller - Author of Build Real Estate Wealth

Join host Brandon Bruckman as he sits down with seasoned real estate investor Joel Miller. With nearly five decades of experience, Joel shares his journey from a curious eighth-grader to a successful real estate mogul. Discover how Joel pioneered the mobile DJ business, balanced multiple careers, and eventually transitioned into hard money lending. Key Topics:Joel's early interest in real estate and radio Transition from DJing to real estate investing The importance of maintaining multiple income streams Insights from Joel's book, "Build Real Estate Wealth" The role of mindset in real estate success Strategies for tenant selection and property management The difference between riches and wealth Joel's approach to retirement and passing on his legacy The evolution of real estate investing over decades Hard money lending as a retirement strategy Building a network within the real estate community The impact of economic cycles on real estate Balancing personal passions with professional pursuits The significance of off-market deals in real estateGuest Information:Name: Joel Miller Book: "Build Real Estate Wealth" Website: JoelMillerBooks.comCall to Action: Visit JoelMillerBooks.com for more insights and to purchase Joel's book. Stay tuned for a deeper dive in our next episode!Social Links:Podcast: The Retiring Real Estate InvestorFollow us on Instagram: @InvestWithInsightFollow us on Facebook: @InvestWithInsightFollow Brandon on Linkedin: @BrandonBruckmanJoin the Facebook group: Invest with InsightListen on Spotify: The Retiring Real Estate InvestorListen on Apple: The Retiring Real Estate InvestorIf you're looking to learn more about DSTs, 1031 exchanges and passive investing, visit www.investwithinsight.comThe firm is a registered investment adviser with the states of KS, MO, WI, CA, AZ, TX, LA, and may only transact business with residents of those states, or residents of other states where otherwise legally permitted subject to exemption or exclusion from registration requirements.

August 8, 202542 min

54: Bryan J. Hayes - Convrzn

SummaryIn this episode, Brandon Bruckman interviews Bryan Hayes, a senior associate at Tenant Services Group and a founder of Convrzn, a pioneer in voice intelligence technology. They explore the integration of AI in real estate, focusing on how voice AI can enhance market intelligence and client interactions. Bryan shares his journey from urban retail to founding a company specializing in voice AI, discussing the challenges and opportunities in adopting this technology. The conversation also covers the future of AI across various industries, including healthcare and government, and the importance of aligning AI with business values.TakeawaysVoice AI streamlines market data gathering, offering real-time insights.Technology provides a competitive edge in real estate transactions.Customizing AI to reflect business personas aligns technology with company values. Embracing innovation encourages rethinking traditional business models. AI can transform client interactions and market intelligence in real estate. The future of AI spans multiple industries, offering vast potential. Aligning AI with business values enhances client relationships. Real estate professionals can leverage AI for better decision-making.Chapters00:00 Introduction to AI in Real Estate 02:30 Bryan's Journey from Urban Retail to Voice AI 05:15 Role of Voice AI in Market Intelligence 08:45 Challenges and Opportunities in AI Adoption 12:00 Future of AI in Healthcare and Government 15:30 Customizing AI to Reflect Business Values 18:20 Embracing Innovation in Real Estate 21:10 Aligning AI with Business Personas 24:00 Transforming Client Interactions with AI 27:30 Final Thoughts and Future DirectionsSocial Links:Podcast: The Retiring Real Estate InvestorFollow us on Instagram: @InvestWithInsightFollow us on Facebook: @InvestWithInsightFollow Brandon on Linkedin: @BrandonBruckmanJoin the Facebook group: Invest with InsightListen on Spotify: The Retiring Real Estate InvestorListen on Apple: The Retiring Real Estate InvestorIf you're looking to learn more about DSTs, 1031 exchanges and passive investing, visit www.investwithinsight.comThe firm is a registered investment adviser with the states of KS, MO, WI, CA, AZ, TX, LA, and may only transact business with residents of those states, or residents of other states where otherwise legally permitted subject to exemption or exclusion from registration requirements.

July 18, 202534 min

53: Matthew Incitti - Hamilton Point Investments

Join host Brandon Bruckman as he chats with Matthew Incitti from Hamilton Point about the dynamic world of real estate investment strategies since the 2008 financial crisis. Discover how Hamilton Point has adapted its approach from distressed asset acquisition to value-add strategies and current opportunities in high-growth markets like Texas and Florida.Key Topics:Evolution of real estate strategies post-2008 Insights into distressed assets and value-add approaches Current market opportunities in Texas and Florida Importance of flexibility and professional management Navigating capital market challengesGuest: Matthew Incitti, Vice President of Sales and Marketing at Hamilton PointConnect with Matthew:Website: HamiltonPointINV.com LinkedIn: Matthew IncittiSocial Links:Podcast: The Retiring Real Estate InvestorFollow us on Instagram: @InvestWithInsightFollow us on Facebook: @InvestWithInsightFollow Brandon on Linkedin: @BrandonBruckmanJoin the Facebook group: Invest with InsightListen on Spotify: The Retiring Real Estate InvestorListen on Apple: The Retiring Real Estate InvestorIf you're looking to learn more about DSTs, 1031 exchanges and passive investing, visit www.investwithinsight.comThe firm is a registered investment adviser with the states of KS, MO, WI, CA, AZ, TX, LA, and may only transact business with residents of those states, or residents of other states where otherwise legally permitted subject to exemption or exclusion from registration requirements.

April 1, 202550 min

52: John Christy - Craft & Sage Wealth

SummaryIn this episode of the Retired Real Estate Investor podcast, host Brandon Bruckman, co-host Joshua Wright, and guest John T. Christy, CFP® discuss the unique financial needs of real estate investors. They explore the common pitfalls that investors face, the importance of holistic financial planning, and the critical role of estate planning. The conversation emphasizes the need for real estate investors to integrate their investment strategies with tax planning and to consider their legacy and exit strategies as they build their portfolios. The episode highlights the often-overlooked aspects of financial advising for real estate investors and the importance of planning for the future. In this conversation, the speakers delve into the complexities of estate planning, sharing personal anecdotes and professional insights. They emphasize the importance of early planning, the challenges posed by complicated estates, and the necessity of strategic partnerships in navigating these issues. The discussion highlights real-life examples of messy estates and the emotional toll they can take on families, underscoring the need for clear communication and proactive planning.Follow John and his firm Craft & Sage Wealth on these socials:Website link: https://bit.ly/43sUwVX Facebook: https://www.facebook.com/craftandsageInstagram: https://www.instagram.com/craftandsage/LinkedIn: https://www.linkedin.com/company/craft-and-sage/YouTube: https://www.youtube.com/@craftandsageTakeawaysReal estate investors often lack communication with financial advisors.Many investors are unaware of the importance of holistic wealth management.Estate planning is frequently neglected by successful investors.The next generation often struggles with unplanned estates.Successful investors need to think about exit strategies early.Planning with the end in mind is essential for legacy management. Personal experiences illustrate the importance of estate planning.Complex estates can lead to overwhelming challenges for families.Understanding the intricacies of estate taxes is crucial.Regular updates to estate plans are necessary as circumstances change.A formal estate plan is better than relying on state defaults.Social Links:Podcast: The Retiring Real Estate InvestorFollow us on Instagram: @InvestWithInsightFollow us on Facebook: @InvestWithInsightFollow Brandon on Linkedin: @BrandonBruckmanJoin the Facebook group: Invest with InsightListen on Spotify: The Retiring Real Estate InvestorListen on Apple: The Retiring Real Estate InvestorIf you're looking to learn more about DSTs, 1031 exchanges and passive investing, visit www.investwithinsight.comThe firm is a registered investment adviser with the states of KS, MO, WI, CA, AZ, TX, LA, and may only transact business with residents of those states, or residents of other states where otherwise legally permitted subject to exemption or exclusion from registration requirements.

February 3, 202536 min

51: Ana Klein, CPA - AKK Tax and Accounting

SummaryIn this episode, Brandon Bruckman interviews Ana Klein, a tax strategist specializing in real estate and founder of AKK Tax and Accounting. They discuss the importance of tax strategy for real estate investors, the differences between a tax strategist and a CPA, and how to engage with a tax strategist throughout the year. Anna shares insights on the strategies wealthy clients use to build wealth, the significance of real estate professional status, and the benefits of estate planning. They also touch on the challenges of IRS audits, the advantages of a virtual business, and the value of life coaching for business leaders.TakeawaysTax strategists focus on proactive planning, not just compliance.Good bookkeeping is essential for effective tax planning.Wealthy individuals often buy back their time by outsourcing tasks.Real estate can offset income from operating businesses.Real estate professional status is difficult to achieve but beneficial.Never gift properties; always pass them through inheritance for tax benefits.IRS audits can be managed with good record-keeping.Virtual businesses allow for flexibility and travel.Investing in expertise is crucial for success.Life coaching can enhance leadership skills and personal growth.Chapters00:00 Introduction to Tax Strategy and Real Estate02:47 The Role of a Tax Strategist vs. CPA05:51 Engaging with a Tax Strategist Throughout the Year09:03 Wealthy Clients' Strategies for Success11:50 Real Estate Professional Status and Short-Term Rentals15:07 Navigating Retirement and Passive Income17:51 The Importance of Estate Planning and Trusts21:09 Understanding IRS Audits and Record Keeping23:56 The Benefits of a Virtual Business27:13 Investing in Real Estate: Current Focus29:54 The Value of Life Coaching for Business Leaders32:47 Final Thoughts and ResourcesSocial Links:Podcast: The Retiring Real Estate InvestorFollow us on Instagram: @InvestWithInsightFollow us on Facebook: @InvestWithInsightFollow Brandon on Linkedin: @BrandonBruckmanJoin the Facebook group: Invest with InsightListen on Spotify: The Retiring Real Estate InvestorListen on Apple: The Retiring Real Estate InvestorIf you're looking to learn more about DSTs, 1031 exchanges and passive investing, visit www.investwithinsight.comThe firm is a registered investment adviser with the states of KS, MO, WI, CA, AZ, TX, LA, and may only transact business with residents of those states, or residents of other states where otherwise legally permitted subject to exemption or exclusion from registration requirements.

November 20, 202451 min

50: Whitney Sewell - Life Bridge Capital

SummaryIn this conversation, Whitney Sewell shares his journey from military service to becoming a successful real estate investor and entrepreneur. He discusses the challenges he faced in his early career, the impact of his adoption journey on his family and business, and the importance of strategic reflection in making significant life decisions. Whitney also highlights the transformative role of podcasting in expanding his network and growing his business, LifeBridge Capital, which focuses on multifamily real estate investments and supporting adoption efforts. In this conversation, the speaker reflects on the challenges faced in the real estate market over the past couple of years, emphasizing the importance of sticking to core investment principles. They discuss recent shifts in market dynamics, the significance of strategic market selection, and the need for steady returns for investors. The conversation also highlights the importance of team culture, community engagement, and personal growth through influential literature. The speaker shares insights on exit strategies and the value of supporting families and investors alike.TakeawaysWhitney's military background shaped his resilience and perspective.Adoption has been a significant driving force in Whitney's life and business.Strategic reflection is crucial for making impactful life decisions.Podcasting can serve as a valuable networking and learning tool.Building a mission-driven business can attract like-minded partners and investors.Challenges in property management can provide essential learning experiences.The importance of family values in business partnerships cannot be overstated.Sticking to core investment principles is crucial during market fluctuations.Recent market shifts have created new opportunities for investment.Investors prefer steady returns over high-risk, high-reward scenarios.Building a strong team culture is essential for long-term success.Community engagement can enhance tenant satisfaction and retention.Personal growth and continuous learning are vital for effective leadership.Exit strategies should prioritize investor returns and satisfaction.Investors appreciate transparency and communication regarding their investments.Creating a family mission statement can strengthen family bonds and values.Supporting families in the community aligns with business values and enhances reputation.Learn more about Whitney - https://www.whitneysewell.com/Social Links:Podcast: The Retiring Real Estate InvestorFollow us on Instagram: @InvestWithInsightFollow us on Facebook: @InvestWithInsightFollow Brandon on Linkedin: @BrandonBruckmanJoin the Facebook group: Invest with InsightListen on Spotify: The Retiring Real Estate InvestorListen on Apple: The Retiring Real Estate InvestorIf you're looking to learn more about DSTs, 1031 exchanges and passive investing, visit www.investwithinsight.comThe firm is a registered investment adviser with the states of KS, MO, WI, CA, AZ, TX, LA, and may only transact business with residents of those states, or residents of other states where otherwise legally permitted subject to exemption or exclusion from registration requirements.

November 20, 202446 min

49: Mike Finger - Exit Oasis

SummaryIn this episode, Brandon Bruckman interviews Mike Finger, a seasoned entrepreneur and business coach, who shares his extensive experience in buying, selling, and operating small businesses. Mike discusses the common pitfalls small business owners face when preparing to sell, the importance of understanding seller discretionary earnings, and the realities of passive income in business ownership. He emphasizes the need for owners to prepare their businesses for sale well in advance and provides insights into the buyer's perspective, including the significance of operational efficiency and the mindset required for successful business transactions.TakeawaysMike Finger has owned and sold multiple small businesses, providing him with valuable insights.Most small businesses fail to sell due to lack of preparation and understanding of sellability.Seller discretionary earnings are crucial for buyers to assess the true value of a business.Buyers should focus on specific industries where they have expertise to increase their chances of success.Passive income in small business ownership is often a myth; active involvement is usually required.Business owners should start preparing for a sale years in advance, not at the moment they decide to sell.Operational efficiency is key to making a business both sellable and ownable.Sellers often underestimate the importance of financial documentation and transparency.Educating sellers about the realities of the market can be a challenging but necessary process.Distressed businesses can present unique opportunities for buyers with the right skills and knowledge.Connect with Mike - https://exitoasis.com/Social Links:Podcast: The Retiring Real Estate InvestorFollow us on Instagram: @InvestWithInsightFollow us on Facebook: @InvestWithInsightFollow Brandon on Linkedin: @BrandonBruckmanJoin the Facebook group: Invest with InsightListen on Spotify: The Retiring Real Estate InvestorListen on Apple: The Retiring Real Estate InvestorIf you're looking to learn more about DSTs, 1031 exchanges and passive investing, visit www.investwithinsight.comThe firm is a registered investment adviser with the states of KS, MO, WI, CA, AZ, TX, LA, and may only transact business with residents of those states, or residents of other states where otherwise legally permitted subject to exemption or exclusion from registration requirements.

November 20, 202447 min

48: Ruben Greth - Yrēfy

SummaryIn this episode, Brandon Bruckman welcomes back Ruben, who shares insights into his evolving career in real estate and capital raising. Ruben discusses his transition from traditional real estate syndication to a debt fund model focused on student loans. He elaborates on the challenges of building a subdivision, the current state of capital raising, and the importance of marketing in attracting investors. The conversation also touches on the motivations of investors and the altruistic aspects of Ruben's business model, which aims to help borrowers while providing returns to investors. This conversation delves into the intricacies of debt, banking, and the dynamics of registered investment advisors (RIAs). It explores how banks operate, the nature of student loans, and the challenges of finding suitable RIAs for alternative investments. The discussion also touches on the importance of spiritual philosophy in business, emphasizing peace and ethical behavior as key components of success. The conversation concludes with practical advice for capital raisers and resources for further learning.TakeawaysRuben has transitioned from real estate syndication to a debt fund model.He has successfully raised over $4 million in a short time.Building a subdivision involves numerous unforeseen challenges. Investors need to understand their goals before investing in developments.The current capital raising environment is cautious, with many investors on the sidelines.Marketing plays a crucial role in attracting investors to capital raising efforts.The debt fund model offers lower risk and higher returns compared to traditional investments.Ruben's business model focuses on helping borrowers while providing returns to investors.Altruism in business can enhance capital raising efforts.Understanding the motivations of investors is key to successful fundraising. Student loans are unique as they lack collateral but are bankruptcy protected. Co-borrowers significantly mitigate risk in lending.Finding independent RIAs is challenging but essential for alternative investments.Alternative investments can serve as bond alternatives for portfolios.Peace should be a guiding principle in business decisions.Good human behavior is crucial for attracting success.Capital raisers should seek experienced partners for better outcomes.Connect with Ruben - https://www.linkedin.com/in/rubengreth/Social Links:Podcast: The Retiring Real Estate InvestorFollow us on Instagram: @InvestWithInsightFollow us on Facebook: @InvestWithInsightFollow Brandon on Linkedin: @BrandonBruckmanJoin the Facebook group: Invest with InsightListen on Spotify: The Retiring Real Estate InvestorListen on Apple: The Retiring Real Estate InvestorIf you're looking to learn more about DSTs, 1031 exchanges and passive investing, visit www.investwithinsight.comThe firm is a registered investment adviser with the states of KS, MO, WI, CA, AZ, TX, LA, and may only transact business with residents of those states, or residents of other states where otherwise legally permitted subject to exemption or exclusion from registration requirements.