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Business LegacyAuthor: Legacy Planner For Serial Entrepreneurs Strategic Advisor
The Legacy Podcast is a series of conversations with business owners who share their journey to financial freedom and the legacy they want to leave for the next generation. Their stories are empowering, educational, and encouraging. Language: en Genres: Business, Entrepreneurship Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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The Intersection of Real Estate and Tax Advisory
Episode 239
Monday, 27 October, 2025
Matthew Wessels, partner at Wessels Realty and Tax Advisors, takes center stage as he shares his compelling journey from the hills of New Hampshire to carving a unique niche in the real estate and tax advisory world. Matthew's story is a testament to the power of combining passions, as he skillfully marries his accounting background with a fervor for real estate development. Our conversation uncovers how he transitioned from the corporate treadmill to co-purchasing his first property, igniting a career that now stands at the intersection of real estate analysis, general contracting, and specialized tax advisory services. Matthew's insights into the Massachusetts rental market showcase both the challenges and opportunities that come with navigating market shifts, political influences, and evolving investment strategies. In a deeper exploration, we reflect on the balance between professional success and personal fulfillment. Matthew opens up about how fatherhood reshaped his priorities, leading to a transformation in his work-life balance through automation and delegation. His reflections on legacy, infused with values of authenticity, courage, and generosity, offer listeners a roadmap to crafting a meaningful life beyond societal expectations. This episode is a treasure trove of wisdom for those eager to learn from a visionary who has successfully integrated personal growth with professional achievement, all while maintaining the courage to follow his distinctive path. Timestamps 00:00:00 - Introduction and Welcome to Business Legacy Podcast 00:00:11 - Meet Matthew Wessels: Real Estate and Tax Advisory Innovator 00:00:37 - Matthew's New Hampshire Roots and Education at Bentley University 00:01:20 - Transition from Corporate Accounting to Real Estate Investment 00:02:45 - Building Wessels Realty and Tax Advisors: A Multifaceted Approach 00:04:10 - The Unique Blend of CPA Expertise and Real Estate Development 00:05:25 - The Complexity and Opportunities in Real Estate and Tax Advisory 00:06:30 - Market Fluctuations and Resilience in Massachusetts Rental Properties 00:07:55 - Political and Economic Influences on the Housing Market 00:09:10 - Trends in Homeownership and Investment Property Challenges 00:10:30 - Matthew's Role in Educating and Mentoring Aspiring Investors 00:11:09 - Real Estate Market Insights and Strategies 00:12:05 - Overcoming the Fear of Property Investment 00:13:30 - The Impact of Market Shifts on Cash Flow and Property Value 00:14:40 - Balancing Professional Growth and Personal Life 00:15:50 - Matthew's Reflections on Fatherhood and Work-Life Balance 00:17:10 - Legacy, Values, and the Courage to Follow a Unique Path 00:18:05 - Navigating Work-Life Balance and Legacy 00:19:00 - Emphasizing Happiness, Generosity, and Authenticity 00:20:30 - Matthew's Advice: Embrace Being Different and Follow Your Own Path 00:21:45 - Closing Thoughts and Where to Learn More About Matthew Wessels 00:22:45 - Conclusion and Final Thoughts from Paul Dio 00:23:30 - Closing Remarks and Invitation to Leave a Review Episode Resources: Connect with Matthew here and find more out about what they do: https://www.wesselsrealtyandtaxadvisors.com/ Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit businesslegacypodcast.com. Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit businesslegacypodcast.com to access the shownotes and additional resources on the episode.
