Best Tyler Chesser Podcasts (2025)

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Tyler Chesser's Playbook: Achieving $2.1M Exits and $150M Targets in a Volatile Market 45:48

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10d ago45:48

45:48

In this episode, Brad chats with Tyler Chesser, co-founder and managing partner of CF Capital. Tyler leveraged his background as a top multifamily broker to scale his portfolio and develop CF Capital into a respected partner for investors. He shares his philosophy of constant improvement and details his journey from corporate America to real estate…

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John Casmon on 'Failing Forward' and the Power of Midwest Real Estate 1:04:58

14d ago1:04:58

1:04:58

In this episode, Brad chats with John Casmon, former marketing executive, founder and managing partner of Casmon Capital Group , and host of the top-rated Multifamily Insights podcast. John shares his journey from corporate America—where he survived two company bankruptcies that spurred his need for a "Plan B" —to a full-time real estate investor w…

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Turning Potential into Performance: A Conversation with Lauren Brychell 31:31

19d ago31:31

31:31

In this episode of Legacy Builders with Kyle McGee, host Kyle McGee sits down with Lauren Brychell, founder of Equity Elevated Consulting and author of Beyond the Lead. Lauren shares how she accidentally stumbled into the world of capital raising and went on to raise over $75M across commercial real estate and alternative investments. From masterin…

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The Family Bank: Wealth and Wisdom Across Generations with Blake Johnson 45:10

25d ago45:10

45:10

In this episode of Legacy Builders with Kyle McGee, our host Kyle McGee sits down with estate planning attorney Blake Johnson to talk about what it really takes to build wealth that lasts. Blake shares how to create a “family bank,” why parents should manufacture challenges instead of removing them, and how faith and intentionality shape a family’s…

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From Drafting Tables to Dream Homes: The Journey of Jason Langkammerer 44:42

1M ago44:42

44:42

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John Wijtenburg on Transforming a $100M Resort and the CRE Growth Operating System 28:47

1M ago28:47

28:47

In this episode, Brad chats with John Wijtenburg, founder of LXK Group, an expert in commercial real estate operations and systems, who helps investors and operators scale their portfolios while maintaining their core values. John shares his journey from an economist at Fannie Mae and an apartment broker to a successful hotel operator and asset man…

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Building More Than Homes: Blaine Flynn on Life and Legacy 53:51

1M ago53:51

53:51

Blaine Flynn’s journey is anything but ordinary. From dropping out of high school at 16 to building one of the most respected home construction companies in Northwest Florida, his story is rooted in faith, family, and the mantra, “Why not me?”. In this episode, Blaine shares the lessons of resilience, the fine line between confidence and arrogance,…

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John Todderud's Journey from Tech to Multifamily Syndication 31:48

2M ago31:48

31:48

In this episode, Brad chats with John Todderud, the founder of Cardinal Oak Investments and a former tech professional who transitioned into multifamily real estate. John shares his journey from buying small, rural properties to scaling a full-fledged syndication business. He opens up about the biggest lessons he learned from his "worst" and "best"…

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Beyond the First Deal: Scaling a Real Estate Portfolio with Ian Cruz 34:03

2M ago34:03

34:03

In this episode, Brad chats with Ian Cruz, a former CPA and boxing coach who has successfully transitioned into multifamily real estate. Ian shares his journey from his roots in big four public accounting to becoming a value-add multifamily investor focused on the Cincinnati, Ohio market. He discusses the importance of building a strong local team …

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Belief Before Breakthrough: A Legacy Conversation with Tyler Chesser 52:20

2M ago52:20

52:20

In this episode of Legacy Builders with Kyle McGee, our host sits down with Tyler Chesser—co-founder and managing partner of CF Capital—to unpack his remarkable journey from a corporate career in marketing to building one of the country’s most trusted multifamily investment platforms. Tyler shares the mindset shifts, personal development breakthrou…

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Bruce Fraser on Distressed Multifamily and Macro Investing 43:35

2M ago43:35

43:35

In this episode, Brad chats with Bruce Fraser, a Forbes Real Estate Council Member and Managing Partner at Elkhorn Capital Partners. Bruce shares his unique journey from running a successful hedge fund for over a decade to becoming a multifamily investor. He explains how his background in macroeconomics led him to focus on hard assets, specifically…

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From Exporting Wine to Building Empires: Alice Chen on Business and Legacy 49:02

2M ago49:02

49:02

In this episode of Legacy Builders, host Kyle McGee sits down with Alice Chen—entrepreneur, investor, and private equity fund manager—to explore her incredible journey from mergers and acquisitions law to building businesses across industries and scaling wealth through innovative strategies. Alice shares how her upbringing shaped her entrepreneuria…

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From Cybersecurity to $217M in Real Estate: Tenny Tolafari's Journey 28:51

2M ago28:51

28:51

In this episode, Brad connects with Tenny Tolafari, a cybersecurity professional turned real estate mogul and co-founder of Xsite Capital. Tenny shares his incredible journey from working 60-hour weeks in corporate America to building and managing a $217 million real estate portfolio. He recounts the full-circle story of a cold call that led to a v…

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Football, Faith, and Foundations: Lessons and Legacy with Will Lowery 1:05:32

2M ago1:05:32

1:05:32

What does it take to turn a walk-on into a national champion and then into a business leader shaping entire communities? In this episode, Will Lowery shares his incredible journey—from grinding it out on Alabama’s legendary defense under Nick Saban to carving a career in real estate development at 68 Ventures. We dive into the discipline, mindset, …

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Lessons from a $650M Portfolio: Insights from Real Estate Veteran Dusty Eddy 33:23

2M ago33:23

33:23

In this episode, Brad chats with Dusty Eddy, founder of Eddy Capital Group, and a veteran real estate investor with over 23 years of experience. Dusty, who has led over $650 million in multifamily investments and completed 15 full-cycle deals with impressive returns, shares his journey from an institutional background to building his own firm. He d…

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Be Comfortable Being Uncomfortable: A Conversation with Forrest Derr on Growth & Legacy 50:32

3M ago50:32

50:32

In this episode of Legacy Builders, host Kyle McGee sits down with Forrest Derr, an operator, strategist, and servant leader whose career has been defined by resilience, adaptability, and growth. From his first paper route at age 15 to nearly two decades in executive operations, to launching his own fractional COO firm, Forrest shares the lessons l…

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From Start-Up to $1 Billion Portfolio: Lessons in Commercial Real Estate with Carlos Salguero 53:32

2M ago53:32

53:32

In this episode, Brad chats with Carlos Salguero, an entrepreneur and real estate expert with over 20 years of business and investment experience. After starting four seven-figure companies and exiting one for an eight-figure sum, Carlos is now focused on helping others invest in commercial real estate and building a $1 billion portfolio. He shares…

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Vision, Mindset & Fulfillment: Building a Legacy with Jacob Hicks 49:04

3M ago49:04

49:04

In this episode of Legacy Builders with Kyle McGee, host Kyle McGee sits down with success coach Jacob Hicks, whose mission is to help leaders, entrepreneurs, and professionals find clarity, craft winning strategies, and live a life of true fulfillment. From his roots in sales to building a thriving coaching practice, Jacob shares the lessons he’s …

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Planting the Seeds of Legacy: A Conversation with Kurt Wilkin 47:27

3M ago47:27

47:27

In this episode of Legacy Builders with Kyle McGee, host Kyle McGee sits down with Kurt Wilkin, CEO of Hire Better and managing partner at Beatcave Capital. With over 25 years of experience guiding high-growth companies, Kurt brings raw honesty about the entrepreneurial journey—the wins, the failures, and the lessons that truly matter. From buildin…

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40 Years of Real Estate Experience with Arn Cenedella 36:40

3M ago36:40

36:40

In this episode, Brad chats with Arn Cenedella, founder of Spark Investment Group, who brings over 40 years of real estate experience, including 35 years as a realtor in Silicon Valley. Arn shares his transition from single-family to multi-family real estate investing, the lessons learned from his biggest investing mistake during the 2008 subprime …

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Turning Dreams into Better Lives: A Legacy Conversation with Camilo Giraldo 59:44

3M ago59:44

59:44

Camilo Giraldo’s journey is the embodiment of grit, vision, and legacy-building. From his family losing it all in Colombia to landing in Florida with just $1,000, Camilo has built a real estate, construction, and tech empire. In this episode, we explore his entrepreneurial hustle, the mentors who shaped him, his unwavering morning routine, and the …

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High Performance to High Impact: Joe Evangelisti on Purpose, Service & Legacy 44:26

3M ago44:26

44:26

In this episode of Legacy Builders with Kyle McGee, our host sits down with Joe Evangelisti—a Navy veteran turned real estate powerhouse and high-performance coach—to unpack what it really means to build a life of impact. From flipping 88 single-family homes in a single year to transitioning into multi-million-dollar self-storage developments, Joe’…

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Ministry in the Marketplace: Lessons in Leadership and Legacy with Mike Aman 56:02

3M ago56:02

56:02

Mike Aman’s journey is a powerful story of faith, resilience, and purpose. From facing bankruptcy three times to building and selling a thriving 20-year communications company, he discovered that true success isn’t measured in profits alone—it’s found in people, impact, and legacy. In this episode, Mike shares how surrendering to his faith, leading…

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Streamlining Success: David Hrizak on Real Estate, Mentorship & Living Fully 42:14

3M ago42:14

42:14

In this powerful episode of Legacy Builders with Kyle McGee, we sit down with David Hrizak, co-founder and CEO of The Streamline Companies, to explore his 29-year journey in real estate—from humble beginnings on the South Side of Chicago to creating a vertically integrated real estate empire in Arizona. David shares the defining moment that changed…

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Cultivating Curiosity: Navigating Legacy and Leadership with Lisa Wallenda Picard 42:01

3M ago42:01

42:01

In this captivating episode of Legacy Builders with Kyle McGee, host Kyle McGee sits down with Lisa Wallenda Picard, a trailblazer whose path has taken her from the big top of the Ringling Bros. Circus to the halls of the USDA, National Turkey Federation, and now the helm of the National Fisheries Institute. With a rich background in public relatio…

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Trust, Time, and Tenacity: Financial Journeys with Richard Wright 43:02

4M ago43:02

43:02

When Richard Wright’s parents helped him buy a house in his early 20s, he didn’t realize they were handing him the foundation of his future success. Now managing over $60M in assets, Richard reflects on how a small act of support became the legacy that shaped his career, mindset, and mission. In this episode, we talk about building wealth with inte…

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Teaching, Treating, and Trust: Building a Lasting Legacy with Dr. Jeff Buchalter 53:59

4M ago53:59

53:59

What do pain medicine, real estate, and leadership have in common? For Dr. Jeff Buchalter, they’re all part of a legacy built on integrity, curiosity, and compassion. In this episode, Kyle sits down with Dr. Buchalter to explore his entrepreneurial journey, the risks and rewards of private practice, how to lead with purpose, and why building a stro…

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Pensacola's Power Play: A Discussion with Greg Harris on Culture and Community 57:37

4M ago57:37

57:37

From Canada to the heart of the Gulf Coast, Greg Harris has built more than a championship hockey team—he’s built a movement. As owner of the Pensacola Ice Flyers, Greg shares how passion, community, and a bold leap of faith created a legacy far beyond the rink. In this episode, hear how his leadership philosophy of “be predictable” and “be a pro” …

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From Mobile Homes to Mindset Mastery: A Conversation with Alyssa Holbrook 47:16

4M ago47:16

47:16

In this episode, we sit down with high-performance coach and real estate investor Alyssa Holbrook to explore the inner transformation required to build a truly meaningful legacy. From buying her first mobile home at 14 to coaching top performers through mindset breakthroughs, Alyssa shares powerful frameworks on identity, resilience, intentional li…

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Legacy in Action: Building Experiences that Matter with Jonathan Griffith 52:10

4M ago52:10

52:10

What happens when a minor league baseball team becomes a major force for good in its community? In this episode of Legacy Builders with Kyle McGee, we sit down with Jonathan Griffith — President of the Blue Wahoos and Studer Entertainment & Retail — to talk about the real work behind building unforgettable fan experiences, company culture, and a le…

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Scaling with Purpose: The Power of Vision and Values in Business with Mark Faris 1:02:19

4M ago1:02:19

1:02:19

What does it take to go from professional hockey player to founder of a billion-dollar real estate business? In this inspiring episode, Kyle sits down with Mark Faris, CEO of Faris Team and Faris Capital Partners, to talk about building a legacy rooted in faith, family, and full-out execution. From hitting early sales goals to developing a 10,000-u…

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From LP to Operator to Business Owner: Sam Khairi’s Pivot from Real Estate to Entrepreneurship 32:38

4M ago32:38

32:38

In this episode, Brad chats with Sam Khairi, founder of Afto Capital and a former mechanical engineer who walked away from a secure 15-year career to chase freedom through real estate and business ownership. Sam shares his journey from passive investor (LP) to active syndicator (GP), the challenges of entering the multifamily space full-time in 202…

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What It Really Means to ‘Be There’ – A Legacy Conversation with Alan Underwood 54:14

4M ago54:14

54:14

This week on Legacy Builders, Kyle sits down with Alan Underwood—a coach, capital strategist, and father of eight—who opens up about the years that nearly broke him: the loss of loved ones, a crumbling business, and hitting rock bottom emotionally and financially. But that’s not where Alan’s story ends. In one of our most powerful episodes yet, Ala…

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Pain, Property, & Purpose: A Masterclass in Mental Toughness with Gavin J. Gallagher 48:49

4M ago48:49

48:49

On this episode of Legacy Builders with Kyle McGee, our host sits down with Gavin J. Gallagher, Executive Director at Earlsfort Group and founder of the Elite Property Accelerator. Gavin opens up about inheriting a struggling business after the sudden death of his father, rising to wealth through real estate, and then losing it all—his fortune, his…

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From Wholesaling Hustle to 400+ Units: How Marine Veteran Joseph Kimbrough Built a Real Estate Empire 22:32

4M ago22:32

22:32

In this episode, Brad sits down with Joseph Kimbrough, Marine Corps veteran turned entrepreneur, and the CEO of both Baruk Capital Group and Apex Real Estate Investments. Joseph’s journey started with door-knocking and speeding tickets—and led to creative financing on a 400+ unit deal in Phoenix. We talk wholesaling, multifamily syndications, the i…

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Building Culture, Shaping Cities: A Discussion with Ashton Hayward 47:36

4M ago47:36

47:36

From busing tables to growing cities, Ashton Hayward’s journey is a testament to hustle, heart, and hometown pride. In this episode of Legacy Builders, Ashton opens up about his path from New York City executive to transformational mayor of Pensacola. He shares how embracing discomfort, thinking big, and leading with vision helped him spark a cultu…

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Building a Titan Mentality: A Conversation with Chad King about the Habits Behind High-Level Execution 59:46

5M ago59:46

59:46

In this episode of Legacy Builders with Kyle McGee, host Kyle McGee sits down with real estate powerhouse Chad King to unpack his journey from door-to-door copier sales to owning nearly $200 million in multifamily assets. Chad shares the ups and downs of flipping over 360 houses, transitioning into syndication, building Titan Capital Group, and his…

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From Boston House Hacker to Large-Scale Syndicator: Chris Lento’s Multifamily Journey 23:48

5M ago23:48

23:48

In this episode, Brad sits down with Chris Lento, founder and managing member of EM Capital Group, to hear how he went from hacking a four-unit house in East Boston to managing large multifamily syndications across the Southeast. With over 18 years of experience in multifamily real estate, Chris shares hard-earned lessons, a few war stories, and wh…

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Risk, Relationships, and Redemption: A Discussion with Rick Ormsby on Franchise Finance and Faith 44:13

5M ago44:13

44:13

Episode 20 of Legacy Builders with Kyle McGee is live! In this episode, Kyle McGee sits down with Rick Ormsby—Managing Director of Unbridled Capital and a leading voice in franchise investment banking. Rick shares his unexpected leap from corporate life to entrepreneurship, the power of intellectual curiosity, and how faith and integrity shape his …

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Legacy By Design: A Conversation with Richard McCool about Strategic Mindsets and Financial Legacies 54:30

5M ago54:30

54:30

Episode 19 of Legacy Builders with Kyle McGee is live! What does it really mean to build real wealth—and how do you protect it? In this powerful episode of Legacy Builders, Kyle sits down with Richard McCool, wealth strategist and co-founder of Blackwood Financial Group, to unpack what it means to create a legacy beyond dollars and cents. Richard s…

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From Physical Therapist to 800+ Units: Building a Purpose-Driven Real Estate Business with Lee Yoder 26:36

5M ago26:36

26:36

In this episode, we sit down with Lee Yoder, founder of Threefold Real Estate Investing, who went from physical therapist to full-time multifamily investor with over 800 units under management. Lee shares how he followed a calling to build something, overcame fear and resistance, and leaned into faith, family, and real estate to change the trajecto…

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Legacy in the Making: A Conversation with John Hosman on Purpose, Pivots, and Building Boldly 52:17

5M ago52:17

52:17

Episode 18 of Legacy Builders with Kyle McGee is now live! Join host Kyle McGee as he sits down with John Hosman for a powerful conversation about legacy, life pivots, and the journey of building something that lasts. From career changes to bold business moves, John shares how purpose and perseverance have shaped his path—and how he's laying the fo…

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Mindset and Motivation: A Conversation with Samantha Parrinello About Legacy and Personal Growth 49:12

5M ago49:12

49:12

Episode 17 of Legacy Builders with Kyle McGee is live! In this inspiring episode of Legacy Builders with Kyle McGee, host Kyle McGee sits down with Samantha Parrinello for a powerful conversation about building a lasting legacy and embracing personal growth. Together, they explore the mindset shifts that fuel motivation, how challenges shape charac…

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Evolution and Growth: A Conversation with Gene Whiddon III about Developing Your Legacy 45:05

5M ago45:05

45:05

Episode 16 of Legacy Builders with Kyle McGee is live! Host Kyle McGee sits down with visionary leader Gene Whiddon III for a powerful conversation on growth, evolution, and legacy. From personal transformations to building enduring impact, they explore what it means to adapt, lead with purpose, and leave something meaningful behind. Tune in for wi…

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The Legacy We Leave: A Discussion about Family, Purpose, and Resilience with Tal Clark 41:31

5M ago41:31

41:31

Episode 15 of Legacy Builders with Kyle McGee is live! In this powerful episode, host Kyle McGee sits down with Tal Clark to explore how life’s toughest moments can shape our purpose. Together, they unpack personal struggles, the meaning of resilience, and how to define a legacy that goes beyond ourselves. A must-listen for anyone striving to leave…

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Forging Your Own Path: A Conversation with Robert Rinke about Building Legacies from the Ground Up 1:18:29

5M ago1:18:29

1:18:29

Episode 14 of Legacy Builders with Kyle McGee is live! Join host Kyle McGee as he sits down with visionary entrepreneur Robert Rinke to explore the grit, mindset, and bold decisions it takes to build a lasting legacy from the ground up. From humble beginnings to industry impact, this episode is packed with real talk, practical wisdom, and the inspi…

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Perseverance and Commitment: A Discussion about Pushing through Challenges and Imposter Syndrome with Brian Ward 43:25

6M ago43:25

43:25

Episode 13 of Legacy Builders with Kyle McGee is live! In this powerful episode, we sit down with Brian Ward to explore what it really takes to push through life's challenges. From overcoming imposter syndrome to staying committed when the odds are stacked against you, Brian shares raw insights and actionable strategies to help you keep moving forw…

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Faith at the Forefront: How Your Faith Can Shape Your Journey with Nathan Pooley 44:52

6M ago44:52

44:52

Episode 12 of the Legacy Builders Podcast is live! In this episode, we dive deep into the powerful intersection of faith and legacy. Whether you're building a family, leading a community, or just figuring out your path, this conversation will challenge you to think bigger about the life you're living and the impact you're making. Tune in now and…

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Living Your Legacy - A Conversation About Growing Your Legacy with Tyler Gross 50:36

6M ago50:36

50:36

Episode 11 of the Legacy Builders Podcast is live! Legacy isn’t built on perfection—it’s shaped by the lessons we learn, the mistakes we own, and the commitment to keep going. Tune in as Kyle McGee sits down with Tyler Gross and dives into real stories of growth, resilience, and purpose, exploring what it truly means to leave something meaningful b…

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From Aerospace to Apogee: How Jonathan Nichols Engineered His Multifamily Success 23:13

6M ago23:13

23:13

In this episode of First, Worst, Best & Next, host Brad Weaver sits down with Jonathan Nichols—CEO of Apogee Capital, aerospace engineer turned full-time real estate investor. Jonathan shares his transition from side-hustling real estate with his wife into full-scale multifamily syndication. From a fourplex house hack near AT&T Stadium to a 75-unit…