Episode Summary

In this episode of Groundbreakers, Lee Yoder, founder of Threefold Real Estate Investing, shares how he left his career as a physical therapist to build a real estate portfolio that now manages over $75 million in assets. Lee walks through the early steps of learning syndications, scaling his team, and how focusing on core markets in the Midwest helped him grow efficiently while keeping operations tight.

Key Points Discussed

• Leaving a Stable Career: Lee opens up about his decision to step away from physical therapy—first into a sales job, and then full-time into real estate—to create a business with more freedom and impact.
• Starting Small, Scaling Fast: Lee explains how he went from flipping single-family homes to leading multifamily syndications and raising capital for deals across Ohio, Kentucky, and Indiana.
• Building the Right Team: He breaks down his strategy for hiring—why his first hires weren’t from real estate, and how clear expectations and ownership helped them thrive.
• Lessons from $75M AUM: Lee shares the operational lessons he’s learned from managing 600+ units, including deal sourcing, how he evaluates markets, and his thoughts on investor communication.

Guest Information

• Name: Lee Yoder
• Role: Founder & CEO of Threefold Real Estate Investing
• LinkedIn: Lee Yoder
• Website: Threefold Real Estate Investing

Conclusion

Lee’s story is a blueprint for operators looking to transition from W2 careers into multifamily. His methodical approach, strong Midwest focus, and dedication to team building have enabled him to grow quickly—while keeping values and investor trust front and center.

In this episode of Groundbreakers, Ben Bowerman, VP of Capital Markets at HPP Equity, shares how he scaled from managing 450+ single-family rentals to overseeing a diversified real estate portfolio with over $150M in assets under management. Ben breaks down the strategy behind HPP’s transition into student housing, multifamily, and build-to-rent—and why he believes in holding assets for the long term.

He also shares lessons learned from property management, the power of in-house operations, and how his team built a vertically integrated platform that aligns investor goals with long-term generational wealth.

• From Property Manager to Portfolio Builder: Ben started his real estate career in the trenches—managing hundreds of SFRs. He talks about how that experience shaped his perspective on operations and scale.
• Scaling into Student Housing: HPP Equity’s entry into student housing wasn’t accidental—it was strategic. Ben explains why the team leaned into this asset class, and how they’ve generated strong returns with disciplined underwriting.
• Lessons in Vertical Integration: HPP manages construction and property management in-house. Ben shares the benefits and challenges of controlling the full lifecycle of an asset, from acquisition to renovation and lease-up.
• Investor Education & Communication: Ben emphasizes the importance of transparent investor updates and setting realistic expectations in today’s economic climate. He also shares how his team educates investors who are new to commercial real estate.

• Name: Ben Bowerman
• Role: VP of Capital Markets at HPP Equity
• LinkedIn: Ben Bowerman
• Website: HPP Equity

Ben Bowerman’s story is a masterclass in scaling real estate the right way—slow, steady, and intentional. From property management to private equity, his journey proves that with the right operational backbone, it’s possible to go far without overextending. His long-term mindset, focus on value creation, and investor-first approach make this a must-listen for anyone thinking about scaling beyond their first few deals.

Connect with Ben on LinkedIn to learn more about HPP Equity and their investment thesis.

In this episode of Groundbreakers, Sean Graham, founder of Maven Cost Segregation, breaks down the most overlooked wealth-building tool in real estate: cost seg. After getting laid off in 2020, Sean transitioned into real estate full-time—starting with his own deals before launching a firm that now saves investors millions in taxes every year.

He shares how one property generated $400K in tax savings, why ROI should be measured in depreciation, and what most syndicators miss when it comes to maximizing after-tax returns.

• From W2 to Wealth Builder: Sean’s corporate job disappeared during COVID. Rather than wait for the next one, he leaned into real estate—launching Maven to help others unlock the tax strategies he used himself.
• How Cost Seg Works (for Real): Sean demystifies cost segregation in plain English, from front-loaded depreciation to partial asset dispositions—and why even smaller sponsors can benefit.
• The $400K Case Study: One property. $400K in paper losses. Sean walks through the math behind a real example and what that meant for investor cash flow and yield.
• What Syndicators Get Wrong: Sean shares the biggest mistakes operators make when structuring their deals for tax efficiency—and how to fix them without needing a CPA.
• ROI Beyond the Deal: Why the best operators treat cost seg like a multiplier, not an afterthought—and how to use it to attract high-net-worth LPs.

• Name: Sean Graham
• Role: Founder at Maven Cost Segregation
• LinkedIn: Sean Graham
• Website: Maven Cost Segregation

Sean Graham’s episode is a must-listen for any syndicator who wants to boost IRR after the deal closes. If you’ve ever wondered whether cost seg is worth it, this episode makes the case—backed by real numbers, real savings, and a blueprint for real results.

In this episode of Groundbreakers, Andrea Foley, Director at Generational Wealth Capital, shares how she went from flipping homes in Kansas City to launching a real estate fund focused on hotel-to-multifamily conversions. Along the way, she’s tackled everything from diaper cleaning to owning car wash franchises—proving that building generational wealth takes hustle, grit, and the ability to pivot fast.

Andrea breaks down her unique path, including the creative ways she sourced early deals, how she scaled into larger commercial assets, and why she’s bullish on hospitality conversions. She also opens up about the emotional side of entrepreneurship—juggling family, faith, and financial goals in a volatile market.

• The Flip That Started It All: Andrea’s real estate journey began with flipping residential homes—but she quickly realized the wealth was in holding, not selling. That mindset shift led to multifamily.
• Car Wash Franchises & Cash Flow: Before going all-in on real estate, Andrea and her husband bought into a car wash franchise. She shares what worked (and what didn’t) about getting into small business ownership to generate income.
• Hotel Conversions as an Opportunity: Andrea discusses her team’s thesis on converting hotels into multifamily, the operational complexities, and why she believes this is one of the most underpriced strategies in today’s market.
• Raising Capital Authentically: She opens up about building trust with passive investors, including the playbook she used to move from personal capital to raising funds from her broader network.

• Name: Andrea Foley
• Role: Director at Generational Wealth Capital
• LinkedIn: Andrea Foley
• Website: Generational Wealth Capital

Andrea Foley’s story is proof that you don’t need a traditional background to succeed in real estate. With persistence, creativity, and a clear mission, she’s building a portfolio that reflects her values—and helping others do the same.

Connect with Andrea on LinkedIn to learn more about her fund, her hotel conversion projects, and her journey from flips to franchises to multifamily.

Episode Summary

In this episode of Groundbreakers, Joey Schneider—CEO of Trinity Peak Partners and Head of Investor Relations at Ironton Capital—shares his unconventional path from medical sales to real estate investing. After climbing the corporate ladder and managing a large sales team, Joey realized he wanted more than a high-paying job—he wanted freedom.

That shift led him to real estate, where he started with flips and BRRRRs before building a multifamily portfolio and helping other investors do the same. Now, Joey educates high-income professionals on how to unlock passive income and reclaim their time.

Key Points Discussed

• Walking Away from W2: Joey opens up about his decision to leave a successful medical sales career despite the financial stability, title, and team. He shares the mental hurdles and mindset shifts it took to walk away from “golden handcuffs.”
• Building His First Portfolio: Joey breaks down how he built 28+ units through BRRRR strategies, flips, and buy-and-hold properties while still working full-time. He discusses key markets, deal analysis, and lessons from early mistakes.
• Investor Education: At Ironton Capital, Joey now helps passive investors—from tech execs to business owners—understand how to vet deals, operators, and align investments with their long-term goals.
• From Transactional to Relational: Joey emphasizes why relationships matter more than spreadsheets when it comes to real estate investing—and how trust-building plays a central role in both active and passive investing.

Guest Information

• Name: Joey Schneider
• Role: CEO of Trinity Peak Partners & Head of Investor Relations at Ironton Capital
• LinkedIn: Joey Schneider
• Website: Trinity Peak Partners & Ironton Capital

Conclusion

Joey Schneider’s journey is a powerful example of how to trade prestige for purpose. His transition from medical sales to real estate showcases the value of long-term thinking, calculated risk, and focusing on what truly matters—freedom, impact, and ownership.

Connect with Joey on LinkedIn to learn more about his work with Trinity Peak Partners and Ironton Capital.

Episode Summary

In this episode of Groundbreakers, Jaideep Balekar, Principal at Prosper Capital, shares how he scaled from a full-time role at Deloitte to building a 550+ unit portfolio, and why he chose to vertically integrate along the way.

Jaideep walks through the early days of his investing journey, including what drew him to value-add multifamily, how he found his first deals, and the lessons he learned transitioning from LP to GP. He also unpacks the systems he’s built to manage operations in-house and the red flags he looks for when co-sponsoring deals.

His story is a masterclass in building a business the right way slow, steady, and with a long-term mindset.

Key Points Discussed

• Why Vertically Integrate: Jaideep explains how in-house property management gave him tighter control over expenses, better NOI, and improved resident experience.
• From LP to GP: Jaideep shares how investing passively helped him learn the ropes, but also exposed the risks many LPs overlook including operator misalignment and lack of transparency.
• Choosing the Right Markets: His investment thesis focuses on landlord-friendly states, strong job growth, and low-cost basis relative to new construction.
• Surviving Interest Rate Shocks: Jaideep dives into how his team has adjusted to debt market volatility and what he’s seeing from lenders and LPs in 2025.
• Advice for First-Time Sponsors: From building trust with investors to knowing when to outsource, Jaideep offers hard-won advice for syndicators looking to scale sustainably.

Guest Information

• Name: Jaideep Balekar
• Role: Principal at Prosper Capital
• LinkedIn: Jaideep Balekar
• Website: Prosper Capital

Conclusion

Jaideep Balekar’s journey is proof that building a durable real estate business doesn’t require shortcuts—it takes systems, long-term thinking, and a commitment to doing things the right way. His approach to vertical integration and investor alignment sets a blueprint for syndicators who want to build lasting trust and sustainable growth.

Connect with Jaideep on LinkedIn to learn more about his work at Prosper Capital and how he’s helping investors achieve strong returns through multifamily real estate.

Episode Summary

In this episode of Groundbreakers, Ian Noble, founding partner at RunSteady Investments, shares his journey from building a 15-location dry cleaning business to walking away from it entirely. After spending years managing 90 employees and growing a successful company, Ian realized the business was running him, not the other way around. Burned out and missing time with his family, he made the hard decision to sell and transition into real estate investing.

Now, Ian helps other business owners achieve financial freedom through passive investing in recession-resilient assets like mobile home parks. His story is a powerful reminder that time freedom, not just financial success, is the real endgame.

Key Points Discussed

• Escaping the Business That Owned Him: Ian opens up about how the grind of operating a multi-location business wore him down, and what finally pushed him to sell.
• Mobile Home Parks for Cash Flow and Resilience: He explains why his investment thesis now centers around mobile home parks, which offer stable income, sticky tenants, and low operating costs.
• The Operator is the Deal: Ian shares his criteria for vetting sponsors and why execution risk is the biggest factor he considers when investing in other people’s deals.
• Helping Other Entrepreneurs Go Passive: Through RunSteady, Ian partners with proven operators and structures fund-of-fund vehicles so busy professionals and business owners can get access to institutional-quality deals without having to manage them directly.

Guest Information

• Name: Ian Noble
• Role: Founding Partner at RunSteady Investments
• LinkedIn: Ian Noble
• Website: RunSteady Investments

Conclusion

Ian Noble’s story is one of intentional reinvention—leaving behind operational stress in favor of freedom, purpose, and aligned investing. Whether you’re a business owner, syndicator, or LP, this episode offers valuable insight into building a life that works for you—not just a business that looks good on paper.

Connect with Ian on LinkedIn or visit RunSteady Investments to learn more about his work and upcoming opportunities.

Episode Summary

In this episode of Groundbreakers, Douglas Escobar, CEO of ESCFreedom Investments, shares how repeated corporate layoffs pushed him to take control of his financial future through real estate. After a long career in insurance and mortgage underwriting, Doug began investing in single-family rentals, exited before the 2008 crash, and later transitioned into multifamily. Today, he is invested in over 2,000 units and focuses on helping busy professionals generate passive income through a fund-to-fund model.

Doug’s story is about building security when the job market couldn’t provide it and helping others do the same.

Key Points Discussed

• Preparing for the Leap: Doug explains how he built a two-year financial runway before leaving his six-figure job and why that safety net was critical to making thoughtful business decisions without pressure.
• Lessons from the Subprime Crisis: Doug shares what it was like underwriting subprime loans before the 2008 crash, what red flags he saw early, and why he exited his single-family portfolio just in time.
• Why Operator Due Diligence Matters Most: The most important variable in any deal, Doug argues, is not the returns on paper—it is the operator. He shares what traits he looks for and how he evaluates their ability to manage downside.
• Fund-to-Fund as a Strategy: Doug breaks down how ESCFreedom Investing uses a fund-to-fund model to give professionals access to larger deals without having to manage the details or take on additional risk.
• Helping Professionals Become Work-Optional: Doug’s mission is to help others achieve freedom from the uncertainty of corporate life. He believes passive income is not just about replacing a salary—it is about reclaiming time and control.

Guest Information

• Name: Douglas Escobar
• Role: CEO of ESCFreedom Investing
• LinkedIn: Douglas Escobar
• Website: ESCFreedom Investments

Conclusion

Douglas Escobar’s journey is a case study in resilience, foresight, and purpose-driven investing. His experience offers valuable insights for anyone looking to reduce dependence on a paycheck and build a future defined by choice and flexibility.

Connect with Doug on LinkedIn or visit ESCFreedom Investing to learn more about his mission and upcoming opportunities.

Episode Summary

In this episode of Groundbreakers, Cody Wiseman, founder of Wiseman Capital, shares his journey from earning $300K a year in tech sales to going all-in on real estate investing. After building a two-year financial runway, Cody left his W2 job to focus on multifamily, hotel-to-apartment conversions, and creating one of the largest multifamily meetups in the Midwest. His story is a blueprint for anyone looking to make the transition into full-time investing while minimizing risk and maximizing impact.

Cody’s approach is a masterclass in preparation, execution, and community building.

Key Points Discussed

• Building the Runway Before the Leap: Cody shares why he spent two years saving, investing, and preparing mentally and financially before stepping away from his W2 job and how that preparation helped him scale confidently.
• Scaling from a Triplex to Hotel Conversions: Cody breaks down his growth from a small triplex purchase to converting hotels into apartments, including the biggest surprises and challenges in making these projects work.
• The Critical Importance of Location: When evaluating hotel conversion deals, Cody shares why location matters more than price, and how buying in the wrong neighborhood can kill even the best numbers on paper.
• Building the Midwest’s Largest Multifamily Meetup: Cody reveals how hosting a local meetup helped him rapidly expand his network, source deals, and establish brand credibility in the Wisconsin real estate ecosystem.
• Why Hands-On Operators Win: Cody talks about getting deep into operations, from city zoning meetings to CapEx planning, and why true involvement separates average sponsors from great ones.

Guest Information

• Name: Cody Wiseman
• Role: Founder at Wiseman Capital
• LinkedIn: Cody Wiseman
• Website: Wiseman Capital

Conclusion

Cody Wiseman’s story is proof that success in real estate is not about giant leaps. It’s about preparation, taking smart bets, building the right relationships, and staying relentlessly consistent. His experience offers a roadmap for anyone who wants to transition from a W2 career into full-time real estate investing without unnecessary risk.

Connect with Cody on LinkedIn or visit Wiseman Capital to learn more about his deals, events, and future projects.

Episode Summary

In this episode of Groundbreakers, Gregory Laskody, founder of MasterCRE, shares his journey from struggling college student to leading over $3B in commercial real estate transactions. After three decades in the industry, Greg has seen firsthand how difficult it can be for new investors and professionals to break into commercial real estate. Now, through MasterCRE, he’s focused on opening access, shortening the learning curve, and creating a more collaborative environment for future dealmakers.

Greg’s story is about more than just big deals—it’s about changing how the industry works from the inside out.

Key Points Discussed

• Breaking Into CRE: Greg shares how he went from failing his accounting classes to working for one of the top real estate firms in the country—and how anyone can carve a path into CRE without the traditional roadmap.
• Why CRE Is Still Behind: Unlike residential real estate, commercial is fragmented, offline, and often gatekept. Greg explains why CRE is slow to evolve and what needs to change to make it more accessible.
• MasterCRE and the Future of Education: Greg built MasterCRE to help aspiring investors and professionals learn the fundamentals of commercial real estate, access deals, and connect with mentors without relying on outdated, closed-door systems.
• Market Outlook for 2025: Greg discusses why capital markets are tightening, what deleveraging will look like, and why many operators will struggle with cash-in refinances in the coming year.
• Why Unpaid Internships Hurt the Industry: Greg believes that everyone brings value, even beginners—and why it’s time the industry moves past unpaid work as the only entry point.

Guest Information

• Name: Gregory Laskody
• Role: Principal at MasterCRE
• LinkedIn: Gregory Laskody
• Website: MasterCRE

Conclusion

Gregory Laskody’s mission is simple: to make commercial real estate more open, without lowering the bar. His experience across $3B in deals, capital advisory, and platform building makes him a unique voice for where CRE is headed. If you’ve ever wondered how to break into commercial real estate—or what’s holding the industry back—this episode delivers insights from someone who’s seen it all.

Connect with Greg on LinkedIn or explore MasterCRE to learn more about his mission to open up the industry.