Raise the Bar

In this episode, Jennings explains that the biggest risk he ever took was a highly distressed 208-unit property in Oklahoma. The asset was half vacant, most of the remaining tenants weren’t paying rent, and it required a $2.5 million rehab while being located halfway across the country. The deal demanded consistent oversight, weekly calls, and frequent trips to Tulsa to keep the project on track. Jennings and his team bought it for roughly $5 to $5.5 million, were all-in for about $8 million, and ultimately exited for $12.6 million. For Jennings, this deal is the perfect example of big risk producing big reward. Bullet Points and Highlights:- Jennings’s biggest risk was a distressed 208-unit property in Oklahoma.- The property was 50 percent vacant when acquired.- Many of the remaining tenants were not paying rent.- The project required a $2.5 million renovation.- The property was halfway across the country, increasing operational difficulty.- Jennings and his team bought it for about $5 to $5.5 million.- They were all-in for roughly $8 million after rehab.- They exited the deal for $12.6 million.- The project required two years of consistent focus, weekly calls, and regular trips to Tulsa.- Jennings views the deal as a clear example of big risk leading to big reward. Links from the Show and Guest Info and Links: Seth Bradley’s Links:https://x.com/sethbradleyesqhttps://www.youtube.com/@sethbradleyesqwww.facebook.com/sethbradleyesqhttps://www.threads.com/@sethbradleyesqhttps://www.instagram.com/sethbradleyesq/https://www.linkedin.com/in/sethbradleyesq/https://passiveincomeattorney.com/seth-bradley/https://www.biggerpockets.com/users/sethbradleyesqhttps://medium.com/@sethbradleyesqhttps://www.tiktok.com/@sethbradleyesq?lang=en Jennings Smith Jr.'s Linkhttps://www.instagram.com/jenningsfostersmithjr/?hl=en&utmhttps://x.com/Jenningsfosterhttps://www.facebook.com/jennings.smith.50/?utm

The last two years have tested every real estate investor’s limits. In this episode, Jennings Smith, CEO of My First Million in Multifamily and co-creator of The Deal Room, joins Seth to break down what’s really happening in today’s market. Jennings opens up about over-scaling, selling off high-risk assets, and pivoting into easier, more stable investments. Jennings also shares how he grew one of the fastest-rising Facebook groups in the real estate space by giving massive value, staying transparent, and teaching others to raise capital ethically and sustainably. Bullet Points and Highlights:- Why raising capital in 2025 feels harder but better- The difference between scaling fast vs. scaling smart- How floating-rate bridge loans nearly broke his portfolio- When to pivot, liquidate, or double down- The real reason some investors failed after 2021- How to communicate value when people ask “what do you do?”- Why community and education have been his biggest growth tools- Behind the rise of My First Million in Multifamily Links from the Show and Guest Info and Links: Seth Bradley’s Links:https://x.com/sethbradleyesqhttps://www.youtube.com/@sethbradleyesqwww.facebook.com/sethbradleyesqhttps://www.threads.com/@sethbradleyesqhttps://www.instagram.com/sethbradleyesq/https://www.linkedin.com/in/sethbradleyesqhttps://passiveincomeattorney.com/seth-bradley/https://www.biggerpockets.com/users/sethbradleyesqhttps://medium.com/@sethbradleyesqhttps://www.tiktok.com/@sethbradleyesq?lang=en Jennings Smith Jr.'s Linkhttps://www.instagram.com/jenningsfostersmithjr/?hl=en&utmhttps://x.com/Jenningsfosterhttps://www.facebook.com/jennings.smith.50/?utm

What happened to the easy money era? In this episode, Seth reconnects with investor and BiggerPockets personality Matt Faircloth, founder of The DeRosa Group. They unpack how the capital-raising landscape has shifted, why fund-to-fund models are gaining traction, and why flipping homes isn’t all it’s cracked up to be. Matt also shares his unfiltered perspective on the future of multifamily, the rise of accredited vs. non-accredited structures, and where smart money should focus next. Bullet Points and Highlights:- Behind the scenes at BiggerPockets and Best Ever conferences- The rise of fund-to-funds and why it matters for capital raisers- Why Fractional isn’t a perfect fit for serious investors- The reality behind flipping vs. long-term real estate investing- How TV glamorizes flipping and why “slow wealth” isn’t sexy- Matt’s take on America’s obsession with quick returns- A preview of what’s next for The DeRosa Group Links from the Show and Guest Info and Links: Seth Bradley’s Links:https://x.com/sethbradleyesqhttps://www.youtube.com/@sethbradleyesqwww.facebook.com/sethbradleyesqhttps://www.threads.com/@sethbradleyesqhttps://www.instagram.com/sethbradleyesq/https://www.linkedin.com/in/sethbradleyesq/https://passiveincomeattorney.com/seth-bradley/https://www.biggerpockets.com/users/sethbradleyesqhttps://medium.com/@sethbradleyesqhttps://www.tiktok.com/@sethbradleyesq?lang=en Matt Faircloth's Linkhttps://www.facebook.com/mdfaircloth/?utmhttps://www.linkedin.com/in/mdfaircloth/https://www.instagram.com/themattfaircloth/?hl=en&utm

In this episode, Matt explains that his first million came from holding real estate long term. The biggest checks Matt has ever cashed were created through buying solid assets, letting debt amortize, capturing cash flow, and eventually selling after years of appreciation or forced value creation. Matt contrasts this with the recent era of short-term multifamily flips, which he views as a temporary market anomaly. His last million is coming from an eight-year hold on a 49-unit property, where Matt added “paper value” by securing site plan approval for additional units on an adjacent parcel. That entitlement process cost around $80,000 but created roughly $1.2 million in additional value. Looking forward, Matt expects to make his next million through business building. Matt is focused on scaling DeRosa and two other undervalued companies by improving operations, investing in leadership, and elevating each brand to its next stage of growth. Key Highlight Point - Matt made the first million by holding real estate long term and allowing appreciation and amortization to build equity. - Matt attributes large wealth gains to buying good assets and staying in them for years. - Matt believes the era of 18-month multifamily flips was an anomaly driven by an unusual market cycle. - Matt warns that future value creation in multifamily will rely more on long-term ownership and cash flow. - Matt’s last million is being earned from selling a 49-unit property held for eight years.- Matt created additional value by securing site plan approval on an adjacent parcel.- Matt spent around $80,000 in professional fees for engineering, legal, and approvals. - Matt and investors expect to gain roughly $1.2 million from that entitlement work alone. - Matt plans to make the next million by scaling existing businesses, including DeRosa. - Matt believes his companies are significantly undervalued and will grow through improved operations, leadership development, and strategic investment. Seth Bradley’s Links: https://x.com/sethbradleyesqhttps://www.youtube.com/@sethbradleyesqhttps://www.facebook.com/sethbradleyesqhttps://www.threads.com/@sethbradleyesqhttps://www.instagram.com/sethbradleyesq/https://www.linkedin.com/in/sethbradleyesq/ https://passiveincomeattorney.com/seth-bradley/ https://www.biggerpockets.com/users/sethbradleyesq https://medium.com/@sethbradleyesqhttps://www.tiktok.com/@sethbradleyesqMatt Faircloth's Link:https://www.facebook.com/mdfaircloth/?utm https://www.linkedin.com/in/mdfaircloth/ https://www.instagram.com/themattfaircloth/?hl=en&utm

What happened to the easy money era? In this episode, Seth reconnects with investor and BiggerPockets personality Matt Faircloth, founder of The DeRosa Group. They unpack how the capital-raising landscape has shifted, why fund-to-fund models are gaining traction, and why flipping homes isn’t all it’s cracked up to be. Matt also shares his unfiltered perspective on the future of multifamily, the rise of accredited vs. non-accredited structures, and where smart money should focus next. Bullet Points and Highlights: - Behind the scenes at BiggerPockets and Best Ever conferences - The rise of fund-to-funds and why it matters for capital raisers - Why Fractional isn’t a perfect fit for serious investors - The reality behind flipping vs. long-term real estate investing - How TV glamorizes flipping and why “slow wealth” isn’t sexy - Matt’s take on America’s obsession with quick returns - A preview of what’s next for The DeRosa Group Links from the Show and Guest Info and Links: Seth Bradley’s Links: https://x.com/sethbradleyesq https://www.youtube.com/@sethbradleyesq www.facebook.com/sethbradleyesq https://www.threads.com/@sethbradleyesq https://www.instagram.com/sethbradleyesq/ https://www.linkedin.com/in/sethbradleyesq/ https://passiveincomeattorney.com/seth-bradley/ https://www.biggerpockets.com/users/sethbradleyesq https://medium.com/@sethbradleyesq https://www.tiktok.com/@sethbradleyesq?lang=enMatt Faircloth's Link https://www.facebook.com/mdfaircloth/?utmhttps://www.linkedin.com/in/mdfaircloth/ https://www.instagram.com/themattfaircloth/?hl=en&utm