Street Smart Success

Street Smart Success

Street Smart Success is a show for accredited investors. Whether you’re investing in Real Estate, Private Equity, Private credit, Debt, or other alternative assets, or you’re just starting out, this is the show for you. Street Smart Success interviews successful entrepreneurs about their backgrounds, careers, and lessons learned.

Episodes

July 22, 2025 34 mins

Despite the common convention, you can buy homes without cash or banks. You can use seller financing, subject-to existing loans, or lease purchases, allowing you to control properties without personal guarantees or large down payments. There are many reasons sellers will sell on these terms, among them because they can command a price they didn’t get on the open market, they don’t want to pay fees, and other reasons. Chris Prefonta...

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When it comes to Real Estate investing, you can be a borrower, or you can be a lender. When you’re the lender, you get monthly payments without having to manage the properties, and you can generate the same or higher returns. There’s a secondary market for buying loans from original note holders at a discount. Fred Moskowitz, Fund Manager and Investor, quit his job in 2015 to become a full-time note investor and has turned it into ...

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Over the past few decades, there’s been a trend towards renting apartments versus home ownership, especially in the past five years. Home ownership has grown increasingly out of reach, and apartment amenities and living spaces have improved dramatically. Additionally, people are becoming more reluctant to make long-term commitments to any given location and want to avoid the responsibility of owning a home. Mike Kron, COO of Manage...

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Because of increased regulations that have resulted in tighter lending standards, banks aren’t making a lot of smaller loans against properties that aren’t stabilized. This has created a sizeable gap in the market for “Micro balance” short-term bridge loans to operators borrowing $200,000 - $1,500,000 with value-add business plans, especially in secondary and tertiary markets. Brock Freeman, Managing Partner and COO of Kirkland Cap...

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As word got out about Mobile Home Parks over the past five+ years, many new players emerged in the space. The fundamentals were appealing, but many underestimated the capital expenditures required and the multitude of operational challenges. Mobile Home Parks can be lucrative, but there are a ton of nuances and speed bumps on the way to stabilization. As many of these players have been unable to achieve their business plans, they’r...

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Ecommerce has plateaued at 16% of total retail sales. Concurrently, the cost of land, borrowing, and construction has made it prohibitive to build new neighborhood retail centers. As a result, occupancy at existing properties in many markets is in the mid-high 90’s and sometimes even 100%. There’s a huge demand for space from restaurants, yoga and Pilates studios, gyms, massage clinics, plus other medical providers like dentists, c...

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It’s easy to oversimplify multifamily operations, and to make assumptions about how a property will perform. Countless nuances and details impact property performance, some are controllable, others aren’t. Many operators get this wrong, and it costs them dearly. There are hundreds of details that impact how financially successful a property will be. Stacey Hampton, Founder of Asset NOI Consulting, helps multifamily owners achieve g...

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In some markets, you can buy suburban office property for as low as $10/ft where it costs $200/ft to build. What’s more, you don’t have to find off-market deals, they’re listed publicly on LoopNet, Crexi, and other prominent sites. As workers have moved to the suburbs and left downtown offices, they’ve chosen to work closer to home. Suburban buildings with one to three person offices in particular are seeing strong tenant demand. A...

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In order for a larger multifamily dwelling to perform at its peak, it needs the right leasing personnel and the right maintenance team. The leasing agent creates the first impression of the property and influences the prospective tenant decision to rent at the property. This can make or break the deal out of the gate. On the maintenance side, an ornery repairman can alienate existing tenants and cause them to leave. Andrew Cushman,...

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Most real estate classes require a lot of hands-on daily management that makes or breaks the success of the investments. Nowhere is this more true than multifamily apartment communities. When you’re dealing with tenants 24/7, there’s always things that need prompt attention.  Ryan Weiss, Principal Broker and Managing Partner at Blue Door Living, has gone from managing 40 units to over 700 units in the past five years and has gotten...

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Investing in newer multifamily assets is a long-term conservative investment, but returns are low. There’s too much money chasing these deals, therefore the market is efficient. If you invest in heavy lift C Class properties, however, the returns are significantly higher. There’s far less competition to acquire these assets, and therefor better deals. Amy Rubenstein, CEO of Clear Investment Group, has an incredible track record acq...

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3rd party property management can be notoriously difficult and aggravating, but it can be successful if you manage it properly. To make it work, you need rigid processes, actionable metrics, and weekly meetings to hold property managers accountable. Chris Lento, Founder and CEO of EM Capital, has been successful managing properties in other states by finding great property managers that help him execute on his business plans. Chris...

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As urban port neighborhoods have been redeveloped over the past few decades into residential and other uses, warehouse developers and tenants have moved to more inland locations. At the same time, ecommerce has created a need for tenants to be closer to their customer bases. These changes, which have created a high demand for inland urban infill spaces, has resulted in great opportunities for investors. Brian Ker, President of Snow...

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Even in challenging markets, it's hard to find great real estate deals because sellers are always slow to capitulate on price. One asset class, however, that promises steady cash flowing deals is sub-institutional industrial. These properties don’t have as large a buyer pool as multifamily or larger properties across other asset classes in general. Jonathan Hayek, Founder of Endurance Properties, has recently acquired cash flowing ...

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The multifamily market has faced major headwinds in many growth markets, but is gradually stabilizing. Occupancy levels are starting to rebound as there’s been absorption of new units, although rents are still largely suppressed. Phoenix, one of the country’s top growth markets, is finally coming off the bottom with record absorption levels. Jeff Sherman, Principal at FSO Capital Partners, oversees 2500 in Phoenix and other markets...

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Fundraising for Private Equity and Venture funds has slowed as interest rate have climbed. Stalled exits and reduced distributions have followed. There are 50% fewer venture companies today than just a few years ago. As a result, multiples for acquisition targets have decreased, thereby presenting an opportune time for active funds with capital to acquire companies at attractive prices. Companies in secondary and tertiary markets, ...

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June 12, 2025 48 mins

Most new businesses fail within their first five years, but investing in a strong franchise system can enhance your odds of success. There are great, recession resistant franchise categories to invest in such as Home Services, Pets, Beauty, Kids, and many others. Investing in a successful franchise mitigates a lot of risk by aligning yourself with a proven concept and a leadership team that teaches you the critical components of a ...

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Although Mobile Home Parks have been great investments over the past couple decades, they have not been immune to the same challenges that other asset classes have faced. These include interest rate escalations plus operating costs such as labor, supplies, and insurance. Despite these headwinds, however, prices have mostly held firm although imminent loan maturities may yield attractive buying opportunities. Jeff Cook, CEO of Cook ...

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Even though prices on multifamily properties have come down 20%-30%, most of these still don’t make sense because higher interest rates and increased expenses have more than offset the price decreases. As a result, transaction volume for quality properties in great markets is still low. Brooks Mosier, Principal and co-founder of United Point Capital, is one of the largest buyers of single-family homes in Kansas City and has leverag...

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To be successful in any niche, you need to find a market inefficiency and a discernible differentiator. Too many sectors within commercial real estate have become commodities as unprecedented volumes of capital have been deployed. One sector that remains relatively inefficient is small balance lending, or “Micro balance loans,” to smaller operators borrowing $200,000 - $1,500,000. Chris Carley, Managing Partner of Kirkland Capital ...

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