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 1, 2025 41 mins

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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With so much information available, it’s easy to get educated on an asset class or an opportunity before investing. Although there’s no substitute for hands-on experience, you can still reduce risk through education. Steffany Boldrini, Principal at Monte Carlo Real Estate Investments, invested in car washes in North Texas and learned the hard way that she didn’t know what she didn’t know. Six years later, Steffany is recouping her ...

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Despite some of the challenges that have faced multifamily in the past few years, some markets have been affected less than others. The Midwest in particular has fared better than most other parts of the country. There are many markets like Cincinnati, Cleveland, Louisville, and many others that have experienced minimal new construction combined with consistent renter demand. As a result, these markets have maintained high occupanc...

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Over the past several years, most of the returns in real estate have been generated because of declining interest rates and cap rates. If you just held on to properties long enough, even without successfully executing on a business plan, you fared well. However, an oversupply of capital resulted in overly unrealistic underwriting for both lenders and operators, and distress has ensued. In more recent years, the tide has changed, an...

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Not only has commercial real estate been faced with escalating borrowing costs and lower rents, but it has also been challenged by rising expenses, especially taxes and insurance. In this environment, it’s become essential for survival to aggressively manage these expenses. Matt Buchalski, Head of Sales for Ownwell, helps property owners lower these costly line items in order to protect and increase their NOI and valuations. Ownwel...

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The world of alternative investing can generate diversification, cash flow and tax efficiency. It can also be opaque and risky and has created massive losses for uninitiated investors. Unlike public companies, there’s a far lower regulatory threshold for private companies to provide transparency to investors. The key to being successful in this world is being able to assess risk quantitatively and qualitatively. Leyla Kunimoto, Co-...

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One asset class that still has great deals on sub-institutional properties is Mobile Home Parks. Although larger parks near major metros are being acquired by REITs, Private Equity, and other institutions, parks with fewer than 100 sites are being acquired by smaller investors with far less competition. Smaller parks in secondary and tertiary markets offer great buying opportunities with value-add components that result in tremendo...

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Although the margins are thin in Multifamily, there are niches that provide outsized returns without undue risk. One example is government-sponsored affordable housing. By creating public-private partnerships, it takes a lot of risk off the table, Jesse Sells, Co-Founder and COO of Impact Growth Capital, recently began a partnership with the Southern Nevada Regional Housing Authority for a $300 million development to develop 600 ne...

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Real Estate is a block-to-block business, especially multifamily. There are too many nuances involved to manage multifamily without boots on the ground. This is where a lot of operators went wrong over the past several years. In addition to buying in markets they didn’t know, many inexperienced operators followed the herd by overbidding on properties and used risky debt to make deals pencil. Most of these operators and their invest...

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