Roger Becker
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.
Author
Roger Becker
Category
Podcast website
Latest episode
Jul 9, 2026
Where to listen?
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Episodes
605: Paying Discounted Prices For Distressed Properties Results In Big Profits 16.05.2025 53:07
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...
604: Well-Managed C Class Properties Can Achieve High 90% Occupancy With The Right Management 14.05.2025 42:49
Like many other markets, the Dallas-Ft Worth market got oversaturated with new apartments over the last couple years. As the torrent job and population growth continues to flourish, however, new supply is getting absorbed, even C Class properties. Occupancy in these buildings is increasing because there’s a shortage of workforce housing. The key is being able to manage these properties effectively...
603: Cash Flowing Opportunities In Stable, Tertiary Markets 12.05.2025 37:02
Even though the Real Estate market has contracted significantly as a result of interest rate hikes and rising operating expenses, it’s still difficult to find great deals, especially in large metros where there’s still a lot of money on the sidelines looking for deals. By comparison, it’s easier to find cash flowing opportunities in tertiary markets. Brian Ferguson, Founding and Managing Partner a...
602: Achieve Strong Returns Plus Healthy Diversification 09.05.2025 36:11
Anyone who’s been following the trajectory of commercial real estate over the past few years knows there’s a lot of distress in the market. If you’re in the enviable position to deploy capital, however, this can be good news. With distress comes opportunity, and the market is currently presenting great investment opportunities on both the debt and equity side. Beyond Real Estate, there are also op...
601: Public Markets Are At All Time High Evaluations, Private Markets Are Less Frothy 07.05.2025 42:24
Passive investing in private offerings can yield above market returns, it can also be a complete disaster. Apart from evaluating proforma numbers, it’s critical to evaluate the General Partner and the team. The numbers are generic, the intangibles, including the character of who you’re investing with, are less quantifiable and therefore harder to vet. There are too many newer, and generally inexpe...
600: Major Multifamily Challenges Turn Into Great Opportunities Ahead 05.05.2025 38:05
The multifamily business has been brutal for most operators over the past few years, especially for ones who took on bridge debt. There’s been too much new supply, and skyrocketing interest rates caught most operators off guard. For low-income workforce housing, the tenant base has gotten crushed by inflation which has resulted in higher delinquencies and higher vacancies. At the same time, howeve...
599: Section 8 Housing Provides Long-Term, Steady Income 02.05.2025 35:49
The multifamily space has many niches and myriad ways to maximize invested dollars. One of the more specialized multifamily niches is government voucher programs, otherwise known as Section 8. These can be great properties to invest in because the need for this kind of housing is immense, tenants stay for many years, and rents are guaranteed by the government. There are complexities to implementi...
598: Generous Profits In Luxury Vacation Rentals And Development 30.04.2025 49:28
One asset class within commercial real estate that many people don’t think about is luxury Short-Term Rentals. Houses that cost between $2 and $5 million typically rent for $500-$1,500 per night and generate $200,000 or even more per year in revenue, comparable to small apartment buildings. Investors can use these properties themselves, they enjoy the cash flow, plus they benefit from capital pres...
597: Buy At The Right Price And Get Long-Term Fixed Debt 28.04.2025 39:51
Investing in private real estate deals can be fraught with pitfalls, so you need to get to know who you’re investing with before investing. In the past five years, many multifamily operators in particular, paid too much for properties and got the wrong kind of debt with too much leverage. Unfortunately, many investors have lost their principal as a result. At the same time, there are better multif...
596: Passive Investing Generates Great Returns 24.04.2025 40:22
Investing passively is a great way to generate cash flow and appreciation, without having to deal with day-to-day operations. You just need to develop the skills at vetting operators and specific deals. David Shirkey, a fellow passive investor, has done a great job finding quality operators and profitable deals over the past eight years. David has made successful multifamily investments plus sever...
595: There’s Big Opportunity In Buying Lower-Middle Market Companies 22.04.2025 53:44
Over 90% of U.S. businesses generate less than $5 million profit per year, yet these businesses are the backbone of our economy. Although the majority of Private Equity investments are in larger companies, many smaller companies are investable and need access to capital and expertise to grow. Ariez Dustoor, Partner at NB Group Investors, invests in founder or family-owned Wellness related or multi...
594: Industrial Outdoor Storage Is Still Mostly Owned By Ma And Pa Owners 18.04.2025 36:10
In the last several years, industrial Real Estate has become a highly favored asset class, largely because of ecommerce. A thriving subset of this category is Industrial Outdoor Storage, a 2 billion asset class. Industrial Outdoor is a great asset class because it’s still mostly ma and pa owned, there’s very low capital expenditure, and little day-to-day management. These properties are comprised...
593: Once In A Lifetime Opportunity To Buy Office At Pennies On the dollar. 16.04.2025 43:30
In certain 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 go through the toil of finding off market deals, they’re listed publicly on LoopNet, Crexi, and other prominent sites. As workers have left downtown offices, they’ve chosen to work closer to home. Buildings with smaller one to three person offices in particu...
592: Hidden Discounted Homes 14.04.2025 37:36
If you’re entrepreneurial and looking for a way to generate a lot of income with little initial capital requirements, flipping homes is an age old, timeless formula. It just requires courage and tenacity that many don’t have. There are always distressed sellers and hidden opportunities in any market cycle and any market. Tony Youngs, Owner of Real World Enterprises, has been flipping houses in Atl...
591: Nothing Beats Boots On The Ground 11.04.2025 42:30
In Real Estate, and multifamily in particular, you need to have boots on the ground to ensure things are running as expected. It also helps to live in the market in order to have intimate knowledge of the investment. This is one way to mitigate risk. Multifamily is a 24/7 business, and too many things go wrong when you’re managing from afar. Dustin Miles, Managing Partner at Momentum Multifamily,...
590: Industrial Properties At The Right Price 09.04.2025 36:13
The forecast for industrial real estate is bullish in growth markets for the foreseeable future. As long as you can buy the right properties, and don’t overpay or overleverage, it’s a recipe for success. Single tenant properties, in particular, have management efficiencies that make them particularly attractive. Brent Leiberman, Founding Principal at Levelan Partners, acquires and develops well-lo...
589: 73% of Americans Live In Communities With Fewer Than 5,000 People 07.04.2025 29:58
Buying properties in tertiary markets with five to ten thousand residents within a 30–40-minute drive from a larger city can generate outsized returns. Often times long-time owners in these markets aren’t aware when their rents are significantly under market, and they aren’t current on what their properties are worth. Farris Gosea, Founder and CEO of Farris Gosea Capital, has amassed a large portf...
588: Multifamily-Cash Flowing Properties In Indiana 04.04.2025 25:33
Despite the escalation of asset prices over the past decade, there’s still great value In Midwestern tertiary markets. In multifamily, you can still buy properties for $65,000-$75,000 per unit that generate strong cash flow. Although these are small markets, many of them have strong and stable employment fundamentals, and therefore consistently high occupancy levels. Stan Remling, Partner at Follo...
587: When It Comes To Investing, Boring Is Beautiful 02.04.2025 31:07
There’s a big difference between investing and speculating. Speculating is exciting. Investing is less exciting, but more predictable over time. Great investors like Warren Buffet, Charles Munger, Howard Marks and others, are boring investors. With the right asset classes and the right operators, Real Estate is a slow and steady, boring investment vehicle, but can also entail risk. Over the past c...
586: Beyond Real Estate Investing 31.03.2025 26:35
Apart from Real Estate, there are many private placement vehicles to invest in, including Oil and Gas, pre-IPO companies, and many others. Some of these opportunities are less well known, but present higher returns than commercial real estate. Marshall Sykes, Founder and Owner of Capitano Investing Group, has been involved in over 20 syndications across multiple asset classes. After some initial w...
585: Pricing Corrections In Multifamily 28.03.2025 32:56
Given pricing corrections over the past couple years, some of the best mid-market multifamily deals in the last decade are now being acquired at well below replacement cost. There are more buyers that need to sell and there’s less competition for these assets than higher priced deals that attract larger institutions. Cameron Croy, Director at Walker & Dunlop Investment Partners, helps deploy...
584: Chicago Focus And Disciplined Growth Pays Dividends 26.03.2025 31:17
Submarket-specific focus, complete vertical integration, and 20 years of experience mitigates a lot of risk. Chicago has been the number one market for multifamily rent appreciation in the country over the past couple quarters. Rents to average income are considerably lower than most other large markets and there are several Fortune 500 and large tech company employers. There’s also been limited n...
583: Tax Abatement Strategies Produce More Profitable Investments In Multifamily 24.03.2025 36:11
Prices on most value-add workforce class B and C multifamily properties are too high to execute successful business plans. Construction costs have escalated and obtaining higher rents is not a certainty as renters are being squeezed by inflation. Rob Beardsley, Founder and Principal of Lone Star Capital, started with workforce value-add multifamily, but has pivoted to affordable housing with mostl...
582: Interest Rates Can Go Up 300 Basis Points 21.03.2025 58:13
Current events and policy will determine inflation levels and interest rates that effect our broader economy and Real Estate values and investments. Volatility around tariffs and other decisions will make a significant impact that effects all sectors of our society. Greg Makoff, Senior Fellow at the Mossavar-Rahmani Center for Business and Government at the Harvard Kennedy School, and author of De...
581: Buying Land To Sell To Developers Generates Big Returns Without Huge Capital Outlays 19.03.2025 40:20
Although prices have come down as much as 30% or even higher on Class B and C Value-Add multifamily, they haven’t come down enough for most seasoned investors to want to jump back in. There still needs to be further concessions to make the deals pencil, and to be worth the risk entailed with value-add. Buying and selling land in growing markets, however, can generate very attractive rates of retur...
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