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
350: House Flipping Can Be Lucrative, But It’s Not For Everyone 23.08.2023 50:05
Flipping houses can be a great way to make money, but only a handful of people are truly successful at it. There’s a lot you need to know and there are many ways to make costly mistakes. Roger Blankenship, Founder of FlippingAmerica.net, has successfully flipped over 1500 homes, but lost it all back in 2014 by expanding too fast, overextending himself, and having the wrong employees. Roger’s goal...
{RE-RELEASE} 224: Even With An Impending Recession, Multifamily Is Still Positioned To Appreciate Over The Next Several Years 21.08.2023 46:29
Even though the U.S. economy is in a state of flux and there are other domestic and global uncertainties, trends continue to be in favor of growth in the South and Southeast in terms of population job growth and migration. The rate at which this is occurring is unparalleled and opportunities for solid investments in multifamily real estate will continue to present themselves. Charlie Young, Partne...
{RE-RELEASE} 227: The Best Way To Make Money In Any Interest Rate Environment Is Still To Buy The Property Way Under Market 18.08.2023 42:23
You hear a lot about value add Real Estate in terms of creating value in acquisitions these days, especially as prices have skyrocketed over the past few years. Although there’s great gains to be made with the right value add improvements to a property, the most expedient value add is buying the property for significantly less than it’s worth. Ben Kogut, partner at HJH Investments, has been having...
349: Great Deals In Multifamily Real Estate In The Next 6-12 Months 16.08.2023 34:23
With loan terms maturating and escalating borrowing costs, many Real Estate properties are going to be in trouble. With these escalating costs combined with higher operating expenses and contracting rents, many properties will be sold at deep discounts in the next 6-12 months. This will present great buying opportunities for acquirers. Cameron Pimm, Co-Founder & Principal of Urban Landings, ha...
348: Disruption In The Construction Of Apartment Buildings 14.08.2023 35:27
This country is facing a housing affordability crisis with few foreseeable solutions. Shortage of supply, increased construction costs, and the costs to operate have escalated. If the cost of construction could be reduced, however, it would be the first step to solving the affordable housing conundrum. Mike Kaeding. CEO of Norhart, is innovating the way apartment buildings are being built with mor...
347: Lots of Real Estate Distress Will Present Great Buying Opportunities Over The Next Few Years 11.08.2023 53:12
1.5 trillion dollars in Real Estate debt is coming due by 2025. This Is starting to cause major distress across asset classes, markets, and sponsors. On top of increased borrowing costs, expenses such as insurance, taxes, and labor have increased faster than rents and delinquencies are becoming more common. On the other side of the equation, great deals for investors are on the horizon to acquire...
346: Get Solid, Consistent Returns Against Lending Or Owning Single Family Homes 09.08.2023 55:19
Single family homes are the most conservative asset class to both operate and lend against. Right now, inventory levels are the lowest they’ve ever been, so prices have maintained despite dramatic interest rate increases. Matt Owens, CEO and Owner of OCG properties, has bought, renovated, sold or held over 1000 single family properties in the last 15+ years. Matt currently has a debt fund where he...
345: There’s More Operational Inefficiency In Smaller Multifamily Buildings Without On-Site Staff 07.08.2023 34:43
Although there are multifamily properties of all sizes that are not managed well, smaller buildings without on-site staff and ma and pa owners tend to be more likely to be run unprofessionally. These properties pose opportunity for new buyers with more professional management infrastructure and processes. Will Matheson, Co-founder with his twin brother of Matheson Capital, has had incredible succe...
344: Get Hands-Off, Passive Income By Investing In Short-Term-Rentals 04.08.2023 37:03
One asset class for passive investors that often gets overlooked is Short-Term Rentals. Like in other asset classes, there are companies that will manage the whole process starting with identifying the properties and managing them from start to scratch. You can get monthly cash flow with properties in great vacation destination markets with a lot of appreciation. Leslie Anne Morris, The Cabin Lad...
343: Controlling All The Operational Aspects Of Apartments In-House Leads To Increased Profitability 02.08.2023 46:06
By controlling all the construction and property management processes, you can successfully operate Multifamily properties, as long as you don’t overpay for the properties and you know how to manage expenses. Matthew Shields, Founder and CEO of Significan, has been buying and operating Multifamily properties mostly in Northeast Ohio and Atlanta since 2017, and generating excellent returns. Matt is...
342: Choosing The Right Operator Makes All The Difference 31.07.2023 46:14
Passive investing can generate cash flow, appreciation, and tax benefits through depreciation. By investing with others, you don’t have to spend time managing properties which may not even cash flow. They key is finding operators with the right experience and skills to make sure your investment is secure. Whitney Elkins Huttten, Director of Investor Education at Passiveinvesting.com, is a partner...
341: Low Risk, Conservative Returns From Hard Money Loans 28.07.2023 59:20
If you want to invest in Real Estate but don’t want to be a hands-on operator, a great way to participate is through hard money lending. When you invest with the right company, it’s a conservative investment that provides high yield, consistent passive income with better liquidity than hard assets. Brock VandenBerg, President of Talimar Financial, started out lending his own money to house flipper...
340: Leverage Will Make Or Break Real Estate Deals 26.07.2023 52:07
40% of floating rate Multifamily projects acquired over the past few years will not be able to get refinanced. This will cause distress for operators and opportunities for acquirers. Additionally, increased insurance costs, especially for older properties, and increased property taxes are further burdening properties’ net operating incomes. As a result of these challenges, experience and the abili...
340: Dislocation Generates Opportunity 24.07.2023 38:20
As the cost of capital has increased dramatically, and generating yield has gotten more challenging, institutional investors are increasingly looking for specialized niches within sectors to invest in. Outside Storage, Cold Storage, Senior Living, and Affordable Housing are just a few examples of burgeoning niches. Institutions also prefer vertical integration and invest heavily in underwriting th...
339: Who You Invest With Is More Important Than What You Invest In 21.07.2023 34:15
When it comes to investing, there are always risks. Despite countless resources on how to vet operators and deals, the most important decision you’ll make is who you invest with. Proformas and projections are at best, educated guesses, and things rarely go according to plan, so the differentiator is the operator. The best operators have moral fiber, and as important, successful track records, com...
338: Fortune Favors The Brave 19.07.2023 43:53
Increasingly, Real Estate investors on the coasts are deploying money into the Midwest. Not only are these markets less expensive, but many of them are thriving like never before, and are less volatile. Markets like Columbus, Indianapolis, Kansas City and several others are seeing massive job and population growth. People are leaving the coasts and moving to these markets for a higher quality of l...
336: 8% Yield With No Leverage With Chicago Industrial Properties 17.07.2023 44:54
Nothing has caused more heartache and stress in Real Estate than too much debt. Leverage can work great in upmarkets, but it can cut the other way in a downturn. Joel Friedland, Principal of BRIT properties, has been buying infill industrial properties with all cash since learning the hard way during the 2008-09 financial crises. Joel and his investors are seeking very conservative investments wi...
335: The Midwest Is Experiencing Job And Population Growth 14.07.2023 34:33
Nothing ensures success more than focusing on what you love and what you’re truly good at. Real Estate is a multi-trillion-dollar industry with many avenues to pursue, but you’ll thrive the most by identifying your strengths, and as important, your weaknesses. Logan Freeman, Co-founder of FTW Investments, made some costly mistakes early on, but now specializes in select asset classes and markets i...
334: Today’s Market Requires More Experience And Discipline To Be Successful As The Obstacles Mount 12.07.2023 41:07
Over the past several years, most operators in Real Estate did incredibly well, often regardless of experience. The rising tide lifted all boats. Today, more experience and skill will be required to acquire properties at the right price and operate them successfully. Having an established network of local brokers, local lending sources, and vendor contacts are becoming more critical in a market wi...
333: RV Parks Are The Next Hot Asset Class 10.07.2023 44:11
In commercial Real Estate, most asset classes are already saturated with competition. It’s difficult to identify opportunities that are still relatively undiscovered and provide great cash flow at the same time. An exception to this is RV Parks. Over 10,000,000 families in the U.S. own RVs and they’re hitting the road in greater numbers than ever before. As a result, many RV parks are operating at...
332: Self-Storage Is Still In The Early Stages And Mostly Run By Smaller Operators 07.07.2023 41:52
One asset class that performs well in any economy is self-storage. When people are downsizing, they need self-storage. When they’re moving, changing relationship status, or running out of space for any reason, they need self-storage. Self-Storage is also great because rents are typically month-to-month, so you can raise rents with relative ease and not a lot of resistance from tenants. Charles Kao...
331: Government-Sponsored Housing Is A Lucrative Niche 05.07.2023 48:17
Finding strong cash flowing properties has become increasingly difficult over the past several years as the amount of money chasing Real Estate has risen dramatically. Most properties typically require a value-add business plan which can take months, if not years, to complete before generating cashflow. In-place cash flow, however, is a rarity. One exception is government-sponsored Section 8 homes...
330: In The Current Market, Skill Of The Operator Is More Mandatory Than Ever 30.06.2023 34:47
The market for multifamily right now is seeing severe headwinds. Escalating insurance costs, rising property taxes, and rising interest rates are just a few. As such, sponsors need to deploy special deftness and adaptability to survive over the next couple years. On the transaction side, sales volume has fallen 70% from last year as the buyer-seller bid/ask delta still remains high. Even though th...
329: Northern New Jersey Towns Have Seen A Large Resurgence 28.06.2023 42:35
Investing in older, infill markets that are poised for repositioning and growth can be a recipe for huge appreciation. Over the past decade, several cities in Northern New Jersey with easy access to transportation have seen explosive growth in values. Gentrification has led to changes that have made these areas desirable to live in for upscale demographics. Aaron Fragnito, Co-founder of People’s C...
328: Flipping Houses Can Be A Path To Riches If You’re Willing To Put The Effort Into It 26.06.2023 37:48
One of the oldest, tried-and-true ways to make money in Real Estate is to flip houses. Although not easy, it can be started with almost no money, just a lot of effort. Most people fail at it, but some do well, a select few make millions. If you don’t have capital, there are hard money lending companies and private individuals who will lend you all the money you need to buy and rehab a house. When...
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