Real Estate Investing for Cash Flow with Kevin Bupp Podcast
1) The Painful Failure That Pushed Me to Pivot (and Made Me Millions) w/Joe Downs
The fear of failure stops many from ever getting into real estate. But what if it's the failures that actually make you wealthy? Today's guest woke up in his 30s, broke and burned out, having traded y...Show More
The Painful Failure That Pushed Me to Pivot (and Made Me Millions) w/Joe Downs
39:37 | Dec 15th, 2025
2) Skip the Sunbelt: Why "Micropolitan" Multifamily Markets are Unbeatable w/Cory Jacobson
While most operators chase the Sunbelt states, one overlooked market type is making small- and mid-sized multifamily investors wealthier. It's got near-zero vacancy, with strong employment anchors, an...Show More
3) The Opportunity You've Never Heard of in CRE ("IOS" Real Estate)
This could be one of the, if not the, most under realized opportunities in commercial real estate. It's a blue ocean market operating in a boring business space that most investors (and service provid...Show More
4) The Most Underrated Metric in Multifamily (Not Cap Rate/Cash Flow) w/Joe Root
One key metric could tell you immediately whether a multifamily real estate investment is worth buying—but most people ignore it. It's not cash flow, it's not cap rate, and it's probably something you...Show More
The Most Underrated Metric in Multifamily (Not Cap Rate/Cash Flow) w/Joe Root
40:41 | Nov 24th, 2025
5) #962 Former Pro Snowboarder Dan Brisse's Playbook for Durable Multifamily
Pro snowboard legend turned operator Dan Brisse breaks down how obsession and discipline translate to durable multifamily returns covering capital calls, bridge debt pain, why he's buying newer B+/A- ...Show More
6) #961 Affordability Rates & the New-Build Advantage with Keith Weinhold
The housing market isn't broken, it's shifting. And smart investors are shifting with it. Keith Weinhold returns to explain why affordability is squeezed, why owners aren't selling, and why prices rem...Show More
7) #960 Why Discipline Beats Deals: Lee Yoder's Real Estate Journey
Physical therapist turned investor Lee Yoder breaks down how he left a stable W-2, lived below his means, and scaled from a duplex to 800+ units in six years. We cover flipping vs. cash-flow rentals, ...Show More
8) #959 Payments to Properties: Charles Carillo’s B-Class Multifamily Playbook
Charles Carillo founder of Harborside Partners and host of the Global Investors Podcast joins Kevin to share how he went from building a billion dollar payments company to scaling a B-class multifamil...Show More
#959 Payments to Properties: Charles Carillo’s B-Class Multifamily Playbook
32:50 | Oct 27th, 2025
9) #958 Hard Assets, Smart Money: MOB riches, safe leverage & the 2025–26 opportunity
Ben Reinberg is the Founder and CEO of Alliance CGC. Ben’s journey began in accounting and has since grown into a commercial real estate career with decades of experience building and managing a diver...Show More
#958 Hard Assets, Smart Money: MOB riches, safe leverage & the 2025–26 opportunity
41:05 | Oct 20th, 2025
10) #957 House Hacks & Mobile Home Parks: Build a 7-Figure Portfolio
Jordan Moorehead is a real estate power house who has built a diverse and impressive portfolio across multiple asset classes. Jordan Moorhead is a Louisville native, licensed sales agent in Texas, li...Show More