From Losing It All to Building a $250M Portfolio: Kevin Bupp’s Blueprint for Freedom
Release Date: 09/05/2025
HI Beats AI: How to Generate More Referrals Through Human Connection with Michael J. Maher
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Michael discuss: How Michael accidentally launched a referral engine in his first year by hosting a housewarming party for his very first clients — and walked away with 11 referrals from a single event. The “What’s Next” concept: Every interaction should naturally lead to a future interaction Why events are especially powerful for introverts: you don’t need 50 one-to-one conversations when an event creates hundreds...
info_outline
Why Success Still Feels Empty (and How to Build a Business That Feels Like Freedom) with Erin Bradley
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin shares how: Success can look great on paper and still feel empty. The hamster wheel is real — and it usually started with fear. Growth doesn’t have to mean more effort. To rewrite the identity, not the to-do list. Turn your database into a community. About Erin Bradley Erin Bradley is a speaker and...
info_outline
The Shortcut to Your Goals: Belief, Grit & Mentorship with Ruben Gonzalez
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Ruben discuss: How perseverance (not talent) was Ruben’s edge — he decided early to stop quitting. How Ruben reverse-engineered a plan around his strengths and chose the luge because it rewarded tenacity and outlasting the quitters. The power of mentorship as a true “shortcut”: borrow someone else’s belief, follow their proven path, and stop arguing logical reasons you can’t do it. Proximity + authenticity win:...
info_outline
Do Less, Create Momentum, and Step Into 2026 with Erin Bradley
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin shares: Why 2026 is a “new beginning” year Before you add more… subtract first: the breakthrough lesson that changed everything How consistent activity tends to create results in about 90 days, regardless of season Freedom is built through systems + support How the biggest leaps (hiring, investing, visibility, grief seasons) were done while scared — and still worked ...
info_outline
From Tragedy to True Wealth: Nathan Barkocy’s Story of Time Freedom
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Nathan discuss: The life-altering moment that changed everything: a training ride that ended in a 60-mph collision, a coma, and the long road of learning to walk, talk, and live again. How adversity can become fuel instead of dead weight — and why “tomorrow is never promised” reframes how we use our time today. The difference between knowledge and wisdom, and why mentorship + proximity to high-level thinkers compresses your learning curve. A powerful redefinition of wealth:...
info_outline
Building Wealth That Supports Your Life with Sharon Lechter
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Sharon discuss: How early exposure to money conversations and entrepreneurship shaped her lifelong mission around financial literacy and empowerment Why one of her “worst” business decisions ultimately led to her best life decision — and how closing one door often opens many others The powerful distinction between chasing income vs. building assets — and why assets only get “sexier” with time. Sharon introduces the core message of her...
info_outline
Creating Community & Possibility with Edith Espinola
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Edith discuss: How growing up in a tight-knit family shaped Edith’s desire to create community and connection in both life and business. The importance of seeing people — truly hearing their stories and understanding how human dignity affects every decision they make. How hard seasons can become catalysts for finding purpose, building resilience, and creating support systems that strengthen entire communities....
info_outline
Raising Your Belief Lid: The Agency Operating System with Angela Totman
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Angela discuss: How a career pivot during college opened the door to an unexpected, purpose-driven path in entrepreneurship and financial education. The Agency Operating System, an acronym-based framework designed to realign your identity, energy, and actions so you can grow in life and business simultaneously. How accountability is actually a form of self-love — and why most people avoid it due to fear of being “called...
info_outline
Joy Is the Strategy: Rewiring Success with Jennifer Liss
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Jennifer discuss: How “fun first” became Jennifer’s unconventional success strategy after burnout in two careers Why most high achievers block joy — and how childhood moments often hard-wire that pattern The simple daily question that doubled her income almost overnight How curiosity, not hustle, becomes a reliable business strategy Jennifer’s C-M-O Framework for magnetic marketing: Clarity, Magnetism, Offer ...
info_outline
Freedom Has a Feeling: Step Into Your Next-Level Self with Erin Bradley
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin shares: Why freedom has a feeling — and how most real estate pros postpone it instead of accessing it now. The origin story of Pursuing Freedom and how misalignment — not effort— created burnout during the early success. The moment I stopped tolerating what wasn’t aligned and started leading with authenticity, joy, and “vacation energy.” How stepping into your future self requires choosing new standards, new boundaries, and new levels of belief. The...
info_outline 
Listen in as Erin and Kevin discuss:
- How Kevin went from losing everything in 2008 to building a $250M real estate portfolio.
- The “boring” asset classes that fueled his success (and why they work).
- The mindset and daily exercise that helped him rebound from rock bottom.
- Why discipline and long-term thinking outperform “quick wins” in real estate.
- How Kevin helps everyday investors create true passive income.
About
Kevin Bupp is a seasoned commercial real estate investor, top podcast host, and author of The Cashflow Investor, with over $1B in real estate transactions under his belt. On his podcast, "Real Estate Investing for Cash Flow," he shares his 20+ years of experience, guiding millions of listeners on how to find and invest profitably in commercial real estate.
Based on his decades of personal experience, supported by well documented housing and demographic trends, Kevin has identified Mobile Home Parks and Parking Lots as the top commercial real estate investments in the current market.
Increasingly known for his highly-regarded private equity firm, Sunrise Capital Investors, Kevin leads the firm’s vision of providing financial and time freedom to passive investors via access to real estate funds managed by Sunrise. These funds put Kevin’s commitment to mobile home park and parking facilities into practice through their focus on acquiring and managing these asset types.
Beyond real estate investing, Kevin gives back to the community with the "72 Hours to Key West 280 Mile Bike Ride," a charity event that has provided meals to tens of thousands of families in need during the holidays.
How to Connect With Kevin
- Website: https://kevinbupp.com/
- YouTube: https://www.youtube.com/c/KevinBupp
- LinkedIn: https://www.linkedin.com/in/kevinbupp/
- Facebook: https://www.facebook.com/RealKevinBupp
- Instagram: https://www.instagram.com/buppkevin/