From Losing It All to Building a $250M Portfolio: Kevin Bupp’s Blueprint for Freedom
Release Date: 09/05/2025
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
From Exhaustion to Empowerment: How Rebecca Green Built a Business She Can Retire From
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Rebecca discuss: Rebecca shares how she built her first real estate team while raising two babies under two—and what she learned about letting go of control. She reveals the turning point when she stopped chasing volume and started prioritizing profitability and peace of mind. Learn the mindset and systems that helped her step off the hamster wheel and finally build a business she could retire from. Rebecca opens up about walking away...
info_outline
Joy as Strategy: Amy Wilkinson on Soul-Led Success, Future-Self Guidance & the “Vacation Energy” Advantage
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Amy discuss: Why “feeling good” can be a legitimate business strategy—and how Amy built multi-location success by following what resonated rather than what was “supposed to” work. Masculine vs. feminine operating modes: getting out of the head (constant doing/figuring out) and back into the body, heart, and receiving. The future-self practice: “Have tea with the you who already made it” and act from that state today. ...
info_outline
The Joy Frequency: Tuning Into Abundance with Cathy Heller
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Cathy discuss: how shifting from striving to receiving opens the flow of abundance Cathy’s journey from record deals to spiritual mentorship — and why “God is my CFO.” share why joy, not hustle, is the magnet for prosperity and purpose practical ways to “tune” yourself daily to your soul’s radio station of love and possibility a heart-centered reminder that synchronicity, not strategy, is often the true source of success … and much more. ...
info_outline
From Corporate to Real Estate Success: Authentic Growth with Gaby Proctor
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Gaby discuss: Gaby’s transition from 15 years in corporate media to becoming a top-producing real estate agent in Austin. How she and her husband navigated working together in business and marriage — learning to balance strengths, delegate, and grow as a team. The role of honesty and authenticity in marketing — why showing up as yourself (accents, ballcaps, lake life, and all) attracts the right clients. The...
info_outline
Designing Wealth and Business in Alignment with Your Energy with Katrina van Oudheusden
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Katrina discuss: Katrina (“Chef Katrina”) shares her journey from Disney chef to digital marketing entrepreneur and coach. She reveals how women’s natural infradian rhythm impacts productivity, creativity, and sales — and how syncing business tasks with cycles can reduce burnout. Why traditional male-based productivity systems (like 5AM routines) don’t always work for women — and what to do instead. The “Create Her Money...
info_outline
Process is Freedom: How EOS Helps Entrepreneurs Build Better Businesses and Better Lives with Mike Paton
Pursuing Freedom: Helping Realtors & Mortgage Lenders Build Profitable, Scalable Businesses and Lives They Love — No Hustle, No Burnout
Listen in as Erin and Mike discuss how: EOS (Entrepreneurial Operating System) provides simple, practical tools to help entrepreneurs run better businesses and live better lives. “Process is Freedom”: Having systems in place doesn’t limit you—it frees you to focus on what only you can do. Growth always brings new ceilings; what got you here won’t get you there. Reinventing yourself and your business is key. Investing in systems and support...
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/