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From Losing It All to Building a $250M Portfolio: Kevin Bupp’s Blueprint for Freedom

Pursuing Freedom

Release Date: 09/05/2025

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Pursuing Freedom

                                  Listen in as Erin and Andrea discuss: Why authenticity is Andrea’s most powerful business strategy. The unique path from theater to real estate — and how it made her unstoppable. The mindset that helped Andrea thrive through market downturns. How “vacation energy” and passion projects attract ideal clients. Why giving back creates surprising opportunities in business. About As a Realtor®, Andrea serves the Oakland, Berkeley and surrounding East Bay communities as...

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Pursuing Freedom

                                      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.      ...

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                                          Listen in as Erin and Alice discuss: How Alice went from wine exporting to running a private equity fund and coaching entrepreneurs on AI. What most solopreneurs misunderstand about passive investing—and how it can transform your lifestyle. The real reason AI isn’t optional anymore (and what to do if you’re overwhelmed). How Alice uses ChatGPT and custom tools to replace entire teams and scale her business with fewer headaches. The mindset...

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                                          Listen in as Erin and Cassy discuss: Why “toning it down” can limit your potential — and how to embrace your authentic self in every space. How Cassy’s book Unapologetic empowers readers to break free from conformity and step into boldness. The importance of building your “tribe” to lift you up when self-doubt creeps in. Why intentionality with your time is essential for avoiding burnout and creating the life you want. How to spot (and...

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                        Listen in as Erin and Brittney discuss: How Brittney went from librarian to leading 125+ agents in a thriving Texas brokerage—starting with zero real estate experience. Why “borrowing belief” is a secret weapon in business growth (and how to use it). The real formula for success: Massive action + unwavering faith (and how to build both). Brittney’s mindset toolkit for leadership, momentum, and avoiding burnout. Tactical advice on time blocking, tracking lead gen, and building integrity with...

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                                          Listen in as Erin and Mallory discuss: How Mallory scaled from helping with a few apartment sales to running a $200M team — in just 7 years. How she spent two full years learning the basics and building a real business foundation before scaling. How her team thrives on clear SOPs, post-deal roadmaps, and constant refinement (even after success). How hiring the right assistant changed her life — but she had to go through several wrong fits...

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                                        Listen in as Erin and Joao discuss: How Joao went from buying one duplex a year to owning 92 properties in just three years — all through strategic networking, mentorship, and the BRRRR method. How joining masterminds and attending live events help overcome introversion and build partnerships that accelerated his success. Why multifamily buildings can actually be simpler to renovate and scale than single-family homes. How Joao uses syndications to...

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                                      Listen in as Erin and Lindsay discuss: How pursuing joy—not just profit—transformed her real estate career. Why moving from DC to New Hampshire was the smartest “scary” decision she ever made. The 5 pillars of Lindsay’s Happy Agent Method for building a business that aligns with your life. How to create a virtual brokerage culture that empowers agent autonomy and sustainability. Why embracing change in today’s real estate market is critical—and...

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                                      PF Pod 282 Promo

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.

                                    PF pod 282 quote

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