From Market Crash to Multi-Million Dollar Wisconsin Portfolio: Secrets & Strategies episode artwork

EPISODE · Nov 25, 2025 · 59 MIN

From Market Crash to Multi-Million Dollar Wisconsin Portfolio: Secrets & Strategies

from The Wisconsin Investor · host Corey Reyment

Send us Fan MailIn this episode of The Wisconsin Investor Podcast, Corey sits down with seasoned investor Ben Keleny, who built a multi-million-dollar portfolio with long-term rentals, short-term rentals, boutique hotels, and even a church renovation. Ben shares how he capitalized on the 2008 market crash and expanded his investments across Wisconsin and South Carolina.Learn about Ben’s strategies for navigating market changes, using the BRRRR method, and leveraging creative financing. He also discusses the power of mid-term rentals, the challenges of self-management, and tips for new investors looking to scale their portfolios.Don't miss out on this episode packed with real-world advice and strategies to help you succeed in Wisconsin real estate!Timestamps: 00:00 – Intro and Giveaway Announcement 05:00 – Ben's Journey into Real Estate 15:00 – How Market Timing Changed Everything for Ben 22:00 – Managing Different Property Types (Short-Term, Long-Term, and More) 30:00 – Financing Deals: BRRRR, Private Money, and Lines of Credit 40:00 – Tips for New Investors & How to Make Your First Deal Happen 48:00 – Pivoting in Today’s Real Estate Market and Staying Opportunistic 54:00 – Final Words and How to Get Involved in Real Estate Today🔑 Key Takeaways:How to use the BRRRR method and creative financing to grow your portfolioThe difference between short-term and mid-term rentals in today’s marketHow AI and technology are changing property managementThe importance of having multiple exit strategies for each property✨ Giveaway Details: We're giving away some amazing prizes to our loyal listeners! Three winners will receive:A 1-hour Real Deal Strategy Call with CoreyA $250 Amazon or Visa Gift CardA Wisconsin Investor Starter Kit (merch, books, coffee!)How to Enter:Subscribe to our YouTube channelFollow us on Instagram or FacebookComment "DONE" on our pinned giveaway post on Facebook or Instagram and tag two friends!Bonus entry: Share the pinned giveaway post on your social media and tag @TheWisconsinInvestor!If you enjoyed today’s episode, please support the show by leaving a review and subscribing. It helps us reach more listeners like you and keep bringing valuable insights every week!You can also connect with Ben directly at [email protected] or check out his YouTube Channel @CheersLB for more content and real estate tips.Thank you for supporting the podcast, see ya next week!

Send us Fan Mail In this episode of The Wisconsin Investor Podcast, Corey sits down with seasoned investor Ben Keleny, who built a multi-million-dollar portfolio with long-term rentals, short-term rentals, boutique hotels, and even a church renovation. Ben shares how he capitalized on the 2008 market crash and expanded his investments across Wisconsin and South Carolina. Learn about Ben’s strategies for navigating market changes, using the BRRRR method, and leveraging creative financing. He a...

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From Market Crash to Multi-Million Dollar Wisconsin Portfolio: Secrets & Strategies

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This episode was published on November 25, 2025.

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Send us Fan MailIn this episode of The Wisconsin Investor Podcast, Corey sits down with seasoned investor Ben Keleny, who built a multi-million-dollar portfolio with long-term rentals, short-term rentals, boutique hotels, and even a church...

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