📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master

🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club

The host interviews Matt, a former arena football quarterback and investor, about turning a nest egg from an earlier retail venture (selling the “wacky whistle,” which expanded from Hawaii to Dubai’s Global Village) into a football-themed short-term rental business, PigskinJourneyman.com. Matt explains how he built and self-manages themed properties near sports destinations—starting near Lambeau Field in Green Bay, expanding to South Bend near Notre Dame (including a two-house “Rockne compound”), and adding a pool property near the Pro Football Hall of Fame area in Massillon/Canton, Ohio. They discuss amenities and design, tools like Turno and PriceLabs, seasonality, platform reliance vs. direct bookings, operational workload, and regulatory risk. Matt shares 2025 plans to open a Jim Thorpe–themed property in Jim Thorpe, Pennsylvania, and considers future restructuring and possible expansion into boutique hotels or other ventures.

00:00 Podcast Twist Intro

01:18 Wacky Whistle Origins

02:00 Dubai Retail Chaos

03:59 Product Longevity Mindset

06:15 Real Estate Pivot Begins

06:54 Football Brand Story

09:20 Family Football Inspiration

10:29 No Guru Policy

14:21 Canton Market Strategy

17:26 Purchase Rehab Numbers

20:21 Revenue Ops Systems

22:26 Rockne Compound Expansion

24:18 Two Houses One Compound

25:14 Compound Pricing Strategy

27:13 Minimum Nights Party Risk

27:43 Dynamic Pricing With PriceLabs

29:29 Direct Booking Challenges

31:16 Next Market Jim Thorpe PA

33:17 Who Books These Stays

36:39 Scaling Risks And Diversification

37:35 Future Markets Hawaii Texas

39:13 Graduating Beyond STRs

42:13 Life Logistics And Time Zones

45:18 Wrap Up Links And Advice

Connect with me:

LinkedIn: https://www.linkedin.com/in/lanekawaoka/

Facebook: https://www.facebook.com/TheWealthElevator

Instagram: https://www.instagram.com/TheWealthElevator

Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016.

Check out our Top-50 Investing Podcast, The Wealth Elevator.

Hosted on Acast. See acast.com/privacy for more information.