Back-to-Back Real Estate Case Studies
Two investors. Two real deals. One night packed with real-world lessons.
Join us in Wausau for a special back-to-back Case Study night featuring Jake Strassburger and Jeremy Dobson, as they take you behind the scenes of deals they’ve actually worked through—including the challenges, financing strategies, unexpected obstacles, and lessons learned along the way.
️Powering Up with a Portfolio Deal
Presented by Jake Strassburger
Jake will break down a multi-property deal and share how he combined creative and traditional bank financing to make the deal work. We’ll cover deal structure, analyzing multiple properties, due diligence, and the importance of not giving up when challenges arise.
Old House, New Lessons
Presented by Jeremy Dobson
Jeremy will walk through the transformation of a heavily distressed property, sharing lessons on risk, renovation, financing, contractors, cost control, and maximizing value—while also building a real estate business that supports family life rather than consuming it.
Come hear the real stories behind the deals, learn from the challenges, and take away practical strategies you can apply to your own investing journey.
Don’t miss this unique night of real deals, real challenges, and real lessons!
Case Study Presenters
Jake Strassburger and Jeremy Dobson
Jake Strassburger
About 2.5 years ago, I made the decision to leave my W-2 career and pursue real estate full-time, fully committing myself to building something of my own. Since making that transition, my experience and portfolio have grown rapidly, expanding from 12 doors to 60. Rather than learning from the sidelines, I’ve focused on learning by doing—acquiring, improving, renovating, and managing properties firsthand.
A major part of that journey has been staying closely involved in the physical side of real estate, particularly construction and property improvements. I’ve developed a strong understanding of renovations, repairs, construction processes, and the factors that truly drive value in a property. Instead of outsourcing every aspect of the work, I intentionally stayed close to the process so I could understand the real costs, timelines, quality, and challenges involved in executing a project successfully.
That hands-on experience has shaped the way I approach real estate today. It has allowed me to become more confident in identifying opportunities, evaluating properties, managing improvements, and making informed investment decisions based on real-world experience rather than theory.
Real estate remains the core focus of what I do, with my general contracting business serving as a complementary part of that larger vision. As my portfolio continues to grow, I’m transitioning away from being as involved in the day-to-day hands-on construction work and focusing more heavily on management, strategy, and long-term portfolio growth.
My goal is to continue building a strong, sustainable real estate portfolio grounded in practical experience, disciplined decision-making, and long-term ownership.
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