Podcast Episode #553: How to Invest or Participate in Franchise Businesses - Jon Ostenson
Episode #553: Dentist Freedom Blueprint Podcast
How to Invest or Participate in Franchise Businesses - Jon Ostenson
What comes after dentistry or a career in active income? For many professionals, the hardest part of stepping away isn’t the finances—it’s the question: what’s next? In this episode, I sit down with Jon Ostenson, franchise expert, investor, and author of Non-Food Franchising, to explore how business ownership beyond your practice can offer purpose, tax advantages, and legacy opportunities.
Jon reveals why franchising is one of the most overlooked paths to semi-passive income, and why it’s about much more than burgers and fries. From home services to senior care to pet wellness, franchising provides vetted, scalable businesses with systems, support, and tax benefits baked in. Whether you’re looking to involve your family, diversify your portfolio, or transition into your next chapter, Jon shares exactly what to look for—and what to avoid—when exploring this path.
Minute Markers:
00:00 – Intro
02:36 – Meet Jon Ostenson
08:24 – Why healthcare professionals are drawn to franchising
13:03 – Evaluating emerging vs. established brands
16:16 – Understanding agreements and protections
18:08 – Examples of successful non-food franchise models
20:05 – Health, wellness, and pet care opportunities
21:03 – Tax benefits and write-offs for franchise owners
22:01 – Building family legacy through franchising
24:30 – Investment ranges and financing options
26:33 – Generational wealth transfer and mentorship opportunities
28:15 – Case studies of family-run franchises
30:13 – Leadership as the ultimate differentiator
Jon Ostenson Website | LinkedIn
Book: Non-Food Franchising by Jon Ostenson
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P.S. Whenever you’re ready, here are some other ways I can help fast track you to your Freedom goal (you’re closer than you think) :
In this episode, we finish up the second part of my interview with Rob Swanson and his eight rules of investing. (If you haven’t listened to part 1, be sure to go back and give that a listen before jumping into this one.) Today, we pick up where we left off, covering rules four through eight and talking about everything from decision-making to cash flow and risk reduction.
Listen in as Rob shares his incredible insight and experience in real estate and investing to give us a few rules that help make our decisions and investments more solid. You will hear about the importance of looking at margins before buying and what boxes need to be checked when it comes to predicting a solid income stream. Rob also discusses how to define and mitigate the different risks involved so that you can come out on top.
Alastair MacDonald is a private advisor to established entrepreneurs, investors, and business owners, as well as a TEDx speaker who lectures on economic, social, and financial forecasts. Join me today to hear part two of our conversation at the Freedom Founders Mastermind, where we dive into the concept of certainty, how to hedge against a volatile economy, and why the abdication model is no longer one that works.
Listen in to learn the reasons why Alastair is not worried about consumer price inflation (and what he’s really worried about instead) and why the 401(k) is not always the investment that it is made out to be. You’ll learn why he is most concerned about the issue of division and polarity in the Western world, why your business is your best asset in a volatile economy, and how you can maintain its viability to weather the most intense economic storm.
1. Get Your Free Retirement Scorecard:
Benchmark your retirement and wealth-building against hundreds of other practice professionals, and get personalized feedback on your biggest opportunities and leverage points. Go to www.FreedomFounders.com/Scorecard to take the 3 minute assessment and get your scorecard.
2. Attend A Workshop:
If you’re committed to Freedom, but still building a practice, paying down school debt, or growing investment capital, our hands-on Freedom Blueprint Workshops are your entrance ramp onto the fast track! Visit www.freedomfounders.com/workshop to claim your seat!
3. Apply To Visit The Mastermind:
If you’d like to join dozens of dentists, docs, and practice professionals on the fast track to Freedom (5-7 years max), visit www.freedomfounders.com/step-1 to apply for a seat.
4. Want to Work Directly with Me?
If you’d like to work directly with me and a small group of my closest investment colleagues, with direct access to the dealmakers and asset classes that I invest in, just send a message to my Executive Assistant (Lindsey@FreedomFounders.com), and put “Fast Access” in the subject line. Or, call (972) 203-6960 Ext 144 and leave a brief voicemail for Lindsey. Let her know you’re interested in the Fast Access program – we’ll set up a time with you to talk, find out about your goals, and see if there is a fit.