41. Everything Happens for a Reason: My Path Into Real Estate & STRs
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Episode Summary
In this personal, behind-the-scenes episode, I share how I went from a Six Flags kid in Gurnee, Illinois, to UW-Platteville grad, to wedding and hotel work, to a miserable janitorial sales job… to finally finding my lane as a real estate agent and short-term rental investor. I walk through the domino moments—meeting a Zillow agent who became my mentor, getting laid off during COVID, almost opening a paint-your-own-pottery studio, discovering Airbnbs, and how we bought our first, second, and third properties (plus a “two-for-one” partnership that’s in motion). If you’re curious how someone actually pivots into STRs without a trust fund or a $200k salary, this one’s for you.
Key Takeaways
- Your path won’t be linear—and that’s okay. Every “wrong” job taught me what I truly wanted (and what I didn’t).
- Mentors matter. A single Zillow tour led to the agent who mentored me and changed my career trajectory.
- Don’t chase money, chase fit. Long-term rentals weren’t our fit—hospitality was. STRs clicked.
- Start imperfectly. Our first market wasn’t ideal, but it got us in the game and funded the next doors.
- Momentum compounds. Property #1 led to #2, then #3—then partnerships for #4 and #5.
- Niche = clarity. When I niched into STRs, the work got easier, more fun, and way more effective.
Why Listen to This Episode?
If you’ve ever thought, “I didn’t go to school for this—am I too late?” or “I don’t have a perfect plan or pile of cash,” this is your permission slip. You’ll hear what it really looks like to pivot industries, learn in public, and build an STR portfolio step by step—messy mic moments and all.
Mentioned in the Episode
- Start your Airbnb Profile: Receive $48 back when starting your Airbnb profile and I'll have your back every step of the way!
- Want to learn how to launch an Airbnb?: Every dollar counts when it comes to investing. Save $50 with the Promo-code: 5STARPODCAST
- Connect with Me on Instagram: Follow me @airbnbroadmappodcast for behind-the-scenes content, tips, and updates.
Let’s Connect
Thinking about getting into short-term rentals? DM me on Instagram at @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out.
Work With Me
- Buy or sell an STR in Wisconsin with me at Front Porch Realty (powered by Real Broker LLC).
- Invest anywhere in the U.S.—I’ll connect you with a vetted STR-savvy agent in my network.
- Take my self-paced course, Airbnb Roadmap Accelerator (under $500): step-by-step from deal finding to launch and systems.
- Close on your first STR with an agent I connect you to, and you’ll get 100% of your course tuition refunded.
- Want a warm intro to a local pro, lender, or CPA? Message me “INTRO” on IG.
Chapters
- 00:00 — Mic on (finally), what today’s episode is (and isn’t)
- 02:46 — Teaser: our new two-for-one STR deal with friends in Texas
- 04:30 — Growing up in Gurnee, Six Flags summers, loving thrills not lines
- 05:06 — College, weddings, events… and realizing weekends weren’t mine
- 07:12 — Hotel front desk: the spark for hospitality
- 09:29 — The toxic sales job that broke me (and taught me)
- 10:59 — Pottery studio dream, mentorship, and a near-miss lease
- 15:45 — COVID pivot: the blessing in disguise
- 18:09 — Buying our home, meeting the Zillow agent who changed everything
- 20:19 — Joining a team, getting laid off, and momentum begins
- 22:41 — BiggerPockets binge: LTR vs STR and choosing our lane
- 25:03 — Why STRs fit my skills and personality
- 25:59 — Writing our first offer at Dunkin before a wedding (we got it)
- 28:18 — Property #2: funding, chaos, and lessons
- 30:44 — Property #3 during pregnancy, simple loan structure, smooth launch
- 33:09 — Leaving the team, launching my own company
- 34:54 — Niching into STRs and never looking back
- 37:21 — Why I started this podcast: stop repeating answers, start scaling help
- 39:44 — The truth: first market wasn’t ideal—and that’s normal
- 42:11 — What’s next: scaling to properties #4 and #5, and the course offer
Subscribe and Share
If this gave you the nudge to start—or restart—your STR journey, hit Follow/Subscribe, drop a quick 5-star review, and share this episode with a friend who keeps saying “one day.” Your support helps more beginners find transparent, hype-free advice.
