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What does it really mean to build a lifestyle around real estate investing in Chicago? In this episode of the Straight Up Chicago Investor Podcast, Erik Swanson walks us through his unique journey from audio engineer, touring with world-famous bands like Aerosmith and Green Day, to full-time real estate investor and bar owner. If you’ve ever asked, "Can I escape my 9-to-5 and live life on my terms through real estate?" this episode is for you.
Erik's Journey: From Rock Tours to Real Estate Freedom
Erik didn’t start out in real estate. His early 20s and 30s were spent on the road as an audio engineer, touring internationally and earning great money while living on the go. But after years away from home, Erik realized he wanted to build a life with more roots, more flexibility, and more time.
Armed with cash and curiosity, he turned to books like Rich Dad Poor Dad and dove into the world of multifamily real estate. He began with a three-flat in West Logan for $250K and scaled to a five-unit in Belmont Cragin—all while learning construction, managing tenants, and making smart financing decisions along the way.
Top Questions This Episode Answers
Q: How do you get started in Chicago real estate with no experience?
A: Erik read Rich Dad Poor Dad while touring and started his investing journey by working with a local agent and using an FHA 203k loan to buy a three-flat. For those Googling "how to buy your first rental in Chicago," this episode gives a real-world blueprint from someone with zero real estate background.
Q: What is the best way to scale from a 3-flat to 20+ units in Chicago?
A: Erik gradually traded up by leveraging equity, partnering with other investors, and eventually moving into syndication. He shares how building systems, hiring the right contractors, and developing strong lender relationships (especially with Renovo Financial) were crucial.
Q: How do you fund real estate deals when banks say no?
A: Erik used everything from HELOCs and credit cards to construction loans and private capital. For anyone Googling "creative real estate financing in Chicago," Erik's journey shows what's possible with persistence and planning.
Q: How do you manage rehabs in Chicago while working a full-time job?
A: In the early days, Erik was doing everything—laying tile, installing toilets, and even moving in without a finished bathroom! If you're searching "how to rehab while working full time," you'll love Erik's story of resilience and resourcefulness.
Q: What happens if your building gets shot up?
A: One of Erik's properties in Belmont Cragin was involved in a drive-by shooting. He shares the full story—from tenant calls at 4 a.m. to patching bullet holes—and how he ultimately decided to sell. It’s a reality check for those Googling "is Belmont Cragin safe for investment?"
Q: What are the best landlord tools for part-time investors?
A: While not a tech-heavy landlord, Erik emphasizes the importance of having a reliable team, clear systems, and good communication. For "best tools for Chicago landlords," think less tech and more process.
Q: How do you raise private capital for real estate deals in Chicago?
A: Erik raised money for both real estate and his bar business, Navigator Taproom. He talks about earning investor trust through transparency, owning mistakes, and building confidence. If you’re wondering "how to raise money for real estate deals in Chicago," this episode offers a masterclass.
Q: Can you really travel the world and manage a real estate portfolio?
A: Yes. Erik has visited over 100 countries and continues to run deals remotely. He explains the systems, partnerships, and communication tools that make this possible. This answers the question, "Can I be a digital nomad landlord in Chicago?"
Q: What's the long-term play?
A: Erik is shifting his focus to larger syndication deals and helping others grow their portfolios. His mindset is all about partnerships, systems, and delivering consistent investor returns.
🔧 Real Estate Lessons From the Field
- Start with what you know: Erik began by self-managing a small multifamily and doing hands-on work.
- Build relationships: Contractors, lenders, and investors are all critical to scaling.
Don’t wait for perfect: He moved into units mid-renovation and figured it out as he went. - Reinvest wisely: Instead of splurging, Erik put his profits back into more deals.
- Own your mistakes: Transparency with investors and tenants builds long-term trust.
Chicago Market Highlights
- West Logan: Erik's first property was a 3-flat for $250K—those deals don’t exist anymore, but the lesson is to act when opportunity arises.
- Belmont Cragin: Cash-flow positive but not without risks. Erik's experience proves the importance of understanding neighborhood dynamics.
- Crystal Lake: GC Realty managed a 42-unit here that faced a massive water main break—a great reminder of the importance of local city relationships and responsive property management.
Erik's Key Takeaways
- Real estate is the path to time freedom.
- You can build wealth without quitting your W2 right away.
- Failures are part of the process—embrace them.
- People invest in you before they invest in the deal.
- Travel, freedom, and financial independence are possible with the right systems and team.
Show Notes
00:00 – Erik’s early projects and learning curve with hard money and construction loans
00:49 – Erik joins the show and shares his first real estate moves
01:43 – Water main break at a Crystal Lake property and the city’s response
04:25 – Housing Provider Tip of the Week: Sell to your tenants first
05:27 – Erik’s backstory, audio engineering career, and touring with bands
08:31 – Burnout from travel and first steps into real estate
10:15 – Buying his first 3-flat in West Logan using FHA 203k
13:36 – Realizing he could cash flow and cover the mortgage
15:05 – Scaling to a 5-unit in Belmont Cragin
17:01 – The drive-by shooting incident and exit strategy
19:32 – Rehabbing during a relationship and construction stress
21:40 – Launching Navigator Taproom in Logan Square
24:28 – How COVID hit the hospitality and real estate industries
28:45 – Navigating layoffs and completing a 4-unit rehab mid-pandemic
31:36 – Scaling up with investors, capital, and private lenders
33:57 – Under contract for a 63-unit in Louisville
35:21 – Fundraising challenges: Real estate vs. restaurant capital
38:01 – Embracing problems, learning from mistakes, and scaling with partners
41:22 – Why experience trumps net worth
43:44 – What’s next: Syndications, capital raising, and global travel
46:46 – Systems for managing real estate while visiting 100+ countries
50:41 – Final questions: Advice for new investors, favorite books, and where to connect
Connect With Erik Swanson
Guest Name: Erik Swanson
Guest Company: Fernweh Property Group
Guest Link: https://fernwehpg.com/
Because finding good tenants and property management shouldn’t feel like online dating.
Dear Investor,
If you are an investor in either the city or suburbs of Chicago, I would love to speak with you about how we can help you on your real estate journey. At GC Realty & Development LLC we help hundreds of Chicagoland real estate owners and brokers each year manage their assets with both full service property management and tenant placement services.
We understand that every investor’s goals are unique and we love learning about each client’s individual needs. If there is an opportunity to help you buy back your time by managing your rental property or finding quality tenants, please check us out.
Best Investing,
Mark Ainley
Founder, Partner, Podcast Co-Host, and Investor
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