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I love Daniel Baker and what he has done. This episode was a lot of fun and it is all thanks to his positive viewpoint of his experiences.
From starting with a single house hack to building a multi-property portfolio, Daniel Baker’s story is a blueprint for persistence in Chicago real estate. In this episode, Daniel shares how grit, hustle, and leveraging the right partnerships helped him succeed in one of the most competitive markets in the country.
Whether you're a first-time investor or an experienced Chicago property manager, this episode delivers practical lessons on growing your portfolio, surviving setbacks, and thriving in the long game of real estate.
Questions We Answer in This Show
Q: What does grit look like in the Chicago real estate market?
A: Grit shows up in the form of consistent action—even when it’s not fun. Daniel talks about taking late-night calls, showing units on weekends, and learning how to finance creatively when banks said no.
Q: How do property managers in Chicago handle leasing when starting out?
A: Daniel shares his approach to managing vacancies, running background checks, and the learning curve of placing quality tenants while still working a full-time job.
Q: What’s the key to scaling your portfolio while staying sane?
A: Leveraging systems and people. Daniel emphasizes the value of hiring a Chicago property management company to handle day-to-day tasks and allow him to focus on acquisition and strategy.
Q: What advice does Daniel give to landlords frustrated with bad tenants?
A: His advice is that It starts with better screening and communication. He discusses how he learned the hard way and why investing in screening systems or hiring experts can protect your bottom line.
Q: How do you recover from a bad real estate deal in Chicago?
A: Daniel shares a story of a deal that almost went south and how a strong network and focus on long-term vision helped him pivot and turn the property into a win.
Q: What should investors know about operating in tougher Chicago neighborhoods?
A: Don’t assume every area works the same. Daniel talks about understanding neighborhood dynamics, community engagement, and tailoring property management strategies accordingly.
Q: How does a first-time investor know when to self-manage or outsource?
A: Daniel recommends starting with self-management to understand what’s involved, then hiring a property manager in Chicago once your portfolio expands past your personal capacity.
Q: What is one trait Daniel believes separates successful investors from the rest?
A: Consistency. Showing up, even when you don’t feel like it, is the number one trait he sees in investors who build long-term wealth.
Q: What is Daniel’s favorite Chicago neighborhood to invest in right now?
A: He shares his insights on emerging pockets with potential, including how he analyzes school ratings, walkability, and nearby development.
Q: What are Daniel’s go-to resources for managing his rental business?
A: He uses platforms like Buildium and Rentometer, while also relying on local Chicago property manager meetups to stay ahead of changing laws and tenant expectations.
Daniel Baker’s Roadmap to Real Estate Success
in Chicago
Daniel’s journey began with a duplex house hack in the western suburbs. Like many Chicago landlords, he underestimated the workload that came with self-managing tenants, maintenance issues, and city compliance. But instead of backing off, he leaned in.
After his first few deals, Daniel realized the difference between working in your business and on your business. He transitioned from being the maintenance guy and leasing agent to hiring experts—starting with a part-time virtual assistant and eventually a property manager in Chicago who could handle tenant calls, rent collection, and inspections.
Daniel now mentors newer investors who want to get into the game but don’t want to make the same costly mistakes. His message? There is no perfect deal. Learn the numbers, screen your tenants well, and never underestimate the value of a great property manager.
Show Notes
02:45 – Daniel’s first house hack and what he learned
06:10 – The reality of self-managing rentals
09:30 – How grit helped him survive a bad tenant situation
12:55 – Scaling from one property to several units
17:40 – Why he hired a Chicago property manager
21:15 – Neighborhood insights: Where he’s buying now
25:30 – Daniel’s favorite landlord tech stack
28:45 – The importance of building a team
33:00 – Advice for new landlords navigating tough tenants
36:20 – What makes a good investment in Chicago
39:00 – The one trait that matters more than money
Daniel Baker’s Top Advice for Chicago Landlords and Property Managers
- Screening is everything. Avoiding one bad tenant can save you $10,000 in lost rent, legal fees, and turnover costs.
- Don’t be afraid to delegate. Whether it’s maintenance, leasing, or bookkeeping, outsourcing to professionals like Chicago property managers allows you to scale.
- Track your numbers. Daniel keeps tight control of income, expenses, and time-on-market for each unit.
- Stay educated. He credits podcasts, local meetups, and mastermind groups for giving him the tools to grow.
- Think long-term. Real estate wealth isn’t about quick flips—it’s about smart buys, solid tenants, and holding strong during tough seasons.
Guest Info
Guest Name: Daniel Baker
Instagram: @danielbakerinvestor
Website: Coming soon — Daniel mentioned he’s launching a Chicago investor newsletter. Stay tuned!
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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