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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
A lot of people hear the word persuasion and immediately think pressure, manipulation, or trying to win an argument. That is not where this conversation goes. In this episode, Josh Bandock breaks persuasion down into something much more practical for Chicago real estate investors, landlords, property managers, and really anybody trying to move a deal forward. Whether you are talking to a seller, a resident, an investor, a contractor, your spouse, or your own team, you are constantly trying to get alignment.
What stood out in this conversation is how much of persuasion has less to do with talking and more to do with understanding. Josh explains why people feel first and reason second, why most people lead with logic too early, and why the best communicators know how to uncover what is really stopping someone from moving forward. That applies just as much to a buyer hesitating on a property as it does to a resident going silent, a prospect dragging their feet, or a team member not fully buying into a plan.
There is also a bigger lesson here for Chicago investors. We spend so much time thinking about numbers, underwriting, rents, repairs, and financing that we can forget how much of this business depends on communication. A good deal still has to be explained well. A service still has to be sold. A relationship still has to be managed. If you cannot make people feel understood, even the best logic in the world can fall flat.
Housing Provider Tip of the Week
Before the interview, the team shared a maintenance tip that fits perfectly with the bigger theme of the episode. When something breaks at a rental property, the time to figure out who to call has already passed. You need to know in advance who handles HVAC, appliances, handyman work, painting, and everything else that can go wrong. Even better, you need backups for your backups.
That first 48 hours matters. If you are a self-managing landlord or about to buy a property, having responsive vendors lined up ahead of time can save days of delay, reduce costs, and create a much better resident experience.
Questions We Answer in This Episode
Q: Why should Chicago real estate investors care about persuasion?
A: Because persuasion is happening all day long in this business. You are persuading sellers to work with you, buyers to trust your pricing, investors to believe in a deal, residents to cooperate, contractors to stay aligned, and even family members to support what you are building. Josh makes the point that having a good idea is not enough. The real difference is getting other people to embrace it.
Q: What is one of the biggest mistakes people make when trying to persuade someone?
A: Leading with logic too early. Josh explains that people feel first and reason second, and sometimes they never even get to the reasoning stage. That means the standard approach of dumping numbers, facts, and analysis on someone is often ineffective. In real estate especially, people love to say, “Look at the numbers,” but the brain does not actually process decisions that way first.
Q: What should people ask instead of “What do you think?”**
A: Ask, “How do you feel?” That question gets to something deeper and more honest. It gives you a more unfiltered response and helps you spot hesitation faster. It also helps reveal whether the actual barrier is the person in front of you, their partner, financing, a competing opportunity, or something else entirely.
Q: How does asking about feelings help in a deal?
A: It gives you real intel before the person leaves the conversation. If someone says, “This sounds awesome, I just need to talk to my partner,” that is different from, “I do not know, I need to talk to my partner.” One suggests outside approval is the issue. The other suggests the hesitation is already inside them. That difference matters if you are trying to get to the truth instead of getting brushed off politely.
Q: What is persuasion actually supposed to be?
A: Josh argues that persuasion is not about winning, conquering, or proving you are right. It is shared action. It is about helping people move willingly toward something together. That is a much better long-term framework for investors because the goal is not just to get one deal done. The goal is to build relationships, protect your reputation, and create outcomes where people are willing to work with you again.
Q: What mindset makes someone more persuasive?
A: The mindset that it is about them, not you. Josh calls this the persuader’s mindset. Instead of obsessing over your own position, your own logic, or your own urgency, you need to understand the other person’s goals, fears, needs, and interests. If you are 50 grand apart on a price but you do not understand what they actually want, you are probably making the wrong argument.
Q: What is one practical question investors should ask more often?
A: “What would stop you from doing X?” That question gets straight to the barriers. Once you know the barrier, you know what has to be addressed. If the issue is financing, that is one conversation. If the issue is a competing deal, that is a different conversation. Persuasion becomes much easier when you treat it as removing barriers instead of overpowering objections.
Q: How can you handle people who ghost after a showing or good conversation?
A: Josh recommends not coming back too aggressively and not always pushing for a yes. Sometimes it is better to soften the follow-up and even invite a no. A check-in that lowers pressure can work better than another hard ask. He also recommends using follow-ups based on what you learned from them earlier, like tying your message back to their goals or sharing a short story about someone in a similar situation.
Q: Why are stories so powerful in real estate communication?
A: Because people remember stories more than explanations. Mark and Tom talk about how often stories help them in property management and sales. Instead of reciting rules or numbers, they explain what happened the one time they did not follow a certain process and why that created a problem. That makes the lesson real, memorable, and persuasive.
Q: How did Josh approach writing and publishing his book?
A: It was about a decade in the making. The ideas started around 2016, and the process involved becoming an expert, building a platform, developing a proposal, working with a literary agent, and then going through multiple rounds of editing with a publisher. He also explains that before a publisher signs you, you need a strong answer to one question: why are you the person who should write this book?
Q: What kind of writer is Josh, and how did he actually get the book done?
A: He describes himself as an outline writer, not a process writer. He built the structure first, then executed against it. Much of the book was written nights and weekends, often in 30 to 60 minute blocks during the week and longer sessions on weekends. Later, he secured time to write it full-time, but the early progress came from consistency and disciplined work.
Q: What did the editing process teach him?
A: That shorter and clearer is better. The largest version of the manuscript was around 160,000 words. The final published version was roughly half that length, and only a fraction of the original wording remained. The lesson is one that applies directly to investor communication too: do not water down your message. Say it clearly, say it efficiently, and respect the attention span of the person on the other side.
Q: What is the “granny test”?
A: It is a simple communication filter Josh uses: would your granny understand what you are saying? If not, you are probably too abstract, too technical, or too buried in your own language. That matters in real estate because when a prospect does not understand what you said, they usually do not argue with you. They just quietly move on.
Q: How does AI fit into persuasion and communication?
A: Josh sees AI as both helpful and limited. It is powerful for gathering information and creating raw material quickly, but he does not believe it can replace emotional intelligence. You can use tools like ChatGPT to help frame ideas, but you still have to communicate with human beings in a way that matches their concerns, motivations, and feelings.
Q: What advice did Josh give to someone who has not yet bought their first property in Chicagoland?
A: Understand what would stop you from making that investment and deal with those barriers honestly before you move forward. If you do not have the time, money, or resources needed and you ignore that, you are setting yourself up for trouble. His point is simple: do not walk into real estate without first understanding the problems you are likely to face.
Top 15 Timestamps
00:49 Why persuasion matters in business, investing, and everyday life
02:28 Housing Provider Tip of the Week on maintenance vendor planning and backups
04:22 Josh explains why persuasion matters for real estate investors, landlords, tenants, and contractors
05:24 The inspiration behind How to Get What You Want
06:39 The core neuroscience idea: people feel first and reason second
07:34 Why asking “How do you feel?” works better than asking “What do you think?”
11:26 What persuasion is not: winning, conquering, or just proving you are right
12:31 Josh’s definition of persuasion as shared action
16:32 The persuader’s mindset and why it has to be about them, not you
18:27 How to identify barriers by asking what would stop someone from moving forward
19:37 Why getting the other person to make the case can be so powerful
21:11 How to re-engage someone who disappears after a showing or conversation
23:48 What it really takes to write and publish a book
29:55 Why clearer, shorter communication is usually more persuasive
36:29 How AI can help with communication and where human emotional intelligence still matters most
Takeaways for Chicago Landlords and Investors
If you lead with logic too early, you can lose people before the real conversation even starts.
Asking how someone feels can uncover more than asking what they think.
Most stalled deals are not solved by pushing harder. They are solved by identifying the real barrier.
Better communication starts when you stop thinking about your argument and start thinking about their goals.
Stories often persuade better than numbers because people remember them.
If a message is too long, too technical, or too vague, most people will not challenge it. They will just move on.
Good follow-up is not just repetition. It is using what you learned to re-enter the conversation in a smarter way.
Whether you are selling a service, managing a resident issue, hiring a team member, or pitching a deal, clarity matters.
AI can support your process, but it cannot replace human emotional intelligence.
Before buying your first Chicago investment property, be honest about what could stop you and solve that first.
Guest info
Guest Name: Josh Bandock
Guest Company: Illinois Policy Institute
Guest Link: https://www.illinoispolicy.org/author/jbandoch/
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,
Founder, Partner, Podcast Co-Host, and Investor
