Rick Chess, attorney, real estate strategist, capital-raising expert, and trusted advisor, is passionate about helping entrepreneurs, investors, and business owners navigate complex decisions that can dramatically impact enterprise value and long-term success. Throughout a career spanning more than five decades, Rick has raised over $100 million for multiple organizations, guided companies through acquisitions, governance challenges, and strategic growth, and helped owners prepare for successful exits.

We explore The Capital Raising Framework — Focus on Individuals, Not “the Market”; Be Ready to Sell; Start With Who You Know; Connect on Emotion; and Find a Problem to Solve. Rick explains why raising capital is ultimately about understanding people, not pitching ideas, why investors care more about their needs than your opportunity, and how trust-based relationships create opportunities that compound over time. He also shares lessons from raising capital, building influential networks, serving on boards, and helping entrepreneurs avoid costly mistakes when pursuing funding, growth, and exit strategies.

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How to be a Trusted Advisor with Rick Chess

Good day, dear listeners. Steve Preda here with the Management Blueprint Podcast. And my guest today is Rick Chess, who is a real estate and exit strategist. He helps business and real estate owners, and the trusted advisors who guide them, turn complex decisions into strategic moves that grow enterprise value and maximize sale outcomes. Rick, welcome to the show.

Thank you. Appreciate it, Steve.

Well, it’s great to have you. And I’m going to ask you my favorite question, which I always ask: What is your personal ‘Why’, and what are you doing to manifest it in your practice?

When you go back in my career, 50-some years, where I’ve been most happy is either growing an organization. That can be a community, that can be a business, it can be an association. And then, at some point, individuals in that association want to move on, whether that’s to retire, to go someplace else, or whatever. And I find that in that world, there are certain things where they might have a Steve Preda who helps them with how to manage day to day. But they get to certain big issues that they’ve never done before, and maybe they’ll never do again. That’s where I like to come in because I know I’m critically important to them.

So you’re a trusted advisor. You like to grapple with the big challenges people have in their lives, whether it’s a big real estate transaction, getting ready for an exit, an acquisition, or something like that.

Yeah.

Yeah.

So, I mean, the things that would be—for instance, most folks, if they’re talking about real estate, they have some idea how to fix a toilet. They have some idea how to buy a property. But when they get to a certain point, it’s like, “We need to raise $10,000. We need to raise $100 million,” whatever the amount is, because there’s either a great opportunity or they want to keep moving upward. And they have, again, a Steve Preda who can help them through the process. How they get that capital often is what trips people up. So that’s where I kind of first got into this.

I was an acquisition guy. I knew how to spend other people’s money, but I didn’t know at that time how to raise the money. And I’ve done it several times. I’ve raised $100 million for three different companies. And like everything in life, like with Summit, there is a process that you go through. And I love doing it. I just love doing that kind of stuff.

Okay. So when you are doing capital raising, fundraising, M&A deals, or real estate transactions, is there a framework that has helped you, that you figured out along the way? And think about something that is three to five steps. Maybe it’s a mental model of how you look at things, or maybe it’s a process. How would you describe that framework that you have, or that has helped you, so that the listeners would also benefit from it?

The listeners are best served if they step back from their preconceived notions of, A, how they think capital is attracted, because they usually are wrong. And they step back from how wonderful they are. And those two things are difficult. Because the reality is, no one is waiting to give you money. That’s foolish. You’ve got to sell the concept like you have to sell everything else. And what you sell is not what you think is wonderful. It’s what the market is going to think is wonderful. It’s like with any other product you’re making. “Hey, I made this great widget.” And the population looks at it and says, “I don’t need it. I don’t want it. I don’t know what it does.”

And depending on whether you’re trying to raise $100,000 from friends and family or $100 million on Wall Street, you look at who it is that you know. Because people that you know might at least return your phone call. So if you don’t know Bill Gates, thinking that you’re going to go to Bill Gates and get a billion dollars is, well, stup*d. But if you’re just trying to raise money from friends and family, and you have an aunt who lives three states away that you don’t see very often, and she has some money, okay, then you start with who you know. So, for instance, thinking about one of the many ways that you can raise money, there’s something called intrastate. And it is something that’s allowed by the Securities and Exchange Commission. If all of your money is raised within your own state, there are certain allowances for that.

But if you do one transaction outside the state, it all collapses. So like everything else on the business side, where there are certain rules that you can’t violate without getting into trouble, it’s the same thing when raising money. And I get so many people saying, “I’m going to list this on Wall Street, and I’m going to make…” It’s like, “No, you don’t. You better be prepared. If you’re going to list something on Wall Street, you’d better have $25 million that you can risk just to get it out there. And nine times out of ten you’re going to fail.” Not because there’s anything wrong with you.

It’s just that if you’re going to climb Mount Kilimanjaro with a pair of Keds, a T-shirt, and some shorts, you’re not prepared to climb that mountain. It’s no different when raising capital. And also think about when you were a kid. At a certain age, your parents let you cross the street to see your buddy. Then ten years later, they’ll let you get in the car and drive, but you’ve got to get home by midnight. It’s the same thing with raising money. And there aren’t a lot of folks who have done what I’ve done. So talking to your local lawyer or accountant—who may be wonderful people—but if they’ve never raised money, they’re not the people to talk to.

One of the ways people get taken advantage of on a regular basis is they’ll go to a securities attorney. The securities attorney will charge them $100,000 and write this great offering document, and no one ever gives them a penny. Because lawyers generally have no clue what’s happening in the marketplace. I own my own securities broker-dealer. I’ve also raised money for three different companies. It’s not easy. But like having read your book, Steve, if you follow certain paths, there’s at least a chance for success. Same thing here.

Fascinating. So what I’m taking away in terms of a framework: Be aware that people are not out there waiting to give you money. You have to sell them. So that’s the first step. The second one is: start with who you know. Don’t start on Wall Street. Start with the people you know, where you have some trust, the people you understand, and where you have a chance to get there. And then look at some special circumstance that’s going to give you a leg up. For example—

Absolutely. Again, this is coming right out of your book on the business side. You create a widget. So what? But you create a widget that solves a problem. Ah. Then you have something. So it’s the same thing. When you get over onto the money-raising side, it’s: who do you know? Where do they live? How much money do they have? How do I approach them? But then, in the end, it’s not what’s in it for you, it’s what’s in it for them. And for them, if it’s friends and family, your mama may give you some money because she thinks you’re cute.

Your aunt might give you some money because she’s related to your mama. But at some point, you’re going to people who really have a checkbook. They have money in the checkbook. They’re not going to give this up just because you’re cute or you have a great idea. You’re either going to get them because you have something they’ve never heard of, or you have something that really feels like it could solve one of their needs. And their needs are not always what you think. Some people think, “Well, what they need is high cash flow.” What if they don’t need cash flow, but they’re really interested in a cure for cancer?

What if you think, “Well, it’s really going to go up in value”? Well, they have all the money they need. They’re not looking for that. But is this something that is going to allow their nephew to come work for you? Yeah. When you start thinking that you know what other people are thinking, that’s when you’re going to fail. When you can step back and just ask them, “Well, what’s important to you?” If you can’t have a conversation, one, you’re never going to date anybody, and you’re never going to raise any money.

And don’t be slick. You can be slick for three sentences, and at that point they’re going to reject everything you say thereafter. So don’t talk about how much money you’re going to make and all the rest of it. No. Talk about them. Talk about them. Talk about them. Your document should talk about them. Your questions should talk about them. Now, does that mean there are certain people who won’t put money into your deal? Yes, because it doesn’t fit. If you sell high-heeled shoes and a runner comes in, they’re generally not going to buy your high-heeled shoes. They’re not going to invest money in high-heeled shoes.

But if that high-heeled shoe actually is a running shoe, and you can break off the heel and then… I mean, I don’t know. You could come up with something there. And the folks that say no are sometimes your biggest advocates. What? The folks that… Yes. Because you’ve been able to get into their head, and they’ve shaken it around, and they’ve looked at it and said, “No, that’s probably not right for me. I’m not into high-heeled shoes, but I have a friend.” If you’ve done a sincere job, a thoughtful job, you’ve really asked them questions, and you’ve connected on an emotional level, they’ll open the next door. And that’s what it’s about. It’s often a lot of the same things that you teach people about how to sell their company. It’s how they sell—

Rick, this is fascinating. So how do you connect with people on an emotional level? What’s the trick there?

First thing is: why are they going to take a meeting with you? Why they take a meeting with you answers almost everything that we’ve just asked. If they’re taking a meeting with you because you’re related, okay, that’s the emotional connection. If they take a meeting with you because some friend of yours called them and said, “This is a great way to make money,” that’s another reason. If you found them in an article in the paper—yes, there are things called newspapers. They print them. There are words in them. And there’s somebody in there who has shown an interest in something you do.

Then you’re talking to them about that interest. You want to try to avoid cold calls. Really, it’s a waste of your time and a waste of their time. It’s a random thing. It’s like asking every girl who walks by in college, “Do you want to go out on a date?” Sometimes it works. You get slapped a lot, get arrested, and what have you. There’s this thing called the internet, Steve. And what shocks me is how few people—not just my age, but young pups—say, “Well, that’s for watching YouTube videos.” No.

Through the internet, you have so much information. So maybe I can’t find anything about Johnny Jones, but his kids are on there and what sports they play. Huh. Okay, so I used to do judo. I did three years of judo in high school. If somebody’s doing karate or whatever, I have an opening. I have something to talk about. Now, it’s great if what you have to talk about then connects to something else that they want. It’s a linking process of connecting various things together. It’s what I did… I told you I was a member of the General Assembly in Pennsylvania way back in the ’70s.

And I learned there that if I could get people talking about themselves, or their next-door neighbor, or some relative… What’s funny is people are much more likely to tell you about somebody else. So when I go into a company—this is just a side note—when I’m doing due diligence and I really want to know their financial condition, I’m not going to get it from the CFO. I’m going to get it from somebody over in property management. Why? Because the property management person knows not to tell me anything secret about property management, but they’ll talk about finances all the time. And it’s the same thing. If I’m in a family and I want to know about Daddy, I talk to the daughter.

If I want to know about a neighbor, I talk to a neighbor. I can go to the post office. Everything you ever need to position yourself to sell is out there waiting for you. But you’ve got to get out of your head what you think the market is about and start thinking about individuals within the market. And accept that when I’ve raised money, 70% to 80% of the people I call on don’t do a deal with me. But of that 70%, half of them lead me to somebody else. And I keep up with them. They become my support group. They become my unofficial advisors. Because I’m a decent guy, they want me to succeed. And once they know I’m not bugging them anymore, I say, “Hey, you told me I should go talk to such-and-such.

Here’s what I heard.” And then the network just expands. And occasionally, that person who said no has somebody new come into their life and says, “You need to go talk to Rick Chess.” And sometimes the next time I’m raising money, their situation is different. So the person who told me no originally has seen me work the market and close the deal. It’s amazing how attractive an opportunity is once you can’t put any more money into it. And so you let them know, “I know it wasn’t the right time for you to come into my deal, but we did buy this company. We’ve doubled their…” Whatever it is. You continue to work with them. If somebody is willing to give you time on the phone, on Zoom, at a coffee shop, or wherever, they’re your friend for life. They don’t know that yet, but you’re going to make them your friend for life. It’s the old six degrees of separation—the Kevin Bacon game.

Everybody’s related to somebody somewhere. And it’s what makes this fun for me. You were talking before about growing an exit. I love the process of putting together the network and feeding the network. There are people I’ve known for 50 years that I still talk with.

You’re very good at connecting people and making them look good with other people that you connect them to. It’s very gratifying. So this is a long game, right?

Absolutely.

It’s a long game because you’re being decent. You listen to people. You find something that helps them. You learn what they need, what is the itch that needs to be scratched, and then you connect people who can help them scratch that itch. And then they will reciprocate, and it becomes a self-perpetuating process.

Well, I mean, an example is the work that I do in North Carolina with a family that owns 44 hotels. A woman who was my CPA left the CPA firm and became the family officer for a large family here in Richmond. A friend of hers who does advisory work with family offices was giving up on a client. So she told my friend, who used to be a CPA. She introduced me to them and said, “Would you be willing to serve on the board of a private company?” I said, “Well, do they pay?” I used to be on the board of a public company, and after a certain age, you’re not attractive anymore.

After a certain age, they want you off the board because the institutions say, “We want a mix on the board. So I got introduced to these people, and I’ve had a great time. Members of the family have hired me for other work, and it just goes on and on. But I’ve learned that you’ve got to pay it forward. So I have students of mine from VCU who I’ve helped place in jobs. I keep up with them. I give them ideas. And they’re often shocked to find that I’m still in touch with them. I’m not asking them for anything. I’m just saying, “Look, I paid it forward to you. Now it’s your turn to pay it forward to somebody else.” And some of them are doing it. Some of them haven’t caught on yet.

But it is the circle of life, and it’s all tied together. And there are skills you have that I don’t have. There are skills I have that you don’t have. We both have folks that work with business brokers because they have a different drive. But it’s also self-selecting. There are a lot of people you’ve met that you don’t do business with. There are a lot of people I’ve met that I don’t do business with. If you’re going to get into raising money, doing governance, or doing exit planning, whatever it may be, one of the most important things is saying no. Or, “No, I don’t want to work with this person.” You can always be friendly with them. Yeah. But I try to fire a client every month. Somebody that just doesn’t fit for me ethically. Yeah. Or I don’t think there’s anything more I can do for them.

I pass off legal work to other attorneys in Virginia. I’m the chair of the Real Property Section of the state bar. There are 1,550 attorneys. I have plenty of attorneys that I can pass things on to, and they’re happy to get the business, and I’m happy. I’ve got somebody that I’ve referred that’s happy that I’ve referred them. My biggest challenge, my wife would say, my son would say, is that I’m a squirrel chaser. Something new and interesting comes along, and I want to get involved with it. And I’ve wasted so much time. So I’m working with this hotel group down in North Carolina. The last time I had worked with a hotel company was 30 years earlier. Two owners couldn’t agree on a direction.

I worked with them for six months. We made a decision. It was great work. I learned a lot about hotels. But I then went 30 years without applying the same skills. And that’s one thing that, with age, I’ve realized. I am better off saying: “I’ll help you with capital, I’ll help you with governance, and when you’re ready, I’ll help you exit.” That’s it.

Yeah.

If it’s not one of those three, I’ll talk about it.

Yeah.

I’ll listen to you. You don’t want to engage me.

Yeah. I mean, people want deep expertise. They don’t want generalists. They want someone who knows what they’re talking about and who can link them to other resources who also know what they’re talking about. And in today’s age, I think this is becoming more important again. Because of the internet, there was a disintermediation going on, but now there is a reintermediation, I believe. Because there’s so much noise out there, you don’t know what is true and what is fake. AI is creating a lot of fake stuff.

The only people you can really trust are the people who are in front of you, or someone recommends them whom you trust. It’s a transparency thing. So I think what you’re doing is very valuable. It’s going to become even more valuable. And knowledge is ubiquitous. You can ask ChatGPT, and it will give you an answer. But how do you get the trust? How do you get the emotion? How do you get the relationships? That’s all human stuff. And if you still have that, then you’ve got what is valuable.

Well, I have a friend of mine who wrote a book, and he wrote it as a fable. What I love about it is that I know the true story behind the fable. And what comes across in every single chapter is that, with that trust, people who were afraid took a step. And often that is the hardest thing. So I go to the gym six days a week, and the gym is hard. Getting in the car to drive there is the hard part. Once I’m there, I’m around friends, I work hard, I sweat, I get better. Getting in that car and driving down the drive…

So in your fable, in your book, and in most of where I’ve had success, I would love to say it was because I was brilliant. Eh, sometimes I will say I was brilliant. But let me give you an example. United Dominion Realty Trust, now based in Denver and originally based here in Richmond, has been around for 35 years. It was one of the original five REITs in the country—real estate investment trusts. I came in as acquisitions director. They hadn’t closed a deal in a year. I closed three in the first three months. I grew the firm tenfold in 10 years, and I had great people. Buddy Scott as an analyst. Catherine Surface as an attorney.

But what I did was look at it and say, “Does anybody know what we’re trying to buy?” Because they had no acquisition criteria. So I wrote a one-page acquisition criteria document and put it out to everybody who had ever submitted a deal. Oh, and we weren’t responding to the submissions. So a submission would come in, they would look at it and say, “Okay, that doesn’t work.” But they never told anybody no. So one of my rules was that anything that came in would get a response within 48 hours.

And it should be specific. “We don’t like this because of the city.” “We don’t like this because of the roof.” Something specific, because I knew they’d pay attention. And by responding within 48 hours, we went from struggling to get submissions to doubling our submissions within a year. Because people were like, “Oh, we know what they want. We know they will respond.” And then—and this probably sounds outrageous—we celebrated. We put out a newsletter every month. This is back when you mailed things, so we’re going way back into the dinosaur era. But anytime a broker brought us something that we bought, we would do a full-page spread on the broker. We were marketing him or her.

People loved us. And they would tell others about us. So owners would know that if they came to us, we’d make a fair offer and we’d move on. So I would love to say that’s because I was a great attorney. I would love to say that’s because I was insightful. It was just like, “Well, damn, this is obvious.” And reading some of your stuff, I’ve seen you point that out to people time and time again.

You give me too much credit. But yeah, I mean, if you’re there, they say that if you work hard for 25 years, you can become an overnight success. So yeah, it does get obvious when you’ve been studying it long and hard. Well, listen, Rick, that’s been wonderful. So what is your final thought for an entrepreneur, a young entrepreneur or founder who’s coming up? Maybe he’s in real estate. Maybe he’s trying to be successful. What’s the most important mindset for an entrepreneur to become successful?

Well, I mean, you’ve got to know something. I mean, you either need to really know construction, or you’ve got to really know how to lease a space. If you’re going into it like they do on HDTV, like, “Oh, we’re going to find this property and it’s going to be…” You’re going to fail. So get good at something. Accept the fact that you’re not going to be good at everything. Find people who fill in the spots where you aren’t good. In the old days, you might have had to hire them. In today’s world, there are fractional CFOs.

And then when you get down to picking your experts—your attorneys, your accountants, the people that cost you real money—ask them a simple question: When was the last time they did whatever it is that you’re trying to do? Not when was the last time they prepared a securities document. When was the last time they prepared a securities document that succeeded? And that’ll knock out two-thirds of them right there.

Love it. That’s fantastic. Well, if you’re listening to this and you want to be successful in business, or you have a business and maybe you’re getting close to retirement and want to figure out how to transition it, how to exit right, and how to structure it… Or maybe you have a family company and you’re trying to put together a board, and you need someone who really understands governance. Or if you’re trying to do a transaction, a merger, or an acquisition, and you need a trusted advisor who will connect you to the right people and help you make it happen, then call Rick Chess. Rick Chess is here in Richmond. He is on LinkedIn. And you have a website as well, Rick, right?

Yep, yep.

What’s your domain?

It’s chesslawfirm.com.

Chesslawfirm.com. So you can go there, and Rick is going to respond because he always does within 24 hours, or 48 hours max, and he’ll help you. So Rick, thank you very much for coming on the show and sharing your wisdom with us. And if you’re listening to this and you like this show, please follow us on YouTube and Apple Podcasts. Give us a review, and make sure you listen to every episode because we have very exciting entrepreneurs and subject matter experts sharing their knowledge. So thank you for coming, and thank you for listening.

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How to be a Trusted Advisor with Rick Chess

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336: How to be a Trusted Advisor with Rick Chess