December 18, 2025 – Juvo Chat Leads Ted DeBettencourt and Renters Warehouse Brenton Hayden

0:04 Intro 1
Broadcasting from AM and FM stations around the country. Welcome to the Small Business Administration award-winning School for Startups Radio, where we talk all things small business and entrepreneurship. Now, here is your host, the guy that believes anyone can be a successful entrepreneur, because entrepreneurship is not about creativity, risk, or passion: Jim Beach.

0:26 Jim Beach
Hello, everyone. Welcome to another exciting edition of School for Startups Radio. I hope you’re having a great day out there, riding the roller coaster life of being an entrepreneur. I have a great show for you, whether you’re having a good day or a bad day on the roller coaster. This show will help. It’s going to give you some motivation and some education, and that’s what we all need.

So, first up today, I have Ted Debettencourt. Cool name, Debettencourt. He is a legal marketing expert, and we’re going to talk about that. We’ve got lots of other conversations that go on along the way too. And it’s an amazing build story. He built a great business, and I’m excited to learn and share the story with you.

After that, from Renters Warehouse, you’ve probably heard their radio ads. CEO Brenton Hayden is with us as a greatest hits. So excited to share this file with you. Of course, for those of you who don’t know, we lost our server from the first 10 years of our show, and they went out of business. And so we’re slowly having to put the greatest hits back up on our new server so that you can hear them, because they’re not worth having if you can’t hear them. So there we are.

I haven’t defended our thesis in a while and let you know what I stand for and what I want to do with this show. I hope that this show, the 2,800 episodes that we have done, create a mosaic for you. I don’t expect you to listen to every single interview every single day. I expect you to pick and choose what is useful for you. To that end, we work incredibly hard on keeping our index up to date and offering the index so you can go and listen by topic, see the other real estate gurus that we’ve had on, or do you want to find out about other AI guests? It’s all easy to find. Of course, there’s the search, and we’ve just added an incredible new feature where we are transcribing all of the shows and then posting them with also the category so that you can scan the entire show very quickly, in about two seconds, seeing what questions we ask, what topics are, a deeper dive into just being introduced. So, great, great information. And then, of course, you can use that transcription and cut and paste it and put it wherever you want. We just want to support you and make that available to you. A lot of you would prefer to read. Those people are still out there. So, anyway, yet another new feature that we’re adding.

Oh, and I haven’t defended the thesis. I’m out of time. Yeah. People don’t use more than $5,000 because risk is bad. Copy, borrow, steal someone else’s idea because you don’t have to be creative to be an entrepreneur. You just have to be innovative. And passion is awesome for the church, the synagogue, the mosque, in the bedroom, but you don’t need to be passionate about your thing anyway. Those are the pieces that I want to defend with these mosaic tile interviews.
All right, we’re going to get started right now, or in a minute, a second.

3:47 Jim Beach
Welcome back to the show again. Thank you so much for being with us. Very excited to introduce my first guest today. Please welcome Ted Debettencourt to the show. He was a third-generation Martha’s Vineyard native. Imagine growing up on Martha’s Vineyard. That must have been the coolest thing ever. And I’m just really envious of that, because I’ve been there. It’s just gorgeous.

He went off and got a JD and an MBA and started in Boston legal marketing. Did that very productively for a while, but he was also getting frustrated with the chats and how the chatbots were being so horribly answered, and so he started another company to do chatbot management. It’s called Juvo Leads, and it is now what we’re going to talk about.
Ted, welcome to the show. How are you doing?

4:41 Ted DeBettencourt
I’m doing great, Jim. Thanks for having me on. Excited to be here.

4:45 Jim Beach
So, growing up on Martha’s Vineyard, I mean, that’s like the Jaws movie minus, all right.

4:52 Ted DeBettencourt
Yeah, I think they just did the 50th anniversary last year. Like, it’s been out for a while. But, yeah, that’s, uh, Amity Island is named in the movie Jaws, but that’s where it grew.

5:00 Jim Beach
Were you just out crabbing and sailing all the time? Was it just like having—

5:07 Ted DeBettencourt
Not a lot of crabbing. I actually get sick in boats, which is kind of funny. If you grew up there, it’s a lot different than vacationing there. So if you grew up there, it’s just like any other place, except you’ve got to pick a boat to go anywhere. But if you have a summer house there, you’re probably doing a lot more, to be honest.

5:26 Jim Beach
Okay. Did you have school on the island, or did you have to leave the island to go to school?

5:32 Ted DeBettencourt
No, we did school on the island. I think my graduating class was like 120. We had sports and everything. The only problem with sports is game day. You have to take the boat and go over. So it’s like an all-day affair.It makes it a lot more involvement of islands, of course. 

5:51 Jim Beach
Yeah How interesting. Law school. Bad, bad. Why? Why? Boo-hoo. And then we like that. Tell us about the legal marketing company. I have run across several people doing that. Seems like a huge niche.

6:10 Ted DeBettencourt
Yeah, it’s a, well, you know, lawyers need leads online. They can’t do traditional sales like other businesses, so they get most of their leads online, lead generation. So after law school, I realized I didn’t want to go be a lawyer, so I got my MBA as well. And I was like, well, how do I leverage the two to kind of start a life, build a business?

I was like, well, I like the business side of law, but I didn’t like the practice of law. So I was like, well, a lot of businesses, law firms particularly, try to get more leads online. And so I started that business. I was doing it for a company in Boston for about three months. I said, well, shoot, everything, you know. The plan was to do that for a few years and then spin out.

I got fired there after about three months. I got accused of taking the client list and emailing them, and I wasn’t, but I did take the client list because I was trying to study what the law firms are doing so I could understand more. But I remember sitting at my desk, got to three months, and had police escort me out of the building. And they accused me of stealing the client list. I wasn’t, and I sorted it, but it wasn’t for the purposes they wanted. But, you know, scared the jeepers out of me.

But then I said, all right, well, I will do everything that they were doing, but do it better. But I didn’t touch any of those clients because I know the legal ramifications. So I started a legal marketing business. Grew up to about probably 30, 40 clients, mostly in the market, some in the Boston market, and then it kind of expanded from there.

So I had that business going for a while, but that business is hard. Legal marketing as a whole is hard because every client, they have their own particular needs. So it’s not like you do one thing, you just hit repeat and, you know, you scale it. So every client has their particular needs. They have different things you have to do, and you really need to have someone that really cares about the law firm spend a lot of time maximizing those efforts there. So it’s not really scalable unless you can scale your time better. But I found that a little bit harder.

So then I was doing that, and then I was using some vendors for my clients. And the vendors I was using, like, the idea was great, using chat on the website to maximize leads, and I knew it got more leads. But the companies I was using kept screwing up the chats. And like, the law firms, a few times, the chat company would turn down their car accident case, which are, you know, could be millions of dollar cases. And I saw the lead, and the law firm called me, absolutely, “Ted, you know, you just lost me a million-dollar case. What’s going on here?” And I was like, holy crap, that’s not good.

So I fired that company and then started answering chats myself. And, you know, they told a car accident case they don’t handle those types of cases. And it was like, you know, it wasn’t even, it wasn’t even like a sticky situation. It was pretty straightforward, and they should have handled it differently, and they didn’t. They cost the firm the lead. I got blamed for it, rightfully so, I guess.

So then I said, all right, well, I can’t have this happen ever again. So I fired all my chat companies and started doing it myself because I know I could do it better. And then, you know, eight years later, you know, we have a little under, a little over 1,000 firms we work for.

9:26 Jim Beach
We call that the Caroline clause. One day, my business—and we left Caroline at the office to answer the phones. She had worked there for three or four months and really didn’t know anything, and didn’t know the business that well. And Visa called and started asking her questions about when we were accepting payments for her services that we offered months later, and she cost me $700,000 in a three telephone conversation. Cool.

And the line, Ted, that I used—I’m so embarrassed. So this was 25 years ago, so I’m a better person now. But I told poor Caroline, “You’re taking the food out of my children’s mouth.” Yeah. She just disappeared. Ted. Who would think.

10:21 Ted DeBettencourt
Yeah, well – At the end of the day, it’s, you know, is it her fault or is it your fault for not training her back?

10:27 Jim Beach
Hey, none of that stuff here. We don’t do any stuff like the reality checks or honesty or self-reflection. None of that here. You’re 100% right. It’s my fault for not telling her not to talk to Visa. You know, your answer should have been, “I have no idea what you’re talking to or about. You need to talk to someone else.” You know, this is 100% my fault. But you really didn’t have to point that out. My God.

10:55 Ted DeBettencourt
Well, hey, I’ll take credit for when that law firm—when that company screwed up the chat. Yeah, okay, I was on the hook for it. It was my fault, so I acknowledge that. So, you know.

11:07 Jim Beach
Just that simple example, does that really summarize the case? I hate you, because it always—it’s someone who doesn’t understand, you know. It just seems like really bad AI that they, you know, you have to type the same thing eight times, and they go in circles, and they just suck. You know, that’s the accepted way.

11:31 Ted DeBettencourt
Yeah, there is some bad AI out there. And, you know, moving to more AI will get a little better, I presume. We’re seeing it get better. But what we do is we spend a lot more time with the clients, onboarding them, understanding their needs.

And I, honestly, when I first started trying to get into this, the first question was: I hate chat. I find it annoying as heck. Like, I just want to use a website; get out of my face. But the reality is, when we do—we’ve probably done over 200 A/B tests since we’ve started the business—when you put chat on a website, you might not like it, but you’re going to like what that gets you.

And if what matters is leads, we can statistically prove—and we give everyone a free 30-day trial—that when you put chat on a website, chat that works, Juvo Leads chat, will get them at least 50% more leads. So we give them that free 30-day trial. We make that guarantee up front.
And then after the 30-day free trial, we sit down with them on Zoom, and I say, “How many leads did you get last month?” Or, “How many forms did you get? How many leads did you get this month? Is it 50% more?” Great. Let’s continue. If not, they walk away and they spent $0. So even if you don’t like chat, most business owners care about the leads on the website, and that’s why they use us, because they get at least 50% more.

12:42 Jim Beach
Oh, that’s pretty impressive. So how do you go about answering 1,000 different companies’ chat? Do you have one guy who does six companies and another guy who does nine companies, based on volume?

12:57 Ted DeBettencourt
We break it in the team. So there’s different verticals we serve. So, you know, some of our biggest verticals are criminal defense, personal injury. If a person is in a car accident in Alabama versus, you know, California, the questions we ask aren’t going to be too different. Like, there are different statute limitations, different insurance questions you ask, but the needs of the customer are typically the same.

So we break down teams in the practice areas and business lines. So the team gets trained on those business lines, and then we just have to teach them the variation per client. A lot of our clients have a lot of variation, but some, you know, we have probably 50% of our clients, the chat scripts are fairly similar across the board.

13:35 Jim Beach
Okay! So how many accounts can one person handle?

13:42 Ted DeBettencourt
Oh, it really depends. Maybe up to 20, 25. Okay. It just depends on the similarity of the transcripts, 

13:51Jim Beach
Right! And where do you put these people?

13:56 Ted DeBettencourt
We hire a team. They’re all remote. We have team members in the U.S. and team members in the Philippines. Every chat that comes in is graded on a 12-point scale. So our agents are hired, fired, promoted, demoted, and bonused based on how fast, how empathetic, and how well they follow the rules for the particular transcript.

There’s no scoring difference between our Filipino team and our U.S. team. It really just depends on what time of the day the chat comes in and what team member is up for that chat.

14:21 Jim Beach
Okay, so what’s the technology that routes it to the right person in the Philippines?

14:28 Ted DeBettencourt
Great question. So a lot of people think we probably have a million and a half lines of code. Most of that chat code is on the back end that we use to determine who answers. The quality control we have is probably where most of our code is, making sure that, you know, chats are answered fast and well and empathetically.

So a lot of the code is that. The other part of the code is everything we wrote is in-house. It’s our code determining what agent is up for that chat, and determining the right agent gets it, and, you know, they have the right information in front of them to answer that chat properly. So that’s all our code is.

But yeah, a lot of people think in chat, like, “Oh, the little chatbot on the website.” Like, yeah, it’s some of that. But the reality is, you know, four-fifths of our code is on the back end, controlling exactly that: the quality control, and then making sure it goes to the right people.

15:17 Jim Beach
All right. Very impressive. Ted, I’m really impressed. You’ve done a great job. How did you pay for all of that code and growth and stuff? Did you bootstrap with the legal marketing money, or how did you pay for all this creation?

15:36 Ted DeBettencourt
Well, I have a co-founder. So I’m the sales and operations guy. He’s the finance and tech guy. So we—I was chat agent number one. So I think we both put $1,000 into it back in 2015, 2016. It was more just, so we could say we did. We put $1,000 in, and I was answering chats probably the first year because we didn’t really know what we were doing.
So the first year, I was just answering chats and made it work, and got a few clients, built more code, got some more clients, built some more code. But we both had jobs: running my legal marketing agency, my partner had a job doing other tech stuff, and we kind of did it as a side project and just let the sales from the business finance our growth.
It kind of started there, like 2015, 2016, like 16. Like, if I think about it now, it’s like, well, I don’t know how the heck this was working, but we just put a lot more manual into it. And then as we got bigger, we could say, “Okay, well, now we can take this off a person’s plate, and you use code to build it.”

So just over time, we’ve gotten bigger and bigger and had more automation and code in place to help there. But everything’s bootstrapped. And, you know, when we get a big client, well, now we can put more money into focusing on this. So it was all bootstrapped, no outside finance or anything like that.

16:51 Jim Beach
I love it. Well done. And how do you go about marketing now and get new customers?

17:01 Ted DeBettencourt

A few ways. The main way we do is we go to a lot of the industry trade shows, boots on the ground, meet in person. We sponsor a lot of events. Word of mouth. At this point, there’s really only like two or three big players in our space now, so we’ve got the brand recognition at this point where a lot of leads come to us. So, you know, we do Facebook, don’t touch Google much. It hasn’t been effective for us. But word of mouth and reputation and boots on the ground at industry conferences.

17:33 Jim Beach
All right. And how do you manage having, I don’t know, whatever—how many employees do you have now? 20, 25?

17:43 Ted DeBettencourt
No, we’re up to about 90 or so.

17:45 Jim Beach
90 employees. Wow. Okay, how do you manage 90 people overseas that you probably have never met? Oh, I mean nothing, but manage all those people?

17:59 Ted DeBettencourt
No, we have multiple people —that only manage multiple people. So we have three layers of management. You know, everyone on the team is hired by us. So, like, we’re not outsourcing anything. It’s like, at one point, we were up to about 50. I made all the hires myself, and now we have HR and stuff. So we have multiple management layers and different quality control.
You know, our biggest non-chat team is our quality control. Literally manually reviews every chat that comes in. And we use AI a little bit to help, but it’s really still just manual review to look at the chat to make sure everything is going right. So our chats are graded. And then we have different managers that oversee different teams. Each team has seven chat agents, and then we have managers of those, and then a management layer of that, and then one direct VP of operations that handles the chat management side, and they report to me.

18:55 Jim Beach
Wow. Very impressive. Ted. And how old is that company now?

18:59 Ted DeBettencourt
We’re coming up on the 10-year anniversary. So we’re about to be 10 years old.

19:01 Jim Beach
Impressive. Congratulations.

19:03 Ted DeBettencourt
Thank you. Thank you. That’s been fun. Been fun journey

19:07 Jim Beach
I heard that you wanted to play our little game, the Quick 10.

19:11 Ted DeBettencourt
I do want to play the game, the Quick 10. I’ll be as quick as I can.

19:14 Jim Beach
Okay. Are you currently sober? I’m required by state law to ask. Do you want the standard wager?

19:19 Jim Beach
What’s the standard wager? Well, I don’t know what this is now. So what’s the standard wager everyone else made?

19:28 Ted DeBettencourt
Well, you sold it well.

19:31 Jim Beach
Number one, your favorite creativity hack.

19:35 Ted DeBettencourt
Get on the treadmill in the morning and don’t put on any music. Let your mind wander and come up with ideas.

19:40 Jim Beach
Number two, favorite bootstrapping trick.

19:46 Ted DeBettencourt
I throw a million and a half ideas into ChatGPT so I can save my partner the time from having to hear all my dumb ideas.

19:53 Jim Beach
Number three, name your top passions.

19:58 Ted DeBettencourt
Church. Kids. Exercise. 

20:02 Jim Beach
Number four, the first three steps in starting a business are—

20:09 Ted DeBettencourt
Plan to have no life for two to three years until you get it figured out. Try harder than your competition.Care more about your clients than anybody else. 

20:20 Jim Beach
Number five, the best way to get your first real customer is—

20:24 Ted DeBettencourt
Meet people in person and share your passion with them.

20:27 Jim Beach
Number six, your dreamiest technology is—

20:33 Ted DeBettencourt
Skip.

20:34 Jim Beach
Number seven, best entrepreneurial advice.

20:40 Ted DeBettencourt
Find a niche problem that you can solve in a unique way, and then figure out how to scale it.

20:45 Jim Beach
Number eight, worst entrepreneurial mistake.

20:51 Ted DeBettencourt
Giving up.

20:54 Jim Beach
Number nine, favorite entrepreneur and why.

20:59 Ted DeBettencourt
I can hire a cheap company overseas to build it for me.

21:02 Jim Beach
Number 10, favorite superhero.

21:04 Ted DeBettencourt
Superman.

21:08 Jim Beach
All right. Excellent answers. While we calculate your score and find out the winner of the wager, how do we get in touch with you, Ted—hire you, find out more about you and the team, all that?

21:19 Ted DeBettencourt
Sure. If you’re interested in learning more about how chat can get you 50% more leads for your website, and like the idea of free 30-day trials, check us out. Go to our website: Juvo—J-U-V-O—Leads—L-E-A-D-S—dot com. Start a chat on our website, and we’ll be happy to chat with you and set up a consultation.

21:37 Jim Beach
Fantastic. Well, I’m very impressed with what you’ve done. It’s an incredible story, Ted, so thank you for sharing. Oh, oh, I just got your score. Ted—oh, sorry, we outsourced it not to the Philippines, but to India. And maybe that was the problem. You got a 94, and you have to have a 95 to win the wager. I’m really sorry.

22:04 Ted DeBettencourt
What was the wager? Now that you opened, I asked what I lost, Ted.

22:10 Jim Beach
We always play for a Tesla. Oh, nothing. So, well.

22:12 Jim Beach
So they’re getting really cheap now. You people are almost throwing them away, so it’ll be cheap for you. Get us one maybe someday. Yeah, appreciate you sending us that right over. Yeah. All right, Ted, great story. Thank you for being with us, and we’d love to have you back.

22:28 Ted DeBettencourt
Yeah, thanks, Jim. Pleasure being on the show, and look forward to keep listening to you guys.

22:32 Jim Beach
Thanks a lot, and we will be right back.

22:49 Intro 2
Well, that’s a, that’s a, that’s a wonderful question. Oh my gosh, I love the opportunity to do this. Thank you, Jim. Wow, that’s, that’s, that’s a great one. You know, that is a phenomenal question. That’s a great question. And I don’t have a great answer. Great question. Oh, that is such a loaded question, and that’s actually a really good question.  School for Startups Radio. 

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23:44 Jim Beach
Get going. I am very excited and honored to introduce you to my first guest today. We recorded an interview, oh gosh, months ago, and I blew it. Somehow, erased it. The tape had peanut butter on it. The dog ate my homework, one of those excuses. And I’m just honored that he would graciously come back on the show and not be a spoil sport about it. Just a really, really classy guy.

I’d like to introduce you to Brenton Hayden. He is the founder of Renters Warehouse. You have heard all about it. You’ve seen their ads. It’s one of the fastest-growing real estate companies ever. He is the 2014 Ernst & Young Entrepreneur of the Year winner. He’s won the Maverick of the Year Award. He has Best Management Team of the Year awards by the American Business Association. He won the International Real Estate Company of the Year, the Gold Stevie Award, the Inc. Higher Power Award, the United States Army Honored Employer Award. Oh, my goodness.

But after Renters Warehouse, he’s actually stepped up to chairman and relinquished his CEO role. He’s now running a bunch of other companies in some really interesting industries. We will talk about that. Welcome back to the show. Thank you so much for not being mad at me.

25:04 Brenton Hayden
Not a problem. And this is—that was one of the nicer very, it argues, very proud of—every one of those accolades. I know some of every one of those accolades. I know some of those are personal, but many of those, most stories of low risk, because I’ve recruited a lot of friends and family to work for me over the years, and to see them get awards for doing great things at the business is also great. So thanks for mentioning that. Well, thanks for having me on your show. Happy to be here.

25:38 Jim Beach
You’ve got an amazing background, especially for someone that’s still only 22 years old. You’re a whole—you’re all of 30 now, really?

25:50 Brenton Hayden
All of 30 this year. It was a big, big shindig. I grew up in Minnesota with my closest friends. You don’t turn 30 twice, so I thought I’d do it right the first time.

26:01 Jim Beach
Well, excellent. Well, congratulations on that, and congratulations on all the incredible success. You’ve started out in the real estate industry, but you’ve run limousine companies and so many different things. How did you get started? What was the first entrepreneurial thing that you did?

26:18 Brenton Hayden
The first entrepreneurial thing I did was definitely the cliché lemonade stand. My dad had a house in Minnesota, and I was on a busy street, and I only lived with him on the weekend. And bet your buns every weekend, I had that card table out with a new sign and better—a better Country Time pink lemonade than the last. So that’s where the entrepreneurial spirit started for me. It evolved into mowing lawns later, trading baseball cards, hogs, and other things like that later. And I’m just a very self-sufficient guy, right? I’ve always wanted to make my own way. And it started then.

26:59 Jim Beach
And every time that you had a lemonade stand, of course, you went to the city government and got a license, I’m sure. Oh yeah. Does it just make your blood boil when you read about a 12-year-old girl has a lemonade stand closed down because she didn’t get a license? Does that make you just want to go kill someone in government like me?

27:21 Brenton Hayden
It’s very disappointing. It’s totally inappropriate, and it’s just, it’s just not right. It does, it does make me upset. You know, I could go on about red tape in business, or the overreaching power of government in business, or just the power of media and news agencies out there and how, you know, they have unregulated power with respect to perhaps defaming or highlighting the business. So there’s just, there’s a lot of things in business that aren’t fair. That’s one of them.

27:58 Jim Beach
Yeah, it makes me super mad. And in a larger sense, you’re very active in politics now, aren’t you?

28:05 Brenton Hayden
I used to be very active in politics. I’ve decided, after the amount of brain damage that gave me being involved behind the scenes in politics, that that’s no longer something I want to put my time into.

28:15 Jim Beach
Are you going to run for office, then?

28:17 Brenton Hayden
No. Nope, never. In fact, that made it real easy for me to just make that a never-never situation. You know, the public light is far too negative, and that’s something that is a problem that plagues our society, the media. And frankly, I want nothing to do with it, right?

28:41 Jim Beach
Well, I would love to run for office, but I have, like, an entire graveyard of skeletons in my closet. So if I were to ever run, there would be a new article every day about all of the horrible things that I’ve done. And so—

28:55 Brenton Hayden
Here’s the interesting thing: you really don’t even need to have real skeletons in your closet. They’ll just make them up about you anyway. And then the news will publish it, or, yep, or some other way. And that’s the plague. That’s the problem with politics, is people can say and do whatever they want, and there’s really no accountability for that. And frankly, politics—that quite a bit.

29:16 Jim Beach
That is very true. When Rubio got lambasted for his speeding tickets, and it came down that he had two tickets in 19 years, and that was the headline. I was like, that’s got to be the dumbest thing ever. If that’s the worst they can get on him, we should elect him Pope for goodness sakes

29:37 Brenton Hayden
Mitt Romney, for example, the guy—the most clean, crystal-clean guy I’ve ever seen. And then they, you know, they find a sad face to talk about the one business that closed, as it was, you know, not going well as an antiquated business. Whatever the stakes are, politics—and frankly, being a figure in business—will subject you to that sort of public scrutiny that is just something that is really unappealing.

30:00 Jim Beach
You used to work for Kellogg’s. You were the Rookie of the Year, a territory manager, beat quota 10 quarters in a row. Why did you leave? What was the bug in your shorts that made you want to leave something safe and secure like that? Probably would be CEO of Kellogg’s if you had stuck around.

30:21 Brenton Hayden
You know, I really had a great time working for that company. It was one of the best companies I’ve ever worked for. I’ve only worked for a few, but that’s one of the best companies I’ve ever worked for, and would recommend it to my family or friends to work there again. Frankly, they didn’t let me go. I screwed up. I made a mistake, and I was fired. Later, it has to come back, but nonetheless, I made a mistake and I was fired. I was a 21-year-old hotshot, kind of kicking butt over there, doing big things, and I inappropriately tried to credit an invoice, and I didn’t do it correctly, and just didn’t handle it with good customer service, and I pissed the wrong guy off. And that wrong guy had a lot of clout and didn’t like the way I handled the situation. I was at fault, and I owned that, and that guy used his clout to make sure that I lost my job over the situation. Now, I don’t think Kellogg’s would have fired me or wanted to, but their hand was forced. And to me, that taught me a lot about business. It taught me a lot about respect, a lot about customer service, a lot about clout and political juice, power. It taught me a lot about many things, but I learned a lot while I was at Kellogg’s. I valued my time a lot. I think the circumstances in which I was let go were not appropriate. I shouldn’t have been fired. But nonetheless, I made a mistake, and it was their prerogative to have me gone, and then so be it. But I used that as fuel to figure out what I was going to do next. I mean, let’s have something good taken away by a simple mistake. You can do one or two things: you can fall in a pit of despair, or you can climb out of it and do something different. Frankly, somehow, some way deep down in me, I used it as fuel—motivation and power—to get my life back on track and do something bigger and better.

32:19 Jim Beach
I was let go by Coca-Cola after saving them a billion dollars. I now, 25 years later, say it was the best thing that ever happened to me. Was being asked to leave Kellogg one of the top three or four things that’s happened to you professionally?

32:35 Brenton Hayden
Absolutely it was. I would have risen the ranks. I would have done well, but I would have peaked, and I would have peaked at something well below where I’m at today.
And frankly, I have been happier, more financially secure, and I’ve learned and done so much more working for myself and doing the things that I’ve done that I would not have had the opportunity to do if I was still at Kellogg’s.And so absolutely, I would put it up there as a top five. You know, one of the better things that—it’s one of those best bittersweet things that ever happened to you, right? It wasn’t good when it happened, but it turned out to be for the best.

33:16 Jim Beach
And how did you land on your feet? What was the first entrepreneurial thing that you did in your recovery phase?

33:21 Brenton Hayden
Well, it was a phrase somebody gave me, a phrase that really was something I held on to deep into my soul, my morale. And it was: “Your story is being written right now, with or without you, and the ending is entirely up to you.” But like I said, that story is being written right now, with or without your help. It’s up to you to take control of your own destiny, your own story, and rewrite the end. And I used that as kind of my first stepping stone to say I’m going to rewrite the ending. And I had been fired. Somebody told me to follow the money. What else could a 21-year-old do with no college degree? And this was 2005, and they told me, “You should get into real estate.” If we know about 2005, 2006, those were booming years—probably inflated, but booming years.

Well, I did. I went to work for the top real estate guy in all of Minnesota. He did about $70 million a year in sales. Funny side note: I ended up buying his company two years ago. But I worked for him as a buyer’s agent, and I fielded phone calls from a lead source that he had, and many of those people needed help to rent their home, manage their home, before they could buy another or sell the one they have. And so I kept approaching my broker that we need to get into the professional landlord game, or the property management business. He said, “Just refer it to somebody. Just refer it to somebody. This is a great time for real estate. We need to be buying and selling.” Well, I was relentless about it. Every week in their meetings, I’d tell them about how many people need that help. I kept telling him that so much, and quantifying, and trying to change his mind. And I think he became frustrated with me.

And around the time he decided he wanted to start his own company and leave one of the big box brokerages, he decided that I would have been too competitive, and potentially somebody that was going to be a competitor to him, and that was too focused on this property management thing than buying and selling homes. And he actually fired me. He called me into a meeting one day. I was thriving. I didn’t make any mistakes. And he said, “Brent, I see you as competition. I don’t see you sticking around too long. And frankly, you keep talking about this property management, property management, and I’m starting my own company, and I just don’t think it makes sense for you to come with.”

35:48 Jim Beach
Wow! Was that a worse kick in the teeth than the Kellogg’s experience?

35:54 Brenton Hayden
It was, because at that point, I was already down and out. And I’d pretty—I had taken a pretty entry-level job, making about 30 grand a year, plus commissions. And it came out of nowhere because this time I kept my nose clean and did right and didn’t screw up this time, you know, and I tried to be a good team member, and I thought I was. And frankly, we had a good relationship past that. But, yeah, that was a punch in the gut. But then again, that was one of the better top five things that ever happened to me too, because I had previously heard that phrase: “Your story is being written without you right now, without your help. It’s up to you to take control of the end.”

Well, that phrase went right through my head during the 15 minutes that I had to evacuate the office, take my stuff, and get out. And I left that office, I grabbed my stuff, and I realized that I won’t really have anywhere to go. Oddly enough, I’d only been with him six months. Prior to that, I had been fired from Kellogg’s, and it took me two months to get my license, and I didn’t have any income, and I actually had been evicted from my apartment. Well, here I am fired from two jobs: one really great within a year; the other one was something I was finally starting to be good at, make some money, and get my life back on track. I was fired from that, and it was just that timing, because now I was going to be evicted from my apartment. So a week later, I was actually evicted from my apartment. So: fired twice, and evicted, just completely down and out—21-year-old. And I had to start calling around: buddies, friends, whoever I could live with. I was too full of pride to go back to mom and dad. So in fact, I couldn’t find anyone to live with, and so I lived in my car for 11 days at a park that had a shower. It was a Lions Club park in Minnesota. And during a fit of perhaps depression slash inspiration, I wrote on a yellow notebook—something I still rather carry around with me—seven pages of stream of consciousness, back to front, of what I was good at, what I wasn’t, what I liked and what I didn’t, where I was going, how to get there, the money I needed, what my retirement looked like, and just, just, just all of that. And at the end of it, I had crafted a plan that had me retiring by the age of 27. It had me starting my own business that eventually would allow me to take care of my dad, my family, and get the dream cars I wanted, and played to my strengths and eliminated my weaknesses.

And it was with that that I set out on a mission to create the best damn professional landlord company in the country. And you fast forward eight and a half years—sorry, nine years—I now own one of the largest property management companies in the entire country, with about $2 billion worth of real estate under management. So it was those lumps and bumps and punches in the teeth that I think gave me the gumption, clarity, and the fact that I just needed—I had to succeed. I’m living in my car. I’m showering at the park. I’ve been fired. Now my resume is hosed. What do I do now? And so I had to succeed. And frankly, when you have a need to succeed like that, and you’re really focused and ethical, that’s all I did is I applied it in business, and I was able to dig my way out of that hole and eventually create wealth for myself.

39:26 Jim Beach
We had a guest on, I think two days ago, who said that if you don’t write goals down, they’re not goals. It’s just BS. You wrote those seven pages front to back. Would all of that have happened had you not written it down? Was the writing of it—let’s say you just played it over in your head, you sat in your car at the Lions Club park and you went through the entire story verbally—was the writing essential to the success and the actual fact that it happened, you believe?

39:57 Brenton Hayden
Absolutely, absolutely, absolutely. It was not just so much the words. It’s the process, right? It’s being in the mindset to say: what am I good at? What am I not? What are my goals, and are they realistic?

And, you know, at Kellogg, they taught me this analogy called SMART: Specific, Measurable, Attainable, Realistic, and Timely goals. All of your goals need to be marked using that acronym. And so as I was writing this letter that was going through my head, I was making sure that I was actually putting out realistic goals. And frankly, that got me into things like calculating money I would need. What are taxes, and what would it be like after taxes? And how many years, if I earned this much money, would it drop to the bottom line? And how many years? How much percentage would I have to save if I did that to make this work? And so then that was the big part. I think that’s 50% of the way. The other 50% is checking in on those goals and breaking those goals down into smaller, more actionable, more realistic goals that you can complete in a shorter window.

For me, generally later, as I started to realize traction towards my goals, I started to break my goals down into 90-day periods, and, you know, make micro decisions or micro goals that led to the bigger goal, and checking in on those, looking at those, determining if you’re on or off track to meet those. Always putting that Specific, Measurable, Attainable, Realistic, Timely SMART acronym lens on it helps me actually execute and achieve them.So it’s one thing to write them down and to feel good about them and to be thoughtful about what you’ve written down. It’s another thing to actually execute and, you know, take seven and a half years to get there. So I think it’s all about checking in and actually seeing—who is—also the other half of the equation.

41:47 Jim Beach
Why did you leave Renters Warehouse? You didn’t leave, but you let your buddy become the CEO and you moved upstairs to the chairman role. Why?

41:59 Brenton Hayden
I was 28.I had just turned 28, and I was on vacation with my wife in St. John’s, Virgin Islands, and I was sneaking away to do new work, and she was always annoyed by that. We didn’t go on enough vacations, and when we did, I was always working. And so she was annoyed by that, and she called me out on my BS and said, “Listen, you wrote—you know, you talk a lot of game about this young retirement and this yellow notebook. I got it all together, and yet here you are sneaking out for emails. 28, you know, not really living up to your goals,” and just called me out on it. And it was more of like she wanted to get mad at me about wasting time on vacations. It wasn’t like a conversation where she wanted to motivate me to retire. She just wanted me to know, you know, this isn’t going to work.

Frankly, I took it the other way. I said, “You know what? You’re so freaking right. You’re absolutely right.” I started to self-reflect and say, “What am I scared about? Why did I get this far breaking my goal down into 90-day increments? I do that for this many years, and then I forget about the ending. What the heck is up with that?” And I realized I was only scared. I didn’t know what to do. I didn’t actually—I think I realized I really didn’t actually think I could hit my goal, but I was relentless in my pursuit of it. And my relentless pursuit, I just kind of lost track of whether I would actually hit it or not.
Well, her jab at me made me very aware that, okay, I’ve reached my financial goal. I’ve reached my age goal. Is my business able to support Brenton being gone? And frankly, that was the only other thing I couldn’t master. I said, “You know what? I think it needs one or two people yet before my company is ready.” In fact, I set out to recruit a president and the chief marketing officer, because at the time, my role kind of evolved into more marketing and franchise operations. I brought in a president of my franchise company. I recruited the chief marketing officer for all my companies. And I spent six months working with them, training them in. And at that point, I realized I have the financial means, I’ve always aged for my goal, and I now have the team to capably run my business long after I’m gone. What’s holding me back? Nothing. So I decided. I just did it. I quit. I just said, “Kevin, you’re CEO and president. Now it’s your show. I only want to meet with you on Tuesdays for 90 minutes. That’s it.”

Now, my president had been with me five years, just a different president of the franchise operation. So he had a lot of experience. I had a lot of faith in him, and he was my right-hand man. So he’s been running the business now for almost two years, doing very well. The business is up. Still growing. Still profiting. In fact, profiting better than ever. I’m still drawing a salary, but I work as a chairman of the board. But by the way, the board’s only me. So frankly, I basically just take meetings twice a week with my two different CEOs, and that’s how I run my business. I have a tool that I use that was taught to me called Traction. There’s a book out there written by Gino Wickman, who wrote this book called Traction. It’s that book that I use to operate my business remotely, and not having to be in the business, but rather on the business. So I use that every day to keep me a finger on the pulse of what’s going good, what’s not going good. And ultimately it led to me being retired. I eventually moved from Minnesota, where my business was, and I now live in Miami, Florida, and started investing in other things, as you alluded to earlier. There is some consideration right now, here today, where I’m considering selling stock in my company to a private equity group and becoming a minority shareholder, and that may change some things. I may have to go back to work for a little bit as an executive with the company to help the new partner kind of take over, or I may just decline that deal, and seeing the new writing on the wall and the potential my company has, having been away from it for two years, working on it rather than in it, and then actually decide to go back to it, because there are some huge opportunities to grow.

But, you know, my whole life is up in—well, right now. And the whole idea behind me retiring when I was 27, 28 was not so I could go play golf and video games and get fat and, you know, wake up late on Tuesdays. It was so that I have the ability to wake up each day and decide what I wanted to do that day, knowing that my business or anything else was not really dependent on me to survive And so there are some days where I work a full week, and there are some days where I don’t work at all. There are some months I don’t work at all. I don’t go to meetings. I don’t work at all. And then again, like the last month, I’ve actually been working quite a bit, because I have some big initiatives and projects that are important to me and actually fun things I want to work on, instead of things I have to work on. And that’s really where I draw the line of my form of retirement. Some of the things I do in my formal retirement are work, but only on the stuff I want to, that I like to do, because that’s, that’s my choice. And if I’m burnt out or tired and I want to sleep in, I do that too.

47:31 Jim Beach
I love it. That’s an amazing story. Congratulations on being able to accomplish that. I took my wife in, I don’t know, ’99, ’98, something like that, to the same resort where Bill and Melinda Gates got married. And we had a big suite, and we had one of the kids with us, and we’re having a wonderful time. And when we checked out, they gave me my bill. It was like $9,000 or something. And then they said, “And Mr. Beach, we have another bill for you. It’s your telephone bill.” And it was like $14,000. This was before cell phones. Really, my telephone bill was more than my suite and food and accessories and spa bill because I’d spent so much time on the telephone. And of course, that marriage ended up in a—get this, this is a big shocker—divorce, right? Because it fell apart. And so I’m glad you did better on that front than I did. Really congratulate you on that. What are you doing now, then? What are these things that are making you get out of bed in the morning now? What do you have passion for right now?

48:36 Brenton Hayden
My form of retirement involves me becoming an angel investor in young companies, young people all across the nation, in things that I know, like real estate, real estate services, and technology-enabled services. And frankly, I like to help people that kind of come from nothing but have a really good plan and the ability to execute, and they’ve founded the business. Those are people I really like to work with.

Now I’m no longer looking for those investments, as I’ve exhausted a lot of my resources very quickly on some really great opportunities, which I’ll tell you about. One of them is a laboratory in Minnesota called LeafLine Labs. It is a grower, researcher, and retailer for the state of Minnesota for their medical cannabis program. So we are in the edibles and oil-based cannabis programs exclusively for the state of Minnesota. Minnesota is a very—cannabis law. You must—can only be dying in order to be able to get access to it. But it fully legalizes—or, sorry, this law that I just referred to comes into play July 1. In fact, it just starts. And so I partnered with a really profound group of investors to be the supplier, researcher, and retailer for the state of Minnesota cannabis business.

My friend—one of my friends and mentors—also is in the real estate business, but happens to start restaurants and nightclubs. Well, I’m not really into the nightclub business, and I don’t know anything about restaurants, but everything he touches in those spaces seems to turn to gold. So for many years, I’ve been begging to invest with him. And finally, I got an opportunity, and I’m glad I waited for this one, because it’s kind of a Scotch speakeasy bar, you know, Monday through Thursday, with a speakeasy kind of hidden. And then the rest of the time it’s a big nightclub, Friday, Saturday in Minnesota. And that actually opened July 2. Yes, I’m not too thrilled about the business as much as I’m thrilled about working with the team he has assembled, because they are home run hitters in that line of work. And I’m a Scotch guy, so I intend to partake in the unlimited bar tab at that speakeasy. So that’s exciting. I’m also involved in some technology companies. One’s called 15Five, which is a software-as-a-service for human resources departments, facilitating collecting and coordinating feedback from your employees and different team members. It’s actually a tool that I use at Renters Warehouse and all my franchisees, where I first learned about it. Then they eventually invested. And then I’m also a big sports fan, and I’m actually a die-hard NFL fan. It was natural for me to do something in sports, and I partnered with a sports betting application called Onside Sports, and it’s one of the top-selling fantasy sports betting applications in the App Store today.

To name a few of those—those are some of the newest ones I’ve done. On top of that, I invest in real estate. Yeah. And those are kind of the things that kind of fill my time. Those five investments are really quite a full-time job right now. So when I say I’m not looking for more, one, I ran out of resources, and two, I’m out of time to dedicate to extracurricular business ventures like that. So while I’m not working in Renters Warehouse, I’m certainly being an advisor to a lot of businesses on the side that’s keeping me very busy.

52:22 Jim Beach
Well, it’s a very interesting basket of opportunities. I hope they all do well for you. I just did a fundraise for a speakeasy company here in Atlanta that’s planning on going national. So you and I need to get our two friends introduced to each other. Yeah, we do.
I also have Crohn’s disease, and so your medicinal marijuana oil is interesting to me from a person I actually—Minnesota. Yeah, one of the—Crohn’s is horrible, and I have it really badly. I’ve had several, several surgeries. And so I’m going to move to Minnesota. And if I could only find a real estate agent in Minnesota, everything would be great.

53:03 Brenton Hayden
That’ll take great care of you. My father-in-law has Crohn’s, and I know the pain issues that come with that, and I don’t put that upon anybody. And I’m sorry to hear you have to deal with that. But nonetheless, Crohn’s disease is one of the few illnesses that really benefit very much from cannabis oils.

53:24 Jim Beach
Well, it has been an honor and a pleasure to listen to you. I am inspired by what you’ve done. It’s an amazing 30 years, and I hope you’ll come back on the show soon and give us an update of how all these—your current basket of investments—is going. Thank you so much for being with us.

53:42 Brenton Hayden
Today, really, really was my pleasure, and thanks for having me. More than happy to come back on.

53:49 Jim Beach
All right, thank you so much. We will be right back. You.