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20 min read

Becoming a Solopreneur Later in Life

Becoming a Solopreneur Later in Life

Dan WaldmanUp until his early 50s, Dan Waldman owned a furniture store. He decided to sell that business and instead of staying in his chosen profession, he moved into commercial real estate brokerage, a field that isn't so simple. As you'll hear in this episode, Dan proved all the doubters wrong, and then some.

What you'll learn in this episode

  • Why Dan decided to become a solopreneur in his 50s
  • Challenges of transitioning to a solopreneur later in life
  • How the transition conversation may go with your significant other
  • Whether the transition was easier or harder later in life
  • How to position yourself against bigger companies
  • How to get clients in the beginning
  • How to get referrals from current clients
  • How to combat isolation
  • How to stay focused as a solopreneur

Connect with Dan Waldman

  • Contact Dan at (781)492-1586

Resources Mentioned in the Episode

Want to share your experiences and learn from other one-person business? Be sure to join our community! It's free :)

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Episode Transcription

Joe Rando (00:01):

Honestly, when I heard Dan was doing this, I was quietly concerned that it was too big a leap. But as you're gonna hear, Dan proved me wrong. And then some

Intro (00:09):

Bigger doesn't always mean better. Welcome to the One-Person business podcast, where people who are flying solo in business, come first. Specific tips and advice to find success. As a company of one, here are your hosts, Joe Rando and Carly Ries.

Joe Rando (00:27):

Hello and welcome to the One-Person business podcast. I'm one of your hosts, Joe Rando,

Carly Ries (00:33):

And I'm Carly Ries.

Joe Rando (00:35):

And today we're talking about switching to solopreneur mode, late in life. I hope to dispel the myth that you can't teach an old dog new tricks. To help us explore this, Dan Waldman's gonna talk about his transition to solopreneurship in his fifties. Not that fifties is old, but it's certainly later than one typically thinks about taking this kind of a leap. Up until his early fifties Dan owned a furniture store in Plymouth, Massachusetts. He decided to sell that business and instead of staying in his chosen profession, say by getting a job in furniture retail, he moved into commercial real estate brokerage. Now I know a good deal about commercial real estate brokerage, and it's not so simple. And honestly, when I heard Dan was doing this, I was quietly concerned that it was too big a leap. But as you're gonna hear, Dan proved me wrong, and then some. I've had the extreme pleasure to know Dan from his days in the furniture business and he is one of the nicest people to grace the planet earth. So I want to say Hello Dan, and welcome to the One-Person business podcast.

Dan Waldman (01:38):

Thank you, Joe. And I feel the same way about you.

Joe Rando (01:42):

So Dan, tell us a little bit about what you're currently doing and maybe talk a little bit about some of the awards and some of the bigger deals that you've done.

Dan Waldman (01:55):

Sure. Since 2008, I have been in commercial real estate. I do sales. I do leasing. I help people with 1031 exchanges. I've been very fortunate, over the last 10 years I've won the Co-Star Power Broker award nine times. Wow. During COVID, I did not win it. So, except for that one year I've won nine out of 10 years and that's currently, on a macro level, what I do. I do a lot of sales. I sell anything from retail malls to self storage facilities and I do leasing and, I get a lot of gratification helping people find 1031 properties.

Joe Rando (02:43):

Cool. That sounds like a very happy story. I mean you've really done well. I know that Co-Star Power Broker award is an achievement. And I know some of the deals that you've done that are pretty big and as a solopreneur, all the more impressive that you've done that. So tell us a little bit about why did you switch to becoming a solopreneur in the first place?

Dan Waldman (03:06):

Okay, so after I transitioned out of the furniture industry, I had a choice. I was looking for another business to go into, and it was pretty hard for me to find a business. So a dear friend of mine said to me, "Danny, you're in your fifties. You're either going to come work for me at a big insurance company, or you're gonna sell stocks, or you're gonna go into the real estate business." And, I did have a few customers that were commercial real estate brokers, and they always purchased nice furniture. So I said, "oh, I think I want to try this". And in the real estate business in Massachusetts, you pass a test, you become a broker and you have to work for a company for, at the time it was two years. It's now extended to three years. And I'm very grateful. I worked for a wonderful company but I knew as soon as I was allowed to go off on my own, I would. And that's exactly what I did. Literally after two years, I took the test and I was allowed to work for myself. And, that's how I became a solopreneur.

Joe Rando (04:28):

So, you know, it sounds like so straightforward, but, you know, there must have been some challenges to this whole process of making this transition. What were they and how did you get through them?

Dan Waldman (04:41):

<laugh>, it's the one thing about commercial real estate, even if you have the perfect property on day one, it's going to take six to nine months before you're compensated. So naturally there's a lead time. There's a big, big lag time. And, I don't know anybody that has the perfect property on day one. It takes a long time to build up a network of clients, a network of referrals. So that was a huge challenge. I mean, I went off on my own. Well, let me backtrack for a minute. When I worked for this company, I did very well. I sold plazas and I sold some other things. But when I went off on my own, it literally took me three years before I made my first sale. But when I did make that sale, it was an incredible sale. I worked very, very hard on that. I'm happy to tell you about it, if you like.

Joe Rando (05:36):

I think that would be fun to hear a little bit about what the deal was. And also the fact that obviously you had a cushion to get through three years without starving.

Dan Waldman (05:47):

No, no, I did. And that's a big thing. I'm very, very fortunate because I had, you know, the sale of the business and that was a great situation for me. And then, I'm also married to a professional, so unlike a lot of guys, I had income from two different sources. So I was lucky. I didn't have the usual pressure a lot of people have, because again, for three years, I probably lost money between the gas and the insurance. So what happened is, I went off on my own and, I saw a shopping mall and the owners agreed to see me . They said, "we want to sell this mall for $10,500,000. "

Dan Waldman (06:37):

And, the mall was south of Boston. It was a hundred thousand square foot mall. And I looked at the numbers and I said, guys, the mall will not sell for that price. And they said, do you have any suggestions? I said, yeah, we have to finish leasing it up. And I said, if you let me lease it up and you guarantee me that when we get to a certain net income, you will give me an opportunity to sell it. And they did. They actually stuck with me for a year. We got the place leased up. They wanted $10,500,000. We sold it for $10,860,000. So we sold it for $360,000 more than what they needed. And it wasn't just the money. Here I was hustling for three years, and now my work was beginning to pay off.

Carly Ries (07:24):

Wow. And Dan, I'm just curious, really quick. So you said you had a very supportive spouse but how did that initial conversation with your wife go when you're like, so curve ball, <laugh>, this is what I want to do now.

Dan Waldman (07:39):

Well, let me just say this. I actually did not sell the furniture store. I actually sold the real estate to a car dealership. So here I am, 52 years old, and we have some money in the bank and my wife just assumed, oh, you'll find another location to either rent or buy. And I don't want to equate it to Tom Brady, but it was one of these things after so many years in the same industry, I said to my wife, I really don't want to do this anymore. Uh, I've not seen the kids. Furniture is very holiday driven. Labor Day, Martin Luther King, all those are big days where frankly, I'd rather be with my two daughters and my wife. So, I think my wife thought I was a little bit crazy because I was making a nice living, but she was very supportive.

Dan Waldman (08:29):

She said, "okay, so you don't want to open a furniture store, find another business." And, that was a challenge. I did not find another business. And then it was a friend of mine, Bob Danahy, very grateful to him. He sat me down. And it's actually even more than that. After he gave me three options, his fraternity brother from Holy Cross, a guy named Bill McCall, who's like the godfather of real estate, agreed to see me. So we go down to post office square. We go up to the top floor. He is the king of real estate brokers. He has a huge company. He sits me down. We're in the conference room and we talk for two, two and a half hours and I said, "Mr. McCall, do I have a job?" He said, "No, but I like your personality. And, I can't hire you because you would cost me too much money to train, but he says, I like your personality. I think you're gonna be okay. Start from the bottom and work your way up." And that gave me a lot of confidence. And I'm very, very grateful to Bob and Mr. McCall to this day. They've actually changed my life.

Joe Rando (09:42):

It's knowing those people and getting in front of the right people and getting pointed in the right direction makes all the difference. Doesn't it?

Dan Waldman (09:50):

Oh, I can't tell you how grateful I am to these two guys. They helped me out. I was looking to buy a business, but I still have my own business. I'm very, very entrepreneurial. And, it's a great situation. I've worked really, really hard, but I am so grateful to be in the commercial real estate business.

Joe Rando (10:12):

So I have a two part question. So obviously this was not easy as you've pointed out. And I'm curious the challenges of making this transition in your fifties, versus had you done it say in your twenties, was it harder to do it, do you think? Do you think it might have been easier if you'd done it younger in life or maybe would the lack of experience and wisdom made it more challenging when you were younger?

Dan Waldman (10:38):

No, I definitely feel it's a young person's business. You have to start when you're young. I don't see too many people my age getting into this business and if I, you know, just brag a little bit, I don't like to brag, but, to hit where I am financially, in this timeframe is very unusual. I wish... My wife, kids around. She said, "I wish you would've started this in your twenties" but hey, this is how life is. I'm healthy and I still have a lot of years to go.

Joe Rando (11:12):

That's great. So Dan, you've got a successful, real estate brokerage company. It's a company of one. What is your "Why" for staying small and do you ever think about hiring other brokers?

Dan Waldman (11:28):

Um, <laugh> I think financially it would be a great decision, but as strong as a salesman as I am, I'm that poor as a manager and I'm just not a great manager. I love sales. I love people. I love helping people, but I just don't have the patience to train somebody and to really help, to help them. I rather focus on the sales, but, you know, financially it would be great to have 10, 12 guys and I get phone calls every, maybe not every week, but several times a month. Hey, can you help me? Can I join you? Can you at least mentor me? How are you making it? I keep seeing your name all the time in, you know, the New England Real Estate Journal. I do try to help and mentor people and I've had lunch with young guys, but I just don't have the patience to really bring anybody on

Joe Rando (12:26):

Yep. You know, yourself. So this industry is populated by some very large companies. You've got JLL, Jones, Lang, Lasalle, Marcus and Millichap. You've got some very strong regional firms, Atlantic Retail, and a bunch of others. Yet somehow you manage to really be doing a great job of staking out your share. How do you do that? How do you position yourself against these other, more powerhouse, bigger companies, so that you can win some of these deals, get some of these listings?

Dan Waldman (13:07):

Well, on a couple of the deals, believe it or not, some of those firms have actually referred them to me because, it was too much of a challenge and maybe the geographic area wasn't quite what they wanted. I position myself as, I get a lot of opportunities where, it's not just real estate, but maybe it's real estate with the associated business, like self storage. And a lot of the guys don't want this because it's kind of a different analysis. Or even a car wash believe or not. It's a different type of analysis cuz you've got to analyze the real estate and also the business. So that gives me a little advantage. The second thing is, I look for opportunities where I can be part of a team.

Dan Waldman (14:01):

And by that, I mean going back to, for example, a retail plaza, going back to the big sale I had after a three year drought. Here we were, we're a team, there were two owners and myself and we knew the game plan. The game plan was to fill it up. So you need a leasing agent and then to sell it and you need a sales agent. Here I bridge both of them and I think with the bigger firms, and they're great and I do a lot of business with them and a lot of the guys are my friends, but they hand it off. So you have a broker who will lease it up and then he hands it off to the sales guy and then they hand it off to the 1031 guy. I'm part of the team from the beginning to the end. And, I think that makes me a little bit different than a lot of the other brokers.

Joe Rando (14:55):

Awesome. That's a great way to distinguish yourself. I love that. So again, you know, how do you go about getting clients? What do you do to find new people? Because the same people aren't always buying and selling real estate. So you have to be finding new people that are selling, new people that are buying. And I'm just curious what kind of an approach you use to finding those people.

Dan Waldman (15:20):

So in the beginning, and I would recommend this to anybody and you could do it throughout your whole career. You really have to cold call. And it's hard, and you can't take it personal. Because you get a lot of people that hang up on you. So I was very lucky. I did the traditional cold calling and I made some sales and you know, when I take on a client, I really get to know them and like them. And after a couple of years, these same people are the ones referring business to me and it's interesting their lawyers refer business to me. So right now I actually don't cold call. A second way I get business, and this is a very interesting story, from September 24th, 2019 to October 1st, 2019, a period of eight days, I sold nine self storage facilities and except for two of them, they were all referrals because the agents were a little intimidated. They didn't know how to do the analysis. So, they referred it to me and I sold them and of course they got a referral fee. So, seven of those nine sales were referrals.

Joe Rando (16:36):

That's so interesting. What a great way to do it. I mean, you've got your competitors actually sending you business so to speak

Dan Waldman (16:43):

Well, exactly. And, of course I give them a referral fee, but, because it's a little bit different than selling an apartment building, they didn't really want to bother with it. And the same thing happened with .. It may not sound sexy or glamorous, but I've sold a couple of car washes because the guys didn't really want to analyze the business component. And I enjoy that. I look at the real estate, I look at what the business makes and I sit down with the owner and we talk about it and if he agrees and so far, they've all agreed with my analysis, we move forward and we sell it.

Joe Rando (17:24):

That's just so great when you enjoy doing something that other people don't really want to do, and you can make a good living doing it. That's <laugh>, that's an awesome way to position yourself.

Dan Waldman (17:39):

Joe, next Friday. So, a week from today, a lawyer called me up and this family, they lost dad and they own a ton of real estate and they called me up. I met with them and they said, you know, we have office buildings, we have warehouses, we have retail malls. What should we do? So literally a week from today, my analysis is pretty much done, I'm meeting with their mom, the six kids, and we'll see where it goes, but I have a plan for them. And we'll see if they will accept the plan or we'll work together to modify it, to meet their needs.

Joe Rando (18:19):

Wow. Dan, you're working as a solopreneur and I'm curious, do you ever feel lonely? And if you do, what do you do to combat the isolation of working alone?

Dan Waldman (18:31):

You know, I don't feel lonely. I'm gonna tell you why. I've been very, very lucky because although I work by myself, I have five or six guys that are brokers. They're younger than me, but we've become very, very close. And there's not a day that goes by where I don't get a phone call from two or three of them. They're sharing their deals. They're sharing mine. In fact, on a couple deals we've actually worked together. So I have some really, really close friends. And, no, I don't feel lonely. You know, I never feel lonely.

Carly Ries (19:04):

Dan, did you intentionally put that group of guys together for that purpose or did it just kind of happen naturally?

Dan Waldman (19:12):

No, it happened naturally. I meet one guy and we got close and then another guy, and sometimes I introduce those two guys and we have a really close network. I have a very close network of five or six guys. They are all my friends now and we talk real estate. We talk about the Patriots, maybe 10% of the time and 90% we talk about real estate.

Joe Rando (19:39):

That's great. So, Dan, what is something you wish you would've known ahead of time before starting this journey? If you go back and tell yourself something.

Dan Waldman (19:53):

Yeah, it is critical for young people. When they get into this business to realize it is gonna take time. In my case, you know, I was lucky. I worked for a firm. I made a couple of good sales during that two year period. But when it went off on my own, it took a long time. It took three years until I had the big sale. So it takes time. And again, even if your favorite uncle says, I want you to sell my apartment building. Until you receive your first check, it could be six months to a year. It doesn't happen fast.

Carly Ries (20:29):

Were there ever times during those three years where you're like, huh, I'm over it. I want to give up. Or were you just so determined to make it work that you kept going?

Dan Waldman (20:38):

No, I was like the Viking. I burned my boat. I was gonna make this work. I was now 52, 53. I had nowhere else to go. I didn't wanna sell stocks. I couldn't find a business. And there's nothing wrong with stock brokers, they are great <laugh> but I knew I had to make this work. It's the only business in the world where 95% of the time, you meet wonderful people. You learn from these people, and then they hand you a huge check. So it's a great business. I'm learning, as much as I'm helping them, they're helping me.

Joe Rando (21:18):

So Dan, with respect to being a One-Person business, not so much the real estate business, the real estate commercial brokerage business, but just being a One-Person business, what are your most favorite and your least favorite thing about being a One-Person business?

Dan Waldman (21:35):

I'm gonna start with my least favorite. I'm terrible with the paperwork. I should hire a virtual secretary, which my older daughter is telling me to do all the time. I don't like the paperwork, even filling in the forms for the errors and omission insurance. To me, it's drudgery. I just don't like the paperwork. I'll tell you what I really, really like. I love helping people. And if we have a moment, I'd like to tell you a story. It was not my biggest sale, but to this day, it's my most rewarding sale.

Joe Rando (22:07):

Please tell us.

Dan Waldman (22:10):

Okay. So in Metro west, because I don't wanna share too many personal details because there's a lot of personal. I was doing leasing and right down the street there was an ugly retail mall with an even uglier self storage facility behind it. I went in there and the woman was 69 years old and she was shoveling snow on a big truck. And she got off. We started talking and she gave me the background on her husband. Her husband was a crane operator and he was smart enough to build duplexes in a certain Metro west town. And he sold them and he had to do a 1031 and he bought this property. And I said, well, where is your husband now? She says he has a slow terminal disease. And I said, so you mean you shovel the snow and you clean the toilets.

Dan Waldman (23:06):

Literally she said, yes. And I went to visit her a couple more times and I told her, I said, you know, I think I can sell this. She shared her income and I said, I think I could sell this and I think I could find you what they call 1031. And you could take care of your husband because the checks will be wired every month. And she says, I don't really think they have things like that. So I gave her a list of four or five lawyers, two or three accountants and she called and they said, yep, yep. Danny can do this. Yep. If he gets you that price, you don't have to work and you'll make the same amount of money. So we sold the self storage facility. Right now there's about an 80,000 square foot huge national one on there.

Dan Waldman (23:52):

So I had to find them a 1031 and I would go over to their home and I would show them a Starbucks in Houston or a Papa, a Taco Bell in another city. And the gentleman said to me, I have grandkids. I want to show my grandkids something. I have to find something locally, Danny. Well, it turns out that on the Cape they were building the first, let's say, Dollar Store. I called the owner up. I called the developer and he says, I already gave it to a broker. I called the broker and said, you know, what do you want for this? And he said, we're asking two six. And I called my client back. And I said, listen, I found a wonderful Dollar Store, 15 years. It's not even built.

Dan Waldman (24:39):

You could take the kids to the Cape. And I said "what do you think?" And he said, well, listen, we can't go above two, two. I called the broker back. I said, listen, I'm willing to take my clients down there tomorrow. We could all meet. It's two, two, and you don't have to do another day's work. He says, Hey, that's fair. So we all met the next day. The building was about 90% complete and we made the deal. You talk about pride of ownership. And to this day, I always get my Christmas cards from them. And the wife told me that I changed their life and the husband is so proud to take their grandkids down there. And that's a true story.

Joe Rando (25:21):

Awesome, Dan. So it's not about just making money. It's about helping people, which doesn't surprise me coming from you.

Dan Waldman (25:29):

Nope. It was literally one of my smaller sales, but it was the most rewarding because they could spend time together. They didn't have to shovel the snow. He was so proud to show his grandkids he owned this building right on the Cape and it's a beautiful building. And, it's a fabulous company, strong, strong credit. And to this day I get Christmas cards and I get calls from them. And it really meant so much to me, that sale. Awesome.

Carly Ries (26:01):

That is the perfect story for this time of year. This for listeners, this is gonna be published mid-December 20/21. So depending on when you're listening to it, it's very timely

Joe Rando (26:11):

Top advice for staying focused. Any advice for people, you know, kind of keeping your eye on the prize.

Dan Waldman (26:21):

This is what I do, and everybody has their own method, but I use my Google calendar. Every night before I go bed, I look at it and cross off what I accomplished and what I need to do in the morning. And anything that is critical, I start my day about 6, 6:15, those are the first things on my calendar. By nine o'clock, I get a lot of work done and those priorities are usually met by nine, 9:00 AM.

Joe Rando (26:53):


Dan Waldman (26:54):

So that's how I stay focused. Everybody has their own way but that's how I stay focused. Another thing I'm a little bit different than the other brokers, because I don't believe in a ton of listings. I believe in five or six, that way I can focus a couple of hours on each one. And that's how I do it. I don't take on more listings, till I know I have another one under agreement and the money is hard and that's how I stay focused.

Joe Rando (27:21):

Very good. Tell me about maybe the biggest mistake you've made as a One-Person business .

Dan Waldman (27:31):

Well, I've made a lot of mistakes. The biggest mistake I would say is I don't know how to say no. So maybe I'll take a property that is maybe a little too small and it takes up a lot of time. I just don't know how to say no, and I have to get better at that.

Joe Rando (27:50):

We have a whole podcast about that. So be sure to check that out.

Dan Waldman (27:53):

<laugh> well, I'm gonna listen. I will be listening because I need some help.

Joe Rando (27:57):

Tell me your biggest aha moment when you became a One-Person business . What was the, that one time, the beginning, maybe where you went? Ah,

Dan Waldman (28:05):

I would actually say it was, after a three year drought, selling that retail plaza for you know, plus 10 million. That that felt pretty good because, it kind of proved that, Hey, I, I can do this. I stuck in there for three years and Hey, if I can do this. It's funny, success breeds success. From that, I started getting other deals and other deals I was working with did close. So, all of a sudden things started falling in place. So the biggest aha moment was in September 13, 2013 when I sold that Plaza.

Joe Rando (28:45):

Awesome. So do you have any kind of a resource that you think would help our listeners on their solo journey?

Dan Waldman (28:53):

You know what, the best thing to help a broker is to find a mentor. And, I did have those two guys who helped me get into the industry, but I really never had a mentor once I got into the industry. And I think if you have somebody, a little bit older or somebody who has some experience, that would be a great thing,

Joe Rando (29:17):

Great advice. And one that, that you're not the first to promote. So now we're gonna start having a little bit of fun. And our first fun question is what's your favorite movie that always puts you in a good mood.

Dan Waldman (29:31):

<laugh> listen, I love Costner and Field of Dreams. I think that's a great movie.

Joe Rando (29:38):

All right.

Dan Waldman (29:38):

Yeah. I just love that movie.

Carly Ries (29:40):

That is a great movie. I need to go back and watch that. I've been watching him in Yellowstone, which has very different vibes.

Joe Rando (29:46):

<laugh> oh, this is very different. Yes.

Dan Waldman (29:49):

I have to tell you my wife and I look forward to Sunday 8:00 PM. We love Yellowstone.

Carly Ries (29:54):

It's so good. But in terms of feel good, maybe not so much <laugh>

Dan Waldman (29:58):

No, no, no. Although I will tell you, my wife is counting the days for Outlander.

Joe Rando (30:05):

That's the one, the Scottish.

Dan Waldman (30:07):

Yeah. My wife loves that movie. Loves the series.

Joe Rando (30:12):

Okay. Next is your favorite song to pump you up.

Dan Waldman (30:16):

Hey, Born To Run, Bruce. Come on. You know how old I am? I love Bruce.

Joe Rando (30:23):

Bruce Springsteen's awesome. Okay. And lastly, how do you define success?

Dan Waldman (30:33):

I would define it as reaching a level of wealth, so you can spend more time with your family and enjoy life, because life goes by so fast.

Joe Rando (30:43):

Amen. Well, Dan, that brings us to the end here and I just want to thank you so much for your time and your insights. I'm curious if we do have anybody that's interested in maybe connecting with you to mentor, is there any particular way that, they should do that?

Dan Waldman (31:04):

Just call or text me at (781) 492-1586. I'm happy to help any way I can.

Joe Rando (31:12):

Wow. That's very generous. Thank you so much. Well, we've reached the end of another edition of the One-Person business podcast. Thanks Dan. And thanks Carly for being here.

Dan Waldman (31:26):

Well, Thank you. I enjoyed it. And I want to wish you and everybody listening a wonderful holiday,

Joe Rando (31:31):

Happy holidays to you as well. We will be back again soon. If you enjoyed this, please be sure to subscribe. A lot of the topics covered will be in the show notes as well, and with links to information. So check those out as well. And we'll see you next time. Thanks a lot.

Closing (31:51):

You may be going solo in business, but that doesn't mean you're alone. In fact, millions of people are in your shoes, writing a One-Person business and figuring it out as they go. So why not connect with them and learn from each other's successes and failures. At LifeStarr, we're creating a One-Person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversation at