Make It a Pleasant Ride: Interview with Howard Dvorkin, Founder of Consolidated Credit and Debt.com

I recently went one-on-one with Howard Dvorkin, founder of Consolidated Credit and Debt.com.

Adam: Long before the days of debt.com, you were an accountant. What made you decide to pursue a career as an accountant?

Howard: I needed a job, and listen, to be very candid with you, I was actually good at it in school. It’s one of the things that I excelled at. Now, I never said that I was a good accountant. I’m just an accountant, and I got my CPA. I started out with a company called Laventhal and Horvath back in Washington, DC, in the National Tax Department, and moved over, did a lot of stuff, a lot of exposure to workouts and restructuring.

I think within two months of when I was there, I’m on the phone with a very famous corporate raider. I won’t mention the name, but he took over an airline. The senior partner who was training me, and truthfully loved me, and I loved him, and he’s a great guy, and I still talk to him 40 years later, brought me in on this call. I remember him giving advice about this merger, and he said, “What do you think about this, Howard?” The corporate raider, who is well known, and I’m sure you know the name, had very colorful language, and he said, “Who the f is Howard?”

So for the rest of the week, my name was “who the” throughout the office. It was pretty funny.

Anyway, I worked and saw some unbelievably sophisticated things. I got moved up through the ranks extremely quickly. I made senior in like a year, and then went up from there. It was an amazing opportunity.

An opportunity opened up in the Florida office, and it was mostly restructuring, because a lot of people down in Florida got caught by the savings and loan debacle back in the late 80s. I was transferred down to Palm Beach, which is not such a bad place. Two weeks later, Laventhal went out of business. Arthur Andersen rolls in and fires everybody but myself and another guy.

I was used to being moved up quite quickly, and there were some promises made if I moved down to Palm Beach. Unfortunately, those promises evaporated. I got to see what the Big Eight at the time was about, and I really didn’t like it.

I was told, “Yeah, you’ve made it quite quickly.” I was bringing in business, and I think by nature I’m more of a salesperson than anything, and a marketer, pretty good marketer, by the way. I was told it would be 15 years before I made partner there. I was like, I’m not waiting around here for 15 years, I’m out of here.

I took my little book of business and started with another firm temporarily for one or two tax seasons. While that was happening, I created my own business plan. I think I got married, quit my job, and bought a house, all within three months. The only thing that lasted, well, I did get the house. Now that I think about it, I think that’s the only thing I got. But yeah, it was scary.

I went from making a very nice salary as a senior accountant, or more than a senior accountant, to zero.

And I do have the distinct pleasure, and I say this jokingly, but I’ve gotten fired from virtually every job I’ve ever had. I say that because I’m kind of proud of it. If I don’t respect people I work with or work for at the time, it doesn’t work out well for me. I need to respect those people, and I need to like them.

In the accounting world, you meet all sorts of people. Sometimes they’re likable, sometimes they’re not very likable. I related well to the partners. I didn’t relate well to the managers I was supposed to be working for, because I didn’t really have a lot of respect for them, because of their leadership skills.

In the accounting world, people are pretty technically sufficient. They built their career on their technicality, their ability, and their brightness. But there aren’t that many good communicators, and they were far and few between. I’m a better communicator than I was an accountant.

I was able to bring in business, and unfortunately, at the bigger firms, they didn’t want the kind of business I was bringing in. That was challenging, because I bust my hump to bring in business, and then they’d be like, “No, no, we don’t want that kind of business. We want Fortune 500 stuff.” I’m like, that’s not going to come from me.

So that’s my story of accounting. But truthfully, I enjoyed it. It’s the basis of business. I still have on my business card, CPA. I keep current with all my accounting credits. Every year, I probably take between 40 and 80 hours of continuing education, and I enjoy it.

But the reality is, I’m a businessman, and I’ve always been a businessman. Even as a child, I made money. I’ve always been able to make money and enjoy what I do. It’s not so much about the money, it’s more about the kill. I love the kill still, and as long as I achieve that, win, I’m a happy guy.

Adam: What are the most important lessons for anyone today working in the field of accounting?

Howard: I would say, be bold. With AI, with the onslaught of AI, you could get virtually every answer.

And by the way, I haven’t given up my accounting ability, even when I broke out and started a business. Because of the nature of the business, I would get these clients, and we were up to 400 returns a season. That was a tremendous amount of returns for myself. I farmed it out to a gentleman that was a friend of mine, but 400 returns between two people were a fair amount of business.

So again, I was able to bring in business, but then I figured out what I was earning. This is going back 30 years ago. I was realizing probably 85 bucks an hour, where my other business was generating hundreds of dollars an hour. It made no sense that I continue, so I sold the practice.

What I realized, truthfully, is that you need to communicate. If I could tell younger folks, work on your communication skills. I know it’s an old thing, but take a Dale Carnegie course on public speaking. Work on yourself. Invest in yourself. It’ll be the best investment you ever make in your life.

People think because they know a lot about a subject, they don’t need those soft skills, but those soft skills are important.

Once I left accounting, I started the credit counseling business, which is the largest credit counseling business in the world, Consolidated Credit Counseling. Between that and debt.com, we’ve assisted 13 million people over the course of the last 33 years. I just had my anniversary on the fourth, 33 years in business, which I’m pretty proud of.

I will tell you, the ability to communicate and the ability to talk, and certainly now I’m in my 60s, my true skill set is being able to communicate to people, work a room, socialize with people, and more importantly, get people to like me.

I get opportunities that a lot of people don’t get because I’m approachable, I’m a good communicator, and I follow up. When somebody does something nice for me, I still write a hand-signed thank you card. That’s an art that doesn’t happen too often these days. People think it’s okay to send a text. I disagree. You’ve got to have that human touch. Maybe I’m old school on that.

We have a big real estate division, and people will text me, “Hey, I’m interested in buying your property.” This is a multi-million dollar property, and you can’t pick up the phone? You have to text me? Come on. People expect they’re going to score a $10 million property by sending me a text. It’s ridiculous. I realize a lot of that’s automated, but it doesn’t make a lot of sense.

People in their career, especially if you’re in your 20s, 30s, you’ve got to learn to pick up the phone and talk to people, because you can’t hide behind your texts. You can’t hide behind your email.

I’m the worst emailer ever. I get about 400 emails a day, and frankly, I’m the meanest human being on the face of the planet about email. Somebody will send me a two-page email, and the people close to me know I’m only going to read the first screen. That’s it. Ask the question in a couple sentences. You don’t need to send a two-page email to me. It’s like yes, no. Very curt.

I guess it’s the Jersey street kid coming out in me. People aren’t used to that. I’m a rough kid from the swamps of Jersey. Sometimes, the niceties, I don’t have that gene. I’m very direct, and you can’t take offense that I’m so direct.

I had somebody approach me to buy some artwork the other day, and I’m like, “No, it’s terrible. I don’t like it.” They were insulted. I’m like, I told you what I thought. People can’t handle directness.

I think the younger generation needs to get a little thicker-skinned and understand there’s no participation trophies in business. It’s winners and losers, and hopefully you’re on the right side of that.

I still do my CPE, my continuing education as an accountant. I saw a course on negotiation going on down the street, and I decided to go to the course. This is what I do for a living, so I’m pretty rough. The instructor was some corporate weenie, I don’t know what his job was, maybe contract negotiation, and he’s like, “Everybody has to have a win-win.” And I’m like, no, they don’t. My job is to destroy what’s in front of me. I want my opponent on the floor bleeding and crying, and myself being the winner. That’s what I’m built for, that’s what I do, and that’s what my clients expect me to do.

My clients expect me to negotiate on their behalf and not be nice, just get the result. I’m handsomely paid to do that at times. Some people take offense to it, and I don’t really care at this point. I never really did. I’m not trying to be a jerk, I’m telling you my job is to negotiate the best deals for my clients, and that’s what I do.

Adam: What are the keys to career success in the field?

Howard: The one thing I would suggest is, you have to work hard. Certainly, during busy season, you’re working really hard, sometimes seven days a week for 18 hours a day. That’s part of the job. But don’t forget, you have to have a life. More importantly, you have to intertwine your life with your career.

Join social clubs. If you like playing golf, join a golf club. Don’t play so much that it impedes your ability to do your job. Get involved with different groups and try to take leadership positions in that group so you’re able to talk to lots of people, get your name recognized, and get known. Get involved with charities. There’s a lot of help that charities need. Get out there in the community and be known.

The problem I always had with the accounting profession is that we work incredibly hard. By the way, I say we because I still think like I’m an accountant, although I haven’t done a tax return from the ground up in decades. I do review probably 600 tax returns for our organization, because we’re a national firm, and between my personal and all the states we operate in and the local municipalities we operate in, there is a lot of stuff I still review.

But get out there, refine your skills so you’re known, and get involved.

I remember when I first started my business, and I was still wavering between being an accountant and being a credit counselor, I would go teach class to disadvantaged families about finances. Was I going to get any real clients out of that? No. But I thought it was the right thing to do.

Even when I was an accountant, it was when the Cold War ended, and the Berlin Wall came down, and all these Russians emigrated to the United States. They didn’t understand taxes. I would sit there on the weekends and prepare hundreds of returns over the course of two or three weekends. It was challenging.

But you go out there, you get involved, you talk to people, you meet people. It’s pretty interesting, the kind of people that you meet.

For younger folks, I think it’s challenging right now. It’s a tough time. We employ at least four accounting firms. Two are national accounting firms, and two are local accounting firms, depending on the sophistication of the project.

There’s so much turnover at these accounting firms, especially the large ones. You get comfortable with somebody, and then they disappear. You get comfortable with somebody else, and they disappear. It’s fun from my standpoint, because they tend to put me with very sophisticated people, because, believe it or not, I still pretend I know what I’m talking about when it comes to tax work. They’re afraid to put me with a rookie because I’ll blow them right out of the water.

We’ll talk about different stuff, and I’ll be like, “Oh, Section 108, yeah, that applies here.” And they’re like, “What do you know about that?” I go, “Kiddo, I’ve been at it for a long time.” It’s pretty interesting.

You’ve got to be technically sophisticated. But the reality is, a lot of work is going to be produced utilizing artificial intelligence, which we’re seeing right now for a lot of tax research. I used to hang out in the law library or the tax library at the different firms I was at and read treaties and things from different countries. Now I just pull it up on my phone and get the same answer, rather than spending three hours researching.

Also, outsourcing, where a lot of work is going overseas and being automated. There’s a lot of software being developed where, if you have a lot of K-1s, the forms that used to be put in by hand, now these software packages read the forms and put them into a spreadsheet automatically. What would take you weeks is now done in minutes. It’s amazing.

So my suggestion for people entering the business, embrace technology. Understand artificial intelligence. Understand what’s applicable and get through the garbage. It’s fun to play on social media, but it’s not going to get you anywhere. Embrace AI and start to take courses on it. If you don’t, you’re going to get lost in the dust.

We are embracing AI as fast as we can. What I told you earlier was about negotiation. We built a robot that negotiates with creditors now, and you cannot even tell you’re talking to a robot. That’s the amazing part.

I had the manager walk up to me with a grin, and he said, “I’ve got to show you this.” He shows me the name of the agent that does negotiations. Each agent did about 10 to 15 negotiations for the week. I go, “Great.” I go, “What’s this? There’s 126.” He goes, “That’s our bot.” They can’t even say robot anymore, now it’s a bot. Our bot did 126 in one week. I go, “How much is that costing us?” He goes, “About 2000 a month.” I go, “When are you getting rid of these people?” Sure enough, he says, “Already done. We reassigned them.”

So AI is here. It’s here to stay. Will it replace all the skills? No. Thus, I bring back the soft skills, the communication skills. That’s important, because you can have a computer spit out a tax return, or help you do an audit, or whatever auditors do. By the way, I’ve only been on one audit and it was horrible, so I never went back for another audit.

But I will tell you, talking to people is a very important thing.

The part that always bothered me about the accounting profession was, we do four years of undergrad. A lot of states require two years and a master’s, and we don’t get compensated as much as a lawyer would. It’s disheartening that the young lawyers are living better lives than the accounting guys. The accounting guys are working their tails off and getting paid less. I think the industry has to catch up and realize, when you’re talking taxes, taxes are 40% of one’s income, so it deserves the respect and attention that lawyers already get. It always bothered me that accountants aren’t appreciated as much as maybe they should be.

It’s interesting, I have a lot of friends that are accountants, still accountants, hyper successful folks, and they make the real money not in accounting. They do different things. Maybe they own a real estate development company, and they use those accounting skills to build houses and things like that.

It’s interesting that we’re trained as accountants to do a lot of things. I’m not quite sure how I got into the debt business or any of the other businesses that I’m in, but somehow I understand those businesses. I’ve been able to build a pretty large family office, which I’m told is large, with a bunch of different businesses. We have seven operating businesses with about 700 people working for us or with us. It’s kind of cool, and we do a lot of different things.

I mentioned technology, and I could barely operate my cell phone. I’ve sold two or three tech companies over the last 10 years, sold them for millions and millions of dollars, and here I am. I can barely operate my phone, and I’m building or selling database solutions or management platforms, CRMs for companies. It’s pretty interesting.

Adam: How did you go from employee to successful entrepreneur?

Howard: I don’t know if I’m successful. I’ll tell you if I hit 70. When I hit 70, then I’m successful.

But listen, I’ve made my mistakes. I’ve made plenty of mistakes. I’ve blown up a lot of stuff, but somehow, in God’s good graces, I’ve recovered. Frankly, I hire really good people all around me. The people that I’ve employed and that work with me are unbelievable. They’re smarter than me. You’ve got to check your ego. You can’t be the smartest person in the room. You need to listen to people, and you’ve got to surround yourself with smarter people with different skill sets.

I will tell you, I have a couple skills, two, that’s it. I have very good street smarts. My strategy, my long term strategy, and communication skills have worked for me. Other than that, I have no skills.

To get back to your answer, I kind of never wanted to be an accountant. It’s just I was good at it. It was easy in school for me, so I said, okay, I’ll be an accountant.

I was at American University. There were some very wealthy kids there, and all my friends, my fraternity, were going into their father’s business. I grew up without a father, so I didn’t have that opportunity. There was no business to go into. I turned around and said, okay, I’ll go into this. They’re paying the most. But I always knew I didn’t want to do this long term, simply because I always wanted to be an entrepreneur.

Even as a little kid, I was an entrepreneur. Whether it was raising money for Muscular Dystrophy, my sister and I would host haunted houses and carnivals at our house and raise money for charities.

I think my first real business was a snow-blowing operation. You wouldn’t know about that because you grew up in LA, but growing up in New Jersey, we got snow back then, a lot. I lived on a street with a lot of doctors that had to make their rounds, and I made a deal with them that their driveway would be done by seven o’clock in the morning, cleared, and they could get out.

The first year I did it, I think I was a freshman in high school, and I had 10 guys working for me. The next year, I didn’t make that much money, maybe 1000 bucks for the whole season. I took that money the following season and bought a snow blower. I was on the snow blower, my buddy had a plow, so he plowed, I snowed, and we had one guy shoveling. I went from 10 people to three of us, and we made like $5,000 that season. Thank God it snowed a lot that year. We continued that, and it taught me that automation works. Try to automate everything.

When I started in the credit business, I took the skills I learned from accounting and said, why isn’t this automated? So what did I do, the guy that can’t even operate a cell phone? I’m not sure I owned a cell phone at that time. I learned the best I could to program a software package, and I built my own software package to automate this. I would go into competitors and they’d be writing checks by hand. I’m like, this is crazy, why don’t we automate it? So I automated it.

Finally, somebody developed decent software, and we bought the software and really got going. Then we built our own software and automation.

Once I did this and got really comfortable with this industry, I was able to expand into other businesses. If you look at our portfolio now, we have a lot of financial relief or debt relief companies. We have tech, not technology companies. We own a very substantial aviation company and some other businesses. We have a real estate division, and we own quite a bit of real estate, and then a platform for trading securities. We do a lot of different things, and I enjoy it.

People say, “Why do you do so much?” It’s because I love it. I enjoy the mental stimulation.

When I was a kid, I always tell my son, “The world is run by C students.” It’s very true. I was not an A student early in my years. I was probably not even a C student a lot of the time. I was borderline learning disabled, not because I was stupid or because I had challenges, it’s because I didn’t care. It bored me. I would rather do different things than sit there and do my math and my English studies.

I grew up in a nice family, had a great family, and then my dad passed away. It was very tragic how it happened, which is a shame, but it taught me a lot. I hung out with very bad people and did a lot of really bad things as a youth, as a teenager.

Finally, I looked at myself, and I said, I don’t want to be here anymore. I changed my life. I buckled down on school. I had a path to nowhere, and then I changed course. I think I was a sophomore in high school. I ended up graduating not top of the class, but top 10% of a very large class, which I was pretty proud of. That was good, because I was one of the few kids that went to college from my graduating class.

Because I was such a screw up, my mother decided she wasn’t going to pay for my first year in college. So I paid for my first year by finding the cheapest school on the planet. It was West Virginia University. Tuition was $459 a year, or a semester. I think my beer tab at the local bar was more than that. So it was like, great, I’ll go there.

Truthfully, I didn’t learn a lot, although I did excel in the accounting class there. I transferred to American University and learned a lot, was exposed to a lot. That was life-changing for me, because here I am a kid from an unsophisticated blue-collar town, and American University was very sophisticated. You were in Washington, DC, interacting with successful people or people from successful families.

I was recruited by one of the large national firms and had a job. I went down to South Florida for spring break. Fort Lauderdale was all the rage back then. My buddy turns to me and says, “Hey, my parents want me to check out the University of Miami. Will you come with me?” I’m like, no, I’m going to work for Ernst and Young, or whatever their name was at the time. He’s like, “Come on, man.”

So we went to the University of Miami campus. Our first stop was the bar on campus. The second stop was the pool. My buddy turns to me and says, “This is pretty cool. I think I’m going to go here. You mind if I go?” I go, I’m with you. He’s like, “I thought you had a job.” I go, “That can wait.”

I always joke with people, when I came down to Florida for spring break, I never left, which is kind of true, because I did leave after graduating. I got an MBA with a degree, which is the craziest degree that you were able to get a degree. I specialized not only in taxation, because it was easy for me, but also in entrepreneurship. I’m not quite sure how those two collided, but they did.

I went to Washington and started working there. After a couple years, I was going up the escalator at about 5:30 in the morning. I’m a very hard worker to this day. There was this homeless guy laying in the escalator path, and I had to step over him to get off. I’m like, this is not what I want 20 years from now, this is not where I want to be.

I had friends down in the Fort Lauderdale area, so I said maybe I’ll go back there. It worked out because I would have never been able to do what I do and build businesses the way I do it because of the lack of regulation and the cheaper labor rates here versus the Northeast.

Adam: How has having a CPA impacted your career?

Howard: Oh, automatically, if I tell people I’m a CPA, they think I’m really boring. By the end of the conversation, they’re like, you’re not really like a CPA, fun. And I’m like, yeah, that’s why I didn’t last that long.

Listen, I busted my hump to get that CPA license. I’m not giving it up. I have plenty of friends that have given it up. I’m holding on to it so maybe on my tombstone it’ll say, “Howard Dworkin, good father, good husband, CPA.” Somehow I doubt that.

But it has helped me. The first time it helped me, I was trying to save every dollar. I quit my job, bought a house, got married, and I started this company with $7,000. It wasn’t that much money, but I cut every corner possible.

I was doing the registrations for the state of Florida, and the requirement was you had to have a bond. I went to all these insurance guys and they’re like, “We can’t get you a bond.” This industry was riddled with bad, unscrupulous people, so nobody wanted to bond it.

I talked to this underwriter, and I said, “I don’t get it. I have an MBA from Miami, I worked for Arthur Andersen, I have a CPA license, and nobody will bond me.” It wasn’t even that big of a bond, a couple thousand bucks. The guy goes, “You’re a CPA?” I go, “Yeah.” He goes, “I got you covered.” That was pretty cool.

But honestly, credibility. The CPA license tells people you’re credible, at least hopefully you’re credible, and you do good things. I protect that. I never try to do anything that would harm it or put it in jeopardy.

I like being a CPA. I like hanging out with CPAs. In my organization, we have hundreds of employees, and a lot of the senior-level people are CPAs.

There is a difference in the quality of personnel when you hire CPAs. You might pay 10 or 20 thousand more for somebody that has a license, but it tells me something about that person. We’re all part of this fraternity of CPAs, which is important to me. We understand each other, we think alike, and we’re trained differently versus other professions. Marketers and things like that, we just look at things differently.

Adam: What do you believe are the key characteristics of a great leader, and what can anyone do to become a better leader?

Howard: I’m going to tell you, it’s interesting. I did an internship at Deloitte a long time ago, and the managing partner would not say hello to you. I’d be walking through the hall, granted, I was in college, it didn’t really matter, but I would say, “Hello, Mr. So and So.” The guy would not acknowledge your presence. Finally, being the person I am, I said, “Excuse me, Mr. So and So.” He says hello, and I was shortly fired after that.

But I will tell you, I learned this in the accounting world. I used to work for a fellow named Bob Jones in Washington. Bob was brilliant. He was a brilliant accountant, and he could communicate at a level with IRS agents, or he could talk to Larry the forklift repairman. We had both of those.

I think Bob was credited with signing Bill Clinton’s tax return at the time. I think I was there when he was working on that. I may have even worked on it. Sorry, President Clinton probably got audited because of me.

Bob had the ability to talk to anybody, regardless of the level.

I’ll tell you a quick story. My wife is in the equestrian world. We have investments, farms, she loves horses. I never thought I would grow up and be a human ATM machine, but somehow I did.

We built an equestrian center in North Carolina, Tryon Equestrian Center, and we have partners. The partners are very successful people. It was the opening, the place was still under construction. We had a Fourth of July party, and we invited everybody that participated in building it.

You had a clear delineation between the contractors, the suppliers, and the equestrian people. I went to the bar, and I said, “Give me a six pack.” I went over with my work boots, because I knew who was going to be there, and I sat down with all the construction guys for the whole night and had a great time. It was much more fun than hanging out with the fuddy-duddies.

The ability to communicate to everybody and be personable to everybody, and interject comedy into what you say, that matters. Some people would say I’m rude. I say some weird stuff. My goal in life is to put a smile on people’s face. I love making people laugh. The more they laugh, the stupider I get, and the more they laugh because I’m so stupid in the stuff I say.

I will go to every length to embarrass myself to make people happy.

Regardless of what level you’re at, don’t believe your own clippings, your own headlines. Adam, you found me. I’m not sure how you found me, but I’m sure it’s because you probably made a mistake, truthfully.

I’ve been interviewed literally thousands and thousands of times over the last 25, 26 years. Don’t believe your own press clippings. Don’t believe your own headlines. Remember where you came from.

I was having dinner with a young man a couple months ago, and he’s kind of full of himself. It’s like, sonny boy, you need to remember where you came from.

There’s an old saying, I have a friend, and I’ll attribute this to Leon Cooperman, who’s an unbelievable investor, very well known throughout the investing world. He says, “I only hire PhDs, poor, hungry, and driven.” That’s what I hire. Not super smart people. You want somebody hungry and driven.

Just don’t forget where you came from. Even if you make partner of a national firm, remember you started right where those people started, and it’s our obligation to bring those people up.

I take that very seriously. We have training classes, and I go into our customer service training classes and talk to those guys for an hour, maybe two hours. They’re nice people, they come from different backgrounds. A lot of people weren’t even born in this country, but they’re good people. You have to relate to people. You have to say hello, kibbutz with people, enjoy being around people.

No matter how much pressure you’re under, you’ve got to put on a game face a lot of the time. Last month I had tremendous pressure, and you’re getting the same Howard as a result of it.

So my suggestion is, never forget where you’re from, always treat people with respect, and don’t believe your own headlines.

Now listen, I will tell you that a lot of our businesses run call centers. The average tenure of a call center employee is 18 months throughout the country. Our average tenure is eight and a half years. These people are dedicated, they’re smart, they haven’t had a break.

It’s funny, I look at the people that have been with me. Some have been with me 20, 25, 30 years. I’ll use one gal. She started, I recruited her out of Arby’s, and she was an Arby’s assistant manager. She probably got 25 cents more than a cashier did. She came to us and started as a receptionist, and she would jump in wherever she needed to be.

Twenty years later, she moved into my neighborhood, which is awesome, from cashier to moving into probably one of the wealthiest zip codes in South Florida. I was like, that’s awesome. She put herself through master’s programs, and she’s really done well.

A lot of the people, especially if you’re an accountant, they don’t have the education level that you have. They didn’t have the drive that you had, but they are people. Doing nice things for them, they appreciate.

During the holidays, we still give Christmas bonuses. Once in a while, I get a thank you for that. It’s not that much, but it’s something. We do holiday parties, and we do a big holiday party. People can come black tie or whatever they choose. This is their chance, it’s their prom to go to a fancy party. They really appreciate it, at least I think they appreciate it.

We’ll spend as an organization probably half a million dollars on stuff, between longevity bonuses and parties. Don’t be surprised if you’re in our office and you see a keg getting rolled down the hallway, passing out different things. Thank God we do it in the morning, so any effects wear off by the time they’re ready to go home.

It’s making people feel wanted, making people feel special. We do a big Halloween thing around here. Everybody dresses up, and it’s really fun. Some outfits are outlandish. Usually, I try to go for the shock value or embarrass myself as much as I possibly can. I should probably destroy some of the pictures out there.

Again, embarrass yourself. I know where I came from. I’ve been unbelievably lucky to surround myself with incredibly talented people over the course of the last 33 years. I enjoy seeing people, meeting people, hearing about people.

It’s funny, I have one kid, and he may even be watching this podcast. When he was a little boy, his mother and father worked here in different departments. We had this glass table in the lobby, and he was three years old, and he flipped the top, and the glass shattered everywhere. So forever, I don’t even know his name, but I’ve always referred to him as table breaker.

He became a CPA working for a national firm. This is a great story. The partner that we use, I said, “Do you know this kid?” He goes, “Yeah.” I tell him the story and the nickname, table breaker. They had a whole firm event, and he goes, “There’s one guy here that worked in our office years ago, and we just want to say table breaker,” and the whole firm went crazy. He came in here, and I’m so happy for him. He became a CPA. He ended up getting married to another CPA in the office. Not sure the fraternization rules, but I’m very proud of Darnell. He’s a great kid, and I love those types of stories.

At my level, I just want people to do well and be happy. I’ve never been money motivated, to be very candid. People say that’s BS. You’re always talking about money. Maybe I’m always thinking about it, but I’ve never done things just for the money. I think money is a report card, and if you’re good at what you do, you get compensated appropriately.

I love seeing people be successful. If there’s any reward that I want at the end of my career, it’s how many families chose to be with me and are successful, and their kids are successful. Not because of me, because of their hard work, but it’s important to me to see that.

I love the stories of receptionists starting at $8 an hour, and now they’re running departments with hundreds of people under them. It’s pretty cool to watch. To me, that’s success. If I’ve been successful, there it is.

Adam: What is your approach to negotiations? What are your best tips on the topic of negotiations?

Howard: People hire our firm, debt.com, to negotiate on their behalf. I grew up on the football field. I learned to become a man on the football field in my hometown. I didn’t grow up with a father, but football taught me a lot. It was violence and roughness and hitting and beating. I take those lessons and apply it to business. It’s not because I’m a nasty guy, it’s because that’s how I roll.

I grew up a fat kid with a big mouth in an Italian neighborhood, and would walk outside and get the shit kicked out of me. Excuse my language. I probably was in between 50 and 60 fights throughout my life, fist fights. I lost most of them until I didn’t, and then once I learned I could beat everybody up.

I used to joke that people decided my nose deserved to be in a different spot on my face, and they tried to move it there. I busted my nose a few times or had it busted by people. So I take that aggressiveness.

The biggest compliment I ever heard of a gentleman I do business with, even today, he said, “That guy, Jack, would walk away from any deal.” He would walk away from any deal. I thought that’s the greatest attitude.

If the deal isn’t perfect, then I don’t want to do it. I’ll walk away from any deal. I don’t care if I get the deal. There’s no deal that’s going to change my life at this point. If I’m not happy, I won’t do it. It’s simple, either you go my way or I’m not doing it. I’ve walked away, and I’ve probably been wrong a bunch of times, but I’m old enough and stubborn enough that if I don’t like what I see, I don’t do it.

Getting back to what our clients expect, our clients at debt.com are in financial hardship, and they owe money. Our job is to negotiate on their behalf. If we don’t like the deal, we’ll give it to somebody else. There’s always somebody else that will take it.

We are extremely aggressive in what we do and in the delivery of services to our clients. We’re good at it. We’ve helped 13 million people resolve their debt problems, and we have resolved billions and billions and billions of dollars that we’ve helped our clients resolve for many, many years. Thirty-three years at one thing, you get pretty good at it.

But again, helping people, you’ve got to realize, I’m no better than my clients. I was in the same position as my clients at one time, and I know where they’re coming from.

There is nobody on this planet that understands the psychology of a person in debt better than me. I don’t say that from an ego standpoint. I say that because I was one of those people. I understand what goes through people’s minds when they don’t have money for the mortgage, rent, when their car is getting towed, when they’re getting evicted. I understand that. It’s not a good feeling.

That’s probably what distinguishes us from most competitors. I try to instill that throughout the organization, from senior-level management to the people that do maintenance and janitorial. We are client-focused. Period. We will do whatever we have to do to serve that client properly.

Don’t get emotionally involved. Don’t let your emotions get involved. Be willing to walk away if you don’t get what you want.

I was advising one of my nephews on a house to purchase, and he fell in love with the house. Personally, I think he’s overpaying, and I told him that. They weren’t willing to budge on repairs that needed to be made, and he did what he wanted. I said, “You know what? I told you how to negotiate. I’ve given you my best advice. It’s yours. I don’t want anything to do with it going forward. You figure it out.”

When you’re negotiating, whether it’s buying a house, buying an accounting practice, selling a business, remove the emotions. It’s a business transaction.

You’re talking to somebody who has bought and sold at least 50 to 60 businesses over the course of his career. I know what I’m talking about. I understand negotiation probably better than most.

I’ll tell you a cute story. It happened last year. We had this tenant in one of our buildings, and he got in trouble with the government. He personally signed on the lease. We had to put about a half a million dollars into his tenant improvement to build out the office the way he wanted, with glass and mahogany and the whole bit.

Then he put another $750,000 into the space. It was beautiful. The nicest build-out we’ve ever done.

They send me a letter, his lawyer, and he said, “Listen, we’ve gotten in trouble by the government, and we have $100,000 to give you.” I’m like, no. I wrote back, “Maybe it’s professional skepticism, but I don’t accept your offer, and I think there’s more.”

He calls me up, and he’s like, “I didn’t realize who I was dealing with.” I guess he Googled me and realized what my business is. I go, “Yeah, you’re kind of at a disadvantage.” He goes, “I realized that.”

He settled. I gave him a little break on what he owed, just to accelerate it, but we multiplied his original offer by tenfold. It was a very nice settlement.

It was funny because the comment, “I didn’t realize who I was dealing with,” was complementary, and certainly to my PR team. I guess they did their job.

Be matter of fact. Don’t get angry. When you’re dealing with somebody, whether it’s a business partner or a vendor, I don’t care. There’s not one single deal that I won’t walk away from.

We had a vendor this morning. He’s been a vendor for 30 years. He’s a great guy and a friend. He called me yesterday and said, “I just got news that you’re canceling our contract.” I go, “Really?” I didn’t know. I knew we were talking about it. He said, “Yeah.” I said, “Let me look into it.”

He called me again today. I said, “Dude, you’re overcharging us by a lot, and you’re not doing that much work.” He’s like, “Okay, let me look at it and make it right, because I don’t want to lose you, and we’re friends.”

He’s a friend, and I guess we fired him. I feel bad for him; he’s had health issues, so maybe we’ll keep him, but at the end of the day, he’s got to be competitive.

Negotiation, don’t get emotionally involved. That’s my best suggestion. A lot of people can’t separate their emotions, and chances are you’re going to lose when you can’t separate that.

Adam: How can those without strong technical proficiency successfully leverage technology?

Howard: My advice is, truthfully, I am not a technology guy, but I’m a dreamer. I’m like, what if it did this, and what if it did that?

I’ll give you an example. During the great recession, the government came to us and said, “All these people are defaulting for mortgages. Can you put a bunch of videos together to help people work out their mortgage issues?” I said, sure. That was Fannie Mae. For probably two years, 35% of Fannie Mae’s homepage was our videos. It was amazing. It was great. Never made a lot of money from it.

Then I said, this is a crazy idea I had. What if we could keep track of people’s bills in an organized manner, where they’re not doing spreadsheets? Can it be done? The guy’s like, maybe. He comes back a couple days later and goes, “I could build that.”

Then I said, “What about this? Could it do this?” He’s like, “Yeah, I could do that.” All of a sudden, we had a competitor to Mint. If you remember mint.com, which was bought by Intuit for, I think, $165 million at the time, we had a competitor. Then we sold that software off.

Then we had all these really smart computer people. I said, “What happens if we did this? Can you do that?” They come back, and they go, “We could do that.” That turned into an incredibly successful business. It was a challenging business, but it was unbelievable.

Am I technology inept? Yes. Can I get through if I have to? Yes. Am I better doing this with you? Yes.

I often compare technology to when I was a kid, I got caught in a fire, and I was wheelchair bound for a couple months because I couldn’t step on my leg, it was badly burned. I used to watch Star Trek three times a day for like four months, maybe six months. I love Star Trek, the original.

Star Trek premiered in 1969. What was the thing, the communicator? What do you have in your pocket? A cell phone. Very similar attributes.

What about a tricorder? It’s more or less an iPad.

And look at the Dick Tracy watch from the 1950s, a watch you could communicate with and get information. Guess what, the iWatch is one of the most popular watches in the world right now.

Am I visionary? Absolutely not. But do I have an inquisitive mind? Do I like building things? Yes. I used to be close to a professional woodworker to keep me off the streets. I did a lot of woodworking. I could build a house if I wanted to. I don’t have the time anymore, but I like building, I like developing.

My favorite thing is taking a blank piece of paper and writing out an idea, and then seeing that turn into a business with hundreds of people in it.

One time, alcohol comes into my life a lot. I’m not a big drinker, but I remember negotiating a contract. I had this friend of mine, he’s a good friend, very stubborn guy. We went to dinner to negotiate a contract. We ordered one bottle of wine, and we made a deal on the back of a napkin. No lawyer, no lawyering, just wrote down everything on the back of a napkin.

Then we ordered another bottle of wine, and we included all this stuff. That’s the contract. We both signed it on the back of a napkin, and it’s still in the file. We laugh about it.

Am I a technologist? No. Do I like to build stuff? Yes. Do I have a creative mind outside the box? Yeah, I do.

Could I write code? In college, we were forced to take a computer class and write something in Pascal. I don’t think I knew how to spell Pascal at the time. I can’t write anything now. It’s just not my thing.

Adam: It’s a really important message, because you don’t have to be a technologist and you don’t have to be a visionary. All you really have to do is be committed to seeing through whatever goal you set. It starts with setting the goal, and it continues with building the right team, surrounding yourself with the right people who can help you get there. As a leader, your job isn’t to be the smartest person in the room. If you’re the smartest person in the room, you’re in the wrong room, or you’re the wrong person. Your job is to surround yourself with the right people and to empower them. If you want to achieve great things, and you want to utilize technology to help you achieve great things, what better time than now to do that? You don’t need to be a technologist. You need to find people who can translate your vision. That goes back to something else that you shared earlier: the importance of communication. If you have a vision, and you can clearly communicate it to the people around you, and you can compel the people around you to buy into your vision. So often, we think that as leaders, it’s easier to get things done because we have authority and titles. But that isn’t what leadership is. Leadership is the ability to persuade, to motivate, to influence, not through any kind of title, not through any kind of position, but through empowerment, through inspiration.

Howard: It’s interesting, Adam, you’re very talented. Truthfully, you communicate well. More importantly, your thoughtfulness on leadership skills and the recognition of what works and what doesn’t work is inspiring.

Something I’ve always learned: never think you’re better than anybody.

I was walking through the parking lot the other day, getting to the front door, and I saw a piece of garbage laying there. The maintenance guy was outside. I bent down and I picked up the garbage. It was kind of gross, but it was sitting there, and it shouldn’t be in our parking lot. He runs over and he goes, “Mr. Dworkin, don’t do that. That’s my job.” I go, “I got it. Don’t worry about it.”

At the end of the day, we’re all put on this earth to serve. Whether it’s serve God or serve, in my case, it’s serve my wife. I’ve said that a couple times during this interview. But we’re here to serve, and we’re here for a relatively short period of time.

We’re all in this together, and we all have to get through it together. Some of us make a few dollars more than others, but you’ve got to treat people with respect and understand you’re no better than anybody. We’re all here together, and at the end of the day, we’re all going to be not here, and that’s just the way it happens.

So while you’re here, you might as well make it a pleasant ride. That’s what I think I’ve done, make it a pleasant ride for myself and for the people I interact with.