EPISODE 022: Gary Milwit Became a Sales-Coaching Superstar by Doing What He Said He Was Going to Do

EPISODE 022: Gary Milwit Became a Sales-Coaching Superstar by Doing What He Said He Was Going to Do

Gary Milwit is the president and chief operating officer at Stone Street Capital, headquartered in the D.C. Metro area. Gary is a former high school football coach, teacher, and athletic director who left public-sector work in 2000 after being recruited by Earth Networks to run its education and government-sector business. In 2006, Gary was recruited by Stone Street Capital, where he held the roles of senior VP of sales, senior VP of business development, and chief operating officer before being asked in late 2016 to take over leadership of the company. Gary is a multi-award-winning sales leader, trainer, and coach. In 1996 he was named as the Maryland State Athletic Director Association’s Athletic Director of the Year. In 2012 he won the Best in Execution Award from the American Association for Inside Sales Professionals, and in 2013 he was named the American Association for Inside Sales Professionals’ Executive of the Year. Under Gary’s directions, Stone Street Capital won the Institute for Excellence in Sales Best in Sales Training Awards in both 2015 and 2016.

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Fred Diamond: Why don’t you tell us a little more about yourself?

Gary Milwit: I have a wife of 22 years. She and I both started teaching school around the same time. She’s now the CFO of the Montgomery County school system, so I’m very proud of her. I have two kids. One is a senior at Tulane University in New Orleans, and she’s the editor-in-chief of the Hullabaloo newspaper. She’ll like that plug I just gave her. My son is at Rhodes College in Memphis, TN, where he is a two-time letter winner for lacrosse.

Fred Diamond: Gary, when we announced the Sales Game Changers Podcast I must have gotten about a half-dozen suggestions that we come interview you. I’m really excited for this conversation. We’re going to spend the first part talking a little bit about your career, getting some of your insights on how sales professionals can be as successful as possible. And then on the second half we’ll get some of your tips. Gary, how’d you get into sales as a career?

Gary Milwit: Well, let me take you back just a step before I begin, because I’m the guy who doesn’t believe that sales actually starts as a career, because there’s no major in college for sales. We all know that, and we kind of get into sales. But I thought about this for a couple of days now. My first sales job was actually being the athletic director of a public school. We had to sell programs. We had to find booster-club members. We had to raise money, a lot of fundraising. My first sale that I ever really made that I’m proud of was we had our press box built and sponsored by Century Ford in Rockville way back in the day, well before MCI Center or FedEx Field. We had this press box by Century Ford, and it cost me a couple of sessions in the superintendent’s office back then. But that was my first sales job, and that’s where I learned how to be a manager more than anything else.

Fred Diamond: Gary, what exactly do you sell today and what excites you about that?

Gary Milwit: I’m at Stone Street Capital, and I’ve been here now 11 years. We buy annuities. You’ve probably heard about some of our competition out there, but we buy a structured set amount of payments, and we buy lottery-winning payments, and we buy anything that comes in the future and we pay present value for that. Essentially we’re not selling anything. We’re buying. Our salespeople are called buyers, actually. But what excites me about it, it’s a business consumer. It’s a consumer space. Everything that we do has to do with sales and marketing, marketing on the front end, sales on the front end, metric-driven inside sales for the most part… We try to make good things happen for other people, and that’s really why we keep on coming to work every day.

Fred Diamond: That’s very good. Let’s go back to some of those first few sales jobs. You mentioned, of course, you were an athletic director and not necessarily in a traditional sales job. Tell us about some of the lessons from your first real sales job or from when you were an athletic director that has stuck with you today.

Gary Milwit: I actually have done a couple of different types of presentations about sales coaching and the difference between coaching and mentoring and management, and I have two people I would consider to be real, real strong mentors for me.

The first you may have heard of, he’s been in the news lately: Richard Trumka is now the president of AFL-CIO. Richard was my booster-club president when I was at Wootton High School, and he told me one thing and it’ll stick with me. I was 26-years-old when I had that job, Fred, and I was the youngest athletic director in the country [in a] public school. Rich came into my office and said, “I’m going to be your booster-club president whether you like it or not.” He’s a big guy, played football at Penn State, and he said, “All you need to ever do in your lifetime is do what you say you’re going to do and follow up and just do it. If you say you’re doing it, you’ve got to do it.”

It sounds like normal regular everyday advice that I would tell my kid. I wouldn’t maybe tell my kid that if Rich didn’t tell me that back in 1996, actually in 1994. It was life-changing because people expect you to do things that you say, and people won’t think about what they say. In that particular job the goal is 51% of everyone wins. If you have 51% and it’s the right 51%, you’re good to go. You don’t need the other 49%. Rich taught me that. I’m forever grateful. I see him every now and again. When I do it’s always a big hug, and I appreciate that.

The other, a former high school football coach, hall of famer, Bob Malloy, who just retired this year from Good Counsel High School. When I was back at Springbrook High School in 1988 coming off a state championship, I was a young football coach. Bob said, “Whatever you do, don’t end up in the Washington Post for anything.” Because he’s the headcCoach, he talks to his board, what he really meant was “Don’t do anything wrong.” Just do the right thing all the time. Your litmus test is “Do you want your parents to read about this in the Post?”

Right now we’re in an industry that has some controversy that surrounds it. Some of our competitors get in the newspaper for the wrong reasons. It’s very, very easy to get everyone trained and everyone on the same page going, “That’s not what we do. We don’t want to be on the news for anything other than helping people.”

Those are the two that stick out. Those are my favorite two, and there’re plenty of others along the way. In fact, one of my greatest mentors now works here for me. Terry is our operations manager here. He was our senior vice president at Earth Networks when I went there. He taught me about operations and now he runs our operation. It comes full circle.

Fred Diamond: We’re going to go a little bit off script here for a second. You mentioned your employees are called buyers and not salespeople. What are some of the challenges with selling what you sell?

Gary Milwit: If you win the lottery—there are big, big lottery wins every now and again, but let’s just say you win a million dollars. You win a million dollars off a scratch-off ticket that you bought at the liquor store, and you get $50,000 a year for the next 20 years. I could tell you definitively that at a discount in which we have to do, it’s only worth, in today’s money, a little less, maybe around $400,000, maybe a little less. People say, “Why would I give you a million dollars for less than $400,000?” You have to talk to a lottery winner who just won and explain to them the present value of money, and that’s not easy to do. It’s very psychological.

My wife, who’s a mathematician, CFO of the county school system, has $4 billion budget. She mentally can’t get past the fact that there is a discount rate applied to present value. She understands interest rate, but discount rates are very difficult to understand. And it’s not about what the money’s worth; it’s about what we think it’s going to be worth. We have to buy that money and get it later. That’s the most difficult thing. It’s not about the price of the deal or how much I can give you for that money. It’s about what makes that transaction work for you as the winner because you don’t have to buy it all.

We get kids out of college, and we try to train them up and get them to where they are really good at that, and that’s the main thing. You’ve got to really think about the customer and not about anything else. But it’s hard to explain that their credit-card debt is at 22% and our discount rate is at 12%, and all I have to do is sell some money that they don’t even have and they could pay that credit-card debt and make double the amount. That is a difficult, difficult proposition.

Fred Diamond: What is the success rate? Is this the kind of thing where you need to talk to a thousand people to get a sale or one out of ten?

Gary Milwit: Let’s just take, for instance, our online spend. We’ll go on a PPC spend for, let’s call it for the sake of ease $100,000. We’ll get qualified leads out of that, call it 50 or 70 qualified leads. Of the qualified leads, which means that they will have a structured settlement that we can buy, we’ll close 10%. Right out of the first 15 days. Maybe we’ll close 33% over the course of a year, so that’s the success rate. Three point three out of ten will close and do a transaction with us on that. But of the 33% that do, only 10% of all the leads are even qualified. We have to cut and call through all that, so it’s a whole process.

Fred Diamond: Take us back to a specific sales success or win from your career that you’re most proud of. What’s the number-one specific sales success?

Gary Milwit: I’m going to have to take you back to when I was running energy trading software at Earth Networks. Earth Networks is formerly WeatherBug… Some really smart people came up with a software that told energy traders what the weather was going to be like in real-time. The National Weather Service gives you 30 minutes in arrears on the weather, and we would give you real-time. I would go to energy traders and let them know that there was this software that was available that nobody else had and they could actually try to save a penny or two on energy trade, a transaction, if they had real-time data. My best sale I’ve ever made in my lifetime was at Morgan Stanley.

After about a year of being there and giving them some software and some products, I went to dinner with them and their managing directors, and they had a real problem. The problem was they had all those weather data, they didn’t know how to read it. In the old days before regulation, energy companies would trade their own powers. Dominion would have a power desk, a meteorologist, and then they would have the traders. In the back of the Reagan years they separated it all, so they made regulation. And then Enron came, so there was more regulation. Then the banks ended up at the energy trading desk, not the Enrons of the world, and they didn’t have a meteorologist. They didn’t even know what to do with the data.

We had plenty of meteorologists, and lots of them actually used to work for these power companies, but no one knew about it, and everyone was kind of afraid to get into it. I found a couple of meteorologists who were energy trading specialists, and I became a staffing agent, a software company and a hardware company all in the same day, and we made a sale to Morgan Stanley that was in the seven-figure range.

Fred Diamond: Gary, you’ve had a great career in sales. Did you ever question being in sales? Was there ever a moment where you thought to yourself “It’s just too hard” or “It’s just not for me”?

Gary Milwit: Of course. I don’t know anyone who’s ever been in any kind of position where they’re stressed who hasn’t gone, “Oh no, what am I doing?” I tried to tell them I have kids. My daughter who’s, like I said, editor-in-chief of a newspaper, she’s just learning this year that the newspaper doesn’t run unless there’s a sales staff. She’s just literally learning that, how important it is and then how important it is to get just that simple trade done on that level so they can run a newspaper.

My son was here this summer with two of his college roommates as an intern, and he learned that the business doesn’t run unless they’re actually selling. I have always said, “Stress, except if you’re a police officer or if you’re a fireman, stress equals pay.” If you’re under stress and you have some real kind of consternation about what you’re doing, it means you’re going to get paid. So I look at it and go, “Look, I could handle the stress. I’ve been taught to handle stress. I actually don’t mind it, don’t mind pressure.”

But we have a responsibility, so every time I look back and I go, “Should I really be doing this?” or I talk to someone who’s really kind of questioning it, the question is “Do you want the responsibility to bring sales in that support the rest of the company?” If you want the responsibility, you have to accept the responsibility, and if that’s your thing then you should never question what you’re doing.

Fred Diamond: What’s the most important thing you want to get across to selling professionals who want to improve their career?

Gary Milwit: Listen to this podcast would be the first. But in all seriousness, you have to be a lifelong learner. One of the things that your organization does, Fred, probably better than most, you offer education… We talked about that before, how people’s ship kind of moved into the sales desk. They didn’t come out of college and they didn’t come out of the womb and say, “I want to be a sales guy.” There’s no such thing as a born salesperson, and I know you’ve heard the term.

What happens is people end up there and when people end up there, if they have the wrong team around them or the wrong mentor, the wrong manager, they believe that they got there because they’re just really good instead of understanding how they got there and how the whole thing works. If you’re not educated and you don’t educate yourself, then you will believe that you’re a magician and not a salesperson. You have to stay ahead by reading, going online, training yourself, getting coached, finding mentors. It’s the only possible way.

You can get more information on the computer than ever before. For me, I have one book that I read at least twice a year. It’s by a guy named Bill Brooks. Bill Brooks is a former football Coach and a Sales Trainer. I gravitated to him when I first got out of teaching because he was a football guy, and he had a sales-training company. He wrote a book called Sales Techniques. It’s that simple. If you can learn a sales process and understand that there’s an art form and then there’s a science, if you can blend those two things together you can actually become a career salesperson, and that may be the best job there ever was. I personally have never been able to be a career salesperson. I ended up in management before I ended up selling. I had this weird kind of course, and now I’m the president of the company.

But I can tell you definitely that our job here and the way that we make things work here is we bring in kids from college, right out of college, who don’t even know what they want to do. They could have been an art major; I have one right now who was an art major. She’s great. We teach her process. We teach her how to sell, all the sales techniques that you need, the skills and techniques, and what happens is these people start to realize what’s good. If they end up here, great. They always last for a year or two or three. If they get past three, they’ll be here forever, but if not they have made us some money along the way. They’ve made some money along the way, and they could walk into any interview in the country, whether it’s going to be an art studio or a sales job. I have a process, and the only way to get better at what you do is to constantly hone your process. If you don’t have it you’re done.

Fred Diamond: Gary, what’s a major initiative you’re working on today to ensure your continued success?

Gary Milwit: Our major initiative right now as we speak is to build a sales team that will scale. Our whole company really, a company that can scale, not just add people when there’s more work to be done. What I mean by that is we have to train and coach and mentor and be able to handle the whole operational process so that we can add to our marketing spend, get more leads, and not have a lot more work to do—more “let’s do the right thing.”

My initiative right now is hire the smartest people I could find and let them gravitate towards positions, not pigeonhole people, and more importantly, let them create processes. Because processes will trump policies, and I don’t have to write policy. It gets the bad guys, the bad operators. I can have great processes that work, and the people here can actually write the process and create the workflow. If it works, great. If it doesn’t, okay, because we have to be able to make some mistakes.

Fred Diamond: Sales is hard. People don’t return your calls or your emails. Why have you continued? You have a great reputation as a sales leader. What is it about sales as a career that keeps you going?

Gary Milwit: It’s the ultimate game of golf, so to speak. You get to be an individual, you get to play, but at the same time we get to coach. I gravitate towards the inside sales groups because it’s more like a football team. Inside sales I could actually stop, like a football game stops. A whistle blows, you could call a timeout. You could walk out in a huddle, you could bring a kid off, whatever it is. In the world of golf or tennis, the coach is in the stands or on the side. They can’t talk to the player till they get back to the range. That’s your outside sales group. Your outside sales team, you have a bunch of golf coaches. They teach you to swing. They teach you the techniques. But when you’re in the room, unless they go with you, then you’re all alone. You have to be able to do that.

I gravitate towards the football group, which is my insides team. I could stop the play any time I want. All I have to do is just have another person answer the phone. So inbound, lots of people, big energy. But the real answer to your question is it’s not that much failure if you look at it the other way. We succeed five out of a hundred times. Is that good or bad? We succeed five out of a hundred times. Those five times are massively good.

Fred Diamond: Can be.

Gary Milwit: Right, so it’s not 95 failures. It’s 95, you’re 95% closer.

Fred Diamond: Gary, give us one final thought that you can share to inspire our listeners today.

Gary Milwit: You can’t make a sale, you can’t get to the next level unless you can engage someone, encourage someone, build rapport, and earn some trust. And before you can do anything you have to check those boxes. Once you do that you’re allowed to ask anybody anything you ever wanted, because there’s nothing out of bounds. If you earn a little bit of trust, build some rapport, engage somebody, and encourage somebody, you have the green light to ask the question “Can we get this done today?”

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