EPISODE 664: Picking the 2024 Kentucky Derby Winner and Leading Sales Teams with David Peed

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Today’s show featured an interview with sales leader and horse racing handicapping expert David Peed. David was featured on the podcast in 2019. Listen to the show here.

Find David on LinkedIn.

DAVID’S ADVICE:  “Like when handicapping horse racing, it’s doing your homework. My first job as an individual contributor was before the internet was really up and running. I went to the library to study my clients and learn about them. I knew holistically what the agency did, what their mission was. It’s really do your homework. Trust your judgment, trust yourself. Give yourself some credit. More importantly and equally important, follow your passions. They will fuel you mentally and other ways into a successful career.”


Fred Diamond: David, we’ve stayed in contact, and we’re doing today’s interview in April of 2024. The Run for the Roses, the Kentucky Derby, is coming up the first Saturday of May 4th. This show will be posted the week before the Kentucky Derby, but if you’re listening to it sometime in the future, you’ll get some perspective here. We’re going to be talking today about some of the corollaries between horse racing and sales. We could talk about this for hours. David, I’ve had baseball pitchers on this show. I’ve had high intense basketball coaches, and we’ve talked about a lot of sport and how it ties into sales and focus and things like that. But we’re going to be delving into something that you’re an expert on, horse racing. We’re probably going to be exposing a lot of people today to handicapping, which is the term used to pick winners at the horse track and how it relates to sales.

Give us a brief introduction to yourself, then we’re going to get your pick, and then we’re going to ask all these geeky questions that I can’t wait to ask you.

David Peed: My name is David Peed. I’m a longtime government sales executive, many different companies. The first conversation we had, we established or recognized that we both share a passion. There’s not many of us out there, Fred. I try to build longstanding relationships in the sales market. You got a special star by your name because of our shared passion for horse racing.

Fred Diamond: Actually, it is quite interesting. As a lot of people listening to the show know, I’m also an expert on Lyme disease and tickborne illness, and I wrote a book called Love, Hope, Lyme: What Family Members, Partners, and Friends Who Love a Chronic Lyme Survivor Need to Know. I’ve gone on a bunch of sales podcasts and business podcasts talking about Lyme disease and tickborne illness, the epidemic that it is. Just to bring more awareness, of course, but also to show a different side, something that I’m passionate about, because it’s a global epidemic. But it was interesting, again, when I asked you the question years ago and you mentioned horse racing, it hardly ever comes up.

For people, it’s the sport of kings. The athletes, there’s two athletes, there’s the horse, of course, beautiful thoroughbred animals that are just magnificent to see up close. Every time I go to the horse racing track and I look at the horses, I’m just astounded at how beautiful some of the top horses are. Then of course, you have the jockeys, these hundred-pound athletes, I think they’re pound for pound the best athletes on the planet. They’re on top of a one-ton animal going 40 miles per hour on a dirt track against 7 to 10 or 8 other horses, and other jockeys that are trying to win. It’s just an amazing sport. It’s a beautiful sport.

Just one of the quick things too, is during the pandemic, one of the only sports that was on TV was horse racing. There are some channels that are devoted a hundred percent 7 by 24. There weren’t live sporting events happening in baseball or basketball. A friend of mine and I used to watch horse racing around the clock, horse racing from Australia, horse racing from the US, and it also exposed a lot of people to it.

First of all, tell us how you got into this. How did you develop your love for horse racing? Then we’re going to talk a little bit about handicapping. You’re going to give us your Kentucky Derby pick, and then we’re going to tie it all into sales. How did you get into a love of horse racing?

David Peed: Let me first congratulate you or just tip my hat, Fred, for what you’ve done on the research for Lyme disease and arguably comparing Lyme disease and the challenges that you faced in your personal life and horse racing. I tip my hat to you because what you did is amazing.

About the jockeys, real quick, horse racing is probably the only sport that the ambulance follows the athlete around the track because it’s so dangerous. But to your original question, my dad would bet on if two ants were running across the sidewalk. He was a gambler. Horse racing, poker, lottery, he did it all. Paid for my brother and I to go through college, so he wasn’t losing the rent money, but if there was an argument in the house, it was over gambling.

As I like to say, I got the horse racing gene and my brother got the poker gene. But the short answer, it’s from my father and just started going with him when I was five years old. Started handicapping, and in translation for the folks is researching. There’s a couple periodicals that are published that you can read about them. I think when I was seven officially is when I started handicapping. But the passion came from my dad and really going pretty much on a weekly basis with him.

Fred Diamond: Handicapping, let’s talk about this for a little bit. For people who don’t necessarily know, there are some historic documents that were printed. One was called the Racing Form. For every race that you’re watching, so let’s say it’s the third race at Belmont, a beautiful park that they’re redoing, in New York. The third leg of the Triple Crown is the Belmont Stakes. Let’s say there’s 10 horses entered into that race, they will give you the past performances of all those horses. A horse race handicapper will look at that data and try to figure out who is going to win the race, who’s going to come in second, who’s going to come in third.

Tell us a little bit about your process for handicapping a race. The reason it’s important here on the Sales Game Changers Podcast is there’s data available to you, and we frequently speak on the Sales Game Changers Podcast about how to gather and use the right data to understand how you could bring value to your prospects, how you can delineate yourself and differentiate yourself as well. Give us some insights into really what handicapping is, all the data, and how you go about it.

David Peed: Actually, when we talked about having this conversation, so I’ll go back to one of your original statements, you said you’ve had baseball. I’m a big believer in opening yourself up and being transparent, letting people know about yourself. I would argue that I’ve learned that there’s a couple good things that I’m good at in life. One is, I do believe I’m pretty good as a leader in the government sector and the IT infrastructure. I did pretty well at coaching flag football, and lastly, and passionately, horse racing. Again, trying to not parallel in the business world, I think whatever your passion is, you can draw parallels.

The Daily Racing Form, some will call it the horse racing bible. There’s multiple different periodicals that are published, some giving the data in different formats. Reality is, most all the periodicals will give you very similar data, just usually in a different user and a different cost. The Daily Racing Form has gone from when I was a kid, probably $1 to $12. Some of the racing fans will scoff at the cost and say, “Geez, $12.” But reality is, and like in sales, and I think the analogy to my life and the business world, you got to do your research. Data is critically important in this time of where AI and the ability to process data is changing so rapidly. To me, it’s really critical. It’s a critical element in almost too many ways of how I start to approach it as far as when I get in, when I start reading the Racing Form.

But what I’ll highlight is, and again, analogous to the sales process, there’s usually the angles that I’m looking for. An angle, as a handicapper would say is, there’s something happened to this horse that there’s some famous angles, which third race off layoff, which would mean if a horse had raced for a year continually and then took a three month break, three races after that return they would argue would be the horse’s peak performance. Then there’s many, many, many that I look for. Again, in the sales process, I think that’s really critically important that, A, you’re doing your research and you’re getting as much data about the customer as you possibly can. Then more importantly, using that data to your benefit.

Fred Diamond: That reminds me of something here. In sales, we try to get as much data on the customer or the prospect as possible. We get that in a couple different ways. Of course, we could go to the internet, and you mentioned a good point, AI gives us a lot of access to information about what companies might be dealing with right now, from the largest companies in the world to smaller companies. We gather that data. Then a lot of the data that we have to capture though, is from conversations. With people at the company, maybe some partners who are also selling into that company. Trying to get some insights into what’s really going on, because we don’t always have that perfect information. We don’t always know, maybe there’s an executive change that’s happening, maybe there’s a financial challenge that’s happening. Maybe there’s a regulatory thing.

We could find as much of that as we can in the public domain. Basically, the Racing Form is the public domain. They show you exactly how the last, if the horse has been running for a while, I think it’s 8 to 10 races, and you see what their speeds were, what place they came in, where they were throughout the race. There’s a lot of the data. The problem is you don’t get to talk to the horse. You really can’t talk to the jockey either.

Give some insights into that, and related to sales, where you have a ton of information. It used to be, again, just the Daily Racing Form. You had some guys who’d maybe give you some tip sheets, some guys who hang around the track and here’s the top three. But now there’s so many computer programs out there that are using advanced data technologies to map out how the race “should go”. But it doesn’t always happen that way. Give us some of your insights into what we learn that we don’t know at the track. Also tying that into sales where there’s missing information. Maybe you find out afterwards, why did we lose that deal? We just found out we lost that deal because the director of IT had a bad experience with your company 10 years ago. Give some insights into that.

David Peed: It’s been about 10 or 15 years, but I got into owning racehorses about 15 years ago. My dad, who was suffering from Parkinson, who I spoke of earlier, was my entree into this game. I really thought it was going to be something that would distract him from his illness and bring him great joy, and I was wrong. That’s a whole other podcast. But when the people who watch this, when you watch Kentucky Derby, there is nothing wrong with any of those animals. All 20 that load up are going to be in a hundred percent shape. On a day-to-day basis at the racetrack, every horse has an ailment. I want the listeners to know it’s not anything harmful. Nobody would run a horse that would knowingly not be fit. There’s track veterinarians and there’s processes that the racetracks do to do their best to ensure, and they do a phenomenal job.

That said, one of the funny things that the track is, everybody’s got a buddy and everybody’s buddy’s got an inside track to somebody and the owner. As an owner, I know, I have the trainer give me a perspective. The perspective is that the trainer’s told me this horse can’t lose. It’s going to win a race. I think really the translation is that they’re telling you that the horse’s ailment is at a place and time that he’s going to run his best. They certainly can’t guarantee you they’re going to win that certain race, but what they’re really telling you is they’re going to run the best.

I think analogous to what you were saying is that it is critically important to turn over every stone. I’ll do another analogy. There was a movie called Other People’s Money, and it was Danny DeVito. Basically, the movie was around he was a Wall Street M&A guy, and he was going to buy this company, and the company was fighting tooth and nail. But the company, what they were building, it wasn’t going to be longer-term successful. It was a dying industry. I’ve often thought it would be a good thing for whoever, if you are going through business or in the business school, they should make you watch that movie. But back to the horse racing, it really is you have to really do your homework and not leave every stone unturned, because to your point, if said IT director had a bad experience and you don’t know it, you’re just going to waste your time.

Similarly, as I tell people, couple things, if you go to the track with $200 and there’s 10 races, everybody’s thought is, “I’m going to bet $20 a race.” I’m like, “Divorce yourself from that thought and bet the race the way you like it.” Meaning that maybe you don’t bet a race because the horse you like is one to five. You can bet your money, but you only get 10 cents on your dollar. Bet the races the way you like them.

I think analogous to the sales process, you’re focusing on the best. You can chase the wrong deal for the right reason, but reality is doing that homework and making sure you’re focused on the right deals is important. Same with horse racing. It’s focusing on each race as the race lays out.

Fred Diamond: I just want to go back on one thing that you said, just to reiterate. People in the horse racing industry love horses, and the care that they give. Each horse has a number of handlers, it’s fed, it’s taken care of. The purpose is to win races and to make money and then to maybe move on to breeding horses, et cetera, for the right horse. But the love that the people have on the track for the animals is truly genuine. They’re such amazing animals that people would not treat them otherwise.

I want to raise an interesting point you just said here. Every single race, there’s odds. Let’s say again, there’s 10 horses, you’re going to have a favorite, and the favorite’s probably going to be maybe two to one or somewhere around there. Then depending on the horse’s ability that the public thinks it’s going to win, the odds will increase. Maybe the second favorite, maybe three to one, and then 5, 6, 10, 20, 50 to 1, it might be.

Talk about that for a second, about how that relates to what sales professionals listening should be spending their time and energy. Maybe if the 50 to 1 horse wins and you bet 10 bucks, it’s $500. That’s the whale. That’s a home run. That’s going to be a big win. But the odds of that 50 to 1 horse winning are slim. It’s just not a great fit, typically. Yeah, those horses will win. In the Kentucky Derby two years ago, there was a huge upset. A horse that was almost 100 to 1 came in to win.

Talk about your advice for sales professionals, and using the horse racing analogy, on spending your time. You began to touch on that, about do you like people going after the whales? Maybe you spend one bet per week or something on the 50 to 1 shot. Because you’re probably going to lose money if you keep betting the 50 to 1 shots. Same thing as a sales professional. If all you’re doing is going after the home runs, eventually you’re probably going to get out of business because there aren’t as many of them. The likelihood of them happening is slimmer as well.

David Peed: Just for the audience, the odds are established, if you think of 10 horses and there’s $5,000 bet, they just basically do the math of the percent of how much was wagered on the horse to establish. They’re doing mathematical process to establish the odds by how much money’s been bet on each horse. If you had $10,000 bet and $5,000 has been bet on one horse, he’s going to be a heavy favorite. Hence, you’re going to get some long shots.

It’s a great question, and I think my answer is going to make a ton of sense to the sales executives, is that, and without sounding arrogant, I know what I’m doing at the racetrack. I know what I’m doing in government sales. Trust your judgment. I won’t bet on a horse if he’s a heavy, heavy favorite. Because to me, I’m not going to risk $5 or $10 on a horse that I would make just a couple dollars of profit. Not insinuating you’re trying to always hit the home run ball, but if a horse originally was two to one and he goes to eight to one, I don’t look at that and say, “Something must be wrong. The public doesn’t like this horse.” I look at it like, “They’re missing something.”

It really is the same thing on the sales process. It’s basically stick to your guns, trust your judgment. You’re going to win some and lose some. Then one of the worst things you can do at the track, I’ll have people that will bet $2 to win on every horse in the race. Look, if that’s what you want to do, and I’ll tell you a funny story about doing that, and when I did it and why I did it, if that’s okay in a second, because I think you’ll enjoy it. But trust your judgment. Do your homework, and don’t look at it like you’re doing something wrong. Look at it like you’re doing something right. Just resolve yourself, that if you lose, you lose.

In a quick diversion, when my dad passed early in one morning, I went down to see my mom. On my way home, I stopped at the racetrack and I bet $5 to win on every horse in the race. There were seven horses. I stayed to watch the race, and a 99 to 1 shot was winning by a length or two coming into the stretch. I looked up into the sky and I said, “God, please don’t make me make this decision,” because I was actually going to put the ticket in my dad’s coat pocket to send him out a winner. Fortunately, the man upstairs, the five to one shot came in and I happily put that five to one shot. It was just going to challenge me to maybe stay for another race if the 99 to 1 shot won.

But back to the question at hand, trust your judgment. You’re in the business for a certain reason. You’re in the role you’re in for a certain reason. Trust your judgment. In business, as I tell my friends, if you bet against yourself, meaning if you bet multiple horses to win, you’re conceding that one of them is going to lose. More importantly, your return on investment is going to go down. The ROI is really the big driver in business and profit margin. Similar like when you go to the track, the more you dilute your wagering, the less your return on investment is going to be.

Fred Diamond: Again, the Run for the Roses, the most heavily bet on sporting event of the year. I guess probably, maybe the Super Bowl, I don’t know. It doesn’t really matter, but it’s the first Saturday in May. It’s at the beautiful Churchill Downs. It’s on May 4th in 2024. Have you been to the Kentucky Derby in person?

David Peed: I have. I had a guy that worked for me years ago when I was at Qwest Government, before it became CenturyLink, before it became Lumen, that insisted that he take me to the Derby. We were going to a conference in Nashville. I think it’s about an hour and a half, two hour ride from Nashville over to Louisville, Kentucky. He was like, “I’m not taking no for an answer.” I did check that block. I went to about 30-some Preaknesses in a row, my dad. I attended that, which for the listeners, that’s in Baltimore and the last is in New York at the Belmont. But yeah, I’ve been to a derby. It’s wonderful, wonderful, and I think it winds up to be on a lot of people’s bucket lists. Because Even people who don’t follow horse racing have heard of the Kentucky Derby, and I think many will be celebrating on the first Saturday in May with some mint juleps at their house.

Fred Diamond: I got to definitely add it to my list. It’s one thing I definitely want to do. You’re going to gift us here with your selection. Again, we’re doing today’s interview in early April. Some things can change when the show goes live here. Of course, horses get hurt, even one of the favorites. I think either it was last year or two years ago, I forget, the horse was scratched right before the Derby, one of the large favorites. David Peed, put you on the line here, give us your pick for the 2024 Kentucky Derby.

David Peed: If it’s okay, I’m going to give you three horses. Just real quick for the audience, it came on everybody’s bucket list, so they had to come up with a point system to enter it. Because everybody wanted to enter in the Derby, and they actually, quite honestly, had horses entered that shouldn’t have been in the Derby. This is the second time for me in probably 10 years that I’ve liked a horse for a while. I typically will wait till the day before, but I’ll just give the folks really quick.

The favorite for the Derby will be a horse called Fierceness, as long as nothing changes. If there’s any injuries or ailments, they will scratch these horses and they will not run. But the betting favorite on Derby Day, most likely is going to be a horse called Fierceness. I would definitely use him as a trifecta. That’s when you’re picking the first and second place, and the trifecta is for second and third. There’s a horse called Sierra Leone who ran a big race in the Bluegrass Stakes a week or so ago, who will wind up on my ticket. But my pick, and I’ve liked this horse before, he won the Louisiana Derby, is a horse called Catching Freedom. He had four races prior to Louisiana Derby, ran first in two of them, and then the races he didn’t win, he had trouble. He won the Louisiana Derby. He came from last place, passed the whole field. I think he’s a derby horse, and I’ve been excited following him for some time, but Catching Freedom is the pick.

Fred Diamond: That’s a good choice there. Good luck. I know I’ll be watching it on May 4th. I want to thank David Peed for being on today’s show. I remember, when you mentioned horse racing, it was just out of the blue, didn’t expect it. My father also took me to the track, and I went back and told him that. He enjoyed that we talked about it and I’m glad we had the chance to talk here today. Again, I want to encourage the listeners, if you want to know anything more about horse racing, it is a beautiful sport, reach out to David.

One quick question before I ask you for your final action step for salespeople. What’s your favorite track? You mentioned the Preakness, which of course is a Pimlico in Baltimore, but I’m just curious, what is your favorite track to go enjoy races at?

David Peed: Without hesitation, Saratoga is just something out of a movie. Del Mar is gorgeous. You can actually see the Pacific Ocean from the grandstand at Del Mar. It’s right in La Jolla. It’s a gorgeous town, gorgeous place, but not even close to Saratoga. It’s just something out of a movie. For golfers, it would be like Augusta. It’s a throwback. I can guarantee you, the listeners, if you go to Saratoga, you’ll enjoy it. There’s a ton of things to do for folks who are not into the thoroughbred racing, but I think if you go for several days and go to the track one day, I think you’ll wind up enjoying yourself there.

Fred Diamond: I go there every summer as well. I’ve been there a number of summers. It’s about an hour and a half north of New York City, I guess, maybe an hour north of Albany. It’s historic. It’s huge. It usually like an eight-week meet, I guess. It’s like the summer meet for New York, basically. They have some of the classic races like the Travers, and I’ve seen celebrities there. It’s old school too, where you could spend the day and have an amazing meal, and you could go right up to the paddock. They actually walk the jockeys through a public area, and the horses for that matter.

A lot of times in a lot of tracks, it’s a back door into the stable. They put the equipment on the horse and the jockey gets on, and then they enter the track. But in Saratoga, you actually see the horses walk through where people are just sitting, having a picnic and enjoying lunch or whatever it might be. There’s a lot of food there as well. I recommend Saratoga, and I’m looking forward to heading up there one day this summer.

David, give us a final action step. We talked a lot about interesting things here. Give us your advice. It doesn’t have to be necessarily about horse racing, but give us your advice for sales professionals. Again, you’ve led hundreds, if not thousands of sales professionals. Give us your final thought on what they can do to take their sales career to the next level.

David Peed: I think we touched on it. It’s really doing your homework. My first job as an individual contributor was before the internet was really up and running. I went to the library to study my clients and learn about them. I knew holistically what the agency did, what their mission was. It’s really do your homework. Trust your judgment, trust yourself. Give yourself some credit. More importantly and equally important, follow your passions. They will fuel you mentally and other ways into a successful career. That’s my thoughts. I really appreciate you having me.

Fred Diamond: You’re welcome. This was a fun conversation. Again, I encourage any of our listeners, if there’s something else that you are passionate about and you’re a sales leader, reach out to me and I could talk about a lot of these things. Like I said, I’ve had some of these athletes, asking pitchers what’s it like to be on the mound, focusing on mindset. There’s so many other areas of the horse racing game. It truly does relate because there’s so much data and there’s so many factors to consider. There’s also beauty to it as well. Just physically, even if you’re not paying attention to handicapping, just going to spend the day at the track and watching the horses. You’re outside, you’re seeing these amazing athletic animals, and again, the jockeys as well. Just spending the day just observing is also something we could learn as sales professionals as well.

Transcribed by Mariana Badillo

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