Mike Rideout On Coaching, Sales, And Career Development For The Youth

Engaging in sports is a large part of most children’s formative years. How they are coached through that process also has a great impact on how they grow up. In today’s episode, Mike Rideout shares his perspective on youth sports and the importance of guiding kids instead of forcing them. Mike currently works in Business Development at International SOS. But more than that, he is also an incredible coach, mentor, and parent to his kids and their peers. Mike shares some of the projects he worked on in youth development and his passion for helping the youth find their calling. Join his chat with host Evan Brandoff to learn more about how his sales and business development work helped him become a better coach and parent.

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Mike Rideout On Coaching, Sales, And Career Development For The Youth

In this episode, we have Mike Rideout. He had an extremely impressive career in sales and entrepreneurship, starting his own company to support young men specifically, but he is also such an incredible coach, mentor and parent to his kids and his kid’s peers. I’m excited to have him talk about leadership, coaching, sales and so much more.

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Mike, welcome to the show. Thank you so much for coming on.

Thank you, Evan. I’m thrilled to be here. Anything I can do for you. No doubt about it. Congrats on your marriage. I’m very happy for you.

Thank you so much. It’s October 26th, 2021. I see the Halloween decorations in the background. What are the big Halloween plans for the family?

Two of my kids are teenagers, so they’re going to go on their own. They’re off. See you later. My other kid is doing the thing where she’s got four friends who are all dressing the same and scarring the neighborhoods. I tend to be a little bit of a Halloween Grinch. It’s not my biggest holiday, to be honest, but we did some great pumpkin carving. Nothing too special. With the teenage boys, I won’t see them until later in the night. Hopefully, they don’t cause too much chaos in the community.

Mike, we’ve known each other for many years and something that I’ve always admired so much about you is how good of a parent and coach you are, not only your kids but your kid’s teammates as well. I want to start by going back to teenage Mike. What was teenage Mike like?

I grew up with a best friend. We were inseparable starting at three years old. He was the absolute best athlete, still have maybe ever met. Also, extremely good-looking. He was the star of the town. The kid was the kicker, punter, kick returner, punt returner and quarterback. Teenage Mike had to find his way and became more involved in student politics. I was looking for attention and I ran for it. I was the vice president of the junior class, then I was student body president and always an average athlete. I could have been better had I wasn’t in his shadow.

I was trying to make my mark and trying to escape the neighborhood I grew up in, which was low-income projects. I had a mom who drilled into me on a day-by-day basis how I was better than that neighborhood. I don’t need to end up there. That led me to being student body president, doing well in class, getting into a private school that I paid for my own versus going to the state school that people thought I should have gone to. It was insecurity and also ambition. All mixed up together.

You went to a private school. What did you study in school?

I was an English major. I love to read. Frankly, I went into as an accounting major. After my first statistics class, I went to the Dean’s office and said, “I’m going to go with English.” I realized my brain was not math-driven. It was much more about literature, writing and so forth. I was an English major at Saint Michael’s in Burlington, Vermont.

You’ve had an extremely and continued to have an extremely impressive career in sales and entrepreneurship. How did an English Major from a liberal arts school end up going into sales?

Unfortunately, I didn’t have enough direction as a kid to say, “What do I want to do?” Either from parents. I can’t say enough about my mom. I was raised by a single mom, but she wasn’t a college graduate and the type of person who would say, “Let’s sit down and map out what you want to do with your life.”

I got that first job out of school in marketing that one of my former college friends helped me get. Part of that job was to convince schools to let us do some marketing on campus. Your audience will probably be cast by this but we were selling phone cards for Sprint. Get that old, dial in that number and be able to call mom and dad on her phone card, pre-cellphones.

I was booking so many schools so quickly that everyone in the office, I can remember, kept telling me, “You’ve got to go into sales. You have to be in sales.” You heard it enough and I said, “That makes sense if that’s what everyone’s telling me.” I did. I was very social, so it made sense. I went and started applying for sales jobs and got the first one I applied for at a newspaper in Boston, which was the equivalent of the Village Voice. It was called The Boston Phoenix. It was a newspaper that focused on culture, local bar scene, band music scene, and so forth. That was the beginning. Years later, I’m still in sales. I’ve sold everything from $40 ads to $20 million digital campaigns and everything in between.

Sales is a craft. It’s not something that everyone can do.

What’s the most exciting deal that you’ve ever closed?

Exciting is different from fun. Exciting was the $20 million deal between Citibank and Microsoft. That was exciting because, at the time, Citibank wanted to create something like PayPal because they had pipes into every bank in America. They thought they could create a payment system. This is early in the days of person-to-person payments. It took 12, 14 months, SEC lawyers, and a 125-page contract that we were redlining at midnight.

It culminated in flying to Seattle, having Steve Vollmer come into the room to sign on our side. Deryck Maughan, who was the Vice Chairman of Citibank at the time, was flying in on a private jet with his team, and it was impressive. He came in and had 6 or 7 lieutenants. He told them, “You sit there.” He mapped it all out. Steve Vollmer comes in. We go through the final iterations of this deal and sign it right there on the spot. I’m back on a plane. Two hours later, I went back to New York.

It was super thrilling and exciting. It’s something I never expected to be doing. A few days later, that deal ended up in one of The Wall Street Journal. We had that framed and put that in our boss’s office. They weren’t the most fun sale I’ve had, though. I started in health benefits and because it was a small business in that, I was building my book. I was driving Uber for extra income.

One of my writers said, “Why are you driving Uber?” I guess I don’t fit the profile of an Uber driver. I said, “I’m building this small business practice.” He said, “We need to review our benefits.” He then left his phone in my car. Two hours later, I realized and I drove all the way back to the restaurant he was at. I convinced the maître d to let me through, walked in and handed his phone. He gets up, hugs me and the whole table is excited because he was miserable. He had lost his phone.

Four days later, we signed as his benefits broker. He said, “Come into my office tomorrow. I brought my team. You have the same rates as our incumbent but it’s completely clear to me what kind of customer service you’re going to provide, so we’re going to sign with you.” It was pretty amazing. I can pull a deal out of the back of an Uber. That led to my boss telling me to get off my desk and start driving Uber all day. Those are the fun. I’ve had a few of those fun, unique and out-of-the-box sales deals that bring you a lot of satisfaction and joy.

In your mind, no matter what you’re doing, even if you’re not working, are you always selling?

I’m always selling something I believe. It could be ablated. It’s my kids’ abilities on the pitchers’ round or something I believe in, and I’m passionately conveying that in natural dialogue. I’m always trying to convince people to see my side or what the value could be for them, no matter what. Whether it’s trying to convince a Yankee fan to become a Red Sox fan or whatever it might be, all this stuff. There’s no doubt.

For years, I often talked to people in life who could be a great candidate for a LeagueSide. I’ll say to them, “You’ve got to get to know what my friend Evan’s doing.” Until the point where I was like, “I’ll take them.” I’m not always selling. I’m always selling something I believe, and I do get pretty passionate. I’m the guy who thinks sales should be a major in college. I believe that sales is a craft. It’s not something that everyone can do. I do believe it should be a profession that is studied and taken on by young professionals without a doubt.

What do you think that curriculum would entail?

Probably the most important part of sales is knowing as much as possible about the products or services that you’re selling. Maybe even more than the rest of the company. Being able to know how operations and marketing works, the development of the products and how the C-Suite thinks. It would be around presentation skills, also social cues. Listening is the most important aspect. That’s not new. Everyone knows that.

I got my training in sales at Barron’s Magazine in New York. That’s an extremely hard sale because we wouldn’t discount. It was $200 a year for a subscription to a thick newspaper with stock tables in it. What we were able to say is that the people who read it never missed ever. They will walk miles to the next door if they have to get their copy of Barron’s or you’ll walk into a store and there’ll be a little flag and you try to pick up the copy. They would say, “Don’t you dare touch that. That’s Mr. Brandoff’s Barron’s. He’s going to be here in a few minutes to get it.”

I learned that but I also learned from great leaders who said things like, “We have two ears and one mouth so we can talk half as much as we listen or listen twice as much as we talk.” The key for me has always been to talk to the prospect like they’re someone who has a family, has bills to pay, wants a promotion, wants to go into their boss and say, “I found the greatest partner to do this to achieve our objectives.”

Personal finances should be another topic that we educate starting in middle school or high school.

Without a doubt, kids are starting businesses, but they also don’t have any idea how to manage money. It’s true.

They’re going to college or taking on massive debt and don’t know how to structure their finances or the future to be able to set themselves up nicely and also pay off their debt successfully. Maybe we should start a new university together at some point. Speaking of starting something, back in 2009, you started Made Possible. Can you tell us more about Made Possible? What were the problems you were looking to solve?

That was the central theme of my career. I woke up in 1998 at 2:00 in the morning with this big idea that men weren’t being served serious journalism. You call it self-help journalism, if you will, about how to be better at their lives. The mission of Made Possible is to help all young men maximize their potential across all facets of their lives. That means for career perspective, relationships, and being a dad.

The idea was you had all these magazines that marketed $3,000 watches, $25,000 suits, and smutty pictures of women. It was all about the aspirations of what a young man wants instead of some real, grounded advice about how to get there. Made Possible was going to fill a gap for 21 to 34-year-olds, helping them get real practical advice and out all the fat that would allow them to maximize their lives right out of the gate.

It was a deep passion. It took me ten years to start. I worked on it for ten years before I went live with it, left my job, and took it on full-time. It was something I was incredibly passionate about. I worked twenty hours a day on it. Unfortunately, it didn’t work. I blame that primarily on the CEO. It was also not a great time. I was hell-bent on a print model and in 2009, which the economy was tanking and also, print was waving goodbye to us for a digital world. Looking back, what might’ve been a downfall was that I took it on more of a mission than a business.

When I was in my early twenties, I’ve made a lot of those mistakes. I would be hungover too often. I would blow my whole weekend because I was sleeping until noon after a party the night before. I always regretted it. I was trying to tell stories about having a beer or two on Friday night but get first tracks on the mountain Saturday morning when you’re skiing, wake up and hike, do something or join a team. Not enough men, adults in general, but I’m speaking personally, joined teams like they did in high school, college and so forth. That’s what I was trying to help young men do.

One of the pieces of research that came out of it was interesting. We did a lot of research and found out that in a scenario where 5 or 6 guys were in a bar together, 4 or 5 of those didn’t want to be there but felt like they had to because everyone else wanted to be there. They would rather be getting a good night’s sleep and doing something better with their time on Saturday or Sunday morning, but peer pressure led them to do that. They always regretted it. It was a vicious cycle. I was trying to give them the freedom to do that.

It’s also in our society. If you do want to go out and hang out with people or meet people, what options do you have on a Friday or Saturday evening other than drinking or eating?

I tell my sons a story a lot about a guy whom I went to school with at Saint Michael’s. The first year or two, we thought he was the biggest drunk on campus because he was out every night. I came to find out one day that he was the captain of the lacrosse team. He went to class. He came home and did 2 or 3 hours of homework immediately, went to lacrosse practice and was completely done with all of his responsibilities, then went out almost every night but he graduated with a 4.0. The perception was this guy is never going to make it because he made it better than any of us. That was a lesson I wanted to bring to the two young men in America.

The best advice that I got before going to college was if you treat school like a 9:00 to 5:00 job, then you could go out, have fun and do everything. If you put your 9:00 to 5:00 and I didn’t do that but it was very good advice and hindsight.

It’s amazing the amount of great advice we don’t follow. It takes a while, but it takes a year my age to start to realize what those nuggets were that you should have followed a lot earlier. It’s all part of the maturation process. Some of it’s quicker than others, but that’s life. What I thought Made Possible was going to be a revolution. Unfortunately, it didn’t work but I believed in it.

Through Made Possible, it didn’t have the business success that you went to it with but I’m sure you learned a ton and it hasn’t stopped your mission of helping young men. Since Made Possible, what have you done and how have you contributed your time in order to help young men or young people in general?

Maybe it was even subconsciously that I continued on that mission because I had done a lot of work. I was on the board of my Alma Mater at Saint Michael’s. I did a lot of work there in career development for students. I will bring together 6 to 7 professionals in the New York area into a seminar and fill the room with Saint Michael’s students. In the summer, they were home and allowed that to have an interaction between a lawyer, an accountant and a plumber. All the different things I would bring in and help them see what it was like day-to-day to do those jobs and allow them to connect with those professionals for development.

You’re always selling something. You’re always trying to convince people to see your side or what the value could be for them.

I did a lot of that work. I started a golf tournament for the school that raised about $20,000, $30,000 a year in donations that went into more of that programming. It also went towards financial aid. A big thing that I did focus on there a lot was financial aid. I grew up very poor and because of financial aid, 50% to 75% of my education was paid for. I wanted to be able to help other people in that same situation. I did a lot of work with the school. I ended up being on three charitable boards before I was 30 or so, all focused around trying to give back.

Back then, I felt lucky that I escaped. As I got older, I realized, “No, it wasn’t luck.” It was my mom who raised me the way she did, working hard and being ambitious. It wasn’t as much luck, but I wanted to be a model for other kids that they could do things a lot better than their surroundings. Maybe the most important work I’ve done in this area is coaching. I started coaching when my boys were five. I’m about to start coaching my daughter in basketball but I finally put my baseball coaching job down. It worked. They’re in one of the best baseball high school programs in the state of New York at Iona Prep. They have professional coaches and it’s time for me to get out of the way.

What I love most about coaching is inspiring all the kids on the team. It was for my kids, but every team has 12 to 13 kids on it. My goal is to inspire them to be better than they thought they were. Sometimes that’s as simple as giving them better techniques. Once they saw that click, it was everything. It was like, “I’m better at this than I thought I was.” That comes out on the field and is extremely positive in the way I coach. Also, getting kids to focus on the moment. What a lot of adults don’t realize about young kids in sports is that day’s game is the most important thing happening in their life. That’s their job interview, wedding day or whatever it is.

When you know that, you can speak at a deeper level to them and say, “This is an opportunity for you. Remember everything that we’ve learned. Hustle for that ball. Don’t let it drop in front of you because these moments are fleeting and you don’t get these many opportunities in life to play games, to be part of a team, win a game for your team or whatever it might be.” I’d say a lot of things like, “All of you, do one great thing. We’re going to win this game.” They then started to learn that they don’t have to do everything right but if they do one strong thing, maybe it’s great, very good, the team, eventually, most more than likely going to win that game.

I’m also a private coach in baseball as a side gig. I have 10 clients between 10 and 17. In fact, I have two girls that I coach. Those might be my two favorite clients because they’re trying to do something that’s not ordinary. There’s a real satisfaction to know that I’m helping you as go strike some boys out, give them that empowerment. They’re great to coach. They’re fantastic listeners. They want to learn. Those are some of the things I do to try to keep up with the Made Possible mission.

I did do a lot of consulting for startups for young folks who are starting a business and trying to give them as much advice as I could about what I did wrong and right. Those are some of the things. It’s still a mission for me. No doubt. I’m very proud to say that my two sons have never been to the principal’s office. They never come home drunk. They’re excelling at school and sports. I’m trying to raise them in the way I wanted to raise the 21 to 34-year-olds across the country with Made Possible.

I want to stay on the topic of youth sports and coaching. What’s your philosophy on whether kids should stick to their best sport or play multiple sports throughout the year?

There are two ways to answer this. I do firmly believe that they should try lots of different sports. In fact, the one thing that we’re missing from youth sports in this country, in my opinion, is some organized platform where over twelve-month period, kids can try six different sports rather than launching into a whole season at five years old of baseball.

Can it be a month of baseball, lacrosse or hockey? Whatever it might be so that they can identify what sports brought them the most joy, what they felt like they were best at. We don’t have that. There might be efforts out there that I don’t know of but that needs to be more organized because then it does allow them to pick eventually a sport that they liked the most.

Having said that, the kids should be playing three sports all the way through high school. I’m very baseball-focused because that’s my sport. There’s not a single major leaguer in the bigs that didn’t play at least 2 or 3 sports. They will all say that. In fact, the head coach of my son’s baseball team came out and told them he wants them running track in the winter playing basketball or something else because it makes you much more well-rounded. There is a time if a kid has something special going or they are dedicated that Dustin Pedroia type who is 5’7” but said, “I’m going to be a professional baseball player no matter what. You can’t stop me,” focused on baseball. Unless that’s the case, there’s a lot more joy and satisfaction from playing multiple sports.

What’s more important about youth sports is when they start. This is something that I’m on a soapbox about, especially dads and moms too. I talked about it. You should spend the first ages of 4 to 7 or 8 not playing youth sports, instead of playing those sports with mom and dad in the backyard for a number of reasons. It builds a bond that’s unbreakable.

You can’t replace hours on a field with your 1 kid, 2 kids or whatever it might be, teaching them everything you know about that sport. When they show interest in another sport like my daughter would soccer, I don’t even know the names of the positions on a soccer team but I do know the proper way to kick a soccer ball, the right way to pass, how to receive one because I watched hours of European soccer to learn how to do that and teach her how to do it.

Those years are invaluable because if you think about it, you can put your child on a team and might spend two hours a week on that team. We all know how that looks. When soccer, all the kids follow the ball. In baseball, you’re hitting off the tee or some dad throws 52 pitches until you make contact with it. Take those two hours one-on-one. I don’t care if it was biking, swim or whatever it was. That, to me, is invaluable.

When they get to a team at eight, they’re already much better than the other kids on those teams. This is the average trajectory. Those kids are coming in like this. They get better much quicker. They immediately are recognized for travel teams, which then increases the level of coaching and dedication that they get. That’s a big thing for me. I see too much of this thrown a kid on a team and don’t get much out of it.

They get some out of it like the social piece. It’s fun and sports should always be fun. I’ll tell you from experience. Kids have more fun playing sports when they aren’t good at it and when they win. Maybe that sounds old-fashioned but I see it firsthand. Dugout full of kids that lost the game is very different than a dugout full of kids who won a game, especially if they do well and they had some part in it.

To that point, there’s often a big debate in youth sports. Should a coach coach their team in order to win or should a coach coach their team in order to optimize for fun? Is it possible to do both? What’s your take on this?

This is another passion point of mine. This goes back to what I said about trying to think like the kids think. If the 12 kids on a baseball team, 3 of them are good, 7 of them are pretty good and 2 of them are terrible, as a coach, you’ve got to get those kids in the game. Their parents signed up for it. They paid money to expect to see their kids in the game. All kids are born good. You want them to have that fun. On some level, you have to coach around that a little. You have to find the right positions on the field for them to be involved but also not to determine the team’s fate. That’s the old classic stick them in right fielder.

The truth is the right fielder has become the most important position in baseball because every game can be determined on one ball by the right fielder. Maybe third base is a better position for that, which doesn’t get as much action but they’re on the field and they’re helping. The other thing that people don’t realize is that kid doesn’t want to be exposed. If they’re bad and I’m being objective here, they don’t want to be the one up with the game on the line and the one that makes the error to lose the team or game. That’s hard to deal with as parents and so forth for the kids to appreciate. I’ve had more than enough kids say to me, “I don’t need to go in. I’m okay.”

If that team wins, they’re part of that team, celebrating with the team and all that. That’s way better than having ten kids look at you like, “You can’t catch a fly ball. We lost the game because you couldn’t catch a fly ball. All you ever do is a strikeout.” Parents have to take a role here too. If you’re in your 3rd or 4th season of this sport and it’s clear this kid’s not good at it, you probably should think about doing something. There’s a fun story in one of the first teams in the little league that I coached. There was a kid on the team named Andrew. He showed up to the first practice in corduroys and a golf shirt.

My son looked at me and I said, “I know this is not a baseball player.” It proved out that he wasn’t a very good baseball player. A couple of things happened there. He would come to the practices and stay in the car and the mom would be trying to drag him out. I would say to the mom, “Let him be. He doesn’t want to be out here because it’s embarrassing.” We got all these good athletes here and he’s the one that’s not.

When the kids on the team would complain, “Andrew’s holding us back.” I would say to them, “I promise you, Andrew’s better at something than you’re at that thing.” Lo and behold with Andrew, a couple of months after that, we went to a school assembly and he sat down at the piano in front of 500 people and blew everyone away. I looked at my kid and said, “How are you guys at the piano?” Not good. I said, “If you’re set up for piano practice, he’d probably be like, ‘He’s terrible at the piano.’”

There are other talents that these kids might have. Stop trying to force the issue and talk to you like, “Do you want to be going to these games and practices?” “No, I don’t.” Ask them and find out. Coach to win because it brings joy to the group but also, you have to spend the time developing the kids who aren’t very good. You have to separate some time for them to help them. If you have a good assistant coach, you say, “You take these 8 kids and I’ll take these 2. I’m going to work with them directly and get them better to the next level so that they can be part of the group.”

Fitting in is everything as a kid. If you help them get better, you’ll have a loyal player the rest of your life. When you walk through town and you hear, “Coach Mike,” you look over and it’s one of those kids who wasn’t very good, who’s better, they’ll love you forever. It’s an important thing. I said a lot there but I have a lot of thoughts on this subject.

It’s amazing the amount of great advice we don’t follow.

Mike, this is the lightning round. It’s four questions. First question, what is your favorite youth sports memory?

Finishing second in the high hurdles relay at Boston University as a junior in high school in the state. Even though baseball is our number one sport, that was the biggest highlight of my career.

I bet your best friend couldn’t do that. You won up to him.

My best friend was on the team. He was on the relay team. What made it so special for me was I was only 5’7” in high school and the high hurdles were not something that was meant for me. I overcame that, became strong and came in second in almost every race that season.

You’re taller than 5’7”. When did you have a growth spurt?

I’m only about 5’11” but in college, I was 5’7” when I got there. I didn’t start shaving until college.

When you were a kid, what did you want to be when you grew up?

I looked back at my sixth grade yearbook and it said Professor of Math at Harvard. That somehow went away. I didn’t have an aspiration. I wish I did. Looking back, that was my aspiration. If I had it to do all over again, I would have been a teacher and a coach. There’s no doubt about it. I would have loved to have been a teacher.

What is your go-to cause to support?

Development in youth sports without a doubt and helping young people, mostly men, that’s where I was focused on avoiding the pitfalls of life. Create their own path and not allow themselves to be victims of peer pressure that bring them into a vicious cycle.

What do you think is an effective marketing channel for a brand to reach you at the baseball field?

What you folks are doing at LeagueSide is special. I mean that because I call you every couple of months with a new idea of what brands you should be looking at and who needs you the most. Unlike professional sports and even college sports that feel corporate and commercial, there is a purity to what you are doing.

There are parents who struggle to afford youth sports. There is an intention piece. I go to the same little league field 30 to 40 times a season. I’m going to support the brands that support that league. It’s a pure win-win because they’re doing more than just buying eyeballs. They’re helping young kids have better equipment to be able to play.

I’ve had a lot of financial struggles, especially after the startup. The Made Possible failed and I lost a lot of money in that. The last thing I wanted to do was not to allow my kids to have the same youth sports experience that I had. Some of it is very expensive, especially TravelBall and all that. The fact that brands can get involved and help subsidize those costs, it means everything. It might not mean everything to kids who are wealthy and can afford everything but it means a lot to other brands and lots of other kids. I do see it almost like a pure marketing vehicle in what you are doing in that space. I applaud the heck out of what you’re up to. It’s a tremendous platform.

Thank you.

The goal is to inspire the youth to be better than they thought they were.

You’re welcome. I’m proud of you.

I’m proud of you, Mike. This was a lot of fun. Thank you so much for coming on. This was great.

Thank you for having me. I hope I can help. Best of luck to you, Zubin and the whole team.

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Thank you for reading this episode with Mike Rideout. He was incredibly inspirational talking about how to win in sales, in coaching, how to set kids up to have fun, be successful and most importantly, how it is important to put yourself in the shoes of the kids that you’re coaching and also the prospects that you’re selling to in order to have success. It was a great show. Thank you all. We will see you next time. Play on, everyone.

Important Links:

• Mike Rideout – LinkedIn
• The Boston Phoenix
• LeagueSide
• TravelBall