Pitcher, Toronto BlueJays & Founding Managing Partner, Skyward Financial LLC

Ep #5: Ross Stripling

In episode five, we stop in Houston. Dhani Jones speaks with Ross Stripling, Pitcher for the Toronto BlueJays and FINRA-certified stockbroker. He talks with Dhani about the intersection of financial and athletic skill sets.

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Investment, Sports
Ross Stripling
In baseball, it's usually clear as day just the numbers, right? What do they hit against fastball? What do they hit against slow stuff? But in the finance world, everyone has different opinions, man. Some people love charts. Some people love fundamentals. Some people love other metrics. For me, a couple things, man. The first thing I love to look at is the CEO.
Ross Stripling, Founding Managing Partner, Skyward Financial LLC

Ross Stripling's experience

Ross Stripling

Modern Dealmaker & MLB Pitcher

Ross Stripling became a household name after his debut with the Los Angeles Dodgers in 2016. It was during the Major League Baseball offseason where he began his career in financial services at B. Riley alongside father and son team of Lynn Houston and Matthew Houston. Within a matter of months, Ross passed his series 7 exam and shortly thereafter his series 66. As his off-the-field business picked up, he also became a trusted source and voice of reason on matters of finance within the clubhouse. Suffice it to say, Ross has become much more than an athlete.

  • Current Pitcher, Toronto BlueJays
  • Founding Managing Partner, Skyward Financial LLC
  • Vice President - Financial Advisor, B. Riley Wealth Management
  • Former Pitcher, Los Angeles Dodgers
  • Bachelor's degree from Texas A&M University

Episode highlights

How picking a stock is like pitching in baseball




Ross Stripling (00:05):

I invested my own signing bonus and you just fall in love and you navigate it as you go. I have an elbow surgery in the Minor Leagues where I'm looking like I may not play baseball ever again, and I start pursuing a backup plan, right? I get my Series 7, my 66, which makes me a licensed stockbroker. I just start pursuing that while I'm also getting healthy. That was 2014, so now gosh, seven years later, man, I'm that guy. Every announcer, whether I'm on the road or at home, they're like, "Ross Stripling coming in to pitch, the licensed stockbroker," kind of stuff. It's what I'm known for.

Dhani Jones (00:39):

The Pathfinder podcast is presented to you by Ansarada. Ansarada, is the modern deal and virtual data room technology, designed to make M&A, capital raising, divestments, restructures, and IPOs as simple as possible. Since 2005 Ansarada has been trusted in over 24,000 transactions and powered over one trillion worth of deals. Ansarada is a secure space that includes workflow tools, AI powered data rooms, built-in question and answer and integration frameworks. It's the data room trusted by modern deal makers. You can start for free today at ansarada.com. You know I like a winning team, so say it with me, ansarada.com for your next winning outcome.

Intro (01:20):

Welcome to The Pathfinders, the modern deal maker series brought to you by Ansarada. Now here's your host, Dhani Jones.

Dhani Jones (01:31):

Welcome back to The Pathfinders presented by Ansarada. I'm former NFL player, investor, and entrepreneur Dhani Jones. And today, we've got another home run of an episode for you. In case this is your first time you've heard The Pathfinders, here we talk to the people who are transforming, innovating, shaking hands and carving paths forward. Our guest today is Toronto Blue Jays pitcher, and no stranger to deal-making himself, Ross Stripling. In addition to pitching for the L.A. Dodgers and now the Toronto Blue Jays, Ross is also a certified stockbroker and financial advisor. In today's discussion, we'll get into the deal-making lessons he's learned from professional baseball and how he keeps a deal-making mentality on and off the diamond.

Dhani Jones (02:20):

Ross, I must say, number one, welcome to the show. So excited that you're here. And just full board and full transparency being a National League All-Star and at the same time being a financial advisor, that just, in my mind, just blows up this whole notion that an athlete can't be more than just a player, right? A lot of people just say that, even the whole conversation around LeBron James, just shut up and dribble. I remember when I was playing, everybody was like, "Look, just focus on playing the game. We don't want you to do anything else." And you completely just said, "Look, I'm going to not only throw the ball, I'm not only going to strike people out, I'm not only going to become the best, but I'm also going to help people make money while at the same time I'm going to make money and I'm going to do it both on and off the field." Just walk me through in your mind when someone says that, how that makes you feel.

Ross Stripling (03:14):

Yeah. Well put, man. Well, first off, thanks for having me, Dhani. I'm a lifelong Cowboys fan, so I've watched you run around the NFC's tackling my Cowboys for a long time, man. So this is a lot of fun being here. I guess, to answer that question, man, is just I was passionate about it, man. I got a finance degree from Texas A&M. Both my grandparents, my grandfathers were very active in the market. So I got started on the stock market at a young age. I wasn't a super high draft pick, I was a senior sign, but I got a little bit of money out of draft. And I just started tinkering around on the market. I invested my own signing bonus and you just fall in love and you navigate it as you go. I have an elbow surgery in the Minor Leagues where I'm looking like I may not play baseball ever again. And I start pursuing a backup plan, right? I get my Series 7, my 66, which makes me a licensed stockbroker.

Ross Stripling (04:02):

I just start pursuing that while I'm also getting healthy. That was 2014, so now, gosh, seven years later, man, I'm that guy. Every announcer, whether I'm on the road or at home, they're like, "Ross Stripling coming in to pitch, the licensed stockbroker," kind of stuff. It's what I'm known for, and it's a blast. I love it. I love being known. I don't know this for sure, but I do think I'm the only Major athlete that is a licensed money manager and an active Major athlete. So it's a cool little thing to be known for.

Dhani Jones (04:29):

It has to be interesting. You're in the dugout and people are asking you for stock tips or maybe you're out on the mound and people just walking up to you. I know you guys have these conversations because I played football, so it's a little bit different. You all don't necessarily have a huddle like we do, but there's definitely a gathering. I'm just wondering in those gatherings, are you talking about like, "Oh, man, Amazon was up a little bit. I like that one." Or "How are you all feeling about rocket mortgage?" Do those conversations definitely take place?

Ross Stripling (05:01):

A 100%. So it's not like, my catcher is Austin Barnes and I'm in the middle of trying to get Nolan Arenado out and he's coming out and being like, "Hey man, what was Amazon doing today?" In the field of battle, that's not happening. But as a starting pitcher, I pitch and I get four or five days off where I'm in the dugout. My work's done for the day and now I'm just out there being a cheerleader, supporting the team. And that's definitely when those conversations will come up, because you got all the time in the world while you're watching a ball game to talk about stuff. I guess without giving the players name, he was a veteran when I was a rookie and this is eyeopening for me about, I need to watch what I say.

Ross Stripling (05:32):

He is a veteran, he had made a bunch of money and he wanted to dabble in the stock market and we're just BSing in the dugout. One game, and he is like, "Man, what do you like?" And I said, "I like stock X, Y, Z, maybe check it out or whatever." And the next day he came in and he'd bought almost a half a million dollars worth of shares. And I was like, "Okay, I got to really be careful about what I say." Because there's some people throwing out some big money against some of these random stock picks I'm throwing out. So I haven't been as willy-nilly with my pick since then.

Dhani Jones (06:00):

I don't think it was random at all. I think he respects your knowledge and I think he respects the amount of work that you've put into it and being that it was so just off the cuff, it was automatic for you. Right. It was just like throwing a fast ball and making sure it's right into the pocket. Right. I think that when you reach that level and that respect ensues, then all of a sudden life just takes off and just creates a different field of dreams.

Ross Stripling (06:30):

I really had noticed that since I started. I got my license 2015, 2016 and at first people don't really take you serious. One, you're an athlete, two, they think your focus is really baseball or whatever and you got to get over that stereotype. And now I've noticed five years later of being consistent talking about it on social media, talking about it with teammates, it gets around to other teams where like a David Price got traded over from Boston. And the first thing he met me, Hi I'm Ross Stripling. "Oh you're the stock market guy." So the word starts getting out there, which is really cool versus at first I noticed, I really had to get over the hump of people just saying like, oh, you're just out there. I don't know either throwing names out, left and right or trying to make a name for yourself or whatever it is that people think you're doing.

Ross Stripling (07:14):

What could you possibly know versus the six year old stock broker that's been doing it for his career for 30 years? So it's been tough to get over that hurdle a little bit, but now five, six years in I've noticed that people really they start to listen when I open my mouth about it, because I think they are starting to know that I understand it and enjoy it and really passionate about it.

Dhani Jones (07:32):

Well, I think it's just like the investments that you make. If you're a short term trader, it's a lot different than if you're a long-term investor. And if you're a long term investor it takes several years in order to build up that compound interest was Einstein [inaudible 00:07:45] that's the eighth wonder of the world. So it's only appropriate that it would take this amount of time for people to mature around the idea that you are the stockbroker playing baseball, the pitcher stockbroker and people to have that respect. So your own personal compound interest, right? Is happening right in front of your eyes, but was baseball always going to be your career? At what point did you decide that?

Ross Stripling (08:10):

Man, I'm a late bloomer in the baseball world. I come from the Friday Night Lights football high school in Texas, man. Southlake Carroll, it's in the Dallas, Fort Worth area if you've ever heard of it. You just eat, sleep and breathe football in that city from a young age. I just focused on football and basketball more as a kid. That was just the nature of the beast, where I grew up. I didn't pitch until I was 18, man. I did not pitch a ball off the mound until I was 18 years old. So just a late arrival to pitching and really to baseball in general. Walked on at A&M, didn't get any division one offers ended up walking on at Texas A&M and just got bigger and stronger in college in anyways, long way to answer your question.

Ross Stripling (08:47):

I got drafted as a junior and didn't even see it coming. I got drafted in the ninth round, which is fairly high and turned it down in a heartbeat, man. I'm like, "No, I'm going back to school." Baseball was not my number one priority. I was a third generation Aggie. I wanted to get my degree. We had just come off the College World Series. I wanted to go back and play with my teammates again. And I did that, enjoyed every minute of it. Don't regret it at all, got drafted in the fifth round by the Dodgers. And like I told you, when I got hurt, that was 2012 drafted. So 2014, Tommy John, I'm already pursuing another career. Right. Which is this finance thing. I'm already eyes, at least 50% set on something else, halfway out the door.

Ross Stripling (09:23):

And really it took my dad to sit me down and say, "Dude, you were just in big league camp, you got hurt piggybacking Clayton Kershaw in a spring training game. You're right on the cusp. You can't start putting your eggs in a different basket. You got to really focus on baseball." I took rehab really, really serious, but also started the finance stuff, really focused on both those things for that year. And really when I came out of that Tommy John, I was motivated as hell, man. I was like, "All right, I survived 14 months of rehab. I'm ready to take this to another level." And that's really, when I would say, "Laser focused on baseball, I'm going to try make to the big leagues."

Dhani Jones (09:57):

I had an ACL reconstruction and I too, while I was at the University of Michigan, which is by the way, is the greatest university in the world. But I think even amid that struggle that we have as a team, I had a struggle when I had my ACL, you had your struggle when you had your Tommy John surgery. How did you teach yourself or rather, what did you learn as you were recovering? Right. What did it teach you about tenacity and patience? Right. That might be a little bit a part of the ingredients of how you operate your life now.

Ross Stripling (10:31):

Yeah. Man, really good question, and you probably can reiterate some of what I'm going to say. A lot of people say Tommy John is similar to an ACL for a football player. At first, you know the timeframe, right. You know you're facing a year before you are back at an elite level. That's just the way it is. Hundreds and thousands of people have done it before you, besides Adrian Peterson, you're not going to be the one that comes back in six, eight months. Right. It's going to take you a year. So patience is a good word. Ride the rollercoaster, man. Around the three, four month mark, when I'm starting to play catch. I remember thinking my elbow, I need surgery again. I'm not ready to throw. Two months later, I'm like, "I'm so healthy. Why aren't I facing hitters already?"

Ross Stripling (11:14):

You ride that wave and you never get too high, never get too low, stay even keeled, push through some tough spots. And then actually even take the reins off a little bit when you feel like you're flying high. Tenacity is a good word too, that you used and what I touched on earlier, man, I was not in love with baseball or at least had not fallen in love with baseball when I had my surgery. And it really put some things into perspective I think for me, that man, this is what I want to do. This is what I'm fired up about. I see teammates and people around me making it to the big leagues and guys that I think and know that I'm as good as, and I can go do that.

Ross Stripling (11:48):

And that's where you really man, like laser focused tunnel vision, get healthy and get out there and show what you can do because I can do what these guys are doing. Man, it was probably maybe the most depressing year of my life as far as where I was mentally and just grinding. But also some of the most fun I've had and probably maybe the most important year of my life, as far as the stepping stone to get me from there to where I am now. And you probably felt some of those same emotions. It's like you wake up one day, "What the heck am I doing? I could be somewhere else." And you wake up the next day, "Heck yeah, dude, I'm one day closer."

Dhani Jones (12:20):

Yeah. Well, look, in football, our contracts aren't guaranteed, but in baseball you all have guaranteed contracts. So there's a financial component to it in your mind, which I'm sure you spin through, but in a different way than football, because once it's done, it's done. You're not on the field, you're not getting paid. That type of deal.

Ross Stripling (12:40):


Dhani Jones (12:40):

But in football it's a different climb because there's not AA, there's not AAA because in baseball there's although you might have these guaranteed contracts, you don't necessarily guaranteed playing time. So the mental hurdles that you have to get over as a player now, not necessarily being on the field and wondering if you got to go back down to the Minors in order to get all the way back up to the Majors. I'd imagine that's what's probably messing with you more than anything else because you're like, "I'm right here. I'm right here. Now I got to get back on the bus. I don't know if I want to take that trip."

Ross Stripling (13:15):

Yep. Well, I wasn't even off the bus yet, man. I was still in the Minor Leagues. So I was a senior sign out of college in my second year of Minor League Baseball. So I was pulling in 1200 bucks a month for six months out of the year. So that was part of the reason why it was easy for me to maybe start putting one foot out the door because I wasn't making any money. And I had a girlfriend about to be fiance, thinking I can go start my life and build a family and I'm making 1200 bucks a month. And my wife's a first grade teacher making 30 times more money than me. Right. Which is unheard of. So yeah, the financial side of it was a frustrating weight to bear for sure. Because that a year of my life with a college degree and prospects to go make money where I made about $6,000. Right. So that was tough.

Dhani Jones (14:04):

So what was the moment when you said, "All right, I can balance the two. I'm just going to be able to figure this out. I'm going to be able to throw the ball and I'm going to be able to make my picks and I'm going to be really good at both."?

Ross Stripling (14:17):

Good question. Man, I would say it wasn't until maybe two years after I had already gotten licensed and basically I'm doing both full time in a way where actually I have clients now. I have people's money and I am actively managing their money on top of my own. And also trying to get Nolan Arenado and J.D. Martinez and Paul Goldschmidt out. Right. That's two really tough things to juggle right there. And I think I stepped back and organized what I needed to, right. Baseball is the focus. That's how I'm going to be able to make my money right now and support my family. And it's also what I'm really passionate about right now and that life will end. The finance stuff will keep going, but the baseball life will end. Right. The time is ticking on that.

Ross Stripling (15:02):

There's no doubt about it. So I sit back and say, "Okay, what can I really take on my plate with a wife and a son on the way and a full-time baseball job and now 14 active accounts that I'm managing. What workload can I really take on?" And that's where I basically reached out to every client that I had and said, "Look, this is the time that I have to give you, I'm focused on your portfolio and I'm focused on your money. And I swear, you're in good hands, but I might be playing a game at noon on a Friday and not able to answer your texts. And if that's how it is, here's my boss, Matthew Houston, please reach out to him. He can do everything I can." So everyone that I have their money understands that baseball is my priority, but I think they also know that I'm there when they need me and I can take care of them.

Ross Stripling (15:47):

Luckily there's not a lot of things in the finance world that's just like, "Ross, give me this right now. I need a 100 shares of stock X, Y, Z. And if you don't give it to me, you're fired." That's never happened. Right? So luckily I don't have any clients as high maintenance as that, but maybe one day, but for now I got to juggle pretty well, man.

Dhani Jones (16:09):

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Dhani Jones (17:05):

In addition to not only being a stockbroker and playing baseball, you're also giving out advice and you're learning from other people and teaching other people, because you've had the podcasts that you've done as well. And you've been able to balance both what you're doing on and off the field and then doing stuff with CNBC and doing stuff with Fox Business. It just seems like the list is endless, but in the world of which I come from, I think about that as an inherent piece of curiosity. That's one of the most of important pieces. And even as you go into the stock market, it's about being curious. It's about diving into the details market cap and terms like, how big a business can actually be and what you feel like what's going to be on the horizon of the company, but it comes from asking the good questions. Is that what drives you to do a couple of these other things even while you're standing on the top of the pitchers mound?

Ross Stripling (17:57):

Yeah, definitely. I imagine that most athletes have that personality right, where they want to compete in everything that they do and they're driven and motivated. You don't get the highest level of your craft unless you have that personality trait similar to you with the podcast right here. You have opinions and things that you want to say and an awesome network of people to talk to and you can bring things and opinions to the world, man, and things that are on your mind. And also it keeps you busy and it keeps your mind working, right? That's me, that's my personality. I'm always moving almost to a fault, where I probably could be in the moment a little better than I usually am. I feel even right now, I know what's next on my to-do list. I need to go and take care of my son when my wife goes and does something she needs to do.

Ross Stripling (18:45):

I'm always thinking it's just how I'm wired. So I think that trait of mine is how I ended up with just so much on my plate, man. And I love it. I love staying busy. I'd rather be doing this than sitting around watching Netflix any day or playing video games, I'm not a video gamer. So it's just how I've chosen to navigate through my life so far 30 years in. And I love it. I might wake up one day and be like, "Dude, I'm just way too busy. I need to take something off." Which was the podcast. The podcast got tabled for a while, just because just in this 10, 20 minute conversation tell I just got a lot on my plates. So focusing more on baseball and the finance stuff and the podcast comes back later, great.

Dhani Jones (19:20):

But I think sometimes even when you have a bunch of things, a lot of people have this outside opinion, you might be distracted. But in some cases it's actually in my mind satiating a part of your brain that needs to have something to do. Right? And so when you piece this amazing puzzle together, the beautiful picture of the beautiful Monet is what your life has been made up to be. And I think that's a wonderful thing. You've also parlayed not only playing, not only doing the financial deal into Skyward Financial. So now you're also a partner at a firm. Did you help start the firm? Did you join the firm? You said you had 14 clients. Aspirations, I'd imagine is to build a whole portfolio of 14, 15, 20, 30, 40 clients. And then once you get done with baseball, that might be the thing that you do forever.

Ross Stripling (20:10):

Yeah. Yeah, definitely. If baseball ended today, that is a 100% the first step that I would take is Skyward Financial, man, we're located here in Houston. So my mentor/boss is a guy named Matthew Houston, his dad and Matthew. So I guess backtrack for a second, his dad invested with my mom's dad. So my grandfather for 50 years. So that's where the connection happened. So that's where they got me licensed. They were working for another company at the time and what's standard in the business is you build a big enough book of clients. You got enough money, you can go start your own firm, right? Not everyone does it. You can go start your own firm and make a little bit more money for yourself but also feel like you can take a little bit better care of your clients, be a little bit more boutique, not under the umbrella of a big firm.

Ross Stripling (20:52):

So they went and started their own shop and asked me to come with them. I'm not necessarily bringing a ton of value. I don't have those 14 clients, that's not a 100 million dollars I promise you that. But they understand that I have an awesome network around me of guys that I've met in locker rooms and through the podcast and some other things. Guys that I can call on after baseball ends and try and get an account and try and start the money management business and really get a portfolio going. So yeah, I'm technically the third co-founder of Skyward Financial, it's Lynn and Matthew Houston and then myself and I'm so glad to be a part of it, man. It's really two dreams come true. Right? I've been able to now make it to the big leagues, obviously one dream and now able to be a part of starting my own company, a financial firm. So at 31, almost 32 years old to be able to accomplish two of my dreams coming out of business school out of Texas A&M, that's pretty cool.

Dhani Jones (21:43):

Are there some things that you take from the field, things that you take from being on the mound that you apply to how you think about investing?

Ross Stripling (21:52):

Yeah, definitely. So I get asked this all the time and I feel like my answer's ever changing because I feel I should have some awesome answer to this question since it does get asked pretty often. At the end of the day, I think pitching and investing, or let's say pitching and picking a stock are pretty similar. Right. You're getting down to the fundamentals. Let's say I'm facing you, Dhani, and you're very aggressive 0-0. You love the heat or 0-0. Okay. So I'm going to throw you something soft. All right. Now I got you 0-1, what do you hit against slider? What do you hit against fast balls? And what quadrant? What do you hit against change up? If I get you to two strikes, what's your swing and miss? Or if there's a man on first, what do I throw you to get a ground ball, to possibly get a double play?

Ross Stripling (22:31):

All these things that I know when I'm facing a hitter and I'm a numbers guy, right? I graduated with the finance degree. I love numbers. I love math. So I can absorb a lot of this information. A lot of pitchers want to be out there free and easy. They don't want to know that kind of stuff. I'm the opposite. I think it's like having the answers to a test, right? I know exactly what you do against certain pitches and certain counts. I know that. So I'm going to exploit your weaknesses. Picking a stock is the numbers game, man. And obviously there're different ways to do it. You can go off fundamentals, you can do chart analysis. You can go with your gut sometimes, but a lot of times it is what's their earnings? What's their revenue? Are they growing?

Ross Stripling (23:09):

If they growing, why not? Do they have a lot of debt? If they have a lot of debt, what's their cash? Do they have the cash to cover that amount of debt? Do they have a moat around their business? Is there someone that can just come in and do what they do better? Or are they the first ones to do what they're doing in their industry? There's a lot of parallels between them where you can attack them similarly with similar mindsets and I think have success both ways, if that makes sense.

Dhani Jones (23:32):

Yeah, no, that makes a lot of sense. When I was playing football, it'd be the same type of thing, except for it be 11 different people. That you have to be able to identify what their habits are. Right. Obviously you're focusing on the quarterback and what his tendencies might be. If it's third down in four and they're in the middle of the field, they have a higher propensity in order to throw the ball down the field versus run the ball to the outside. So you might adjust the defense and there're some automatics and things that get called. But I think in the world of picking stocks, especially if you're independent and you're on your own, you're in a little bit of an isolated bubble onto yourself based upon the information that you've absorbed from the analyst and from some of the papers that are out there that give your opinion. But I'd imagine in the same way while absorbing all this information, there's one or two things that you really, really pay close attention to.

Dhani Jones (24:30):

In the same way that it might be down in distance on the football field, what are those one or two things that you pay attention to that you really boil down to as part of your thesis as to why you might choose Nike versus Under Armor? Right?

Ross Stripling (24:45):


Dhani Jones (24:46):

Or a fastball versus a slider. Is there something in there, right. Something in the game that you look at that might determine one way or the other?

Ross Stripling (24:56):

Sure. In baseball, it's usually clear as day just the numbers, right? What do they hit against fastball? What do they hit against slow stuff? But in the finance world, everyone has different opinions, man. Some people love charts. Some people love fundamentals. Some people love other metrics. For me, a couple things, man. The first thing I love to look at is the CEO. Who is he or she? What's her track record? Did they start with the company? Have they been brought in? What ownership do they have? Right? Are their interests in line with shareholders? If he or she owns less than 1% of the company, she doesn't really care what the stock price is doing. Right. Well, let's say this is his baby and he started it and he owns 20% of the company still. He's going to want that stock price to go up. Right.

Ross Stripling (25:39):

And he's going to do what it takes to make that thing rise because his wealth is directly driven with the share price. I love to see that. Secondly, sometimes it's as simple as man, what's the product? Do you believe in it? Can you explain it to a fifth grader, if they were to ask? Some of these software companies, their stocks are going crazy and rightfully so, that's the way our world's going and it's going digital and of hurry, but I can't even explain what they do. I don't know what they do. And if you were to ask me, I'd be like, "Yeah, they're a $400 stock, but I don't know what they do. They do CRM somewhere in the cloud or whatever. I don't understand." And those are the companies I'll stay away from versus some of these others that have products that you really believe in like, what do you use every day?

Ross Stripling (26:20):

Are you watching Marvel movies? Are you watching stuff on a streaming service? What kind of car do you drive? That kind of stuff. Those are where you'll like to start investing and build a concrete portfolio of things that you're interested in, that you're going to enjoy following and know a lot about. And then from there you navigate and get to know more and build out a portfolio that way. I know that's a long winded way to ask or to answer your question, but the two favorite things I love is who's running the show and what is their product?

Dhani Jones (26:52):

How come other players don't think like you think? Or why do you think people don't think... This is better, why do you think people don't think players think like you think?

Ross Stripling (27:05):

Well, man, there's always a stereotype that we got a free ride to school. We didn't really earn our way into college kind of stuff. And now we maybe aren't as educated or as intelligent as the common man or woman that's in the workforce. I certainly understand that stereotype. Secondly, most people probably assume we're just laser focused on our craft, man. Which most of us are. 95% of us are. Man, some of my teammates, hitters, a Marcus Semien that just finished third in the MVP. That man would go home and watch video on his iPad of the pitcher the next day, and then get to the field the next day and start watching more film on that guy.

Ross Stripling (27:43):

They're just laser focused. Marcus Semien has three kids, he doesn't have enough time to think about some of the stuff that I'm thinking of. And I'm starting to figure that out that I barely have enough time. Right. I touched on it earlier, this window of making money in professional sports is hopefully 10 years, most of the time, not even. So man, if you can really just crack down and be laser focused on, "All right. How do I maximize my value right now at competing at the highest level of a sport?" It's hard to focus on some of these other things that we've talked about today.

Dhani Jones (28:14):

Do you feel like you're trying your best to bring other people into that way of thinking or into that community? I'd imagine that Skyward Financial could to take on a couple more partners, especially if they're in some other different sports. You might pick someone up from football, someone up from soccer, someone up from lacrosse and then all of a sudden building an entire portfolio that competes with BOA or might compete with Goldman or some of these other institutions that are trying to do the same type of thing. Because sharing common thoughts and coming from a common background, then all of a sudden allows you to educate them in different ways. Where you can now therefore change the stereotype that so many of us have suffered through.

Ross Stripling (28:56):

Yeah, really well said and spot on. I agree. That's the dream and something that I'll certainly pursue baseball wise. Financial literacy, I think is a huge deal among athletes, man. Now with the... What is it? NIL where college kids can make some money off their name and likeness. Financial literacy is a big deal, some of these kids are going to start making money really early in life.

Dhani Jones (29:17):

So two more questions. What's your biggest win? Who do you characterize as your biggest win?

Ross Stripling (29:24):

Oh man. Great question. The answer is my wife. I know that's a corny answer for sure, but Dhani, you live the life. You understand how strong and important... I'll rephrase that. You understand how strong of a woman you need and how important having a strong woman is in your life. And now that our son is nine months old, our year this year, Dhani, we spent two months in Florida, two months in Buffalo and the final two months in Toronto, because I played for the Toronto Blue Jays. We couldn't get into Canada because of the border. And my wife is living unknown day to day where we're going to be, what's going to happen. We get to Toronto, she can't go. So she flies a seven month home or six month home, whatever it is at the time from Buffalo back to Texas. That kid has already been on 25 flights.

Ross Stripling (30:11):

Man, to have a strong, independent woman as a professional athlete is just the most important thing that you could possibly have. She's the rock of our family in every way and someone that I can just count on day in and day out. And I know that's cheesy man, but that is by far my biggest win that I've had in life. All these things that we've talked about today that I have the time to be able to do them, that I can get up and train and then go to the office and help people with their finances and manage 14 accounts and then come home and play with my son and have a wife that's happy and excited to see me and not just pissed off handing me a baby. Is just amazing, man. So that's my biggest win by far.

Dhani Jones (30:47):

The strength of a woman.

Ross Stripling (30:48):


Dhani Jones (30:49):

That's the greatest win. So we always like to end Pathfinders by talking about your meals and deals, what we call where you like to celebrate. So, which is your favorite celebration of a winning deal or favorite place to go for a winning deal? Is it a place, a restaurant, a bar? Is it parties or hanging out with people? How do you like to celebrate all the great things that you've done?

Ross Stripling (31:14):

Man, that's a great question. Since the pandemic, I certainly haven't been out and about as much as I would've liked between a pregnant wife and now a newborn. I miss going out and being social, no doubt about it, man. Some of my favorite memories I've had are, I just have an awesome group of buddies between high school and college buddies that have also became friends themselves, will come visit me multiple times a year. They'll come to Seattle, Boston, obviously, anytime I'm in Texas, they used to come to L.A. all the time. I already had a buddy, the second the borders were up and come up to Canada. So some of my favorite memories ever. So one was my debut in San Francisco where I pitched well, and then I got a win the first time I pitched in Fenway. In both times I had big groups of people there, friends and family.

Ross Stripling (31:54):

And to walk out of a big league stadium and to have, let's say 10 people there that are some of your closest family and friends with big smiles on their faces ready to give them each a hug. And you just go walk to a bar in that city that we're in. So San Francisco, we went to this Irish bar and then in Boston we went to maybe also an Irish bar and those are some of my favorite memories, right? So I just pitched, well, you feel like you're on cloud nine because you had success and then now you're celebrating with your best friends and family. So I think it's a bar after a baseball win. Man, that would be my favorite, what is it? Meals and deals that I could ask for.

Dhani Jones (32:30):

Nothing better than celebrating with friends and family. It's the greatest opportunity to get grounded and to feel those that really energize you and build you up the most. So Ross it's fantastic. I just want to say thank you for all that you have done and that you will do. Because I think so many players like myself, I look up to you, man. I'm going to take some tips from you. I'm going to learn where you're putting your money. Because I'm going to put my money too. Or I might just introduce you to a couple people because not to say that 14 clients is not a lot, I think you need 20, 24 clients.

Ross Stripling (33:09):

Yeah. Who doesn't?

Dhani Jones (33:10):

Ross, I just want to say thank you again for coming on the show and talking to us about your unique career and deal making experience. Please remember to rate and review the show. Until next episode, I'm Dhani Jones and this has been The Pathfinders brought to you by Ansarada.


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