Though starting out as pre-med and a member of the development ski team, Dan Kashman changed courses a couple of times in college and after until he found that his interests and skills made the most sense in the world of marketing. Moving between smaller companies and larger shops with powerful tools, he learned to find the connections between data, technology, and creativity for companies of all sizes, including his own. Find out how changing course and pursuing longevity aren't always in opposition.
Starting out as pre-med and a member of the development ski team, Dan Kashman changed courses a couple of times in college, first getting his ski time in as a ski instructor instead of on the team, then switching to economics. Right after graduation, he worked got an investment banking job but knew very soon he wanted to get his hands more dirty, or rather more snowy. He wrote to a number of consolidating ski resort companies and figured out how to use his Wall Street experience in a different way. Ultimately, he found that his interests and skills made the most sense in the world of marketing. Moving between smaller companies and larger shops with powerful tools, he learned to find the connections between data, technology, and creativity for companies of all sizes, including his own.
In this episode, find out from Dan how changing course and pursuing longevity aren't always in opposition…on Roads Taken with Leslie Jennings Rowley.
About This Episode’s Guest
Dan Kashman is an experienced Chief Marketing Officer and entrepreneurial executive with over two decades of experience in finding the connections between data, technology, and creativity for companies large and small. His marketing consultancy Tenth Mountain is a multidisciplinary marketing firm with clients in all sectors. But as a devotee of the health and wellness space, he is also the founder of Medo, which uses AI-powered health coaching to make preventative health optimization accessible to everyone. Check to get your free Sense Score and a holistic view of your longevity potential.
Dan Kashman: But these big companies were being disrupted by smaller companies. And so I kind of found my way as like the subject matter expert who could bring some of this, you know, kind of more cutting edge connection between data, technology, and creativity to these larger businesses.
Leslie Jennings Rowley: Though starting out as pre-med and a member of the development ski team, Dan Kashman changed courses a couple of times in college and after until he found that his interests and skills made the most sense in the world of marketing. Moving between smaller companies and larger shops with powerful tools, he learned to find the connections between data, technology, and creativity for companies of all sizes, including his own. Find out how changing course and pursuing longevity aren't always in opposition...on today's Roads Taken with me, Leslie Jennings Rowley.
Today I'm here with Dan Kashman and we are going to talk about the early expectations and how he changed swiftly and then how they morphed over time. So Dan, thanks so much for being with us.
DK: Thanks for having me.
LJR: Sure. So the first time I talked to somebody on his program, I ask two questions. And they’re just little ones; they’re pretty easy. They are: when we were in college, who were you? And when we were getting ready to leave, who did you think you would become?
DK: These are great questions. Hard to kind of answer. I think back almost 30 years, but, well, first of all, I grew up in a small resort town here in Upstate New York. And in a lot of ways, the environment in Hanover is very much what I was used to. I was big into the outdoors. I loved the winter. I was a ski racer growing up. So that was a big thing you know, kind of on my list at the time. And I was not good enough to ski at Dartmouth, but I was on the development team and met some great folks there. And quickly realized that since I was training with future Olympians, that that kind of training regimen was probably not aligned with my other goals as a freshman in college. And so I kind of quickly decided that it wasn't for me. I think it was probably after September or October stadium runs that we were doing up and down the stadium that I realized again, I was looking next to me and seeing these folks who were on the U.S. ski team or going to be on.
LJR: In front of you.
DK: Yes. And I was like, I don't know if this is really what I should be doing. So I actually left the Dartmouth ski team, the development team. And I did become a ski instructor at Dartmouth. So I loved that. That was great. So I was an economics major initially actually thought I was going to be pre-med. Somehow I thought I was going to be a doctor. I kind of changed courses pretty quickly. I think I realized that I was pretty commercial pretty early on. I grew up in an entrepreneurial family and It's not like I'm the son or grandson of many doctors. So I think it felt more comfortable to me to be more commercial. So I actually became an economics major, which was great. I loved that, really enjoyed, had amazing professors. And I did a language study program, an LSA in Granada, Spain, which was an incredible time. I spent a winter, split my time between Vail skiing and working as a ski check at the Westin along with a lot of friends. And then half of the winter, I actually went to Mexico City and spent with an architect. And I worked as like an apprentice to an architect in Mexico city. So that was kind of a nice time. And I had tremendous friends. I was in Alpha Delta and a lot of my lifelong friendships kind of started there. The fraternity was actually, you know, a very big part of that community was a very big part of my life at Dartmouth and feel super fortunate. It was an incredible experience, you know, some real formative years. And I think I had a lot of fun. In retrospect I probably should have worked a little harder. I should have taken more advantage academically, but I think I took full advantage socially of what Dartmouth had to offer. And, and really I had a great time.
LJR: Yeah. And with that entrepreneurial spirit though, even though it was the heyday of the dotcoms and the startups, there was no real, like there is now, there was nothing that was kind of preparing us for that. So if you were commercially minded, as you said, like there was one place you were going to go probably.
DK: Yeah. And it's interesting that you say that because it's easy, obviously, to look back now and see like, wow, things were really changing. I mean, we knew about, you know, the internet and Mosaic and Netscape and we had email and like we were ahead, you know, like we should have seen these things coming, right?
I actually, while I was at Dartmouth, I had two kind of key entrepreneurial ventures that I was involved in. So one was I started a ski tuning business. You'll see this like ski theme kind of weave in and out here. [LJR: Okay.] But you know, as a ski racer, you have to, you have to tune your own skis. And I thought, Oh, well, there's all these students. I'm an instructor. There's all these students who, you know, have their skis. I can tune their skis for them, you know. Just bring them to my room and, you know, I'll tune them up. And that was fun. I actually met some really great people through that experience. But it's a very labor intensive kind of thing. And I think I was like charging $20 and it took me like an hour and a half or two hours and I kind of quickly realized that this, that something was like a little off. This probably wasn't the best you know, not, not particularly scalable. But it was fun and it, and it was really…
LJR: And your roommates were probably like, what is all this crap around us?
DK: Exactly. Well, one of my roommates, you know, he is a skier too. So he, he liked it cause I did his skis. But so that, that was one. And then my junior and senior year, maybe just my senior year, I actually worked with the founder of the Hanover Green Card [LJR: oh yeah] who was also a fraternity brother. You know, and that business became a pretty interesting and kind of big business over time. So, yeah, I was involved in some things that were entrepreneurial, but there was no. Dartmouth entrepreneurial center. There was no like startup ecosystem. VC money was not a thing that people talked about. And the early internet obviously was just emerging. I mean, I know some people, 97s, 98s who got jobs at Excite@Home and Yahoo and some of the early internet companies, but that was not a core path, if you will.
LJR: Right. Right. But corporate recruiting got you in front of some banks, I'm sure.
DK: Yes. And so, like a lot of our classmates, if you weren't pursuing graduate school, which was not really on my radar, it was banking or consulting. So I actually joined an investment bank, Hoolahan Lokey, which was based in LA, but I was in the New York office. Yeah. I moved down to New York with two very close friends. And we were both in banking and, you know, and we just moved down to the city and started that career. But actually after just over a year, I bailed on banking. I knew it was…
LJR: Just over a year?
DK: Yeah. So I pretty much, as soon as I realized that this was not the path for me, I said, you know, look, I'm going I'm going to stay on, do my kind of first year, but actually started writing letters—because that's what we did back in the day—to all of these ski resort consolidators. So in the late nineties, what was happening was there was a big consolidation of, of skiing golf resorts. And there were three players doing this Vail Resorts, a company called Intrawest out of Vancouver and another company in the Northeast called American Skiing Company. And I, and I wrote to the Chief Financial Officers of all those companies and I said, look, I see what's happening. You guys are, are raising money. You're going public. I'm an investment banking analyst working on wall street, but I’d love to explore opportunities. And that's how I ultimately ended up getting a job with American skiing company
LJR: Through a letter.
DK: Through a letter.
LJR: Dartmouth connection? No Dartmouth connection.
DK: No Dartmouth connection.
LJR: Amazing, right?
DK: Yeah. Yeah and so I took a job. I was working directly for the chief financial officer. I thought I was going to be living in Steamboat because the company was actually about to purchase two resorts. And they said to me, Hey Dan, you know, we'd love you to run the financial due diligence process for these acquisitions.
LJR: At 22.
DK: Exactly. So I think I probably did a pretty good job of selling my one year of Wall Street experience.
LJR: I’d say.
DK: And yeah, so I ran financial due diligence for the acquisition of Steamboat and a resort in South Lake Tahoe called Heavenly and was told that I'm going to be living in Colorado and kind of going back and forth between those two places. So I packed up my bags, left New York City, moved out to Steamboat. Three weeks later, got a call from my boss saying, Hey, we've decided to accelerate our IPO. And this is where the internet and kind of dotcom mania comes in. It was the fall of ’97. The market was kind of opened up for raising capital. We took the company public. He said, I need you back at headquarters. I said, where's headquarters? He says, Bethel, Maine. I said, okay, I've never been there. Let's go. Didn't know I was actually moving. I, you know, came back and what I thought was going to be a couple of weeks, couple of months turned into four years.
LJR: Oh my God.
DK: So yeah. And so I spent time working at American Skiing Company. We took the company public. I eventually ran investor relations for the company. We actually went public the same day that a company called E-Toys went public. So E-Toys and American Skiing went public the same time. And I think on the first day the trading ended, E-Toys had a website and a market cap, you know, in the billions. And we had a couple of billion in real estate assets and a lower market cap. So it just goes to show you kind of where things were at the time.
LJR: Right. Right. But as of April 2001, you were probably still around, right?
DK: Yes. They were not around. Although, you know, we had plenty of problems too. So, you know, that company ultimately got sold and yeah, and I, and I left in 2001 and I moved back to New York. You know, my girlfriend at the time, now wife, you know, we moved in together and yeah, I started more of an entrepreneurial journey at that point.
LJR: Okay. And I want to get there, but I want to know how much time on the mountain did you get? Zero or someplace north of what a normal person would have had?
DK: Yes. North of what a normal person might've had. But, you know, I had these, you know, illusions of, you know, Oh, it's, I'm going to be skiing every day, all the time.
LJR: Fresh powder, I’ll get out there.
DK: And basically I was like an investment banker living at a ski resort. It was basically what it was. But I got to ski at lunch. My office was, you know, at the base of the, of the mountain.
LJR: Slopeside.
DK: It was Sunday river, a new remain. That's where I spent four years. And it was a good experience. In retrospect, I learned a tremendous amount. Yeah, it was tough being in your early 20s, having left New York and then to move to kind of rural Western Maine was not exactly, you know, a happening place in your early 20s.
LJR: But you ended up with a girlfriend that becomes wife. So how did that happen?
DK: Well, she was from New York actually. We met when we were in New York and
LJR: The first time?
DK: The first time. Yeah. And then we stayed together and then I was commuting back and forth from Maine to New York and Wow. So yeah, and I actually met her through a good Dartmouth friend who went to elementary and high school with her. So that's how we, yeah, always a Dartmouth connection.
LJR: Excellent. Excellent. Good. So you had your time in kind of an industry that you love that's so interesting. I mean, the rest of us wouldn't necessarily have even thought to do that, kind of following the passion, but utilizing at least a year's experience and your academic experience. So, what was the decision process? I mean, possibly some of it was the romantic part, but yeah, so what goes into that? And then taking a another entrepreneurial leap.
DK: Yeah, a lot of it was personally driven. I mean, there was an opportunity for me to actually, when we sold American Skiing Company to a private equity sponsor, they were trying to merge the company with another portfolio company. And there were opportunities there to take on larger roles. And, but yeah, I wanted to move back to New York and, you know, my wife's mom had gotten sick and, you know, she was back in New York and that's really the beginning of, you know, our relationship going from, boyfriend and girlfriend ultimately to getting married. So that was a big part of it. I also, you know, after spending five years kind of doing financial engineering, I was a little, like I was ready to do more both operationally. I was, I think I felt the need to expand my purview a little bit into things that were more operational. I always had, you know, again, on the kind of commercial side, like a market facing side of things that I felt like in finance, at least in the roles I was in, I wasn't really able to utilize. And so I initially started a consultancy. I thought I was going to actually create a consultancy that was going to target the resort industry, because I had so much, you know, experience over that four year period. And there were 500 ski resorts in the U.S. at the time. And most of those, as they still are, are mom-and-pop-run businesses. So I thought there was really an opportunity to help them with strategy to help them with marketing to help them with finance. And I started doing that a little bit. But, you know, I actually then created a business in the in the loyalty marketing and CRM space and I shut down the consultancy because I kind of needed to focus full time on that.
So yeah, pivoted. That was, you know, 2002 time period started this early CRM company called Precision Loyalty. That was really the first like real startup, I would say, that I created and tried to bring to fruition. After four years, we made some amazing progress, but again, we were starting at a time just before 9-11, there was no real venture infrastructure in place. It was, it was a very difficult time to try to like start a technology company, raise money for a business. You know, ultimately the so many pieces needed to come into place and there was so much tech. I was borrowing technology from, you know, other players. And, you know, we were using credit card processing infrastructure. We were trying to like cobble all these things together. That was the beginning of the Dartmouth entrepreneurial network. So that was. 2001, 2002. There was a gentleman named Gregg Fairbrothers who started the Dartmouth Entrepreneurial Network. I was like one of the first portfolio companies. I don't know that they really, they, there wasn't, they didn't even have a name for it, but yeah, that, so that was that business.
I really spent about 12 years in media marketing technology companies. So after I actually had to shut down Precision Loyalty, I joined a company that was pioneering. consumer data for the use of, you know, really it was, it was an interesting concept. The concept was big companies are using your data to target you. You should also have tools to capture your data. And like any other asset, it could actually be monetized, securitized, combined with other people's data, but it was really all about
LJR: Where is that now? We don't have that.
DK: Still hasn't happened.
LJR: I know. Come on.
DK: It was a pretty, it was a very ambitious and amazing concept, but, and so unfortunately that company, while, you know, well funded you know, blew up pretty quickly. I then joined some of the investors in that business in an early search engine marketing company that was building technology and services in search. I helped them kind of grow the business. We got into early search engine optimization and very early social media marketing. So now time period we're talking about like 2005, 2006. So we did some of the earliest social media work for brands like L'Oreal and Honda, Home Depot, American Airlines, things like that. So that was just wild.
LJR: Yeah. And all of these other ventures where you're kind of coming together with other players and all this, are you finding yourself back in those financial engineering roles or are you kind of spreading your wings and doing it?
DK: No. I’m, I’m…So in these other companies, I had more general management roles and I was actually more in a, you know, kind of business development, kind of true, true sense of business development, like beyond the, the selling of product, the development of new lines of business, which was great because that really gave me the opportunity to blend the financial foundation, right? So, you know, these businesses ultimately have to work financially with the more market facing side of things. So, you know, it's that kind of constant balancing of creating product, getting it into market, getting feedback, selling the vision, but also taking that feedback and quickly improving upon it. So it really did allow me to do a lot of that kind of work.
Ultimately the business reprise, we sold to a larger company. It was sold to a large ad agency holding company. And I was fortunate enough after the founders left that business to run that business for a little while. I then joined an early podcasting company that had actually pioneered kind of the YouTube of audio. It was called BlogTalk Radio. That was in 2010. So if we go back now, you know, 14, 15 years, you know, podcasting, there wasn't much going on there and they created tools very much like what we're using right now. And I helped them to kind of move away from being a consumer only business, which was kind of more of the media property to using that same tech and turning it into a really a software company that could sell, you know, that technology to businesses so that they could create marketing content using audio, right? Which we all know today has become, you know, an incredibly robust market. But at the time, you know, nobody was really using it.
LJR: Yeah. Okay. So a string of these things kind of still in the general media tech space. Then things change or I, I love in a couple of other, I don't know if you've noticed this, you talk about changing course, like the skiing—changing course. The, you know, first thing—changing course. Not being a med student—changing course. So courses change. What’s the biggest one.
DK: Yes. What's the next one? So.
LJR: Or the big one.
DK: Yeah, well, I mean, I, went back into kind of corporate, you know, a more corporate environment in 2012. I joined a company called RGA. Now RGA was like a Madison Avenue ad agency, but known for innovation. And a lot of their history was with Nike working on a lot of things there. So one of the companies that we sold, the company that we sold to this larger ad agency holding company, RGA was also owned by that same holding company. So I knew a lot of the folks there. And when I went over there, it was really to help them bridge the gap between a lot of the things that startups were doing at the time, right? So performance marketing, product led marketing, agile development, really kind of quick iterations, test and learn. And I had spent, you know, 12 years or so doing that at this point with what Madison Avenue provided, which was big ideas, big splashy campaigns for big companies. But these big companies were being disrupted by smaller companies. And so I kind of found my way as like the subject matter expert who could bring some of this, you know, kind of more cutting edge connection between data, technology, and creativity to these larger businesses. So, you know, that, that was actually a, you know, for over a five year period, I worked with, you know, some of the most iconic and innovative brands in the world: Google, Nike, Verizon, Tesla, Amazon, Coca Cola, like, you know, the biggest. But then also helped RGA build out a venture studio concept, which was Hey, we have all this amazing talent that works for all these great businesses. What if we could apply some of that talent and expertise to early stage companies, right? And we would invest in those companies as well. And we would partner those early stage companies with our existing clients. So that really became a great mix for me, right? At being able to work with big companies and have, you know, kind of a front row seat to the senior people at some of these extremely innovative companies that are spending hundreds of millions, if not billions of dollars a year in marketing and then early stage startups that, you know, we're in some cases, two people and a PowerPoint presentation, and in other cases, you know, had built out product, but certainly weren't getting access to the world class design resources that, were typically reserved for the, you know, the fortune 50. Not just design, but strategy, copywriting, design, user experience, analytics, et cetera. So that was really great. So I served as a, you know, a bridge between those big companies and these small companies. And it was, it was a really good experience.
LJR: And you had this subject area expertise and yet you're in, this environment that is kind of on its own level. And so what you're bringing is important, but what you're gaining and what you're learning must have just been completely mind shifting for you or even like where you're focused. Like, yeah, you'd been kind of a marketing guy before, but now you have this other level.
DK: Yeah. No, it was, it was, it was the big leagues, right? Like this was definitely like the big leagues. And I love that big platform, but I also love that I was able to kind of toggle between startups and founders and working directly with the people who are, you know, at the most nascent and early stage of a business, as well as people who were the stewards of a brand that might be, you know, a hundred years old already. So yeah, it was a great experience and yeah, the learning…I think one thread for my whole, you know, kind of post Dartmouth career has always been, well, I probably didn't take my learning seriously enough at Dartmouth. After Dartmouth, it has been learning the whole way and like always kind of from the fire hose type of stuff and I love that and I'm kind of having like an insatiable appetite for learning new things and you know if I can learn and apply. And I love this idea of taking…you know, part of the allure for me of working in a portfolio type environment…So at an ad agency or, you know, where you have multiple clients…is this ability to connect the dots, right? Between, you know, across different industries, across different functions, things that we were able to see in one place we could bring somewhere else. You know, some of the experience I, you know, I spent close to two years working on the launch of Beats Music, which became Apple Music. And I kind of handled all the performance marketing and everything related to the launch of Beats Music there. That again was like, as you said, you know, kind of front row to some of the, one of the biggest brands in the world. And here we are, you know, Jimmy Iovine and Dr. Dre, you know, eventually selling that business to Apple for a few billion dollars, you know, right after the launch. That was an incredible, incredible time, you know, in my career. And it was, it was really, it was a great group of people to work with, but also, you know, the, the learnings from that time were incredible.
So then I move again, another shift this time to become the chief marketing officer of a meal kit company called Plated. That shift was again, looking to be more operational at this point. After spending, you know, a number of years more on the services side, even though I've had operational roles within those businesses, I was yearning again, I think, to go back to a more operational role and was fortunate to join Plated as their chief marketing officer. And that was another great experience: Building teams, managing and taking the full responsibility of a large budget, being able to do all of the kind of things that I had advised larger companies on, but was not the budget owner, was not the one with the ultimate responsibility. Now I was, you know, whether it was TV ads or digital ads or direct mail or PR or events or partnerships. You know, we had a very robust operation. And that really is kind of where I am today.
So, so Plated that opportunity kind of came along. That company was also sold to a very large grocery chain. Unfortunately, they closed that business down. And really for the last five plus years, I've been like a fractional chief marketing officer working again with smaller to midsize companies, but have also kind of put together my own kind of SWAT team of marketing experts, you know, that I've worked with really over my entire career. And that's another thing. I think that network that I've built is such a tremendous, like if I was to think back not only on the learning and the, and the expertise, but you know, as you join different companies, as you change course in the road, the networks that you develop, kind of the personal relationships that you develop, like those are key times to, you know, to really expand that kind of overall ecosystem.
So when I started Tenth Mountain, which is my current business, you know, I had an embedded network of specialists in visual design, in experience design, in analytics, in media buying, in copywriting, in project management, in product management that I could tap into. I knew all of these people. I had worked closely with them. We had been in the trenches together working on projects and things like that. So that was really great. You know, as I started my own thing again, you know, I felt like I could rely on that network.
LJR: Yeah. And you had had such a breadth, you know, from either being in the trenches or being at a, Bigger place that had so many different clients, like you could be across all sectors, right? So the things that you do apply so many different places and that keeps you, I'm sure really kind of interested. It's like the best of all worlds. Now you can do all those things that are so different. You have the operational side of being the CMO when you need to be, and yet being very entrepreneurial in that you have your own firm. It's just, it seems like it is the culmination of everything.
DK: I think so. I think we're only halfway. We're only halfway there. Let's please not…
LJR: A culmination. That makes it sound like it's the ending. Right, right. But a logical next step, I should say.
DK: Yeah, no, and it's been good. And I have actually, in addition to Tenth Mountain, I actually about two years ago, I started an AI longevity coaching business. So it's a company called Medo, M-E-D-O. Yeah, that's another startup and that's a health-and-wellness-focused business. So yes, while I have worked across all of these industries and Tenth Mountain has had clients in FinTech and data privacy and pet supplements and personal care. Across the board, kind of, you name it, we've worked across almost every industry. I really do have a passion for health and wellness and, you know, Medo is kind of my way of kind of bringing a lot of the, again, the connectivity in terms of data, technology, and creativity together to help people live better, longer. That's really our mission.
LJR: Yeah. Well, when you said we're halfway there, I'm like, Okay. We have a century in us. Oh, we'll see. We'll see. We'll see. I love it. I love it. Okay. So there are, I'm sure, other parts of your life rather than just work. So I know girlfriend became wife at some point. How does the rest of your life fall into place around these big kind of major…?
DK: Yeah. I mean, we've, we talked only about career, but obviously, you know, so much of life is not your career. So yeah, my wife and I have been married for going on 23 years. Yeah, we have two great kids. My daughter just started. She's a freshman at University of Wisconsin and my son just started high school. I have a six-year-old 80-pound dog and I still love skiing. It's a huge part of my life. My life, I try to, you know, I've tried to get my whole family into it sometimes more successfully than not, but for the most part, we all love to ski and snowboard and, you know, we go to the mountains whenever we can, at least one family trip every year. I still do a ski trip with a lot of Dartmouth guys every year. So we get to get together. Yeah. As you can see here from the musical instruments in the back, I try to play guitar a little bit here and there. I recently got into trail running and yeah, for my 50th birthday, my gift to myself was I've never run more than 15 miles, but I'm going to run a marathon in my home trails. And I did that a week ago, Friday. And so it was super fun.
LJR: Congrats. Excellent. So can you walk?
DK: Yeah, I'm good. I'm good. I can walk. The next day was a little dicey, but.
LJR: I know. I know. Oh I remember. Okay. So all of that sounds like a very full life. And I think it makes sense that you are a course changer, but once you find your stride, like this marathon running, like I think you have some longevity in you. And so I can see this phase lasting for a little bit longer. But the next time you change phases, make sure that you reach out and keep us posted.
DK: I definitely will.
LJR: Good. So Dan, thanks so much for being here and telling us all the roads you've been down so far. We really appreciate it.
DK: Thank you. I appreciate it too and appreciate everything you're doing here.
LJR: That was Dan Kashman, an experienced Chief Marketing Officer and entrepreneurial executive with over two decades of experience in finding the connections between data, technology, and creativity for companies large and small. His marketing consultancy Tenth Mountain is a multidisciplinary marketing firm with clients in all sectors. But as a devotee of the health and wellness space, he is also the founder of Medo, which uses AI-powered health coaching to make preventative health optimization accessible to everyone. Check them out at hellomedo, that’s helloMEDO.com to learn your free Sense Score and a holistic view of your longevity potential.
If you’ve stuck with us this long in the life of our show, we’d say you have plenty longevity potential, regardless of your number. If you’re new to us, though, we’d like to point you to RoadsTakenShow dot com where you can find our full archive so you can catch up with all my guests and me, Leslie Jennings Rowley, on Roads Taken.