The founder of JackThreads and serial entrepreneur, Jason Ross, spoke with host Michael Redd about his early days as a broke entrepreneur, the big gamble of launching (and selling) his own startup, and what it takes to survive the ups and downs of the business world.
“I wrote the business plan and spent two and a half years just working out of my house to get it started.”– Jason Ross
Named after his grandfather, Jason founded JackThreads in 2008 – a members-only flash sale site for the streetwear community – and was working out of a bedroom in Columbus, OH.
By May of 2010, Thrillist had acquired JackThreads.com, the startup Jason helped build to $100m in annual revenues and over two million members (he departed in 2014).
JackThreads was listed as one of Ad Age’s America’s Hottest Brands, Inc’s Fashion Startups to Watch, Entrepreneur’s Top Retail Sites and as the fastest-growing men’s e-commerce company on Internet Retailer’s 500 List.
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In this episode Michael and Jason talked about:
- The mindset needed to be successful in the face of adversity
- How Jason rolled up his sleeves right out of college and bet on himself
- Why entrepreneurship is so iterative and success is not a straight line
- The genesis of Jason’s bootstrapped, $100m idea (and why he sold it)
- On the marriage of passion and high-growth opportunities
- Why you need to surround yourself with the right (and smartest) people
- And much more!
- Jason Ross on LinkedIn
- 30 UNDER 30 2016: Jason Ross, Founder of JackThreads – Inc.
- Jason Ross on Twitter
- Michael Redd on Instagram
Michael Redd: As you know, the podcast is all about betting on yourself. And when I thought about that, meeting you, and hearing your story, I was like, "Well, Jason, would be a great person to talk to about." And you've been an example of that in the city. So, obviously, your background is illustrious, over the last 20 years, in the business world being the brainchild of JackThreads. And then we all know locally, and nationally, internationally, JackThreads was a Columbus based online men's wear retail.
Michael Redd: And it was a members only shopping club, which was on an e-commerce platform. And so, looking and studying you, and really talking with you, and knowing you over the last few months, I've been really intrigued to hear more about your story, and the mindset that you have had since you were a kid, probably. I'll ask this question to start with, what does it mean to you when you hear betting on yourself, or what has that meant to you, betting on yourself?
Jason Ross: Yeah, I think for me, in terms of how I think about my life, it's probably due to some of the ways I was raised. My father went to West Point, West Point graduate, was in Special Forces, and now is like an ultramarathon runner. So, was around somebody all growing up who was very disciplined, and doing things that maybe others thought were not possible. But to us it was like, "No, that is possible." Like, you should set those big goals for yourself. And so, when I think about like how I approached life, I always wanted to take on big challenges, and do really big things. And so, how do you do that?
Jason Ross: And brings me back to a quote, there's this Calvin Coolidge quote that I found like early in my career where he just ... And I don't know the exact quote, but the gist of it is that talent, and education, and genius, they're all commodities, but how to separate yourself is through persistence and determination. And so, if you think about like betting on yourself, and taking on big challenges, well, how do you do that? It's by setting a longterm goal, and persisting through all the obstacles, and the ups and downs along the way, right? Success is not a straight line. There are going to be ups and downs. And if you're not thinking about a longterm goal, and taking steps every day to get there, it's probably not going to happen. And I think that's where most people fall short.
Jason Ross: So, for me, the only way to navigate those ups and downs, and maybe more importantly, the downs is by betting on yourself, and believing in yourself. And if you're not able to do that, then you're not going to be able to accomplish big goals and reach big dreams. And I just didn't want that to be a reality for me. Like I have big dreams and big goals. And I tried to associate more pain with not living a life that way than actually like going through the ups and downs to get to where I wanted to go. And, yeah, the only way to do that was to just take those steps, and place a bet on yourself, and not look back.
Michael Redd: Did that play a part ... And we'll go back into maybe your early teen years as well, but was that part of the mindset that you had even with your first company for a lot of the listeners out there, this was not Jason's first company, JackThreads. I believe you had another business before this. And you transitioned to-
Jason Ross: I did.
Michael Redd: ... So, talk a little bit about that.
Jason Ross: Yeah, no, for sure. I graduated Ohio State, financial degree, 2003.
Michael Redd: Buckeye.
Jason Ross: And right out of school, I never got a job. And so, yes, part of that mindset was I could go today, and with the degree, and probably get a nice job somewhere, and work in a corporate environment, and risk going down that path, or I could take a chance at a young age in my life, and go and just take a bet on myself in terms of doing or pursuing a career path that was really where my heart was, which was entrepreneurship. And it was scary, it was scary. But I met another like-minded student through Ohio State, and we launched our first business right out of school, a sports marketing company. It's not really even worth going into too much detail about what we were doing, but we were just sourcing products from overseas, and selling them into collegiate athletic departments for in-game or in-event like promotional opportunities.
Jason Ross: So, a good example is like a fan comes to a game. And at times, the first 30,000 fans might get a bobblehead with the logo of a corporate sponsor of the university. We were the ones sourcing that product and selling it to the athletic department. And so, it was a great experience. I took a leap to do it, and I think I learned a lot going down that path around just like when you enter into a business opportunity, just what it takes, right? How to sell, how to set up a financial plan, how to just run a business, how to build a team, how to build culture. But ultimately, the important lesson I learned was that we probably didn't plan enough going into it. And it wasn't really a space I was really passionate about.
Jason Ross: And so, a few years in, we were at this inflection point, like, "Do we keep going?" We had made a little bit of money. And we had an investor in the business, and we were at a period where we could basically take the money that we had made and double this person's investment. And it wasn't a lot of money, but we had enough to double this guy's investment, or I could continue running the business, which was something I just really didn't care about that much. I wasn't getting up every day fired up to do it. And I could go down that path and risk losing all his money.
Jason Ross: And so, we made the tough decision to write our investor a check. We gave him his money back in a return, and we ultimately, shut the business down. But it was a great experience for me because what I did after that was I took all the learnings from that, which was, again, didn't really plan too much, I didn't write a business plan. And again, it just wasn't something I was passionate about. And I spent the next year of my life with the little money that I had seeking out, what's the next business opportunity? What's something that I'm going to be fired up about every day?
Jason Ross: What's something that I can do enough planning around to prove that this isn't really a risk, it's a high growth business opportunity? And ultimately, in that year is when I came up with the idea for JackThreads. And I wrote the business plan at the end of that year, and then that started the JT journey.
Michael Redd: Wow. Well, take me back if you can, and if you will, to a moment, a pivotal moment in your life where you took a chance on your life.
Jason Ross: Yeah. Well, I would say, at the end of that experience, I got out of school, I was 23. So, at the time that we shut the business down, I was probably 25. Again, college degree, first business. We didn't make a lot of money. I mean, I'm 25 years old, pretty much broke. And I don't have an idea. I don't really know, like, what am I going to do from here on out? That business is shut down. I have to start from scratch again. I think the urge to want to jump into something that was comfortable was strong. I mean, I always knew I had a degree to fall back on, and I could have easily gotten a job somewhere, and eliminated all that uncertainty, and the nervousness I was feeling.
Jason Ross: But when you ask about taking a chance, I mean, I viewed that year as pivotal because I learned a lot in that first business. And so, I thought like in order to continue on the journey that I really want to be on, which is learning how to start and grow a successful company, and have a career as a successful entrepreneur, you've got to take that learning and then take steps forward to try and not make the same mistakes that you made in the first one, and try to find the next thing that is actually going to be a better fit for you. So, it was that year, which again, I had no money coming in. There was a lot of uncertainty, but I stayed the course, and just navigated through it.
Jason Ross: And I tried to meet with really smart people every day and was researching all sorts of different business ideas. And again, thinking about like how to do more planning around the ideas before I got into them, and to really make sure it was a space I cared about. So, almost [inaudible 00:08:51] that year from like 25 to 26 is like ... And I so easily could have gone and got a job somewhere, but instead chose to just take the chance, and stay on the journey, and live within my means. And it was pretty scary at times not really knowing how you're going to pay rent every month, but boy did it lead to an amazing place. And I'm so thankful that that was the choice that I made. Because who knows, you might end up in a job somewhere, and get comfortable.
Jason Ross: And not to say that that's wrong, because it's not. It works well for many people. But it just really isn't the life that I wanted. And it wasn't going to lead to the impact that I wanted to make. And so, I'm just so glad that I took that risk at a young age, and it turned out the way that it did.
Michael Redd: It almost seem like that decision was ingrained in you from a child even, because I'm going to ask this question, why choose the harder path to start from compared to being more comfortable in a corporation? Why choose the harder path to start from scratch? That's a really challenging, difficult decision. Was that ingrained in you even as a child?
Jason Ross: Yeah, I think so. I mean, again, just basically with the way that I was raised, I think it was ingrained in me. And I do come from a family of entrepreneurs, like on my mom's side, a lot of her siblings have started, and run their own companies. And so, it was something I was around. And I think just, I always had this mentality that ... And maybe it was through seeing some of the things that my parents had achieved, but like nothing great is accomplished without risk. And again, setting like longterm goals, and taking the steps to get there. It does not happen overnight. You have to work so long and hard to really realize big dreams.
Jason Ross: The big dreams that when realized can have a major impact. Yeah. So, I think it was like, you can either face that, and go through it, or you can, I don't know, in a way, give up on yourself and that dream. And I just couldn't do that. I don't want to get down the road 10, 20 years and think what could have been. And, so yeah, I think all those things were fueling me to go in the direction of just taking the risk.
Michael Redd: So, you chose fashion?
Jason Ross: I did. Yeah. You know [crosstalk 00:11:11]. It's funny because in your mid 20s, and specifically in my situation, not having a lot of money, but single guy out on the town, and you want to look good, right? You want to have the right outfit, and have the right accessories, all that stuff, like shoes, everything was really important to all my peer group at the time. But I didn't have any money. So, I was having to find all these things on a budget. And so, I thought, "That's interesting." Right? Like, "What guy doesn't want to look good, and doesn't want access to cool products at a great price? And what guy really likes spending time going out and doing it." I know I didn't, it just was a need that I wanted to fulfill.
Jason Ross: And so, I thought if I could create a service where I'm in that space and looking at all these products that I think are cool anyway, and pulling them together into like a curated store that makes it really easy for guys to get in, understand what brands are cool, how to put products together to get the right outfit or right look. And do it in a way where it's quick, convenient, and there's value in that experience, and the time it saves, but also the money that it saves you. I thought, "Man, that's a win." And that would be a lot of fun. And so, yeah, that was really the genesis of the idea.
Michael Redd: Do you take chances on your wardrobe?
Jason Ross: I did. I definitely did. I would say as I've gotten older, maybe I've got a little more conservative in that, but I'll always keep a few pieces around to separate myself. It's so interesting the way the world has gone. I feel like in the early days of JT, you could go out, and be the guy in the crowd that knew fashion and style. And I feel like now, and maybe it's the way information is so easily accessible, and readily available that in a way like good fashion, it's almost commoditized.
Jason Ross: I mean, you'll have some of the style icons out there that can pull off some crazy looks these days, but you don't typically see that as much when you just go out in Columbus, or some bigger cities. It seems like everybody just knows what's cool. And so, that's been an interesting shift in the world. What about you? When we hang I'm like, "This guy gets it, man. He's got some pretty dope pieces on."
Michael Redd: I am at a age now, Jason, that I just don't care anymore. I think I'm secure in my identity.
Jason Ross: Oh, sure.
Michael Redd: And I think that comes through. However I feel that day is what I throw on, and that's what it is. Obviously, when I played in the NBA, we had a dress code that we had to adhere to. So, I learned a lot from that, that time in my life. And at this point now I'm most comfortable actually though in a hoodie, and shorts, and flip flops.
Jason Ross: Yeah, same.
Michael Redd: But I can go there. I can go there sometimes.
Jason Ross: Yeah, I always admire your shoes. Your kick game is always pretty strong. Yeah. It's fun. I guess, I go in spurts too. I'll get inspired, right?
Michael Redd: Yeah.
Jason Ross: On certain days or weeks. And there are a couple style icons that I'll look to, and maybe look to as inspiration. And I might go pick up a few pieces in that way. But it comes and goes in spurts whereas it used to be more of like an everyday thing.
Michael Redd: As I read more about you, man, I became really intrigued with your mindset. I believe in between that two and a half year process of developing that business plan for JT, you're quoted as saying that you worked at bars and you worked anywhere part time to get enough money, to continue to pursue your dream, man, which is incredible. Tell me about the mindset you needed or what type of mindset have you needed to find success or achievement in the face of adversity?
Jason Ross: Yeah, it's interesting you bring up some of those jobs. And it does lead back to the decision that I had to make. And the decision came from a conversation I had with somebody in the community that I looked up to, and still do, a successful entrepreneur in his own right. But after the first business, the sports marketing company, and I was sitting with this individual, and just talking about all these ideas. And he said something to me that ... And his quote was something along these lines where, you're looking at all these ideas, and maybe talking about trying to start a few of them. And his feedback was it's hard enough to start one business. You can't go out and try to do all these things at once. So, my message to you would be find the thing you care about the most. Back to passion, right? Which was something I learned in my first business. It just wasn't something I was passionate about.
Jason Ross: He was like, "Find the thing you care about the most, and just put the blinders on. And write a plan, make sure you plan it out, and make sure you prove that it's a real opportunity. And put the blinders on, and just make a pact with yourself that no matter what obstacle gets in your way, that you're going to muscle this thing to launch and to success." And so, that year from after my last business, the sports marketing company, the year that I talked about, which was in between that business and JackThreads, that was the mindset that I had was about first and foremost, find what that opportunity is.
Jason Ross: And then once you find it, put the blinders on, and don't let any obstacles stop you. Any obstacle that presents itself, any challenge that comes up along the way, you've got to have this mindset to find your way around it. Well, one of the obstacles was, again, having no money, and having just no way to make sure I could pay the bills, so I could continue to pursue this dream I had. And so, yeah, I made this pact with myself, and the way to keep income coming in was to find creative solutions to do it. And one of those solutions was working in the nightlife industry because I could go into work at 8:00, or 9:00, or 10:00 PM, and have my days free. Right?
Jason Ross: So, I did that for a little while. I have, again, family who are entrepreneurs. And I worked for an uncle who owned a hotel remodeling company. And the beauty of that was he would allow me to come down and work on the jobs as I needed to do it. So, I could call him and say, "Hey, I'd like to come down for the Thursday, Friday, and work on the weekend, just so I can have most of my days free this week, and make a little money." And he was like, "Come on down." Because he knew my work ethic. He's like, "You work harder than most of my laborers anyway." So, he was always willing to let me come down. And ultimately, throughout that process, I was always also constantly networking. And funny enough, the same individual who gave me that quote about like, pick one idea and put your blinders on, introduced me to the CEO of a large business here in the central Ohio region.
Jason Ross: And that CEO, they were launching a new division within their company that had some similarities to what we did in our sports marketing company. And so, that was the reason for the connection. And when I went up to meet with him, I shared my story, and shared my dream. And I was working on JackThreads at the time, and told him that was my real dream but I was working these odd jobs, and I needed a way to make money. And we really hit it off. And so, he offered me a job to help them with this new initiative. Again, that was very similar to the sports marketing company that we had started. So, I did have the relevant experience to help them. But he said two things to me, and I'm indebted still to this individual, but he said, "One, just guarantee me that you'll work 20 hours a week."
Jason Ross: And I said, "Of course, happy to do that." Because that still gave me a ton of flexibility, right? To pursue my dream. So, he said, "Guarantee me you'll work 20 hours a week, and guarantee me that you will not stop pursuing this business. And you will launch this business someday." And I said, "Deal." And I quit that job, and I can't remember how many years later, but I quit that job the same day I was able to pay myself enough money from JackThreads to get by. And so, it was a pretty fortuitous introduction. And I think it worked well for both sides. We had success with the project I was working on. And again, the pact that we made, yeah, I guess, in a way I lived up to my end of that agreement. And I'm very thankful to have met that individual.
Michael Redd: Absolutely. Coming from a family of entrepreneurs, who was your biggest advocate in helping you bet on yourself? I think I did a little digging. And is your father a marathon runner as well?
Jason Ross: Yeah, he does ultramarathon. So, he has been a runner his whole life, but his passion now are these long distance endurance runs. And he'll go out and run 100 miles in one session. It usually takes like, I think the cutoffs are usually around 30 hours. You have to finish within 30 hours. And so, yeah, that's what we grew up around.
Michael Redd: I'm sure that had a huge impact on you.
Jason Ross: Oh, absolutely. Yeah, absolutely. It's interesting, my family dynamics, like my parents were not entrepreneurs. Again, my dad West Point, and the military career, and then police officer for his whole career. So, that dedicated his life to service, and now still he's on the school board in our hometown. And my mom, very much took care of the family, and worked in the banking industry, and a few other industries at times, but it was more her siblings that were entrepreneurs. But I think the mindset of my parents was really interesting. You have the dad on one side who is a very determined, and hard working, and can persist through adversity as good as anybody. And my mom is very tough too, but she is incredibly financially-minded.
Jason Ross: And so, as I look back on that, and I think about a career in business, like what two great skillsets to have ingrained in you. Like an understanding of the importance of finance and financial discipline, and then understanding the importance of persisting through adversity to achieve really big dreams. So, I'm very thankful for that. And obviously, it's just lucky to have the parents that I have.
Michael Redd: I think I know the answer to this question, I think the time that I've been around you, there's still a drive in you. There is still a passion in you to continue to do great things, and have greater impact. Where does that drive to continue to strive, where does it come from?
Jason Ross: It's probably partly the way I was raised, but also I've seen now having gone through the entrepreneurship process, and having had a big win with JackThreads, and seeing the ripple effects of that, right? The opportunities that open up, the jobs that are created, those people that were in our organization the things that they have gone on to do, the companies they've started. The jobs they've created, the wealth they've created for themselves. So, it's just the impact you can make when you're setting these big goals, and going out, and achieving them. And for me, it was through entrepreneurship is incredible.
Jason Ross: And so, I think I just want to continue to do that, right? Like something that I think about all the time, it's something that drives me. And I feel like now I have a pretty unique skillset to be able to do it. And I don't know, you don't want to waste that. Right? Like there's people that I want to help. There's philanthropic causes I'd like to explore over the next few chapters of life. And those are a lot of the things I think about, I think pretty much day in and day out. And those are some of the things that drive me. And luckily through business, and success in business, you can have a platform to create that change, and make that impact. And I've done it, but I want it to keep going, and I want it to keep getting bigger.
Michael Redd: So, with that being said, I'm curious for you, what is your definition of success?
Jason Ross: I think I haven't thought about that in a while. I think for me personally, it's the ability to set these longterm goals, and to persist through adversity. Like, I mean, if I think about what makes me happy, it's when I can look in the mirror every day and ... One way I measure myself is like, how much risk are you taking right now? Because I truly believe that you can't do great things in life without taking chances and risks. And if the answer is that I'm not taking a lot, or I'm not happy with the things I'm working on, then you have to make a change. And so, I don't know. Success to me, because that is so important to me, is just I think living a life where I'm honest with myself, and I'm setting goals, and I'm taking the steps to get there, and fighting through adversity.
Jason Ross: I think if you consistently do that, you will achieve great things. And I think that's really important to me. So, success to me is just living a life where you're taking the steps to make all that possible. And I know if I wasn't doing it, I just wouldn't be happy with myself. And that's just me.
Michael Redd: Any regrets along the way?
Jason Ross: I mean, I think, regrets, is that the word or is it ... I think along the way you maybe make decisions, and you take some chances that don't always work out. So, yeah, in a way you can regret them. I always try to remind myself that what was the mindset that you were in when you made the decision? And what were the factors you were dealing with in life, whether it was personal life, or in the business at that time, that led you to that decision? And because of all those things, like, was it the right decision at the time regardless of how it worked out? So, I try to be objective in the way that I look at them. But of course, I mean, not every decision I made do I think was the right one.
Jason Ross: I do think most of them were the right one at the time, but maybe they didn't work out in that way. And so, I just try to learn from them. I think if you're not looking back and trying to think through what could you have done differently, so that you don't make that mistake again? I think it's really important. Like with JT, I sold JT fairly early in our trajectory. And I know the reason I did it. And I think ultimately it worked out incredibly well, but a result of that was that over the years after selling, it became a job, right?
Jason Ross: I worked for a private equity backed media company, and we had a board, and essentially, I was working for them. And that isn't really why I got on this journey of entrepreneurship. It wasn't to have a business that I started where the strategy was being controlled by a different group of people. And that was essentially in a job. And that's ultimately what it turned into. So, if you say regrets, there's been times when I've looked back on that, and thought like, "What could have happened if I would've hung on to this longer?" But you'll never know. And so, how I've tried to look at it is, well, one, through partnering with that group, it was almost like getting an MBA in business.
Jason Ross: I was around some incredibly smart people, and I was able to hone my skills. And I think become just a much better entrepreneur, and leader, and operator of business. And maybe I wouldn't have been able to have that experience had I gone it alone. And also we had a great outcome, right? We had a great outcome. And who knows? Had I gone on the journey myself, maybe it wouldn't have turned out that way. So, you could use the word regret. I don't really look at it that way. I think it's just like I made a decision, and it seemed like the best one at the time. And what can I learn from that? So, that if I'm facing that same crossroads in the future, that I take those things into account, and I don't make the same mistake if it wasn't a mistake.
Michael Redd: And I think you hit on this a little bit ago, but I'll ask this question, anyhow, why did you sell JT so early on?
Jason Ross: So, in the JackThreads business, it was interesting. I mentioned I was looking for something I was passionate about, and I was pursuing a really high growth business opportunity. And I was trying to marry the two. And so, I did a ton of research, and I found one. And why that's relevant to your question is that when we launched, we exploded out of the gate pretty quickly. And there were a number of other companies that had a similar business model to ours that were also exploding out of the gate. Now, these businesses, unlike me were not bootstrapped. I was bootstrapped. I funded everything myself, and I didn't raise any investments. I did it all with my own money, and an SBA loan. And it worked incredibly well because I own the whole thing.
Jason Ross: And while these other companies that had launched had raised tens of millions of dollars in VC funding, and they were pouring it into growth, and hiring all these huge teams of really smart people. And they were in the press all the time. And so, as I'm growing in like year two, I'm looking around, I'm starting to get all these calls, whether they're from investors, or VCs, or these other competitors who have a similar model, and people wanted to invest. People wanted to buy our business. Others were on these calls talking about like, "Hey, we're going to potentially enter this space, and maybe start selling into men's wear." And so, I started thinking more about, I own 100% of this business. And we've got a great team, we're here in Columbus, but we're all pretty inexperienced." Right?
Jason Ross: Like I had maybe like 15 people at the time. And we were all very hard working, smart people, none of us had really done this before. And again, didn't have any outside capital. And so, I started feeling like, I need to do something to protect, I want to protect this investment I've made. I want to protect this brand I've built, and this business." And a way to do that is to add some capital to the business, take some chips off the table, and surround it with really smart people. So, that all of this noise that's happening out there, all this competition that's emerging, people can't really come in and steal what we've built. And so, that was a big driver for why I sold the business.
Jason Ross: And I sold majority of it. So, I still maintain the nice position in the cap table. But when you sell majority, you're not the key decision maker. I was the person running the business, and still was the CEO, but I now had a board to answer to. And I had other opinions that I had to take into account when thinking about strategy, because there was a controlling interest at the table that was not me. And so, yeah, so that's why I did it.
Michael Redd: Yeah. It's interesting because you birth the baby, and now the responsibility of growing the baby is in someone else's hands.
Jason Ross: Yes. And it's a common thing, right? With entrepreneurs. I think it's like, you give this advice all the time, but if somebody comes along, and offers you a good chunk of money for your business, you really have to consider it because there's so many stories of people who, you could use the term got greedy, and then in two or three years the business, it wasn't at the same level, or it wasn't worth the same amount of money. So, in many ways I think, you can't knock the decision because I just don't know which other direction it would have turned. It set myself up, and it set a lot of people up financially by doing it the way that we did it. But yeah, it definitely was challenging. It was very challenging.
Jason Ross: And I think with all that pressure from the outside, and all the competition that was emerging, and being a first time entrepreneur, and having that feeling of really wanting to protect what you've built. So much of that decision was made thinking about like, "I want to surround us with the right people, and make sure it has a long longterm future." And at the time as a first time entrepreneur, I was confident in what we were doing. And I thought we had a great team, but I thought we could ... I don't know, I just wanted to build a moat around it, if you will.
Jason Ross: And I think we did that with the team that we were able to partner with. However, it resulted in a loss of control, which over the years I realized was a really important factor for me to maintain in the future. And so, I'll think about businesses I get involved in, and decisions that I make in the future, in line with that, who are the people at the table? How is controlling interest designated? And is that a situation I want to be a part of again?
Michael Redd: What I've heard you constantly say in this conversation is about you surrounded yourself with smart people. You surrounded yourself with brilliant people. How important is that for an entrepreneur as they continue to build their startup, and continue in this endeavor? And how important is it for you not to be the lone genius, right? In the room.
Jason Ross: Yeah. Look, I think people ... I say this all the time, I say this to friends who come to me for, you know, "Hey, I'm going to invest in this company. What do you think?" I say this to entrepreneurs who might bring me an, "Hey, I need some advice on this or that." People are the number one most important thing to success in business. I mean, I think every experience I've had, whether it was starting a business, it was sitting on the board of a company, it was investing in companies, just advice that I give to friends, like every experience that I've had in business, and the success or failure of those companies has all come down to people.
Jason Ross: And so, to me, it is like the most important thing. I can't stress it enough. It's like you have to get the right people around you. You have to get the right people on the bus, whether that's your executive team, the advisory boards you put together, people with experience, and the playbook, people that have done it before that have your best interests in mind. I think businesses will live and die with the people choices that the leaders make. And at this point in my career, I can't be convinced otherwise. I mean, I stand behind that so strongly. We'll see where the next 10 or 20 years go, but I don't think it's going to change. I mean, that is just number one.
Michael Redd: Well, launching as an entrepreneur, Jason, today's times we're faced with a new reality with this pandemic, obviously. What advice do you have for any entrepreneur that's now launching out in the middle of this crisis?
Jason Ross: I think, one, with any crisis, there's definitely opportunity, right? Opportunities always emerge from situations like this. And what I mean by that is consumer behavior will inevitably change the way people shop, the way people consume, the way they travel, the way they just think about life will change. And so, I think if you're launching a business today, you just have to be very conscious of the way you were thinking about going about it pre this pandemic might not be the way you need to think about it in the post pandemic world. And so, how can you try to anticipate some of that behavioral change, and the impact that'll have on your business?
Jason Ross: I think that's one thing. And I think too, as we were talking earlier, Michael, it's like we were sitting together in an office, like there are people everywhere, and chopping it up, talking business. And then it seemed like within a day or two later, everything was shut down. And my point in bringing that up is like, we just don't know what's going to happen. I don't know what's around the corner. It seems like things are changing daily, weekly, and there's new information coming out. And with all that uncertainty, I think we need to maintain a relentless financial discipline right now. And I think if you're launching something, obviously, that's really important, just understanding how you're spending every dollar, and being very cautious.
Jason Ross: If you already have a business launch, and there's a lot of talk just from like prominent VCs who do like YouTube interviews, or on CNBC talking about like advice to entrepreneurs, or businesses that are already off the ground, it's like, you really need to think through all the investment you're making right now, like what is truly needed at the moment? And then everything else until some of this uncertainty goes away, I think just put it on hold. And make sure that you're thinking about cash and cashflow. Cash is king. Keep your cash runway as long as you can possibly keep it. Get your burn rate as low as you can possibly get it.
Jason Ross: And really use this time to bring back just an incredible amount of focus, discipline into your business. And so, I would try to hammer those points home. To anybody who's launching, or has recently launched, or is running a business. I think now is the time to just be more disciplined than you've ever been, and thoughtful about the decisions and investments that you're making.
Michael Redd: Totally agree. It's a great time for reassessment and-
Jason Ross: Yeah, and I'm doing it in my own businesses right now. It's interesting, we have a company that does outsourced customer service for companies like JackThreads. And I think it started three and a half years ago, and it's gotten to a size now where it requires much better financial reporting, and much more transparency in terms of key metrics. And it's not that we didn't have that in place. It's that it just grew a lot in the last year. So, we got a little behind, which is pretty common. And so, we've used this time. We were using the month leading up to this to really reestablish discipline, and all of our prophecies, and the way we were looking at our data.
Jason Ross: So, we were ahead of it, but this moment has forced us to push down that path even harder. And it's interesting that I think some people in the org who maybe weren't as behind some of these initiatives, because it's change, right? Change at times is uncomfortable. I think with this pandemic situation, it's really forced people, they're on board with it now. Right? Because they see how important that is. And so, yeah, I think it's important that I don't only give that advice, but I'm also taking it in my own company.
Michael Redd: 100%. This is a great time to pivot. This is a great time to be challenged with not being a procrastinator at the same time. So, I totally agree. Totally agree with you on that. If you could tell your 16-year old self anything, what'd you tell?
Jason Ross: I think I would just say it's all going to work out. That's what I would say. And why is that important? For me, again, I was always wanting to accomplish a lot. And when you're 16, and you haven't gotten out of high school, you don't know where you're going to go to college. You don't know if that's the right decision. You don't know how you're going to get to where you're going to get. I was always just a little nervous, and worrying. And sometimes like the down periods, I'd let them get to me a little bit.
Jason Ross: And I would always push this through, but if I could go back, I'd tell myself, like, "Don't beat yourself up so much. Like you've got the work ethic, you've got the drive, you've got the tools in place. And just stick to longterm goals, take steps every day, navigate the ups and downs. And you'll find yourself in a great place." And so, yeah, I think about that sometimes, that same question. And I think that's probably the message that I would give.
Michael Redd: What do you say to the 40 plus year old that didn't have the support or the inner drive to go after goals? How do you advise them? What advice can you give them to encourage them?
Jason Ross: Yeah. I mean, every second you can turn something around. It's never too late. I mean, it is never too late. And so, I try to just associate more pain with not doing something than you associate with the trials and tribulations of betting on yourself, right? Because it's not easy taking a chance, and taking a risk, and betting on yourself. And all the ups and downs that you're going to have to navigate, and the nos you'll hear along the way. And the people doubting your path. That's not easy. How do you get to keep going in the face of all that? But if you can associate more pain with not taking that chance than on going through the process of betting on yourself, I think it's really important. And you could do it today.
Jason Ross: It takes a second to really decide to take your life in a different direction. It takes a second. And so, if you really want it bad enough, if you really want it bad enough, there's nothing holding you back. But it might take looking inside, and really facing some of the reasons why you haven't taken that chance up to this point. And just being honest and defining reality. But knowing that, if you really want it bad enough, you can change it at any moment's notice. And look, I do this with myself, right? I mean, after JT, it's like over the last few years, yeah, I've been a little more comfortable, right?
Jason Ross: Like had a financial win. And so, it's not that the drive isn't there, but my back isn't up against the wall as much. And so, I have to have these same conversations with myself where it's not that I'm not taking chances, or taking risks, but there are some times when I'm like, I have to just check myself a bit like, "Hey, maybe you've gotten a little too comfortable." And like, "Are you taking enough risks to realize the dreams that you want to get to?" And if the answer is no, then even I might tell myself, "I can make a change right now, to head down a different path." And I try to do that often. And so, it's like I give that person, well, we might be in different situations, the same advice that I try to give myself, and that I try to live by.
Michael Redd: That's good food, man. That is really good food. And people need to hear this.
Jason Ross: Yeah, how do you think about it? Because, I mean, you're an inspiration to many people. And I know part of your mission is to help some of those that are maybe less fortunate to put themselves in a position to help themselves, their family, their community. What's the message that you might give to that same 40-year old person?
Michael Redd: I couldn't have said any better than you. I think there's never a second that's wasted. I think sometimes people need to be reminded of who they are, and their capabilities, which is the purpose of this podcast is to encourage people out there who don't have anybody out there that believes in them per se, or they have a hard time believing in themselves. And I think what you said was so powerful, man, in the sense where today is an opportunity to be creative, to be innovative, and to do something. And I think this podcast is one of the tools I'm using to help people realize that.
Michael Redd: There is an inner drive that I have that I share with you, man. That what's next? What's the next mountain to climb? What's the next thing that we need to accomplish and achieve? And so, yeah, I agree 100% with you, and I hope that answered your question-
Jason Ross: Yeah.
Michael Redd: ... In some of the ways how we can help people. I think sometimes there is a need to carry people who can't carry themselves.
Jason Ross: For sure.
Michael Redd: And I think that's part of what this podcast provides, hopefully, to our listeners. I'll ask you this question. How do you hope that people remember you?
Jason Ross: Yeah, I think I want to be remembered as someone who makes an impact, but does it in the right way. And what I mean by that is that treats people the right way along the journey. And at some point uses their platform for some good things, whether it's in their community, or just globally, causes that they care about. I think that is important. And also it goes back to some of the other questions that we've talked through. And maybe why my mindset is this way, but as somebody who wants to set big goals and accomplish a lot, I think I know why I have that mindset. I don't know for sure, we've talked through some of it, but as somebody who does have it, I want to keep on that journey.
Jason Ross: And I want to use it to inspire others to do the same, because now I've seen the impact that it can have. Right? When you are successful along that journey. Again, the jobs that are created, the impact those jobs have on the lives of the people that get them, what they go on to do, I think is just, I don't know, it's amazing. And so, yeah, I want to be somebody who uses the drive to have a platform, to inspire a lot of other people, and then use that inspiration. Hopefully, we'll have a pretty big impact. And that's important to me. It's like a talent, I guess, that I have, or a mindset that I have that I think I just don't want it to go wasted. I don't think it has up to this point, but if there's more I can do.
Michael Redd: Wow. That is summation of the conversation. There's more I can do. Jason-
Jason Ross: [crosstalk 00:47:18].
Michael Redd: ... It was a pleasure having you, man. Oh my goodness. What a pleasure talking to you, man. It was great to have our conversations that we've had over the last few months kind of spill into-
Jason Ross: Yeah. I've loved [crosstalk 00:47:26]. I've loved [crosstalk 00:47:27]-
Michael Redd: Yeah.
Jason Ross: I think, yeah, it's been great. I love that you share that with your platform. My platform is different. You have a platform, an enormous one. And I love that we have that similar mindset around wanting to use it to create impact, and do good things. So, yeah, I'd love to keep this relationship going for a long time.
Michael Redd: Absolutely. And for all of our listeners, Jason, is a phenomenal golfer, [crosstalk 00:47:52] strokes when we play golf.
Jason Ross: I can't wait to get out there. Yeah. We got to understand that's something I miss, big time. How about you?
Michael Redd: Oh, I'm desperate for it. I'm desperate for it, man.
Jason Ross: Yeah. I look forward to the day we get out there, for sure.
Michael Redd: Absolutely, my friend. Thank you again, Jason, for your time today, bud.
Jason Ross: [crosstalk 00:48:11]. Michael, thanks so much for having me. And, yeah, I hope it was helpful for the listeners. And I look forward to seeing you soon.
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