Jason Polstein has created startups in industries such as apparel, film, SaaS and sporting goods. Currently, his focus is being the Co-Founder and CEO of RIP-IT where he is striving to empower female athletes through beautifully designed equipment. When you visit Jason at his [outrageously remarkable] office you’d think you’re visiting a tech start-up and not an established softball equipment company. There’s a fitness room with showers, full kitchen for the team to eat lunch together and an Amazon-esque warehouse in the back. Quite a slick operation!

In addition to his role at RIP-IT, Jason is also the Co-Founder and Chairman of LateShipment.com. LateShipment.com is a global SaaS platform focused on improving shipping and logistics visibility while simultaneously reducing their associated costs. Yep, we use this service at Blezoo. It automatically retrieves refunds from shipping companies … even if you didn’t realize there was a refund available.

In 2015, Jason and RIP-IT were honored as a Florida Company to Watch by GrowFL. A well deserved honor! I recently ran into Jason and found out he is an Industry Fellow at the UCF Blackstone LaunchPad where he coaches student entrepreneurs. I was eager to set up this interview so I can find out more about RIP-IT & the many lessons he has learned along the way …

[Setting: Jason and I met at my office and caught up for a little bit before walking next door to a casual Italian restaurant. We snagged the last booth, ordered food & started the interview. Side note: when you live in Florida and there is a decent pizza joint that is walking distance it’s a major perk since most Floridians need to use a vehicle to get anywhere.]

Dean: This is awesome [that our schedules lined up] & thank you so much, Jason. When you started RIP-IT, how did it come together? Did you pick the softball industry because you saw opportunity?

Jason: I’d love to say that we had this master plan and that we executed it flawlessly but, no, it totally kind of just fell in our lap. My sister played softball and we designed a [unique] mask for her to use … just for her to use personally. No other ambitions for it besides that. And then we started getting requests from other parents on the team so my dad made one for their kid and one thing led to another. So, we put a website on the Internet one day and started making a few sales and I think once we realized that people were interested in this, I think we started asking the question like “why are we the only ones making something [like this mask] that people are interested in?” Like “why doesn’t the market already have this solution?” I think that’s when we stumbled upon this idea that there are a lot of under-serviced markets out there and that if you can identify them and align your company to deliver value to them, there’s a lot of opportunity there.

Jason’s sister Lauren wearing the original RIP-IT homemade mask

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Dean: At what point did you realize that RIP-IT is a thing, a legit company, and this is what you need to be focusing on 100%? 

Jason: I think it was really early on when we first got our website up there. We got an order for 500 units and it was from a retailer. I think it was at that point when my dad and I kind of looked at each other … my brother was still in college at this point … and we said, hey you know, there might be actually something to this. Maybe we should transition from hobby to full time. So, it was probably a year, I’d say from the first product to that 500-unit order. And if you ask me how that retailer found out about us, I have no clue. And once I got my masters and my brother graduated from law school, that’s kind of when we said, people like this product and customers like products made for them, so that was kind of when we decided to dive into this full speed. We won’t go out and get real jobs, we’ll do this instead and that’s pretty much when we knew that we’ve got something and we just need to execute it.

Dean: What do you think has been the most remarkable thing about the company’s growth? 

We had no experience selling to retailers like Dick’s Sporting Goods

Jason: If I’m thinking holistically across the whole company, it is the fact that neither my brother nor myself had any experience in retail. We had no experience selling to retailers like Dick’s Sporting Goods or Academy. We had no understanding of how to manage a sales team. We literally knew none of this and it was pretty remarkable that over the years, we’ve been able to learn how to do it, and look at how other people have done it in the past, and say ‘can we change the way that business is done in the industry?’ Not just from product sampling, but how business is done with other retailers … can we change that. And I think that’s been our most remarkable thing … that everything we do is focused on making the customers lives better, but at the same time, we view our retailers as partners and we’re always trying to make sure that our programs and the ways that we do business with them is better than what they’re experiencing with other brands.

Dean: So Jason, to be able to build amazing things, it takes motivation, or at least that’s my assertion. Is there something that someone said to you in the past that really helped you or that motivated you to go on this journey?

Jason: I don’t know where the motivation came from, but from a very early age like elementary school, I was always trying to figure out how I could create value or sell something to someone. I mean whether it was baseball cards or anything, my brother and I were always creating these little side businesses growing up. I guess it was just the way our parents raised us. My dad owned his own business so I think it was just maybe in our family culture to kind of think that way …

Dean: Do you think being exposed to your dad’s business helped you be more entrepreneurial because you were watching it or is there something they [your parents] taught you?

Jason: Yeah, I think what I learned from my dad is that running your own business is a lot of hard work. I mean, he put in a lot of hours. It was hard work. He was in construction so it was hot, dirty, and as far as I’m concerned hellacious work and I realized very early on that I really don’t want to do this, you know? But yeah, I think it was probably growing up in that culture is probably where it came from.

Dean: What has been the biggest challenge you’ve faced in your career so far that you can share & how did you overcome it?

That book changed our entire thought process

Jason: So far the biggest challenge was building the systems and infrastructure to scale a business that deals with inventory. I learned early on that when your business generates revenue from the sale of inventory items you can only grow as fast as your current supply chain will allow. For instance, if you are paying your manufacturers on PO or ship and then selling that inventory to third party retailers on payment terms you hit the limits of your customer funded growth pretty quickly. To overcome this, I started learning all I could about supply chain management and I was introduced by a business advisor to the book ‘The Goal.’ That book changed our entire thought process on how to deal with inventory and supply chain management. From the concepts in that book, we identified three key areas where we could improve our cash flow while simultaneously fulfilling more orders on time and in-full. In short, we renegotiated terms with our suppliers to allow for better payment terms, built internal software to manage inventory levels at the SKU level dynamically, and worked with third-party retailers to move closer to a ‘replenish to consumption’ model. As a result, this year we generated the most revenue in our company’s history, filled the highest percentage of orders on time and in-full, and held one-third the inventory as we did the previous year.

Dean: That’s impressive! Especially hitting goals while holding only 1/3 of the inventory … so Jason, I talk about the status quo a lot … what does it represent to you? Like what comes to mind when you think of the status quo?

Jason: I mean honestly when I think of the status quo, I think of opportunity because, in my experience, places where the status quo has been in place for a very long time means that the industry is ripe for someone to come in and do something disruptive in a positive way. I think it’s easier to compete with people who are set in their ways. So like, you know, customers are constantly looking for things to be better and innovative … so anytime you’re dealing with companies that don’t want to change, that just means that their customers are up for grabs.

Dean: You’ve interviewed many individuals, met lots of people, and so you’ve been exposed to many approaches. What’s one tip, for my readers, on how they can stand out? Whether it’s within their own company or trying to get a job … what’s one way that you think they can really stand out?

Jason: It amazes me on a regular basis how little most companies know about their customer. So I’d say like as a business owner or as the owner of a brand, if you want to really stand out, truly take the time to understand your customer and be empathetic to their needs. You’ll start creating products that really speak to them. I think that’s probably the easiest way to stand out and it’s kind of common sense, but in my experience, it’s not done too often. As far as like if you’re looking to get a job and you want to stand out and be remarkable, there are little things that you should be doing like researching the company before you show up for an interview, but the people who really stand out during interviews are the people who show up and say, “Hey, this is my skill set. I can show you in the past how I move x to y, I can tell you how I did it, and by the way, this is my 90-day roadmap of how I can create value for your company once you hire me.” That really shows that this person hasn’t only done something in the past that’s of value, but spent the time to try and understand our business and came to the interview prepared in pitching themselves in how they’re going to generate more value for our company.

Dean: Isn’t it amazing the parallels between finding customers and finding a job. It’s research. Knowing the customer, knowing the company …

Jason: Yeah, it’s research and not being afraid to talk to people. I think a lot of people these days think that research is just getting online and looking at stuff and reading reviews, which is all great and you should be doing that stuff, but really if you want to separate yourself, it’s get out of the building and have a face to face conversation with someone and truly understand them. I mean, in my opinion, that sets people apart by such a wide margin.

Dean: If you didn’t end up making that mask for your little sister many years ago, and eventually starting RIP-IT, what would you be doing right now? What career path do you think you would have gone down?

…but the film won a couple of awards at film festivals

Jason: I think I would have still gone down an entrepreneurial path but in either the software or film industry. In the beginning, when RIP-IT was still a hobby, I had started a website company and was also producing a feature film. The website company didn’t get much traction, but the film won a couple of awards at film festivals and eventually got distribution. At the time, had RIP-IT not existed I probably would have moved to LA and took a shot at producing another movie. At the end of the day, if RIP-IT didn’t exist I am almost sure I would have created some other business. This is because my passion and motivation are trying to find solutions to the problems people face. As an example, a couple of years ago I co-founded a SaaS (software as a service) business that helps businesses save money on their shipping costs and provides them better visibility on ‘the last mile’ of delivery. Maybe the best way to put it is when I see a product or service that doesn’t work right or a group of people who are underserved in a market I get very motivated to create a solution. That is what I enjoy most from my work, and I really can’t see myself being happy in any other career path.

Dean: Who is the most remarkable person you know and why. Now, it can be anyone, but it has to be someone you know …

Jason: The most remarkable person that I know … oh my gosh, let me think about this for a second. You know that’s such a tough one because there are so many people that I know that different aspects of them are remarkable. I mean, the obvious ones are like my parents. I consider them remarkable because to a certain extent, they always believed in what I was trying to do. I think a lot of times people go to start stuff and they maybe get discouraged because people say “oh, you know that’s not possible’ or ‘don’t waste your time there,’ or ‘oh you’ll never be able to make it.’ And I think that everything that I’ve always wanted to do in life, my parents were supportive. You know, they definitely said like ‘hey, this might be hard’ or ‘hey, there might be these challenges ahead, but they were never like ‘you can’t do that.’ So I’d say that it’s the most remarkable relationship that got me to where I am is showing this belief like have confidence in yourself and believe that you can achieve things.

Dean: If you could put humility aside for a second, what do you think is your secret to being outrageously remarkable?

Jason: There’s probably a few parts to this. So the first is have a vision. And when I say have a vision, I mean have a vision that means something to you and make sure that vision is something that’s grand … grand like you want to change the world with whatever you’re doing in a positive way. So I mean setting that grand vision and then come hell or high water, that vision will come true. Whatever you need to do to make that come true, you’re going to do those things and you have to say no to a lot of stuff. So many opportunities come up and you just have to be confident enough in yourself to say no because it doesn’t quite align with what you’re trying to achieve. Every time I’ve screwed up, I look back and it’s like I should not have said yes to doing that thing because that did not align with what I’m trying to accomplish. And then, it’s kind of cliche, but people always say hire people who are smarter than you. I think that kind of applies, but a twist on that is that I would say hire people where you are weak … so not necessarily smarter than you, but if you know you have shortcomings in certain areas, finding those people that kind of like make up for those shortcomings is, I think, super important.

Thank you, Jason. After speaking to you I’m eager to get back in the entrepreneurial batting cage so I can rip it.

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Connect with Jason here & check out RIP-IT’s & LateShipment.com’s website for more on his businesses.

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