The Boss Show

Workplace wisdom with heart and humor

September 18, 2016

Failing – and Succeeding – on TV’s ‘Shark Tank’

Entrepreneur Stephan Aarstol made what some called the “worst pitch ever” on the TV show Shark Tank. He flubbed his prepared speech, resulting in an awkward silence. And yet, Mark Cuban offered him a deal – a deal that led to phenomenal success of his paddle board business. Aarstol visits The Boss Show to share his insider’s story of failure–and success.

View Transcript

Voiceover: It’s a northwest lifestyle weekend on KOMO News. Now a show for anyone who is or has a boss, this is The Boss Show with Jim Hessler and Steve Motenko.


Steve Motenko: Hi there. Welcome to The Boss Show. I’m Steve Motenko. I am known, on the show anyway, and with my wife when I make her call me this, as The Psychology Guy. I’m an executive coach and as well as personal development coach in Seattle and I also do leadership development work in organizations with my friend across the table.


Jim Hessler: Yes, I’m Jim Hessler. I’m The Business Guy. I’m just trying to think what my wife, Paula would do if I made her call me The Business Guy at home. I think our forty-year marriage would be well nigh over. I’m the founder of Path Forward Leadership Development and the co-author, along with Steve, of the book Land on Your Feet, Not on Your Face.


Steve Motenko: Today on The Boss Show we interview an entrepreneur who got a once-in-a-lifetime chance to make a pitch in front of venture capitalists on the TV show Shark Tank, the ABC show which you may be familiar with, fumbled the pitch horribly and ended up succeeding. We’ll talk with Stephan Aarstol later. Why are we talking about his appearance on this TV show when The Boss Show is about workplace wisdom? Here’s the answer. First of all his story is fascinating. You’re really going to enjoy it. It’s a guarantee. Secondly, we did a show, I know don’t know how many years ago it was, where we talked about the Shark Tank. I think it was before we were on KOMO. We talked about the Shark Tank and you brought it up as a potential topic for the show and I poo-pooed it and said, “Well, okay, it’s an interesting show but it’s not in our sweet spot. What does it have to do with workplace dynamics?” You said what?


Jim Hessler: Well, the idea of getting in front of other people and having to make a case for something that you believe in or something that you’re passionate about or something that you’ve analyzed is a critical leadership skill. I made a presentation just recently on building influence and it always amazes me how many people have ideas that they never put into any sort of structure or format and make a formal ask to other people to support their idea. What we end up with is a lot of frustrated employees in workplace America who have ideas and don’t ever have to stand up in front and give an account for the quality of their idea with a critical audience.


Steve Motenko: Well said. You talk about critical leadership capacity and I just want to quickly say that when we talk about leadership we’re not talking about positional authority. We’re not necessarily talking about somebody who manages people, who has a highfalutin title, we’re talking about anyone who wants to have influence on anyone else in the workplace. By definition that’s a leader and I would bet if you like the show, it’s because you see yourself as that kind of leader. Someone who wants to continually have more positive influence then you already have.


Jim Hessler: Yes, assuming that your influence is positive and based in good values there’s no better synonym for leadership then influential. People who can get stuff done. Who can make things happen. You can’t do that unless you can articulate your ideas in a compelling and concrete way. Shark Tank certainly requires people to do that and we see when people don’t do that well they get their butts kicked. Which is the fun of the show.


Steve Motenko: As our interviewee, whom you’re about to listen to, that’s exactly what happened to him. I also wanted to mention that this notion of influence, we do a year-long-plus leadership development program and right smack dab in the middle of it is the notion of influence and how to build influence as a leader. That is built into our curriculum foundation which is our book, Land On Your Feet, Not On Your Face, which Jim mentioned at the top of the show. You might want to check it out, You’ve heard of that place. Search for Land On Your Feet, Not On Your Face and then open to chapter seven, which we actually call … I’m sorry, six, which we call Plank 6 of the Leadership Platform. It will give you some pretty concrete tips about how to build your influence as a leader.


Jim Hessler: I think it’s something we all want. We all want to feel that we matter. We all want to feel that we’re listened to but that doesn’t happen by chance. You have to work your way towards that state of being an influential person. It’s well worth investing your energy and learning how to do that.


Steve Motenko: When we come back we’ll talk with Stephan Aarstol who made one of the most memorable pitches on the show Shark Tank. You’re listening to The Boss Show.


Voiceover: It’s a northwest lifestyle weekend on KOMO News. The Boss Show continues.


Jim Hessler: Hi, I’m Jim Hessler, I’m the business guy.


Steve Motenko: I’m Steve Motenko, I’m the psychology guy and as we promised in the last segment, we have on the phone with us today Stephan Aarstol, who’s an online marketing expert and a serial entrepreneur who made perhaps the worst pitch ever on the TV show Shark Tank and he’ll tell you about it in a minute. But somehow he ended up getting a deal out of it and becoming one of the Emmy award-winning show’s biggest success stories. Stephan, welcome to The Boss Show.


Stephan Aarstol: Hey guys. Thanks for having me on.


Steve Motenko: Sure. You’ve recently published a book-


Jim Hessler: Are you okay with his depiction of your appearance on Shark Tank being the worst of all time? Are you okay with that?


Stephan Aarstol: Yes. I think I’m going to have to be. That’s how I introduce myself. [crosstalk 00:05:58] Shark Tank but still landed a deal.


Steve Motenko: Listen, we’re really looking forward to, I’m just really looking forward to hearing about your experience with it. I just want to say, you’ve recently published a book called The Five-Hour Workday, which is a truly intriguing idea that we’ll take up next week on The Boss Show. For today’s episode we wanted to focus on your Shark Tank appearance. Give us just a little bit, just thirty seconds or so of background on your business career leading up to the Shark Tank. What kinds of things did you do?


Stephan Aarstol: Okay. I got out of grad school in 1999, sort of the heart of the internet boom. Got a job in an internet company and sort of learned that business model over about five years. Then I went off on my own, started a high end poker chip company called


Jim Hessler: What’s a high end poker chip?


Stephan Aarstol: That is really expensive poker chips. The same chips they use in casinos, for your home game. I needed, because that business kind of plateaued after a few years, so I needed to start something else. I figured out how to reduce my day down to first I would only work Monday, Wednesday, Friday then I only worked half a day Monday, Wednesday, Friday and then spent the rest of the time trying to start new businesses. Failing at most of them and then in about 2010 I started … A buddy took me out stand up paddle boarding and I started Tower Paddle Boards and that’s the one that got onto Shark Tank.


Steve Motenko: You say in your book that you got a call out of the blue but you don’t explain in your book what led them to you.


Stephan Aarstol: My business is, all my businesses have been sort of search engine optimization. If you search for poker chips you’ll find us at the top of the search engines. That’s sort of my expertise is getting to the top for free. Anybody that searches for us, including media, will find us and think we’re like a big brand. The time that Shark Tank contacted me out of the blue on the phone we had thirty-five thousand in lifetime sales.


Steve Motenko: Not a multi-national corporation. What made Shark Tank interested in your business? Was it paddle boards? They were excited about paddle boards and they thought you were a leader in industry or what?


Stephan Aarstol: Two things. I think paddle boarding was a huge trend then and about half the companies that get on Shark Tank apply to be. Probably a lot more than that, maybe seventy percent. Then they sort of hand pick the other ones from big kick starters or they go on the Today Show or something or they find them some other way. Or there’s these really hot trends that they follow and then the producers go out, research, find out who’s in that industry.


It was part that we were a paddle board company but the other part was there were eighty paddle board companies at that time but we were this direct to consumer company online and we were selling basically the same paddle boards at half price. Sort of cutting out the middle man and we were doing it differently than the rest of the market. I think that’s what intrigued them.


Steve Motenko: You get a call from Shark Tank. What is your first reaction and remember that this is radio. Family radio.


Stephan Aarstol: The funny, I didn’t really, I’d never heard of Shark Tank so this was in, I was on season three but this was in season two so it was very early. They started telling me about this show. Would you like to be on our show? Here’s what we do. I’m like, you know, I know my company was like a know nothing, nobody company. I’m like what kind of TV would really have me on. Then the guys goes, “Yes, it’s on ABC on Friday night.” I’m like, “What are you talking about?”


Jim Hessler: What’s that old Groucho Marx line, “I refuse to belong to any organization that would have me as a member?”


Stephan Aarstol: That was my initial thought, yes. But as soon as they said ABC I was like, ‘Oh man, this is huge.” I wasn’t even really raising money at the time. I probably should have been but I just wasn’t even thinking about it. But being on TV, I was doing this for the promotion or whatever and then I dove in.


Steve Motenko: So when we come back from the break we want to talk to you about how one prepares to make kind of the ultimate pitch of one’s life to the mega-millionaires who hold your future in your hand. We’re talking to Stephan Aarstol. You’re listening to The Boss Show.


Voiceover: Now back to Jim Hessler and Steve Motenko. This is The Boss Show on KOMO News.


Steve Motenko: Welcome back to The Boss Show. I’m Steve Motenko, I’m the psychology guy.


Jim Hessler: I’m Jim Hessler, I’m the business guy. If you have something to contribute to the show and we think you do if you’re a person with any workplace experience, we’d love to hear from you. Talk to us at is the email and call us at 206-973-7377. You will not get a live operator but please leave a message and give us your permission to use your story on air and we do love to hear from our listeners so thanks in advance.


Steve Motenko: We have on the phone with us today as you know if you’ve been listening to the earlier segments of the show and if you haven’t you want to go to and download the whole show for free. We have on the phone with us Stephan Aarstol who is a serial entrepreneur who started a paddle board company that got the attention of the TV show Shark Tank. We’re talking to Stephan about his experience. Shark Tank calls you. How do you prepare to give a pitch on Shark Tank?


Stephan Aarstol: Well, when they first called me they said … I wasn’t automatically on it. I was put into the system basically and I had to send an audition tape and they said you’ve got like three days to send us this tape. I didn’t really have video experience or anything so I just had to learn it all and in really crunch time. I ended up asking my roommate to be in it and just put her in a bikini and a paddle board and we did this little five minute video. Sent it in. You had to do an ask in the video and so I, not ever seeing the show, I asked for five million dollars for sixty percent of my company.


Jim Hessler: You’re revenues were thirty-five thousand dollars. I love the moxie.


Stephan Aarstol: I have an MBA. I’m not an idiot but I thought this was how you pitch VCs right? One, they’re going to want control of the company and two, they’re not going to invest in no man land between five hundred thousand and five million dollars because it wouldn’t be worth their time right? That was my sense but the producers laughed at me and then I watched a few episodes and changed my pitch.


Jim Hessler: I am frankly surprised at some of the smaller investments they make on that program. They make twenty five thousand and fifty thousand dollar investments. Hardly seems worthwhile if you’re worth hundreds of millions of dollars but they apparently know what they’re doing.


Stephan Aarstol: It’s funny, after being on the show, now I get more of a sense from the investor’s perspective and even when they offer these little amounts I’m like, “Oh that’s crazy. They’re going to lose that money.” I’m much more sensitive to the investor’s side now.


Steve Motenko: You asked your roommate to put on a bikini for the audition tape video and what the producer said, “Bring that woman on?”


Stephan Aarstol: That’s exactly why she came on the show. They’re just like, “Oh, it wouldn’t hurt to bring that blonde on the show.” The producers they’re all interested in entertaining TV. Even me, they were saying, “Well, you’re pretty dry. You’re pretty boring. You need to liven this up.” While the sharks are interested in a good business opportunity. Producers don’t care about that. They want good TV.


Steve Motenko: Of course. How does the process, we’ve got about thirty seconds left, how does the process of taping the show work?


Stephan Aarstol: You go up to LA. I was sequestered for like four days. About two days in I did a dry run. Sort of a dress rehearsal.


Steve Motenko: Do they coach you?


Stephan Aarstol: They, you have a couple guys tell you what to do. When you’re on there it’s just live. They sort of prepare you ahead of time and you can get knocked out at any round so people go to LA and they still don’t get on. Then people even pitch to the Sharks and they don’t air. All kinds of things can happen.


Steve Motenko: You made it all the way through. But then what happened after, when you got up in front of them was something quite remarkable. You’re going to want to stay tuned. When we come back we’ll talk with Stephan Aarstol about what went wrong that almost spelled the end of his quest on Shark Tank. You’re listening to The Boss Show.


Voiceover: KOMO News. The Boss Show is back on a northwest lifestyle weekend. Here’s Jim Hessler and Steve Motenko.


Jim Hessler: Yes, we’re back. I’m Jim Hessler. I’m the business guy.


Steve Motenko: I’m Steve Motenko, I’m the psychology guy and on the phone with us is Stephan Arstol, who made one of the most remarkable appearance in the history of the legendary TV show Shark Tank. Stephan, you get up in front of these multi-millionaire venture capitalists, some quite famous, Mark Cuban, I won’t mention all the names. What happens?


Stephan Aarstol: I had about a two to three minute sort of prepared pitch that they sort of made me prepare. I have a horrible memory so I was literally in the hotel rehearsing this like a thousand times. Like all night. Then I get on studio and they’re about to open those doors and I have four or five slides that go with my little talk and just a minute before they’re going to open the door they hand me this little clicker and say, “Okay, here’s how you work your slideshow.” Then the doors open. I’m almost looking bad like, “I’ve been on set all day really? Now you’re going to hand me this thing and tell me how it works?”


I’m walking out there even looking back and I get out there. Start to go through my pitch. I get about a minute into it. I hit the first slide. It shoots all the way through my slides. I lost my train of thought trying to back track and it was all over. I was silent and stuttering and stammering, in real time probably three or four minutes. It was much worse in real life and then it even was on TV.


Jim Hessler: They must have edited because it wasn’t that bad when you watch it.


Steve Motenko: Oh, it was pretty bad.


Jim Hessler: It was pretty bad.


Steve Motenko: If you want to watch it, Stephan I’m sure you won’t be fond of me mentioning this but just go to YouTube and enter in Arstol, A-A-R-S-T-O-L, Shark Tank and you’ll see Stephan’s flubs for better or worse. Go ahead.


Stephan Aarstol: It’s a red badge of courage now because first time on public TV and I did that and then I’m in my head thinking, “Oh my god, your son’s going to see this. The kids are going to make fun of him at school. You need to pull yourself together.” It was this out of body experience that I had to pull myself back together because this is a live show. It’s not like they’re going to say, “Hey we’re going to re-tape this. Let’s start again.”


Jim Hessler: Interesting. I didn’t realize that.


Stephan Aarstol: You can go running out of there crying or you can just sweat it out and restart. As that aired it was this Rocky like comeback. I was getting beat down, beat down and then I started to come back and got a little momentum. At the end of it I ended up getting an offer from Kevin O’Leary and Cuban and Cuban’s final offer was one hundred and fifty thousand for thirty percent plus first right refusal to invest in any business I do in the future. The reason that happened-


Jim Hessler: That’s an unusual offer.


Stephan Aarstol: Yes. That was the first time in the history of Shark Tank because I had flubbed so bad on the paddle boards and three of the Sharks were out immediately. I said, “Okay, these guys don’t get the paddle boards so I just jettisoned that and then I started pitching them on how I’ve done this with other businesses and [inaudible 00:17:43] and I’m like, I don’t care what the business is. We can use the same model. We can go out and buy a ten million dollar business with you guy’s war chest here, inject what I know, we’ll sell it for thirty million. We’ll do this business flipping business. Those two got interested in that and that’s how I spun it to actually get any investment on the show.


Steve Motenko: When you flubbed up Barbara Corcoran said something like, “I know guys like you. They’re like leprechauns. They talk gibberish and then they run away with your wallet.” How did that feel and how do you recover from an indictment like that?


Stephan Aarstol: I was called a leprechaun and a nerd by Barbara. I should go back to being a nerd or something like this. I think Barbara, when I walked in with this girl in a bikini, I think she didn’t like me from that point. It was all sort of fun and games because even though they’re sort of being brutal to you, you kind of know they’re sort of playing their character on there. You know Mr. Wonderful is going to try to get you in something where he gets five dollar for every sale you do. You know how they’re all playing.


Steve Motenko: He basically wanted fifty percent of you for the rest of your life as I understand it is that right?


Stephan Aarstol: He said basically I’ll give you a hundred and fifty thousand and I get half of everything you earn for the rest of your life. I think that’s slavery. I don’t know for sure.


Jim Hessler: It is interesting how they all have a character to play don’t they? Herjavec’s always the nice guy that’s kind of the opposite of Cuban. He always criticizes Cuban but Cuban’s a pretty good guy too it seems like. I’d like to know more about doing business with him. It’d be interesting to hear.


Steve Motenko: Lets talk a little bit more about your experience and about of course what came out of it when we come back. We’re talking with Stephan Aarstol who made a legendary appearance on Shark Tank. You’re listening to The Boss Show.


Voiceover: It’s a northwest lifestyle weekend on KOMO News. The Boss Show continues.


Jim Hessler: I’m Jim Hessler, I’m the business guy.


Steve Motenko: I’m Steve Motenko, I’m the psychology guy and we have on the phone with us Stephan Aartsol. We’re talking with him about his experience on Shark Tank. Stephan after your legendary stumbling on the show, I’m wondering, we have said, I mentioned at the top of the show today, that Shark Tank is something that everybody who aspires to be any kind of leader in the workplace should be watching because it puts you in the fire, in the crucible of a situation where you’re called on to exercise your influence. To sell a point of view, which is what all leaders need to do. You go in to sell a point of view. Things go horrible wrong and it makes me curious for you personally, what’s your relationship with failure? In that sort of situation do you tend to give up? Do you tend to push through? How do you deal with it?


Stephan Aarstol: I think any entrepreneur worth his salt, basically the way they get anywhere is just through pure stubbornness. Because there is so much uncertainty in the start up world. You’re going to have these failures and you just need to plow through them. In fact what the good ones do, and this is actually what I did when I was pitching Shark Tank, is when something bad happens, you tend to revel in that. You know you’re going to look back a year from now and you’re going to say, “Okay, that was the most memorable part.” All of sudden you have this magic power where you can flip bad circumstances into being the most memorable moment and they become, you actually enjoy them while things are going bad.


Steve Motenko: There’s so much attitude in that.


Jim Hessler: That resonates with me because it does seem like when you hear entrepreneurs talking they talk almost gleefully about their failures. It’s almost, it just seems it’s so much part of the process.


Stephan Aarstol: How you can explain this to people who aren’t necessarily entrepreneurs or really hardcore into the business world, it’s the same thing on vacations. There’s people who can go on vacations and some little thing trips up and it ruins their vacation and they’re just a miserable person. Then other people who have traveled a lot, it’s just like you just let that role. You don’t care. That’s going to be a good memory and that’s how you make vacations extraordinary. Even the same thing in life. You can do the same thing in business.


Jim Hessler: That’s a great analogy.


Stephan Aarstol: Yes. Have you found yourself to be kind of naturally equipped with confidence in your life? That’s allowed you to sail through failures or mishaps?


Stephan Aarstol: No, I don’t think, I thinks it’s definitely something, you know, I’ve done a lot of things so as you get older you have a lot, a lot of experiences and I think just failing at something, getting through it., moving on to the next thing. I don’t think it’s some people are born with more confidence or more ability to deal with failure is really what we’re talking about here. I think you just sort of learn to do it. Maybe I’ve failed more than most.


Steve Motenko: You get a deal from Cuban, from Mark Cuban on the show despite the pitch, the flubbed pitch and what’s happened since?


Stephan Aarstol: Well, we’ve done, we had thirty-five thousand in lifetime sales at the time of the pitch. We have over twenty million since then. That’s been about four years. Two years ago we were named the fastest growing company in San Diego as a surf company. Five people in our company. Most people in San Diego don’t even take surf companies seriously. We have five people. We’re doing five million in revue. They were taking us seriously. Then last year we were named on the Inc. 500 number two thirty-nine of the fastest growing companies in the nation.


Steve Motenko: Wow. Congratulation on all your success.


Jim Hessler: Mark’s happy. Mark’s happy.


Steve Motenko: I’m sure Mark is quite happy. We’ve been talking with Stephan Aarstol. His website is Again if you want to check out his appearance on Shark Tank go to YouTube and look for his last name A-A-R-S-T-O-L and Shark Tank. Stephan, the Twitter handle for his company is @towerpb. Stephan, thanks for being on The Boss Show.


Stephan Aarstol: Thanks guys. Appreciate it.


Steve Motenko: We’ll talk to you next week on The Five-Hour Workday. It’s The Boss Show.


Voiceover: Now back to Jim Hessler and Steve Motenko. This is The Boss Show on KOMO News.


Jim Hessler: I’m Jim Hessler, I’m the business guy.


Steve Motenko: I’m Steve Motenko, I’m the psychology guy and Jim one thing I didn’t get to ask Stephan Aarstol in our interview, we ran out to time, I saw him, I heard him say on a separate interview that Mark Cuban, the legendary multi-billionaire who ended up investing, one of the sharks who invested in his paddle board business, that Mark Cuban is massively risk adverse.


Jim Hessler: Yes, that seems hard to believe. Maybe he’s just really careful and really analyzes his opportunities before he goes after them. But he still has to take risks. He took a risk on Stephan.


Steve Motenko: Yes. How do you get to be a billionaire unless you’re will to take risks.


Jim Hessler: Maybe he didn’t think it was a risk based on what he knew. Yes.


Steve Motenko: Yes. That could be. Anyway, it’s either hard work or risk aversion or some combination of the two, who knows what the formula is. The Boss Show is produced by Boss Media Productions. Our sound engineer is Kevin [Dodral 00:24:49].


Jim Hessler: If you missed any of the show you can get it in it’s entirety online at and you can go there to subscribe to the podcast or contact us for any reason at all.


Steve Motenko: Like maybe you want to bring us into your workplace to do leaderships development work or coach your executives.


Jim Hessler: We’re good.


Steve Motenko: Thanks for listening.


Jim Hessler: Don’t forget, rule number six.



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