Secret To Big Success? Be You! with Scott Duffy

USO 017 | Secret To Big SuccessScott Duffy is our guest for this episode. He has had so many successes in his career. Currently, he is working on Business and Burgers, a show that is sponsored by Microsoft. In this episode, we discuss the secret to big success, which is really quite simple: be you! He shares some personal experiences as well as disasters that he went through, and how he came out of them stronger.

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Secret To Big Success? Be You! with Scott Duffy


I’m with my buddy, Scott Duffy. Scott, are you there?

I’m here. I know it’s a little bit wonky today but we’re entrepreneurs, so we just roll.

That’s right, man, absolutely right. Scott Duffy is one of my favorite people. This is a guy who has accomplished really great things in business. We’re going to tell you a few of those stories. He’s the host of the television show, Business and Burgers that’s sponsored by Microsoft. Scott was handpicked by Microsoft SMB to bring the cool to Microsoft. They’re like, “We need a little bit of help. We need some coolness. Who can we get? We’re going to get freaking Scott Duffy.” I’m so glad to have you with me today, to bring a little cool to The Unshackled Owner. Scott, tell us where you got started. Tell the listeners a little bit of background of how you got into entrepreneurism.

I got into entrepreneurship when I was really young. I really credit my parents. I played Little League Baseball. Outside of the Little League Baseball area, there were three fields. There was somebody that operated a hotdog stand. My dad became friends with that gentleman. He ended up effectively hiring me as a Little League Baseball player. Before and after my games, I would go and I would work for food, like free snacks, there are snow cones and candies and popcorn and things like that. I did it and I did it every weekend. For some reason, I just loved it. That was really how things kicked off.

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I went to work in the training business for Tony Robbins. From there, I shifted from training to technology.

When I was in college, I started a painting business. I had a bunch of folks run around with me painting homes during the summer time. I think for me the real break in, when I was 20 years. I went to work in the training business for Tony Robbins. From there, I shifted from training to technology and moved up to the Bay Area where I was on the ground floor of several small businesses that became big brands like, NBC Internet, The last company I started was like Expedia for private jets. I sold that to Richard Branson’s Virgin Group. In the last couple of years, I have been sharing what I’ve learned about launching and growing companies with entrepreneurs and here we are today.

That’s a great story. It’s funny that you’d say that because my first real business with employees was a painting business, painting homes. That’s so funny. I didn’t know that about us, that we had that same beginning. You started these internet companies. You got in as the internet was really starting to boom. First of all, how do you do a deal with Richard Branson? Give us a little more on how did that come together?

It’s a funny story. I was about to take a job, helping to run a company in New York. On my way out to that final closing meeting, I had lunch with a friend of mine. He said to me, “Before you sign anything,” this is funny how life works. He said, “I just ran to my college roommate and he’s in private aviation.” He was telling me how the industry is just exploding and how fragmented it is and how the industry doesn’t really leverage technology in order to maximize efficiency and things like that. He said, “I think you should talk to this guy before you sign anything and see if there’s something there.” That’s what I did. The next day, I had lunch with the founder of that company. I just fell in love with the direction that private aviation was heading. Overtime, came up with this concept of developing basically what was like Expedia but for private jets. What I did is I showed it around. I started to hire a team and we started to build a product. Now, it was time to raise money.

Life is so crazy. I think a lot of this comes back to the power of building really solid relationships. I was dating my wife. It was about two or three years before the time I was launching my private jet company. One night, I went out with a group of people. The next morning, that group of people all went to breakfast to a diner in New York. The guy I was sitting next to, he happened to be on Richard Branson’s reality TV show. He didn’t win but Richard really liked him and ended up hiring him in a business development type of role. We get to know each other. He was such a great guy. A couple of years later, right when I start to raise money, I get a call. The call is on a Saturday night and he’s at a party, of all things, in New York. He says, “Hey, Scott. I’m at this party. I don’t know if you remember me. Richard and Virgin want to get into private aviation.” He said, “I’m telling somebody the story at this party right now. They said, before you do anything, you’ve got to talk to this guy, Scotty Duffy in LA. You’ve got to call me on Monday.” True story.

What happened was, I did and we talked that Monday morning. I said to him, “What do you need?” He said, “Well, I would really love it if you do me a favor. Would you let our team pitch to you what it is that they’re working on and give us your feedback?” I said, “Sure.” He said, “When are you going to be in New York next?” I said, “It just so happens I’m there tomorrow.” Obviously, I had no trip planned, I just went to the Airport, got on the red-eye and flew in. I ended up meeting with people on the team. I shared my thoughts about what they were looking at doing. They asked what I was working on. They said, “Scott, you should pitch us on that.” That’s the real story about how I got connected to Virgin.

I think it really reminds me of two things. Number one, the power of building relationships. Number two, as entrepreneurs, we just got to hustle. There’s something that I call being on the flow. What I mean by that is you have an opportunity. You can feel the energy, it’s time to strike. There’s a crack in that door that you can go through. You just have to jump on it. You can’t hesitate. That’s what I try to do there.

It’s a great story. I’m going to go further. To everybody that’s listening, you’re hearing Scott’s voice. You’ve never met him. The guy is like this very well contained nuclear bomb. He’s got all this energy. There’s something to be said for being memorable, in a good way, in a positive way. In a way that doesn’t intimidate people but makes him radiate towards you. It’s like you get into their tractor beam a little bit. Scott, I’m not trying to overly blow sunshine at you, but that’s one of the things that I’ve always loved about you. I’m going to introduce you to a buddy of mine over at Adidas later today who’s doing senior things there for your TV show. I said, “You’re going to love Scott and Scott’s going to love you.” You’re the kind of people that everybody wants to be around.

These people remembered you from a breakfast at a diner a year earlier or a couple of years earlier. There are some people that come in to our lives and fade immediately out. There’s something about being memorable, about being positive, about being interesting and interested in other people that will endear you to them. That’s an important skill for entrepreneurs to learn, is how do you effectively curate those relationships? You just said it’s important to build them, but you’ve got to be somebody people will care about and remember a couple of years later at a party. “I know that guy.” There are people you meet all the time that want something from you. That’s different from people that you meet and you go, “I really like that person.”

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I think that the key to being memorable is just being you. Being you unfiltered.

I think it’s two things. One is, my friend who is over at Virgin, we connected a couple of times. It was just for the sake of just checking in on each other between the time we first met and the time that he contacted me about Virgin’s plans. Nobody was trying to get anything. It was just in the spirit of checking in and saying, “How can I help you out?” Being buddies. That was cool. Let’s talk about being memorable for a second, because I think that’s important. I think that the key to being memorable is just being you. Being you unfiltered. You need to understand the room. You need to understand based on what your goals are and the people that you want to attract, what are some of the ground rules. You really have to be you.

I’ll tell you where this started to click for me. This is actually tied to my experience with Virgin. I was in New York. I was doing my first national live appearance on a cable news network, CNBC. It was really cool. It was across the street from a New York Stock Exchange. We were on the steps of, I might mess this up, it’s like the old Capitol building. It’s where Washington was first inaugurated. It was a little surreal that day because they had cleared the entire building with the exception of the CNBC team that was sitting outdoor. I was in the main room where Washington was inaugurated and there was nobody else in there. I was literally standing on the stone that marks where he was standing. I was so in my head. I’ve got to look this way. I’ve got to gesture this way. I’ve got to talk this way, I’ve got to whatever, in order to do a good job and effectively be memorable during my interview.

I remember this amazing woman, Brooke. She was the head of the PR firm that we worked with, Brew PR, which is amazing. Brooke walked up to me, she said, “What’s wrong?” I said, “I’m so nervous. I know I’ve got to do this and that.” She stopped me and she said, “The world already has an Oprah. The world already has this. They already have a Jack Welch. What the world doesn’t have is you. Just be you.”

Great advice.

Just to wrap that story, she said, “If you were being you right now, what would you do?” I said, “Honestly, I’d take off this sport coat.” She goes, “Then just do it.” I said, “They’re going to expect me to have a sport coat on air.”She goes, “Just be you.” I did. I’ll never forget. I sat down and Maria Bartiromo, the first thing she said to me, “Do you want to go put on your jacket?” I said to her, “No, this is just how I roll.” She goes, “All right, that’s cool.” Just be you.

Yes, just be you. It’s a really great piece of advice, guys. We’re talking about being unshackled. Part of being unshackled is building trust with your team, building great relationships, building a culture. You can’t do that in a phony way. You’ve got to do that from the heart. It’s got to be all based on who you are, what you stand for and that engenders trust in your team. Let’s go further on this Scott Duffy story real quick, Scott. You’ve started a lot of businesses, has everything always just come super easy for you or have you ever had any challenges?

I had so many disasters. I don’t even know where to start. I guess we can start with the painting business. I was effectively like a franchise owner for a company, they’re called Student Painters. They taught me how to write business plans and build teams and set up a business. I had a mentor who helped coach me. They gave me the perfect road map. I think I did everything wrong. I remember at one time, I had probably fifteen people on teams that were working for me. I was eighteen years old. I had great coaches. We all do this, from time to time. I went off script. You mentioned earlier getting involved in the internet thing when it was taking off. That’s actually not when I got involved in it. Most people say that the internet became commercial in October of ’94.

I didn’t even know what a website was in ’94. Whatever they think that was, I would have put it a few years later.

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You know that if you just got your shot, if you just got that one break, that one shot, you would work harder, you would be awesome.

By the way, around that time is the launch of the first graphical web browser where you can see pictures and images and stuff. My buddy calls me and he says, “Hey, Scott. What are you doing?” At the time, I think I was working in a bar in Santa Monica or something. I was between being in the training business and I was over it and I was in transition. I didn’t know what to do. Maybe some people who are listening can relate. There’s a time in your life, and maybe it’s now, where you have so much energy and you have so much passion. You know that if you just got your shot, if you just got that one break, that one shot, you would work harder, you would be awesome. Sometimes it takes a while and I couldn’t find it.

My buddy calls me up. He’s like, “What are you doing?” I said, “Not a whole lot.” He said, “Great, I have an idea. You and I are going to start an internet business.” I’m like, “What?” I didn’t even know what the internet is. He kind of told me and I kind of got it but it really didn’t even matter because I had nothing to lose. We ended up trying to start a consumer internet access company. Back in those days, the way you’d mainly get on the internet was you would connect to AOL through closed systems. What we did is we went to partner with a telephone company called MCI. Wanted to sell the ability for people to connect directly to the internet. We called it Internet Express.

It was a disaster. The little bit of money I had left, I lost. Nothing worked. Nothing worked. It was too early. It was all that kind of stuff. Here’s the good part. The good part is I was exposed to some guys at Stanford that were working on a project called Yahoo and a project at Carnegie Melon called Alta Vista and some other stuff.  What I decided is I really connect with this. I love the vision for what these guys are trying to do. Here’s the thing, all the action is in the Bay Area and I’m in LA. In life, we’ve got to adjust. We’ve got to put ourselves in the center of where it is that we want to be and where we want to excel. At that time, I’ve got to move up to the bay area. What I did is I came up with a plan. The plan was to work during the week on the days I get shifts or whatever, and then take my cash, take my extra money and go out to the Bay Area and do what I call the couch tour. I basically sleep on all my buddies’ couches and try and get work.

It took about six months. I eventually ran out of couches. I ran out of cash. I had no money. I was way behind in rent in LA and stuff. I had to make a decision. The decision is, do you quit or do you continue to move on with your dream? What I did is I went to my room, I took everything I had, and went down to a pawnshop in Santa Monica and I pawned it all. I pawned my high school ring, this bracelet that a girlfriend had given me in high school. I had a watch I bought, a Rolex, when I worked for Tony Robbins. I took all that money and I paid everybody that I owed back and decided that same exact day to drive back to the Bay Area, which is what I did.

Goodbye to LA, I’m moving to the Bay Area.

I’m still trying to figure out where I’m going to live in the Bay Area but I’m going to get out there. I’m going to get a job. What I did is I went to a pizza place and I mapped out the companies, and there weren’t many at that time, that are in the internet business that I can maybe get a job with. I printed out my resume. I went and I got a deal on these pizzas and I put my resume in each pizza box. I smashed it as deep as I could in the cheese. The idea was somebody at one of these companies is going to be hungry. If my resume is smashed really in there, they’re going to have to pull it out and they’re going to have to see it before they get to eat some food.

Guess what? Somebody was hungry. A guy named Bill Peck, the father of internet advertising. He called me and he said, “I don’t know if I got a job for you right now, but if I don’t I promise I’ll help you to find one.” It changed everything. It reminded me of something that Tony Robbins said to me when I was working with him a couple of years before which is, “We have good days and we have bad days, but we don’t know which is which until sometime way down the line because we don’t know what we’ll make of the experience.”

Guys, did you hear that? We have good days and bad days but we don’t know which is which until down the road. One of the things I tell people is, when you’re struggling, this is just what it looks like on the way to getting to your dream. Don’t give up on the hard days. Doing something crazy like sticking your resume into a pizza and then delivering it, it’s like saying, “No, I’m not wearing the sports coat. I’m going to be me.” People love memorable. They love it. You did this. This is your beginning. False starts and great successes along the way. Tell us a little bit about how did you get this television show? How did you get Microsoft to sponsor it? Tell us a little bit about what you’re doing. I know the Business and Burgers thing is exploding right now.

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Alan Taylor and I, we provided some content about a year ago for Microsoft’s small business for National Entrepreneurship Week.

It’s so much fun. My partner and co-host, Alan Taylor and I, we provided some content about a year ago for Microsoft’s small business for National Entrepreneurship Week. The content, it did really well and so did the event. Microsoft asked us, they said, “If we were to do anything together and we were to really put resources behind it, what would we do?” It’s so funny because one of the mistakes that I think I make at times is I overthink it. I have a tendency to overthink it. I was sitting down with Alan when we were talking to our friend over at Microsoft and we were eating burgers. He goes, “What would we do?” I said, “Dude, I love burgers.”  He goes, “I love burgers too. Why don’t we talk about business while eating burgers?” I go, “That sounds like a great idea.” It was as simple as that.

When we got started and we started to talk about the idea, he said, “What will it be?” “What if we went to one new city every month?” We went to the best restaurants and brew houses and pubs, looking for the best burger. While we were there, we invited all the top local entrepreneurs and athletes and entertainers to sit down with us and have a burger and talk about the lessons they’ve learned in business. To us, that just sounded fun. We started to do it. We fell in love with it. We started meeting all these amazing people. I think because it was something that we both really enjoyed, we didn’t overthink it. It was fun. It attracted other people. It attracted a certain kind of energy. In about a week, we’re going to be able to announce a couple of big deals and partnerships. It’s been a really fun journey.

I think what sticks out to me the most about the show is this. It’s the incredible story that everyone has to tell about what it took to make something a success. I’m talking about everyone from Brian Smith, the founder of UGG boots, who when he got started, he took a $15,000 or $20,000 loan. In his first year, he sold only 38 pairs of boots. Incredible perseverance. It took years before that business really took off. Last year, it was a $1.5 billion brand.

Our friend Myles Kovacs, the founder and publisher of DUB Magazine. Myles grew up in a really tough part in LA, really tough part, really dangerous part of town. He was kicked out of school when he was sixteen because he couldn’t read. He loves cars. He really loved the rims. He taught himself to read with Car and Driver Magazine. That’s what he did. Then, a guy who couldn’t read at sixteen teaches himself to read with auto magazines and in his 20’s is the publisher of probably the biggest and most renowned magazine in the space. He’s a publisher. He was kicked out of school because he couldn’t read.

I believe that everybody has a story. It is just a matter of how you tell it. I believe that the people who are truly successful over the long term have learned how to take whatever that story is, whatever has happened to them, whatever is going on right now in their life. They figure out how to repackage it in their heads in a way that helps them to keep moving forward.

It’s amazing. People will work harder for something they love than they ever will for money. A lot of times, we force people and especially we force kids into situations, into this box, into this channel and we say, “You must do it exactly this way.” We wonder why the entrepreneurial-minded people rebel against that. Look at all the stories of Edison and Einstein and all these people who were told they were not going to make it because they didn’t conform and yet they go out and change the world. Of course, Apple and Steve Jobs were famous for the commercial that talked about that. It’s really amazing.

I love the theme of this interview and I didn’t know we were going to go there. The theme is turning into, if you want to do big things, if you want to do cool things, you’ve got to reject the status quo and you’ve got to just be you. You’ve got to take off the sports jacket. You’ve got to say, “I’m going to learn how to read from reading Car and Driver Magazine.” You just do it your way. The more contrived you are, the less likely you are to be accepted by people. The more real you are, the greater the likelihood is that people will be drawn to you and give you a shot, because there’s only one you. That’s what I’m getting from this conversation, Scott.

I’m really glad. I tell you what, so many entrepreneurs are trying so hard to follow in the footsteps of some guru and “be like me” in the way that you sell your online course, “be like me” in the way you write your book, “be like me” in the way you get on stage. Instead of just being the people who are really famous who are incredibly unique.

Now, I want to ask you a few specific quick questions just so people can get a peek behind the curtain and know the things that inspire you and drive you. They could go and try to chase those things down. The first question I’d like to ask is, what book, either it’s the book that really inspired you or it’s the book that you’re saying, “Oh my gosh, you need to read this book if you want to be in business”?

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The real key to being successful in business is to master your mindset.

To be successful in business, I thought it was all about learning to be awesome about building teams and managing people and all these business stuff. What I believe now is that all that stuff can be taught and everyone’s got a formula. The real key to being successful in business is to master your mindset. A lot of the books that I read are around that. I just reread for about the tenth time, Zen and the Art of Happiness by Chris Prentiss. It’s a really simple book. It’s a really fast read. It’s just a reminder of what we focus on. That was the last book that I read. I’m looking at my table right now. I just bought Tim Ferriss’ new book. It is sitting up here. I just got a friend of ours, Randy Garn, he just sent me a new book from Clayton Christensen on really what’s your life going to mean and how you get there going forward. I’m excited to open that one as well.

This Zen and the Art of Happiness, I’m going to check it out because I’ve seen that title before. Tell me, if you were looking all the way back from the early days of the painting business to now, if you could go back and you could change something, what would you change? Was there a place you ran into a wall or something and you said, “Boy, if I had just known a little bit better, I could have …” What would you change if you could go back?

The biggest mistake I made when I was young was I thought that I could outwork, outhustle, outlast everyone else and that’s what it would take to be successful. What I did is I worked really hard. I didn’t spend enough time building really solid relationships with people, just focus on people. Not for the sake of getting anything out of it, but just getting to know people. What I learned as I got older was there are a lot of people that work as hard as I do, even though I think I work harder than everyone. There are a lot of people who work really hard. There are a lot of people that are really smart. There are a lot of people that are really persistent.

As you get older, what you find is the people that you grew up with are the ones that are running these big companies. They’re the ones that are doing great things. In order to be successful at this stage, it’s all about the people that you surround yourself with. It’s all about who’s in your network. It’s all about the true relationships that you’ve built with others. If I could go back and tell myself something when I was twenty, it would be probably, “Work a little bit less on your own and get out with people more.”

Schedule a few more breakfast and lunch meetings with people just to get to know them.

Or go to Vegas with them. Honestly, it’s the person I went to Vegas with and whatever we went and did this or we went out that night, we did something that had nothing to do with anything, but you really get to know that person. I think that the other thing that has stuck out over time with me is you really find out who people are when times are really tough for you and when times are tough for them. I think the real person comes out. Again, it’s just something that I look back at and I think about over time.

Invest in your relationships. Invest in people. What’s your favorite quote? Do you have a quote that you have up on the wall or something you love?

I have a few. First thing is first. One thing at a time. People with small visions or limited visions themselves can never have a larger vision of you.

I love that.

You have to be dedicated to the process as well as the product. I think my favorite is, you don’t always need to lead if you have the heart to come from behind.

Wow, that’s a great one. Great words of wisdom. As we wrap up here, Scott, first of all, thanks for being here with me. Tell me real quick, as we head out, what’s the parting guidance, words of wisdom to those that are listening? Some that are really successful in business, some that are just dreaming about jumping out of a job and building a business.

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If you want to be successful on anything, you need to know, you need to start by knowing what success means.

I think it’s to keep your eyes up and on the horizon. If you want to be successful on anything, you need to know, you need to start by knowing what success means. You need to have a clear goal and a clear vision. No matter what it is that happens to you in day-to-day, the ups and the downs, the highs and the lows that go with building and running any business, keep your eyes focused on that goal. Repeat that goal. Come back to that goal every single day.

My friend, Carol Roth at CNBC, she was just talking about Warren Buffett and Bill Gates. They were both given a piece of paper. They were asked, “If you could write down the one thing that’s most important to success.” They didn’t see what the other person wrote and when they handed it in, guess what? They both had the same answer. It was focus. They both wrote down the same word, insane focus. You’ve got to start with that one thing and that focus.

Then number two, no matter what happens to you during the day, when it’s over, you’ve got to figure out how to repackage that thing in a way that moves you forward. If you ask for other quotes or whatever to wrap this up, because it goes along with this thought, as an entrepreneur, I recommend having a really bad memory. If I focused on the things that could get me down every day as business owner, that would just suck. What I choose to do is forget the bad part and spin it and try and get what is the good that came out of every experience.

The funny thing is, it sounds trite and cliché, but the reality is if you start to do that, if you start to ask yourself a better question, when something goes wrong instead of asking “Why do these kinds of things always happen to me?” You ask yourself a question, “What can I learn from this experience and apply to the next call? Or apply to the next investor meeting? What can I learn from that horrible thing that just happened that will help me to close the next sale?”

If you start asking yourself a better question, it’s like building a muscle and over time it will become automatic and it will be amazing, the confidence, the energy, everything that you’re being when you’re around others. That positivity is infectious and it will draw people towards you.

Great, powerful and should be exciting words of wisdom from my buddy, Scott Duffy, the host of Business and Burgers. Be watching for it, be looking at your local listings for when you can find that. Right now, you can find them online. He’s got a number of really great businesses. How can people find you? How can they connect to you and follow what you’re doing, Scott?

The best way is go to You can check out our show, Business and Burgers at I’d love to hear from you. Follow me on Facebook @ScottDuffyOfficial is the Facebook page.

That’s it today from The Unshackled Owner. I’m Aaron Young. It’s been great being with you. Go back, share this stuff with your friends. Subscribe on iTunes or Stitcher and check out my website, You’ll be able to see what stuff is going out there, what adventure is coming up, programs we’ve got, all kinds of free content. Download the freedom formula. Let’s just make sure we give you everything we can possibly give you to help you have the mindset, have the systems, have the connections that you need to become an Unshackled Owner.


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