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Winning The Story Wars with Jonah Sachs
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Episode Summary
Today’s guest is Jonah Sachs, the author of Winning The Story Wars: Why Those Who Tell (And Live) The Best Stories Will Rule The Future. Jonah talks about the difference between inadequacy marketing and empowerment marketing and how to story to get people engage with your vision. He goes into great detail on whether or not we can use myths to our advantages or not; the myths that we’ve had around for years in our story telling. The more digital we become, he says, the more important storytelling becomes. He said, “If you want to get people to trust you, tell them a story of why you’re so passionate about what you’re doing.” Most importantly, he said if you want to be interesting, he has some real secrets on how to tell an interesting story that makes people want to learn.
Listen To The Episode Here
Winning The Story Wars with Jonah Sachs
Today’s guest is none other than Jonah Sachs, who is the cofounder and Chief Storytelling Officer of Free Range Studios in the San Francisco Bay Area. Jonah is internationally recognized as a storyteller, an author, a marketer, a designer, an entrepreneur himself. He’s got a column coming out in Fast Company. He’s written a wonderful book called Winning the Story Wars and has a new one coming out later this year that he’s going to give us a sneak peak on. He literally has helped hundreds of brands and social causes break through with this empowerment marketing approach that fuses storytelling techniques with digital media. That is really the secret to what he’s doing.
For the past sixteen years, Free Range Studios has brought key social issues to the attention of millions with really funny viral videos like The Meatrix and The Story of Stuff. He’s worked with big brands like Microsoft and Green Peace and American Civil Liberties Union. His book, Winning the Story Wars, has won all kinds of awards. He literally talks about drawing case studies from his own body of work. Jonah, welcome to the show.
Thanks for having me, John. I’m glad to be here.
When I first heard about you and first started reading the book, you instantly pulled me in with your story of how you got to play a version of Darth Vader. Would you mind sharing that story? It just made me instantly like you, remember you, and make me want to read the whole book.

Winning the Story Wars: Why Those Who Tell (and Live) the Best Stories Will Rule the Future
I was seven years old. I had just met a new friend at school who had a video camera at the time back in the early 1980s. I’ve never seen a video camera before. He told me that if I wanted to, I could be in his shot-for-shot remake of Return of the Jedi. Nothing could have been more thrilling than doing that. We joined on. We looked at masks. We scouted locations. We dreamed up of how we’re going to shoot every scene. Then, lo and behold, one day, I was cast as Darth Vader, which is, of course, the dream part. Then, when we got to shooting, he pulled me aside and said that while I was doing a great job on the set, he was going to have to dub my voice because I was too squeaky to be Darth Vader, a very crushing piece of information.
At that time, I thought about ending my relationship with this new friend. But strangely enough, we wound up forming a business together fifteen years later. That became Free Range Studios. We’ve been working together on and off ever since. That was a first experience actually with the power of storytelling, because what kid didn’t want to live in Star Wars? I would later come to find out that Star Wars is based on these ancient myth templates that still move people today, in terms of stories that make us care.
The fact that this was going on when you were a young lad, and now you’re certainly not old but a lot of time has passed and it’s still more relevant than ever. That really shows the timelessness of it, doesn’t it?
Yeah. Nobody could have obviously predicted from the 1980s to today what would have happened to our media landscape. It is so different. In some ways, because people have this ability to communicate with each other directly, with brands directly, and decide what media they take in and what they share and what they comment on, in some ways we’re returning to a much more oral tradition-type society; the way we used to communicate. We’re back to everyone owns ideas. Everyone passes them along. They change along the way. That’s how human beings have always communicated. When you go back to our roots of communication, you actually move back towards storytelling and away from some of those broadcast mentality that grew up over the last hundred years, which is really a perversion of the way that people love to communicate. The more digital we become, I believe the more stories become important.
[Tweet “Story Wars: The more digital we become, the more important it is to tell stories.”]
It’s great because you intuitively might think the opposite, but to really be connected to people digitally, the storytelling doesn’t. In fact, in your book, The Story Wars , you talk about Winning the Story Wars, that all wars are story wars, which is such a clever play on words with Star Wars, Story Wars. What is going on in Story Wars? You talk about people have this belief that they want to be part of something, that we’re all in a quest. Is that really the essence of a story war?
The idea is that while we may fight over policies or land or ideology, really what draws people together to give us a sense of us are the stories that we share and the stories that we tell. The stories are these amazing tools for transmitting values, for teaching our children, what do people like us do, what do people like us think? Anthropologists across time have been able to say that the key stories are really what define of tribes or a group sense of us. Without an “us,” there can be no “us versus them.” Then we come up against other groups who have other sets of values, and other stories that they live by. When those stories come into conflict, that’s when we can both feel righteous. We can both feel like we’re on God’s side and yet get into conflict with each other.

Story Wars: Marketers should realize that there’s a battle out there for ideas.
I mean that literally. People have gone to war over these core stories of what our great nation means, who our enemies are. I mean it a little but more figuratively. We fight it out at the ballot box. We fight it out in our brand choices based on, what kind of person am I? What stories do I want to live by? How then can I take actions that make me feel like I’m living that story every day? I think that without a story, it’s pretty hard to get people to go to war. I’m certainly not advocating that we start more wars with stories, but I am advocating that marketers realize that there’s a battle out there for ideas. If you want to win that battle, you have to understand the story that you’re telling.
That battle continues, if you want to get hired, if you want to get your customers to pick you versus all the other choices, or if you want to get investors to pick you to fund your startup. This concept of storytelling and pitching is intricately tied together. We’ve established the need for being a good storyteller a little bit. Can you break down? You talk about peeling away the layers of things to avoid, you call them “story-killing sins,” that you need to really be tangible, relatable, immersive, memorable, and most importantly to me, emotional. Anything you can talk about as it relates to those things, I think would really help people start to understand how they can craft their own story when they pitch.
I think that we have gotten it into our heads, because we have all grown up in this broadcast tradition, or most of us have grown up at least in this broadcast tradition mentality, that if you had the money to be a professional communicator, if you have the money to get on the radio or get on the TV, then you had some authority over the audience. You’re above them. You could spout a bunch of facts at them. You could tell them what to think. You could make claims about what was so great about your product. They figured, “If that guy’s on the radio, he must have some credibility.” That type of communication gets us to talk about the facts and the features and big proclamations. Nobody really gets drawn in to believe that.
Storytellers have always known that if you just get up and yell the moral of the story at people, that’s not going to make it stick. You actually have to put it into a scenario. Show what it’s really like on the human scale. It’s harder work for sure, but really bring it down to that human scale. What emotion is involved here? If you want to rely on your own sense of puffed up authority or just using a little bit of humor to get a cheap laugh, that’s a real 30-second spot broadcast mentality.
If you want to hook people in and make them feel like, “I know this person. I trust this person. This person is someone that I want to do business with.” Telling your personal story, telling the story of how your product came to be, telling stories of how your users will actually come to ultimately engage with the product is all incredibly powerful. For my new book, I’ve been studying. Actually investor intuition is one of the topics I’ve been studying. There are some amazing studies that are pretty new now that are coming out about how much investors make decisions based not on financial data, market data, industry trends, but just on this one question of, “Do I trust the entrepreneur? Is the entrepreneur someone I want to do business with?”
[Tweet “Story Wars: If you want people to trust you, tell your personal story.”]
There’s a lot of data that shows that. That trumps even when the market data goes the other direction. How do you make someone think that you’re someone you want to do business with? Of course, you dress nice, you smile, all that kind of stuff. You show them your resume. Tell them a story that they can relate to, that they can put themselves into. That’s going to create a huge bond. I think that information really backs up this idea if you want someone to invest in your business. You certainly need to tell a story.
What’s the title of your new book?

Story Wars: How do we actually change the way that we behave to adapt to a changing world?
It’s called Unsafe Thinking. It’s about how in changing environments, old ways of operating no longer work. How do we actually change the way that we think, change the way that we behave to adapt to a changing world? So, no particular methodology. I invested in this storytelling methodology quite a bit. I traveled around the world talking about storytelling. One of the things I learned is that becoming an expert in something is awesome. It’s fun. It gives you something to talk about. You meet a lot of people. But it actually slows your learning down. It gives you this idea that if you got a giant hammer, suddenly everything looks like a nail. Storytelling is a great tool, but in some ways, I actually got stupider by becoming an expert about storytelling.
At some point, I had to realize I’m less curious. I’m less interested. I’m growing less because I’m only thinking about one thing. That led me to this idea of, “How do we simultaneously invest in our brands and who we are in the world and our footprint and our expertise, and still remain beginners and learners?” That’s caused me to investigate all kinds of stuff, like the fallacy of expertise, the failures of experts, like intuition and counter intuition, like ideas about values, who are we willing to communicate and collaborate with? Who do we call outsiders and how does better products come from working with people that we find somewhat repugnant? All those things. How do we get out of safety and into that unsafe zone so that we can really succeed?
Expanding our comfort zone is what keeps us growing, yet maintaining our expertise. It sounds like what you’re really saying you can do both simultaneously, not one or the other.
That’s definitely a part of it. There’s this myth that the beginner comes in and changes the field. That actually is a myth. You need to build up. You need hard work. You need deliberate practice. You need to get those 10,000 hours in what you’re doing to really change a field that you’re in. At the same time, there’s this huge trap that you face. That the better you become at something, the less able you are to adapt when the landscape changes. Of course, the landscape is changing. If you’re just playing chess, where the rules never change, you just keep practicing. But life is not like chess. Certainly, the technology market is not like chess. That’s what I’m working on now.
This intuition of investors, making a decision with their gut emotionally and then backing it up with the left brain logic, I love. One of the key ways to get anybody, whether it’s an investor or potential customer, to trust you is to be able to tell a story of why you’re doing something or why you’re so passionate about something. That is where the emotional component comes in that most people don’t know how to do. Is there any tip you have on how to generate a story? You have this really great chapter in your current book, where you’re talking about, “For God’s sake, be interesting.” What are some key tips we can do to at least be interesting when we tell a story?

Story Wars: Put characters in situations on the surface that played that story out in real life.
Let me answer a couple of ways. First of all, a story is really constructed by taking some truth. Something that you know is going to teach your audience something; that your audience is going to say, “That’s what I believe too. But I never thought to say it that way.” It’s some kind of core truth or moral of the story, but illustrate it not just by saying it, but by having characters on the stage that are playing out a drama. At the end, you’ll realize, “That character succeeded because cheaters never win. That character failed because greed always leads to failure. We believe in the power of hard work. That’s what this story is about.” Know what your story is about. Put characters in situations on the surface that played that story out in real life.
If somebody is saying, “That story really comports with my values and my world view,” you’re going to make that hard connection. You’re going to make that emotional connection. How do you make that story interesting? The problem with so much professional branded corporate storytelling is that we don’t want to take chances. We want to go from “the world is bad” to “I use this product and the world is good.” That’s so boring. If you went to a Hollywood movie that was just climbed up on a gentle curve to betterness all the way, you think it’s a horrible movie.
If you want a story to be interesting, how do you set it up so it’s not obvious? You expose mistakes you’ve made along the way. You show some amount of fallibility. You don’t make it so that the solution is obvious. You need some level of surprise, some level of twists and turns, the non-obvious to make it stay interesting. That’s one thing I always coach people on: No one’s going to listen to your story if they know where it’s going from the beginning. Sometimes, that means starting your story in the middle. Don’t just start at point A and go point Z. You’ll start at point M and then flash back, talk about the real trials that you’ve been through, get a little bit vulnerable. Those are some tools along the way. I think definitely, keeping people guessing is what keeps them tuned in.
[Tweet “Story Wars: No one will listen to your story if they think they know where it is going.”]
No one’s going to pay attention to your story if they think they already know the ending. The element of surprise is what keeps a story interesting. Let’s give some examples. You have so many great ones in your book of different campaigns that people have probably heard about. You’re talking about Listerine, the moral of that story is bad breath makes you undesirable, but there’s a core need that’s being celebrated there by being desirable and having good breath.
I use that Listerine story because it’s one of the first examples of where marketers learned to stop just talking about their products and start telling compelling stories around them. In the 1920s, the story behind it is there was this pharmacy antiseptic that was Listerine. They didn’t know what to do with it. They called Madison Avenue and said, “What could we do with this product? We want to sell a lot of it.” They said, “This is good for halitosis.” They’re like, “What’s halitosis?” No one even knew what that meant. They’re like, “Halitosis is bad breath.” They’re like, “Is that even a problem?” “Yeah, we can make it a problem.”
They ran these ads. They’re called the Sad Edna ads where you have this spinster. She’s old and unmarried. At the time, that’s 27 years old or something like that. She’s never going to be married, why? Because she has a problem that she could never know she has. No one’s going to tell her she has. It’s bad breath. Always a bridesmaid, never a bride. There she is looking lonely and sad. This was an enormously successful advertising campaign. Women all over the country reading Ladies’ Home Journal started wondering if maybe they had bad breath. Suddenly, a multi-billion dollar beauty industry was launched on this campaign. I point out in the book that an approach like that is very traditional though. It’s a story. There’s a hero. There’s a damsel in distress. The hero is, of course, the product. The damsel in distress is the consumer. That works when you are flipping through by yourself at home, a magazine, and feeling who do you talk to about how you feel about this?
Imagine sharing on Facebook, a message to all of your friends, “I think you guys all have bad breath.” No one would go for that. This idea of, “You suck, you consumers suck. This product can make you acceptable,” was what I call inadequacy marketing. It’s just the basic underlying premise of most marketing for most of the broadcast era. What I call empowerment marketing is really flipping that script. Instead of saying, “You suck, this brand can make you better,” you say, “You, customer, can do great things. You have a great potential. It may be hard. You might have to fight to get there. It might not be convenient and easy, but you have a great destiny. We can help you get there.”

Story Wars: Don’t make people feel bad. Make them feel good.
That is the change. Don’t make people feel bad. Make them feel good. Don’t tell them how much they lack. Tell them how to reach for those higher values, not just fitting in or making money, or gaining convenience, but having a meaningful life, transcending values on Maslow’s Hierarchy of Needs. That’s the kind of work that I did to tie in patterns of ancient myth that really do that with the new marketing landscape. Perhaps a little bit theoretical, if you’re just sitting down to write your next tweet. I find it very inspiring to think about the difference.
We can absolutely take away how to use that right off of that, because if you’re pitching an investor, let’s say, to fund your startup and you’re painting a picture with your story of what your vision is, that not only is that investor going to make money, but there ideally might be some social impact, making the world safer or better or somehow, that there’s a reason as opposed to just focusing at all the problems you’re solving. Once we get this, for example, if we can prevent drunk driving or if we can keep the schools safe or whatever the problem is that you’re solving with your startup, then the investor’s saying, “I’m making money but I’m also making the world better.” That’s a much more emotional connection that we talked about earlier that good stories have.
You can do that for sure; make the investor feel that they’re a potential hero. You can show how your product makes your everyday users heroes. That means not that just they’re able to get their laundry detergent 25% cheaper but that they’re actually able to better care for their kids and live their higher values. I often liken it to this: imagine you’re at a party and you’re standing next to somebody who basically the subtext of everything they’re saying is how great they are. How long would you stay in that conversation? Imagine you’re standing next to someone, and after five minutes of talking to them, you start to feel really good about yourself. How do you feel about that person? Very different.
You talk about this concept of the myth gap, do we have not anymore myths? I really want to do a little dive into that because there are four elements to a good myth. You talk about there’s an explanation, there’s a meaning, and a story, and most importantly, the ritual of how do we take that into our life. Can you tell us about the myth gap and is there a gap in today’s society? Do you feel that there is still a way to use digital connections with keeping the myth alive?
The basic idea of a myth is not to think of it in terms of fact versus myth. It’s not a lie or a misconception as we often think of it. The first idea is that myths are meaningful stories that all societies have always lived by. Without myths, we don’t really know what we value and who we are. That’s what anthropologists, including Joseph Campbell and many others have said, if you look at a society, you want to understand it, you look at its myths.
Now, these myths combine four things, as you said: explanation, this is how the world works. God created the world in six days and rested on the seventh. That’s how the world came to be. Meaning; it doesn’t just tell you something, but it makes you understand your place in the cosmos, your place in the tribe, your place in society. God made the world, so it’s his world. I should obey him. Story; it doesn’t take place yesterday or in your neighbor’s backyard. It takes place in some mythological other symbolic, creative realm, where anything’s possible. Ritual; The Garden of Eden story, of course, takes place in this forgotten time that you can never go back to, in this lost Garden of Eden. This ritual; how do I live this story out in my life? These stories are not useful if we can’t enact them ourselves. That’s what a myth is.

Story Wars: In our hyper-rational, scientific, technological society, we don’t share those myths like we used to.
In our hyper-rational, scientific, technological society, we don’t share those myths anymore like we used to. We don’t all believe the same thing. We don’t all share these same meaning stories. Carl Jung in the 1920s and 30s started to really worry that we would be the first society without myths and that world war and violence, and all these things that were happening around him were the result of man losing that meaning based on myth. There’s been a clear belief that we are this first society not to have shared myths. I wrestled with that in writing the book. What does that mean? I came to believe actually that we do have myths. But hose myths are now being created by marketers.
Example that I use is the Marlboro man. The Marlboro man came along in the 1950s. Classic storytelling marketing campaign. Philip Morris wanted to introduce a filtered cigarette for men. That’s an entirely new product. Filtered cigarettes used to be only for women. What do they do? They talk about that it’s more healthy. Did they talk about it tastes better? Did they talk about, it’s cheaper? No. They picked a symbol of basically a broken myth. They picked a symbol of this cowboy. At the time, Americans were really wrestling with American identity. Are the cowboys the good guys? Maybe America isn’t good. We’re in the middle of all these conflicts. The way that we’ve treated Native Americans, how do we see ourselves? This is broken myth of the American West. Marlboro comes along and shows us this cowboy smoking a Marlboro cigarette, reinvigorates that exciting myth of the American Frontier.
What does he do? Give us an explanation. There’s a new way to smoke filter cigarettes for men. Meaning; you don’t have to be a cowboy to take on this identity. When someone pulls out a pack of Marlboro Reds, we know what that means about them. That they’re rugged and rebels and all that stuff. Story; nobody walked by those billboards and said, “That guy is not real. He’s just an actor.” We know he’s not real. It’s okay. We still buy it. Rituals are some way to live this story out. Of course, we just go to the store and we buy a different kind of cigarette. These kinds of stories really fill that myth gap in a lot of ways for people. It really said maybe we don’t have legends anymore like we used to, but we can express our identities and ourselves through the products that we buy.
I made the video series, The Story of Stuff, which really talks about how problematic that is to just spend money and consume things as a way of deciding who we are. It is an enormously powerful tool if you can create new myths to get people to do anything from take more pro-social actions to buying your product and using it in a way that makes their lives better, to identifying with an online community. If you could help create new myths, and right now, a lot of our myths are broken. We saw in the last election how the death of the myth of the American dream really opened up a lot of space for new stories to come through. Donald Trump spectacularly capitalized on people’s feeling that that myth is falling apart and offered to bring a new story in its place. You see how powerful it remains to this day.
That, again, may seem overwhelming. But if you break it down into four pieces, am I offering people a real explanation of how life can be better lived or how the world works? Am I giving them an identity, a community to be part of by engaging with this story? Am I using story? Am I not just talking about the rational here and now, but setting it in a fantastic, exciting world, where more is possible? Ritual; is it clear for them how they can get involved and do something that makes it part of their lives? Any marketing effort or pitch can be better if you think along those lines.
You have, at the very end of your book, a whole graphic, you give people a story strategy map. Can you walk us through that very quickly so that people can start to figure out? Obviously they need to buy your book, but if they can start to say, “I understand I need to tell a story when I pitch. It’s going to build up trust and credibility with the people I’m pitching. I know that my story has to have some myth and emotional involvement in it. Now, the basics of storytelling, you’ve given me, but how do I start?” Your three things at the top there would be really helpful from who’s the brand hero etc.

Story Wars: The core insight is your brand is a story.
I build the five-part model essentially that helps people start to figure this out and how do they build their brand as a story. The core insight is your brand is a story. It’s not being told at a single YouTube video. It’s a story; every chapter is being written every day by your audience, by you, by what you say, what you do. You don’t get to control that story but you get to create the coherence for it, the ideas for it, and then let it play out in the world. What I ask people to do is think, at the heart of all stories are core values, what are the values that your company stands for and lives out and that you want to communicate and share with your audience that will matter to them? Don’t just pick the most basic values like the need for convenience or safety or security, but values that can help people live their best lives.
What’s that moral of the story? If your brand is a story, what’s the moral? What’s that core truth that you’re standing for in everything you say and do? Figure that out and you’ve got some real good consistency in your messaging. The other three pieces are, one, don’t think of yourself as the hero in this grand story that you’re telling. Really think about how are we making heroes out of our customers? Two, if we’re not the hero, who are we? When you think of yourself as the mentor, we haven’t really spoken too much about the hero’s journey today, but I use that model. You’re not Luke Skywalker, you’re Obi-Wan Kenobi, inviting someone on an adventure. Obi-Wan Kenobi doesn’t just tell people what to do. He speaks. He creates connection. If we’re a mentor, what’s our human voice? We use brand archetyping, like many people do, to figure out. If we were a person, what kind of person would we be? Whose voice do we speak in?
Finally, the thing that the mentor always gives the hero to bring him on this adventure is some magical gift. What is that gift that you’re giving to your audience, that innovation, that differentiation, that new thing, that makes this interesting, exciting journey actually seem possible? You think of those five things. What are your values? What’s your moral of the story? What’s your brand gift? Who are your heroes and who are you as a mentor? You could maybe not read the book and just go right at it. The book obviously gives lots of tips and tricks for not only how to build that strategy for what your brand is but also then to tell stories to implement it.
You’ve certainly given us a magical gift on how to become great storytellers and the importance of it. I can’t thank you enough. You’re going to be writing a column for Fast Company soon. People can also follow you on Twitter. Would you mind giving us your Twitter handle?
Obviously, if people want to engage you professionally, let’s let them know about your agency and who your ideal clients are that you like to work with at Free Range Studios.
You can find us at FreeRange.com. Anyone who’s got a world-changing vision and wants to do purpose-driven communications or innovation, we’d love to connect. Let us know if you want to help figure out your new story or how to live that story in the real world.
Thank you so much, Jonah.
Thanks, John.
Links Mentioned
- J Robinett Enterprises
- John Livesay Funding Strategist
- Jonah Sachs
- Winning the Story Wars
- FreeRange.com
- @JonahSachs
- Fast Company
- The Story of Stuff
- Unsafe Thinking
- The Meatrix
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Find Who Else Cares About Your Startup with Laura Wagner
Posted by John Livesay in podcast | 0 comments

Episode Summary
Today’s guest on The Successful Pitch is Laura Wagner, who is the CEO and founder of Digitzs, which is changing the way we are going to pay for things. She assembled an amazing team of people from Apple and PayPal and even Kevin Harrington who was one of the original Shark Tank judges. She said, “Everybody wants to be needed and wanted. If you trust and like and admire these people to get them on your team first, then you show investors who else cares about your idea.” She was able to raise millions of dollars on equity crowdfunding platform, Crowdfunder, by having this amazing team of people who believed in her vision to raise money to get it built and now they’re on their second round of funding and have their first revenue coming in.
Listen To The Episode Here
Find Who Else Cares About Your Startup with Laura Wagner
Today’s guest is Laura Wagner, the founder and CEO of Digitzs, which is all about changing the way we pay for things. Laura has an incredible background in this expertise, she’s assembled a team of people from Visa, PayPal and Apple. Laura, welcome to the show.
Thank you, John. Happy to be here.
One of the things that make you so interesting is that you’ve won so many awards in equity crowdfunding. You have the first female founder to reach number one on the CNBC Crowdfunding 50 Index, and number one for the largest capital raised by a female founded company. Clearly, you know what you’re doing. How did you become such an expert in this?
It’s super new, crowdfunding. It’s odd to be called an expert in something that I’ve got about a year and a half in. That’s the opportunity for other people too. I challenge you to beat us on the number one spot. We started in 2015 around April. I’m so non-technical. I’m a non-technical founder. The story will make you chuckle a little bit. I remember the day we launched with Crowdfunder. We put out a press release and had the video ready. About three or four hours went by and I was totally bumped because there was no activity. I was on my Crowdfunder page. I’m like, “Nothing’s happening.” I called my Crowdfunder person, Katie, who I adore and she’s like, “Laura, hit the other tab. You guys have already raised $500,000 of interest in the first two hours.” I screamed. I was like, “Wow.” I was on the wrong damn tab. It’s funny that you call me an expert. It’s been a long road from there.
We’re always talking about how do you figure out a problem to solve that is big enough to start your own business. Can you share a story of how you had a frustration at McDonald’s in the paying business without having cash?

Who Else Cares: We just interviewed a people who owned McDonald’s to figure out their paying points and packaged it up in a very simple product.
That’s how I actually got in the payment space. I fell into it. I’m from Texas. My first day in LA, I tried to go to McDonald’s while I was moving and they only took cash. They wouldn’t take my Visa Check Card. I had to leave hungry, which totally got my attention. My next stop was ARCO ampm gas station. They had this weird thing I’ve never seen before where you pay with your debit card. You put in your pin number and they added a $0.50 fee. I’ve never seen that before. I called the phone number on the top of the pump and probably it’s just beginner’s luck. I asked the guy who answered the phone at ARCO, “Why don’t you guys do this at McDonald’s?” He said, “You’ll never get McDonald’s.” I’m like, “What if I did? Is there money in it?” He’s like, “There’s tons of money, but you’ll never get McDonald’s.”
I went down there to meet him the next day. I started learning a little bit about what was involved with payments. The money caught my interest, of course. It took about a year to get the exclusive marketing rights from ARCO to bring this into McDonald’s. We went after McDonald’s and we won out over 200 companies. We pitched free equipment, free everything. We pay you $0.50. We charge the customer an extra $0.50. We give you a dime of that. Everybody else, all other $1.99 were pitching equipment cost X, transactions cost Y. We just interviewed a bunch of people who owned McDonald’s to figure out their paying points and packaged it up in a very simple product or service and had tons of success.
We hear how important it is to be persistent. You have a very clever way of doing it, about leaving creative and fun voicemails, for example, as a way to stay in front of someone. Can you share that?
[Tweet “Who Else Cares: Leave creative and fun messages when you follow up.”]
That was how we got into McDonald’s. Once I had the marketing rights from ARCO, I started going after McDonald’s. It was important for that particular business at that time to walk that up first. I had to do that first. Once we had that in the bag, I started calling the West Coast division of McDonald’s. There was a wonderful woman, Rose Nash, who was Head of Technology. Rose was inundated with everybody and their dog trying to sell them credit card processing. I called her 29 times and I would leave crazy voicemails. One time I put my radio to the phone and it’s, “One way or another, I’m going to find you, I’m going to get you, get you, get you, get you.” By the time she answered the phone one day, she knew exactly who I was. I said, “A-ha.” She just started laughing. I said, “Don’t move.”
Actually, I went down there to Irvine, to her office, and we stayed in her office until 10:00 that night. I remember distinctly because they were vacuuming the floor, and we did not speak about business until the last fifteen minutes. We talked about relationships, losing weight, everything.

Swim with the Sharks Without Being Eaten Alive
If people haven’t ever read or listened to Harvey Mackay, Swim With The Sharks Without Being Eaten Alive, I was raised on that book. It talks about getting to know 69 things of the person that you’re pitching; the name of their wife or husband, the names of their kids, are their kids into soccer. It may sound manipulative, but it actually gets you on the opposite end of transaction. So many people these days are so transactional. Rose and I, we’re two human beings and we’re just talking about life. We felt good and secure with each other. That was enough for her to let me in at the ninth hour to pitch McDonald’s, when most people had been in line for a year.
If you want to have a successful pitch, get that relationship connection first because people buy ultimately from people they trust, like and know. If you don’t start the trust factor and the likability factor first, you’re never going to win. Now, speaking of winning, when you’ve launched Digitzs, you had to get amazing people on your team before you could even go on an equity crowdfunding platform like Crowdfunder. You have this great phrase about proving who else cares enough to be on your team. Can you share with us how you started your team at Digitzs?
David Jaques was the first CFO of PayPal. He’s the Chairman of our Board. Linda Perry, she ran Visa seventeen years. Edward Katzin sold his company to American Express and filed numerous patents for Visa. I always tell startup founders, you just have to absolutely get people who are way more important than you are and way more accomplished than you are. Surround yourself with those people. Because, at the first glance, if you have a household name, for instance, Kevin Harrington with Shark Tank was one of our investors. The way you go after those people is the same way, relationships.
I just let those people know how much I wanted and needed them to be part of my company. I think everybody likes to feel needed and wanted. That’s a basic human need. Everybody actually likes to be part of something new that they can be in the wanting with. It’s not that difficult. You just have to seek the right people out with the right expertise. Of course, you have to like them and you have to trust them. You have to admire them. If you have that formula, don’t be shy because you would be surprised. Don’t ask, don’t get.
[Tweet “Find out who else cares about your startup.”]
When you were putting this team together for Digitzs, did you look for people who didn’t have the same expertise that you did? I hear that’s a really important thing, that you can’t have three people that all know marketing.
One thing that’s really, really key is that I’m not a technical founder. The key when you’re not technical is to have a technical cofounder. Stacy Moore is my technical cofounder. She has built our platform from the ground up. I’ve known her 25 years. She’s also from Texas. She happens to live here in LA. She’s definitely a unicorn. She’s a strategist. She’s been a partner in every business I’ve had. She also is hands-on. Finding a technical cofounder is imperative to a non-technical founder.
Also, what’s really important here is investors, whether they’re in equity crowdfunding or Angel or VCs, they love it when the team has worked together before because it shows that you guys get along and that you have experience in the shorthand of communicating.
I have no idea why David Jaques still talks to me. He was involved in Pay Wherever which was a prior company that didn’t work out. He was involved and invested in, by the way. I actually think that’s quite key. Most of the folks on the team are people that I’ve had a relationship with and respect highly.
Would your advice be for someone before they go onto an equity crowdfunding platform, to have your team assembled first before you start asking people to invest in the money? As you said, they need to know who else cares.

Who Else Cares: It’s got to have some cache, because you’ve got to stand out.
Absolutely. It really needs to be somebody with some impact. Like with Kevin Harrington with Shark Tank or David Jaques, the first CFO of PayPal, or Linda Perry, who ran Visa for seventeen years. It’s got to have some cache, because you’ve got to stand out. If you threw a bunch of names out that nobody’s ever heard of and they haven’t done anything significant in their life, that is the instant decision somebody’s going to make about your company, which is unfortunate. Most of the time, people are judged that way.
Can you go back to the first $2 million you raised? Was that your seed round obviously, and you had your pre-revenue?
Pre-product. We were just literally an idea.
You have an idea, but you’ve got this amazing team with amazing backgrounds of big brands. If you raise the $2 million, the product will get built. Then will you get revenue from that seed round or is that just getting the product built?
Just getting the product built and getting a pipeline in place.
Obviously, you achieved those results to be able to have the second round, correct?
We achieved it enough to, yes, be able to move into the second round. We just literally processed our first dollar last week. We started this raise in May. It’s going on nine months ago, this $3 million, series A. The whole time we were doing that, we were pre-revenue but post-product.
Do you have a waiting list of people who want to be in? Because I’m very curious, you have certain reservations? Can you explain to us the reservations versus the round? That would really be interesting for the people.
That’s always really confusing to people. On the CNBC Crowdfinance Index, all they can pool in is reservations which are “interest.” If you stumbled upon our profile and you thought it looked interesting, in order to reach out to us, you’re required to either select a dollar amount that you might be interested in investing or not do that at all and just ask for docs. We have a back-end portal with Crowdfunder that we get a text if somebody makes a “reservation.” It goes into our CRM, which we love. It’s called Close.io which is the best CRM ever on the face of the earth.
Why is that?
It’s so simple. It’s ridiculously simple. Every CRM I’ve ever used in my life is just like, you want to buy a Maserati and they lift up the lid and say, “Look at this carburetor in here.” Who truly gives a shit? Nobody. The other thing that Close does is it integrates your email and it just becomes your inbox. It becomes a second inbox which, I don’t know about you, but everything I do is email-related. I can see who I own email to that stands out outside of my entire Outlook inbox. It just makes things super efficient. I highly recommend that.
Anyway, we then connect with the investor and set up a time for me to chat with them one-on-one, which I do. I’d say one out of four times, somebody’s not accredited, which right now, they have to be an accredited investor, which for those who don’t know, you have to have an income of over $200,000 a year or a net worth of a million dollars excluding your home. We do get a lot of outside of the US investors, which they don’t have to be accredited. I would say that a third of the folks who’ve invested are non-US citizens, which is awesome.
Is that because you’re in series A? Did the people have to be accredited investors to invest in your seed round?

Who Else Cares: The difference is when you start to publicly offer something, we have to get third party accreditation.
Yes, they did, because both are public, so they are 506(c) not B. We did a note round of 100k initially. Then we did a note round of 275k before we got onto Crowdfunder. Those were private 506(b). You still had to be accredited, but you can do a self-assessment. The difference is when you start to publicly offer something, we have to get third party accreditation. A CPA or an attorney has to vet that investor or sign a form, or the investor has to send us their tax returns. We have an obligation if we publicly solicit to make sure that we don’t harm them.
That’s not the case for everybody on other equity crowdfunding platforms or even within Crowdfunder. That’s the whole reason for the new law, is that people don’t have to be accredited investors to invest in some of these companies.
It’s still a pretty small percentage where you don’t have to be accredited. It’s getting better, but in order to do a Reg A raise, there’s Title III. I’m not an expert at this, by the way. There’s Title III and you can only raise up to a million dollars. There’s Reg A and you can go up to $50 million. It’s expensive to prep for either one of those raises. What I find when I’m talking to investors is they’ve assumed all crowdfunding is for everybody because of the JOBS Act. One out of four end up not being accredited, but they thought they could invest when we got on the phone. Two out of four hear the pitch and it’s just not right for them. One out of four ends up putting their money out.
The biggest challenge, if you’re not using equity crowdfunding is getting in the right room. You typically have to talk to a lot more people than one out of four to get a yes.
It’s a heck of a lot nicer experience to have somebody come to you than you going out to somebody. They’re actually interested. They are interested to the degree that they set up a call and hear a pitch. I’ve had a blast. It’s the only way for pre-product, pre-revenue companies to get any money these days candidly, outside of family and friends.
Thank you for explaining all this. $11 million out of $3 million that you’re raising. That’s just letting people know that there’s that much interest, but it hasn’t completed yet. You still have some money available to finish that round.
Whatever people show on these websites as the dollar amount, it’s pretty normal that about 20% or 25% of that gets in the bank.
Let’s hear about what it sounds like when somebody says, “I’m accredited. I’m interested. This is a fit for me. I’d like to hear a pitch.” How do you pitch them? With slides? How long is the pitch?
Never ever with slides. We send them an email with a deck and an FAQ and a very long email with as much as detail as we can. When I get on the phone with them, I’m just talking just like I’m talking to you.
I hear that time and again, Laura. Be a human, have a conversation, as opposed to memorizing a script that you can’t go off of. If somebody asks a question, you get lost because you aren’t able to have a conversation. The pitch deck, if you use them, is supposed to just be a frame of reference.
I had screwed up so many times on having a deck in front of me. Back in the day, I always joke that decks are so 2015, because it’s just a barrier between you and the other person.
You still need one. Obviously, you’re going to send them the deck. Sometimes, they probably have questions from looking at the deck, “I see on your competitions slide XYZ, or how did you come up with this valuation?”
A deck needs to be no more than ten slides and very large font, lots of pictures. These days, we are almost never asked for any other due diligence documentation, which is pretty outstanding when you think about it. It’s just the deck, it’s an FAQ, and me.
Have your financial projections changed dramatically from your seed round to the series A?

Who Else Cares: I think just being completely candid with investors is perfectly okay.
The seed round, we really were pretty clueless about what those projections really could be. But we were always very candid about that. I think just being completely candid with investors is perfectly okay. It’s okay to say you don’t know but you think. It’s like, we think there’s gold under the hills, but we don’t know until we get the money to buy the shovels and get our feet dirty. That was our pitch in the seed round. In this round, our projections, of course, projections always change. In tech, everything takes much longer than you think it will. But we also tell them that. I tell every single person, whether they’re accredited or not, that this is a huge risk and it’s a little step above going to Vegas.
Are you trying to get people to use Digitzs instead of PayPal? Is it like Uber versus Lyft? Can you give us a sense of what the pitch is?
We do not sell to individual merchants. If you drew three circles, left or right, on a piece of paper, on the left is where cards are swiped; liquor store, grocery store. On the far right is the experience you might have checking out of an Amazon shopping cart online. In the middle is everything else. In the middle is about five years old. In the middle are three buckets, since I’m from Texas. The first one is mobile apps like Uber. The second one is market places like Etsy. Third one are what we call platforms.
If you drew ten more circles at the very bottom, those would be the ten largest payment processors in the US. This whole page is about $5 trillion a year. In the US, $5 trillion a year is processed at just three card types: Visa, Mastercard and AmEx. It’s growing at 15% per year. It’s a massive, massive market. The middle is a trillion, the right side is a trillion, and the far left where cards are swiped is $3 trillion. We are sitting squarely in a middle market that’s less than five years old, that very few companies can compete in, just due to all kinds of legacy.
Our competitors are companies like Stripe, Vantiv and WePay. They’ve aligned with one of those ten. We’ve used up half of the ten that could even play in this market on the back-end. That’s one of the reasons why it’s so difficult. That’s my pitch. That’s literally the first minute or two of my pitch, to set the stage.
You painted a picture, which is what I tell people all the time.
I’m very visual.
Having people draw those three circles and they can instantly understand, “I know where I am.”
You’re also getting them kinetically. There’s an old saying, “Tell me and I hear you. Show me and I see you. Involve me and I understand you.” Involving them is drawing the circles. Get a piece of paper out, draw the circles. It’s a small thing but it works.
[Tweet “Who Else Cares: Involve them in your pitch so they understand at a deeper level.”]
Do you get questions or is one of your questions, what’s the exit strategy? Or is that too soon?
Always. They don’t invest unless they feel like there is a viable exit. Our exit strategy is actually to sell back to our processor or one of those ten processors at some point. 47% of the M&A transactions last year in the US were niche FinTech companies being swallowed up. Because companies like Digitzs have created new technology, are serving brand-new niches that are hard to serve based on legacy technology underneath them, it’s almost like we’re the electric cars and everybody else is the old gas model cars. But the gas model car factories have a lot of money and they’re going to want to buy the electric car companies.
Can you talk about your marketing strategy, the business model? People sometimes, “If we only get 1%, we’re going to be rich.” Clearly, that’s not what investors want to hear. They want to hear a bottom up strategy. What is your model? You have your first dollar. Are you targeting certain industries? Are you going after the middle circle Uber?
Platforms are what we target. Are you based in LA?
Yes.

Who Else Cares: We make the platform look like a payment processor. We eliminate the noise of the customer having to go get a merchant account.
If you get a parking ticket today in the City of LA, you’re going to go to CityOfLA.com. You’re going to hit a button that says “Pay Your Ticket Now.” It’s going to take you to another page inside the website. The company that hosts that page is what we call a third party platform. It’s no longer the City of LA. It’s a third-party that the City of LA has contracted with to take a payment on their behalf. It’s those platform that Accenture says are a top five trend for 2016. What happens is the platform guy goes to the City of LA guy, and he says, “Hey, City of LA guy, don’t build an elaborate website where you could take parking ticket payments. We’ve got all that software in the Cloud and we can make it look just like your website by tomorrow morning. By the way, we also charge the person using it $2, so it’s free to the City of LA.” The City of LA guy says, “That’s too good to be true. Where do I sign?” The platform guy says, “I just need you, City of LA, to go get a Visa, Mastercard and Amex account so we can connect all the dots for you, so when somebody pays the parking ticket, they see your name in their bank statement.” Unfortunately, half the time, the platform guy loses that sale.
With our API, when it gets to the point in that sale and the guy says it sounds too good to be true, he says, “Just come to our site, the platform site, enter a few piece of information and you’re ready to go in a second.” We make the platform look like a payment processor, so we eliminate the noise of the customer or the merchant having to go get a merchant account, which it’s never one place you have to go. It’s three places you have to go. Three different contracts they have to sign, a week or two of work. It’s a pretty big problem.
You’re solving a big time problem which also causes sales to be lost. By saving not only time, you’re increasing revenue for the platform, is that right?
We increase revenue a couple of ways. That $2 fee for instance. When the City of LA guys, before Digitzs, they would go and get a merchant account and come back to the platform. The platform would connect all the dots. Somebody pays their ticket for $100 and agrees to a $2 fee. $102 goes on that cardholder’s card and all $102 goes to the City of LA. The platform has to send the City of LA an invoice every month that says, “You did a thousand transactions. You owe us $2,000.” With our API, that $2 gets split off and paid directly to the platform next day. The $100 goes to the City of LA. We’ve eliminated their invoicing, which saves them money, clearly. The other thing is we also pay them a commission on the $2.93 that we charge the City of LA to process cards.
As part of your use of funds that you’re raising, is it all going to tech or are you going to be hiring a sales force?
No sales force. We have a brilliant cofounder on board, Ben Way. Ben has helped to launch 200 different companies. He’s advised the White House when he was a kid from the UK. He’s brilliant. Ben is an artificial intelligence internet marketing expert. We have an in-house expert that generates tremendous leads directly for me to have conversations with CEOs of these platforms.
That’s fantastic because a lot of people need sales people, and you’re doing a B2B play so you don’t.

Who Else Cares: Today, not at all worth it to hire a salesperson. It’s much more important to have leads coming into you.
Ultimately, we may have one person super seasoned out having very high level conversations. At this stage, we’re just still in the middle of product market fit. Hiring a sales person, what a waste of money. I’ve managed and hired sales people my whole life. I can tell you, usually in today’s day and age, not at all worth it. It’s much more important to have leads coming into you. Just like we have Kraft and their leads coming into us for investors. If you don’t have somebody replying to an email, showing there’s a need for what you’ve got, it’s a long road.
What’s your biggest surprise so far? I know we all have obstacles in our startups. What would you say is one of your biggest surprises that you didn’t anticipate that you could share with us that people could be like, “Maybe I should think about that?”
We pitched 50 CEOs of these platforms. They all said, “Sounds fantastic.” 27 of them said, “We’re going to do this. It’s amazing. How did you put this together?” When push came to shove, we found out 26 of them were not PCI-compliant, which is a security level that you need when you’re processing Visa, Mastercard and Amex on behalf of other merchants. We had to quickly regroup and build some tools to help non-compliant platforms use Digitzs. That was not something we expected. It was a big kick in the stomach, if you will. You just get over it and do what you got to do.
Let’s talk a little bit about you’re on the Board of a non-profit, A Sense of Home. How did you pick that charity? How does that relate to what you’re doing, if at all, with Digitzs?
It picked me. About a year ago, I was trying to get rid of a couch in my office, and just literally could not find a place for it. Stacey, my technical cofounder, said, “Why don’t you give it to A Sense of Home?” I had no idea who it was. I called them. They picked up my couch. The next day, I get an email with a family and about twenty people sitting around my couch in a house with a celebration. I was so impressed, I just called them back and I said, “What do you do?” They said, “We make first homes for aged out foster kids in Los Angeles.”

Who Else Cares: Our goal, by the time we leave, is to give them a sense of home.
I didn’t know anything about the foster care system at that time, but families get paid to take in foster kids. When they turn eighteen, they usually kick them to a curb because they’re no longer compensated for keeping them in their house. A good majority of these kids end up on the street or about a third of them end up getting what they call Section 8 Housing. A lot of them live on a mattress in an apartment for a year, until A Sense of Home comes along. What we do every Sunday here in LA is we literally, we did one yesterday, we go in with a truck and usually twenty volunteers and put in all donated furniture; everything from flowers to pictures on the wall, to everything in the bathroom and kitchen. Our goal, by the time we leave, is to give them a sense of home.
A lot of people will say, “How do you find the time to do that and launch this huge startup?” Most people will go, “I can either do one or the other. Or I will do that after my company’s sold.” You’re doing it concurrently, so it’s obviously inspirational. I think that’s the big question people have is, how do you find the time?
It doesn’t take a lot of time. It’s actually what I do for fun. You have to have some break from your work. These days, we’re all so cooped up in our homes or our offices with our computers. We don’t connect with people face-to-face. For me, it’s become a really nice way to hug a bunch of people all at one time on the weekend. It takes a couple of hours. I don’t do it every weekend. They asked me to join the Board, which I was so honored, because, Georgie, who founded A Sense of Home, just was honored to be a top ten CNN Hero just a few months ago. It’s a massive honor. They had a big gala that CNN does and she was on there. Richard Gere actually introduced her. Now, they’re getting tremendous traction. The idea is to duplicate it in multiple markets. It’s really been super amazing to watch.
How can someone follow Digitzs and you on social media? What’s the best way for them to keep track of what you’re doing?
It’s @LauraDigitzs on Twitter. We have a Facebook page. It’s Digitzs.com.
Do you have any books or book that you would like to recommend to a founder or someone who’s thinking about getting into equity crowdfunding?
Certainly, your book. I am going to write a book on our experience in equity crowdfunding just to help founders, because there’s a real formula to success. It’s not a complex formula. I think it’s one that people need to be aware of before they go down this road. It’s not for the faint-hearted.
Laura, thank you so much for sharing your expertise and time. We look forward to watching Digitzs change the way we pay for things.
You rock, John. Thanks a bunch.
Thank you.
Have a good one.
Links Mentioned
- J Robinett Enterprises
- John Livesay Funding Strategist
- Digitzs
- Crowdfunder
- Swim With The Sharks Without Being Eaten Alive
- Close.io
- A Sense of Home
- @LauraDigitzs
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Build Relationships and Get an Introduction with Michael O’Neal
Posted by John Livesay in podcast | 0 comments

Episode Summary
Today’s guest on The Successful Pitch is Michael O’Neal, who hosts a podcast called The Solopreneur Hour: Job Security for the Unemployable. He talks about when he creates a podcast episode that’s typically an hour long, he promotes it for four hours. That’s been one of the keys to his success. He’s got this amazing course called The Art of The Interview that I highly recommend you stay tuned and listen to. He really talks about his secrets of getting huge traction. One of them has to do with using social media smartly and the other is relationships, but from a place that you may not expect would be a great place for getting the top relationships and how to do it and get those all-important introductions.
Listen To The Episode Here
Build Relationships and Get an Introduction with Michael O’Neal
Today’s guest is Michael O’Neal, who is a podcast expert. He has his own podcast called The Solopreneur Hour: Job Security for the Unemployable. He also produces a lot of other podcasts such as The Kickass Life and Mechanic to Millionaire. His Solopreneur Hour podcast started back in August of 2013. It already has eight million downloads and he was able to monetize that in six months to six figures. I think that’s some kind of record. He is a big guy into a lot of different things besides podcasting, including music. He’s got this amazing course called The Art of The Interview, which I can’t wait to hear about. Michael, welcome to the show.
John, thanks for having me. That’s very kind of you.
Our mutual friend, Matthew Kimberley, I heard him several times on your show. I know that everything happens through connections. Certainly in the world of investing, investors tell me all the time, “We love to get warm introductions before we hear somebody pitch.” The same is true in the podcasting world, isn’t it?
It really is. I was just having a brunch meeting before this in a co-working session. I was looking at ten new emails in my inbox. Seven out of the ten, “I should totally be on your show.” I can count on one hand in three years the number of times that I have gotten one of those emails and go, “You’re right.” It really requires, at least for me, it requires a heads up from a friend. That third party intro is something I talk about. This course called Conferencetopia, which is free. You go to conferences all the time when you’re in this entrepreneur space. I’ve watched people spend thousands of dollars going to these conferences and then get nothing out of them. Even though they have a great time, they don’t move the needle in their business. I reverse engineered how I had built relationships and built my business from conferences. I made this free course for that.

Build Relationships: One of the major tenets is, “Always get an introduction.”
One of the major tenets is, “Always get an introduction.” If you and I are standing in a crowd and you know your friend knows that person, instead of just walking up to me like, “I’m Michael O’Neal. I have a podcast, blah, blah.” You’d say, “Would you mind introducing me to the mayor?” whoever it is. It’s not only that, but it’s them knowing how to introduce you that makes all the difference in the world.
You’re basically transferring all of the credibility and the trust and integrity that you have with that person when you make that introduction in person or in an email. Don’t you think that’s really what you’re doing there?
I just got introduced to a guy last week and I was at a conference. My buddy, Phil Mershon, who runs Social Media Marketing World, it’s a big conference coming up in March in San Antonio. He says, “Scott, I’d like you to meet my buddy, Michael. Michael has a podcast and talks to other unemployable people like himself.” He says, “He’s also a great drummer. This is Scott, entrepreneur, has an amazing new app. By the way, he was the sax player for Pink Floyd.” There’s context there. It changes how people view each other. It changes how the conversation goes. It really makes a huge difference how people are being introduced. It’s something we don’t consider enough when we go to conferences.
That one thing you talked about, being the sax player for Pink Floyd, that’s the memorable hook, isn’t it? That’s the “Oh my god. There’s a story there.” That’s what I keep telling people when they’re pitching to get their startup funded. Whatever you have that makes you unique and memorable, bring that up to the top when you give a pitch. You have such a great story yourself of how you decided, based on what was going on in your personal life, that you were not going to work for somebody anymore, and figure out a way to overcome your fears. Can you tell us that story and then specifically how you overcame the fear of, “What if this fails?”
To be fair, I never had that fear. That’s something I’ve never really had. I assume it will fail. I just know in the entrepreneur game, we’re going to miss more than we’re going to hit. That a show, in this case, a podcast, has a minute chance that it will be a huge hit. Just like anybody that pitches a new TV show. You file a process and then all the vetting and all that stuff. Then maybe the timing works or the content works, or whatever, somehow, but there’s no guarantee of that. We’ll definitely have more concepts than hits.
With that said, I’m running a pretty solid streak right now. I launched The Kickass Life with David Wood in 2012. That ran until late 2013 or so. That show crushed. It was top ten in health the whole time we did it. Then I launched The Mechanic to Millionaire, which is a buddy, Dave MacArthur, who’s a really successful network marketing dude. That show has been this killer, rabbit-and-hare growth for probably four years now. It just keeps going up and up and up. If I looked a year and a half ago, two years ago, that show was doing 400 or 500 downloads a day or something, which was pretty good even by today’s standards. Now, it’s at 1,500 downloads a day, which is still not Joe Rogan. We’re not getting 90 million a month. But in the grand scheme of things, in our little entrepreneurial podcasting space, that’s a very successful show.
Then I launched this one, and this one was a pretty quick hit. Then I launched The Hines Ward Show. I was the co-host for that one. That has done really well as well. We’ve got two more shows in the hopper.
One being our mutual friend, Matthew Kimberley, is coming up, right?
Yeah. Tipsy Business, which we don’t have a logo or anything yet. Matthew is hilarious. Matthew’s quick, very quick-witted. To me, entertainment always trumps value, if you will, actionable content. I always want to be entertained first. If they can, then those nuggets will fall to the ground because they’re entertained and they’re engaged in the conversation you’re having. Way too few understand that concept. Think about your favorite teacher of all time, they’re entertaining. That’s why you still remember some of their lessons.
[Tweet “Build Relationships: Own a social media platform and be active to get rapid growth.”]
For me, I would go one step further and say the best way for people to become entertaining is to learn how to become a storyteller, because that’s my favorite teacher. He always told great stories about history as opposed to just giving me the facts. Can you tell us an entertaining story of how you were able to get to eight million downloads so quickly? Traction is so important for investors when they’re looking at startups. They want that kind of rapid growth. I’m thinking there’s probably a story there that could be applied to a startup, who’s listening to this and like, “I could use that same skill or strategy or even process to apply to my business to scale fast.”
I think you’ve got to own social in some way. You’ve got to own a platform and really use it. You can pick it, it can be Facebook or Instagram or Twitter, whatever you want to use. You should definitely not be one of those people that’s like, “That’s for the kids.” You need to be active in that conversation. You can’t outsource everything. You’ve got to be the one that responds to these people’s comments. That’s one.
Two, I alluded to it before, which is the relationships that you build at conferences and out in the world are critical to your success. They were a high number of responsibility for the success of my show early on, because I was able to stock those first two or three months with some baller people. Some people that had huge social media followings back in the day in 2013, when you could still get someone to share the show because they hadn’t been on 300 shows by then. That matters. The relationship side really matters. A really diligent head-down promotion is what I did. My show would be an hour. I would spend four promoting each show.
The other thing that I got from Derek Halpern, which I really enjoyed, is you don’t have to be a content creator. You can take that content that you already have and keep repurposing it and keep promoting it. Those episodes I did early on, Matthew Kimberley episode, or you name it, you get really good content from that. So what if it’s three years old? Why shouldn’t I hammer the promotion on that old episode constantly on social media? They go, “That was a really valuable hour I spent. What else do they have?” Then all of a sudden, they’re plunging on your show. I would say the short answer to that question is the relationship-building that you do at events is really what moves the needle for your startup.
If you combine two of the things we’ve already talked about, which is building that relationship up and third party validation, third party introductions with people. You’re having a great conversation at a conference, you see someone that could move the needle in some way for you. ”Would you mind introducing us?” You guys have a great conversation. Before you know it, you’re at dinner and good things happen at dinners at conferences. Things get funded. It sounds cliché but it really, really matters that you can build these relationships and that you take that skill set very seriously in this space.
[Tweet “Repurpose content. Spend 4x time promoting it as you do creating it.”]
I love everything you said there. Own social. Be active, don’t outsource that. Relationships, everyone hears is important, but I like what you say, is the relationship you get started and keep going from conferences as a source=, not networking events, but actual conferences where you all have something in common, and get those introductions as opposed to doing it cold. Those are some amazing takeaways that apply to everything; podcasting, funding, pitching, anything that you want to scale your business.
You should be going to a conference a quarter. That should be the minimum amount. Per quarter is what you should be going to. It not only keeps you connecting, but it keeps you motivated. You see these people that are cranking. You start seeing some of the same faces. Again, that helps relationships get built.
That’s a perfect segue into something else you’re doing that I’m really impressed with and I want to hear more about, which is your mastermind, Sololab. You talk about this great quote that we’ve all heard, “You’re the sum total of the people you spend the most amount of time with.” Tell us what you’re doing in Sololab and who that’s for?

Build Relationships: I don’t think you know what you know until you’re teaching it to somebody else.
My group are people that either have a side hustle going on or they are leaving their 9 to 5, or they’ve been in this thing for a little bit and they’re trying to find their swing, if you will. If you play golf or tennis, you’ll understand that phraseology. I didn’t know that I was going to do it when I started the show. I was just bringing people on that I thought were smart and interesting and had cool stories and we were talking. Every once in a while, I’d get an email that says, “Do you do any coaching?” I say, “No, I don’t, really.” But after the 40th one, “Yeah, I totally do.” I started talking about it on the show.
I don’t think you know what you know until you’re teaching it to somebody else. It’s like as a drummer, I can go back and listen to some of my old music and go, “I don’t even know I knew how to do that.” You just don’t recognize maybe some of the smoothness. I had to talk to Matthew Kimberley a couple of weeks ago in the show. The way he phrases certain things, that is a gorgeously phrased way to sit down and do a sales pitch for someone.
Let’s give an example of that, because I listened to that episode. He’s very smooth with that charming accent, “Would you be interested in having a conversation where I could see if and how I might be able to help you grow your business fast? Is that of interest or not?” Really framing that up fast. Obviously, that sounds very conversational and not robotic, but it’s been thought through and practiced much like a musician practices before they perform.
Like a stand-up, actually. Every word has weight.
It’s a thread that unravels. I tell people when they’re pitching investors, they need to have thought through their opening and their closing just as specific to that rehearsed but not robotic smooth way of inviting someone to join into what you’re offering, and not coming across desperate but really inviting them to join in. It’s the difference between saying at the end of a pitch, “Any questions?” versus having a smooth closing, where you’re asking them to invest and join in the vision.
It would be cool to talk about that initial conversation too. At some point, you want to end up in front of these people and being able to pitch them. But how do you even begin to do that? My buddy, Clay Hebert, got a thing called, “The Six Word Intro.” The idea is, “I help blank do blank.” If someone says, “What do you do?” which you’re going to hear a million times at conferences. You have to be prepared for that answer. You’ve got to know exactly what you’re going to say, and you have to have an idea of what the funnel looks like after that first sentence.
The analogy I can give is Tim Ferriss has this TV show, The Tim Ferriss Show. One of the episodes was that he wanted to learn MMA. He was learning jiu-jitsu. He wanted to learn, they call it rolling, which is moving around and wrestling and trying to get different moves. His whole show was about rapid learning. The instructor said, “There’s too much for you to know. I can’t teach you all of this stuff in three days. But I can teach you one move that you can execute well and I can teach you eight different ways to get into that move.” He taught him a rear naked choke. He taught him six or eight different ways to get into that move in various situations that he would be in while he’s rolling around on the mat with someone.
Picturing that in your head, when you get into a conversation with somebody at a conference, you have your one move. You’ve got to have multiple ways to get into that conversation. That’s not to say that every conversation needs to be a sales pitch or anything like that. It always starts with, “What do you do?” That’s always the first question you’re asked. I can say something like, “I help other unemployable people, like myself, take their hobbies and skill sets and learn to make a business out of them.” That’s how I’m going to answer that question.
[Tweet “Build Relationships: Relationships from conferences are the key to success.”]
It intrigues people, they’ll say, “That’s interesting, tell me more,” which is the whole point of a good pitch.
They’re going to go, “How do you do that?” I can say, “I have a podcast where I’ve interviewed some of the world’s thought leaders over the last three years.” I stop it there and they go, “Tell me more about the podcast.” That develops into a deeper conversation, and then they’re in my Sololab.
You said two things that I really want to underscore for the audience. Number one is, don’t open what you do when you get asked with how you do it, i.e. “I host a podcast.” Instead, open with some statement that makes them intrigued enough to want to know more. Only give them enough to continue to ask more. Don’t do verbal diarrhea on somebody and just go into all the details.
First of all, you haven’t been given permission to tell your story yet. That has not been implicit in the conversation. You can’t start telling it. Two, if you can’t answer those questions in those six words or twelve words or whatever it is, your brand isn’t dialed in enough. You actually have to go back and work on your brand, which could take months. That could really be something that you work on until you can answer that really, really succinctly. That’s the important part.
It took me a long time to get to, “What do you do?” “I’m the Pitch WhispererR. I take people from invisible to investable.” Then I stop. If they want to know more, then I tell them more. “What’s a Pitch WhispererR? How do you go from invisible to investable?” It’s just enough to get people intrigued. The same thing is true in that first 90 seconds when you’re pitching an investor. This has been great. I personally want to ask you for one of your favorite, most entertaining interviews you’ve done on The Solopreneur Hour. You had so many great comedians and musicians. Do you have an entertaining story of somebody that you had on?
I’ve been a life-long musician. I ended up having this conversation with Scott Page a couple of weeks ago at this conference called NAMM, National Association of Music Merchants. Within a minute, I’m fascinated by the dude. I just want to hear about this historic rock and roll guy. He talked about playing in front of 620,000 people in Venice at one show. That’s a lot of humanity right there. He talked about after selling out Wembley Stadium for three nights in a row, having a party in the suite of the hotel that Roger Waters had. In the one suite, at one time, there are 30 people, but it was Paul McCartney, David Bowie, Eric Clapton, Madonna, Sting, and ten other people. It was all musical legends and then ten other people, whoever else happened to be there. That, to me, was actually really difficult to not just totally nerd out. I remember looking at my little Zoom H6 and going, “We’ve been talking music for 47 minutes.”
This amazing course, The Art of The Interview, you’re doing, I want to hear more about that because investors tell me time and again, “When someone comes in to pitch me for funding, I want to have a conversation with that person.” They don’t have to suddenly become this robot or get nervous or hide behind who they are because at the end of the day, they’re investing in them. What can people learn in The Art of the Interview that they can use in their everyday life to get the right people to join their team, to get customers, and ultimately to get funded? It’s all the same skills.
There’s some technical side to it, obviously. I remember having this conversation. I was at a happy hour with a friend of mine. She had brought a friend. My friend had gone off and had a conversation or went to the rest room or whatever. I was there by myself with her friend. It was that awkward, awful small talk that you get in when you’re with a stranger. Somewhere around minute five, I was just sitting there thinking about taking my phone out. I thought, “Wait a second. For a living, people have told me, is a pretty entertaining conversation with a complete stranger every single day. Why am I not doing it?” I mentally flipped the microphone on. I had this great conversation. That’s on me. That’s me not connecting the dots between my actual skill set and how it translates into the real world. That was the subtext of The Art of The Interview.

Build Relationships: People find your show so much more memorable when you’re good at what you do, when you’re a good interviewer.
The other part is, and this is as frank as I can be, most podcasters are awful at podcasting. They’re really, really bad at it. Partially, it’s not their fault. Partially because we’ve had some people that are really successful financially in podcasting that are bad hosts. They’re just not good at the media, the actual broadcast hosting side of being a podcaster. By the way, it’s also not their fault. They never really considered it. They’re more marketers than they were podcasters. When you listen to someone who’s good at it, it’s such a stark contrast in conversational flow, in content, in how the message is delivered. You’ve got people that find your show so much more memorable when you’re good at what you do, when you’re a good interviewer, when you’re good at the show flowing well, when you’re good at introducing people, when you’re good at plugging their stuff.
Here’s a perfect good example. Once you’re interviewed a bunch, you start to see the tendencies of people. You can see where they came up and the schooling they had in the podcast world and who they paid attention to. Think about this, John, how often do you make it to the very end of a podcast? If you listen to other people’s show, percentage wise?
I would say, if it’s a good show, I’ll make it to 90%. More than half of the podcasts that I listen to, I’ll scan the show notes. I’ll be like, “There’s nothing really good until twenty minutes in.” Sometimes you can look at the transcripts.
If you’re listening, you don’t know the show notes, the transcripts, do you listen to 85% all the way through? Are you 75%? Are you 65%?
If it’s somebody really great, like Alec Baldwin, I’m in, because I love it from the start.
All the way to the end? You hear the closing credits?
Yes. It’s because he’s entertaining and he’s himself. He’s a great interviewer and all those things you just mentioned.
Would you say that you don’t do that with others though?
Correct, yes. There’s a definite problem you’re solving.
In my case, I probably don’t make it to the very end. I love podcasts. I live in the podcast world. I probably don’t make it to the ending credits 85% of the time. 15%, I’ll make it to the very end. 85%, I don’t. If you are a current trend of podcast host, you have to understand that you’ve got guests that are coming on your show that are doing you a massive favor. They’re providing great content for your audience. Do we agree on that?
Absolutely, and their time.
They’re giving their time, however they are, however far long they are in the time line. That could be more or less valuable. If you get a Jack Canfield or a Gary Vaynerchuk, you know their time is worth a lot of money. They’re getting a $100,000 for a keynote speech for an hour. With that in mind, as the host of the show who’s getting this massive favor done for you by this guest, the guest hoping, “Maybe I’ll sell a few books. Maybe I’ll get a few new people to my content,” that kind of thing, where do we plug the guest currently?
Towards the end.
Now. At the end.
Yes. Because we don’t want it to be “sales-y” so we have to save that and no one’s listening. Totally understand where you’re going now. I love that.
Number one, we go, “Where can people find you?” As a host of a show, it should have been the first question you ask before you started recording, “Where can people find you so I can help you?” Two, we do it at the very end. That’s one of the things that when you listen to a pro, let’s say anybody comes on Jimmy Kimmel or Jimmy Fallon or Jay Leno, the first thing they do is introduce the guest and say their new movie, blah, blah, blah, is out in theaters on Tuesday. They plug the guest right at the beginning of the show. As a good host, we should be plugging beginning, middle, end. Whenever that guest has a good take, we go, “That was really great. Guys, why don’t you tweet them at,” whatever their Twitter there is. That’s a pro move that 99% of podcasters do not do. That’s the kind of thing that The Art of The Interview talks about.
That leads me to another question, which is one of the things I pride myself on is preparation. If I have somebody on as a guest and they have a book, I do my darnedest to get a hold of it and read it before they get on the show. The same thing with someone like yourself. I did listen to a couple episodes, both of you as a host, both of you as a guest. I know what other things you’re doing. All of that preparation, that’s what I think separates you on any pitch. I’m always telling people, before you get in front of an investor with a pitch or a potential client, you must prepare and not just go in and wing it and expect it’s going to be brilliant without any preparation.

Build Relationships: You’ve got to step up your conversation game. You’ve got to be a little more committed.
You better know that that investor is the coach of their daughter’s softball team. CEO loves dirty jokes on the golf course. That’s how it got done. What I mean by that is there’s enough that happens that’s not “business.” If I walk into somebody’s office and I see a vintage car model sitting up on their desk, we’ll probably talk cars for probably 45 minutes. What that five minutes is going to be a foregone conclusion because we’ve already connected on a deeper level and on a relationship side. Now, you can always do that. Some people that are investors are just those are the guys that flip to the back page. I can’t do much, but then that means you’ve got to step up your conversation game. You’ve got to be a little more committed.
Let’s face it. Most people have a lot of anxiety. Even with an introduction at a conference and going up to someone and starting a conversation. If they can learn those skills, it will totally transform their business. What’s one mistake you see people making in an interview situation? Let’s say, not necessarily as a podcast host, because you’ve gone through those, but just interviewing somebody in a situation at a conference that you’ve been introduced to, you’re trying to get to know them. We’re saying that conversations, when you flip that switch and pretended that it was an interview, then everything went great. I’m guessing you could take some of those skills from your Art of Interview class and apply it to conversations.
I think one that I see happen a lot, and it just happened to me on Tuesday, is non-inclusive body language. I had sat down, there was a girl that sat next to me and knew my friend. It was three chairs in a row, and I was on the end. She just turned her back on me and had this conversation with this person. She could have been the world’s best entrepreneur or business person, I will never do business with her. She just turned her back on me. In fact, in that same scenario, I was speaking with the speaker that was at the event and then another person. We were in a little triangle. I sensed that there’s somebody on my right shoulder, behind me, and I opened up. I welcomed them into the circle and then I made the introduction. You have to do that with people. Even if it’s this deal where you’re lucky enough to get this conversation with Gary Vaynerchuk or something like that, that person, the influencer, will appreciate more, they will recognize what you just did and how selfless it was and how inclusive you were, and that will put you into a different category with them. I’ve seen it happen over and over and over again.
I’ve seen that happen myself where you’re sitting at a round table at a meal and you’re listening to a keynote speaker. Someone will literally turn their chair just to talk to the person to their left and ignore the person on the right. You never know who’s there.
Not good. Bad business.
What final piece of insight or a book you’d like to recommend or a podcast you want to have people listen to, in addition to The Solopreneur Hour, that you think would be helpful for people?
One other addendum to that last thing we just talked about, when you’re in that meeting, be super nice to the underlings. Be really nice to the assistants. Don’t be dismissive. Have a good conversation with the elevator person or the janitor. Believe it or not, they’re major gatekeepers.
I’ve seen that happen many times where you’ll go in to pitch for something and that person walks you out and you get in the elevator, and the receptionist will say, “That guy was great,” or, “That guy was a jerk.” That makes or breaks your deal.
I use an app called Evernote on my phone. I put all the names of all the door guys because it only takes one or two times where you can be like, “Hey, Fred. What’s going on, man? How are you?” Then you never have to wait in line. It happens to me every Wednesday. I play at this club every Wednesday and there’s a line around the block. Do a little handshake and go right in, every single time.
Just from remembering somebody’s name.
It doesn’t take much. Anyway, recommended, if you want to get really good at conversation, I love this show called Off Camera with Sam Jones. Sam does amazing interviews. He’s my favorite on iTunes right now. Plus, he has a Rolodex like you wouldn’t believe. It’s all major celebrity A-listers. What he does is he’s a photographer in Hollywood. He’s worked with a ton of them on a professional level and then started the show. He just has this great super low-key conversational style. He’s very well-researched. It was a common theme that we talked about today.
Follow Michael on Twitter. Your Twitter handle is @SoloHour. The podcast is SolopreneurHour.com on the website. I’ve listened to both. I’ve followed him on Twitter. I highly recommend everyone to do that. Most importantly, I really invite you to sign up for The Art of the Interview. It’s going to change your way that you have more confidence and it’s going to give you the success that Michael has had. Thank you so much for being with me today, Michael.
I should mention the URL. It’s ArtOfTheInterview.co. Thanks, John.
Thank you.
Links Mentioned
- J Robinett Enterprises
- John Livesay Funding Strategist
- The Solopreneur Hour: Job Security for the Unemployable
- Conferencetopia
- Sololab
- @SoloHour
- ArtOfTheInterview.co
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