Leap Academy with Ilana Golan
Seth Godin: Turning 800 Rejections into a Roadmap for Success
Tue, 25 Feb 2025
Where most people give up after a handful of rejections, Seth Godin got rejected 800 times by editors before finally making a big break. For him, every “no” was a clue. He adapted and mastered the system, and soon, the same editors who dismissed him were calling him first. His success wasn’t luck or passion. It was built by showing up, iterating, and playing the long game. In this episode, Seth joins Ilana to reveal why most people quit before they succeed, how to market ideas people want, and why smart strategy, not passion, drives real success. Seth Godin is an entrepreneur, bestselling author, and marketing expert widely recognized for his groundbreaking ideas on marketing, leadership, and business innovation. He inspires individuals and businesses to make a difference by being creative, authentic, and impactful. In this episode, Ilana and Seth will discuss: (00:00) Introduction (01:34) Startup Failures and Early Struggles (02:48) From 800 Rejections to Breakthrough (04:34) Turning Rejections into Strategic Insights (06:25) How to Lead Change Amid Resistance (09:23) Why Commitment Beats Passion (11:12) The Dip: Knowing When to Stay or Quit (14:31) How to Create Value in Niche Spaces (19:32) Building Success with Constant Iteration (23:33) Strategies for Earning Your Worth (27:06) Building Brand Reputation Through Consistency (31:55) The Chocolate Bar Marketing Strategy (34:34) Embracing Failure as Part of the Journey Seth Godin is an entrepreneur, bestselling author, and marketing expert widely recognized for his groundbreaking ideas on marketing, leadership, and business innovation. He is the author of over 20 best-selling books, including Purple Cow, and This Is Marketing. Seth inspires individuals and businesses to make a difference by being creative, authentic, and impactful. Connect with Seth: Seth’s Website: https://www.sethgodin.com/ Seth’s LinkedIn: linkedin.com/in/sethgodin/ Resources Mentioned: Seth’s Blog: https://seths.blog/ Seth’s Book, The Dip: A Little Book That Teaches You When to Quit (and When to Stick) https://www.amazon.com/Dip-Little-Book-Teaches-Stick/dp/1591841666 Seth’s Book, This Is Strategy: Make Better Plans: https://www.amazon.com/This-Strategy-Better-Elevate-Community/dp/B0D47T8S7N Seth’s Book, This Is Marketing: You Can't Be Seen Until You Learn to See: https://www.amazon.com/This-Marketing-Cant-Until-Learn/dp/0525540830/ Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training
Chapter 1: What are the early struggles and startup failures Seth Godin faced?
Seth Godin is the author of 22 worldwide bestseller that has been translated into 40 languages. You are an incredible entrepreneur at heart, plus one of the most prolific bloggers on the internet.
I started my first business in 74, sold ice cream sandwiches and posters. I started a book packaging company, got rejected 800 times. It was a slog of inventing things that people didn't want to buy. The key learning from the 800 rejections is... I totally understand that there's a desire to leap.
Chapter 2: How did Seth Godin turn 800 rejections into a breakthrough?
But if you are picking a path that is crowded, that is easy to get on, and only has one or a few winners, you have made a bad strategic decision.
What are the strategies that will help you rise above the noise?
The first one is...
Seth Godin is the author of 22 worldwide bestseller that has been translated into 40 languages. Seth, you love teaching. You are an incredible entrepreneur at heart, plus one of the most prolific bloggers on the internet. I even bought your chocolate.
And I know you almost never talk about yourself because you want to give so much to others, but I do want to take you for a second to starting your first company, YoYo Dine, which was acquired by Yahoo. Can you share a little bit about that story?
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Chapter 3: What strategic insights did Seth gain from rejections?
Sure. It's great to be here. I would say that YoYo Dine was my seventh company, not my first company. And One of the challenges that we have when we seek to lead and to show up is this sensation that we have to get it all right and have the big launch and everything's got to be smooth sailing after that. But that's almost never what actually happens.
What usually happens is first we look in the mirror and see somebody who wants to build something. And that thing we build might be solo. That thing we build might be freelance and it might be entrepreneurial, something bigger than ourselves. So, you know, I think I started my first business in 74. I built businesses that sold ice cream sandwiches and posters.
When I was in college, Steve Dennis and I co-founded one of the largest student-run businesses in the world. Each one of them had value being created for people and none of them was a household name. And in 86, I started a book packaging company, got rejected 800 times in a row after selling my first book.
And it was a slog of inventing things that people didn't want to buy or inventing things that they bought them, but it was tricky. And what I saw was a company called Prodigy coming along. And Prodigy and then AOL and CompuServe were the thing before the internet. And I'm a game designer from way back, and I designed a game that we ran on Prodigy, and it was extremely successful.
The thing that I discovered, though, is that building software in the 80s or 90s, the 90s by then, was very expensive and difficult to do over and over again. And nobody knew who was going to win, Prodigy, CompuServe, AOL, whatever. But what they all had in common was email. And so we invented email marketing.
And Yo-Yo Dine, which I ran out of my pocket from the book business, incrementally built up by finding clients who wanted to pay us for the next project and the next project until eventually... The web showed up and I thought the web made absolutely no sense. I thought the worldwide web was a scam and it wasn't going to work. That cost me, I don't know, $50 billion.
But eventually we grew to be the largest email marketer in the world. And then I sold the company to Yahoo in 1998.
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Chapter 4: How does Seth Godin view change and resistance in business?
When you get 800 rejections, that's usually where people stop, right? I mean, they stop by the fifth one.
They usually stop at 20.
So what makes you, and you talk also about the fact that you're never going to be ready, and you talk a lot about the perseverance of these things, but what made you continue when you get no's? What makes you continue even now?
In my book, This is Strategy, I talk about the key questions we need to ask ourselves. And they are, who's it for? What's it for? What is the change we're here to make? And if you're hassling people to change their mind, to like what you do, you're never going to get to where you want to go. And so the key learning from the 800 rejections is they weren't all the same.
The rejections at the beginning were, you're a stranger around here. You don't know how we do things. That was it. We're not even going to look at the rest of it because you're not speaking the right language. And over time, over the months that followed, the rejections got more insightful. They were no longer was someone saying, who the hell are you?
They were saying, oh, I see what you were doing here, but we need something more like that. And so I had to develop the empathy to sell book publishers what they wanted, not what I wanted. Once we got over the hump, we ended up doing 120 books, a book a month for 10 years. And we were a trusted partner. Who changed? We changed. The editors didn't change. The editors were the same.
But we changed because we now had their voice in our heads. And so if you're busy hassling and hustling people and you keep getting no's and they're always no, then the world is telling you something. It's telling you you're being selfish. But if you are engaging with people and getting better at solving their problem and they're encouraging you,
then those rejections aren't no, they're no for now. They are, let me tell you where I'm hoping to go, will you come with me letters? And those are the things we're looking for.
Then you also talk in, this is strategy in your book, you talk about time and games and systems and empathy and you touch part of it. And I love that you call it dance together versus combat each other. Can you explain this a little bit?
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Chapter 5: Why does Seth believe commitment beats passion in achieving success?
It used to be a little tiny sapling next to another sapling and it grew over time. And so try to imagine if you had to write yourself a five years ago, a letter, and that letter was to thank the you of five years ago for something hard that you did that we're grateful for today, right?
I'm really glad you decided to speak up to your parents and not go to dental school because five years later, my life is better. I'm glad we didn't have to go to dental school. That's a thank you note. All right. Well, The you of five years from now is going to send the you of today a thank you note as well. What are they going to say?
What are you going to plant today that they're going to be glad five years from now that you put the effort into planting?
That's beautiful because you also talk a lot about making change happen and creating impact and curating things that you care about. And a lot of it is also driven by the strategy that you put together, the marketing you put together. Why is making change so important?
Change isn't important if you're happy with the way things are. That if the snow at the top of the mountain where you teach cross-country skiing is exactly perfect for the right number of days a year, don't change it. That's fine. You should dance with that. That's fantastic.
But if you want to create value, if you want to make a profit, if you want to make a difference, you have to make change happen. And the thing about change, as we said, systems fight it and it always creates tension. The tension of this might not work. The tension of I'm not sure. The tension of this is new. The tension is who are you to do this?
And so what it means to make change is to willingly inflict tension on the system to help make it better.
So you talk a lot about that and you're actually saying, and I love this quote, what you're doing today that creates the condition for tomorrow to be better, right? But I think you also talk a lot about bringing your passion, bringing your all in, right? And if you're all in, you'll be able to do so much more in your life.
If you talk to professional poker players, they will explain to you that going all in is mostly for amateurs. That professional poker players win over time. They don't win all in. And the thing about passion, like authenticity, is for amateurs. In the sense that your friends are owed your authentic passion itself. But if you're a professional... You make a promise and you keep it.
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Chapter 6: What is 'The Dip' and how do you know when to stay or quit?
That we can say, this is going to be open from nine o'clock to five o'clock, whether I feel like it or not. I'm going to do heart surgery on you at three in the afternoon. The best it can be done, even if I just had a fight with my brother-in-law. That you're not looking for the red hot fire of somebody who's doing their hobby.
We're looking for the reliable, branded promise of showing up the way you said you would.
Interesting. So many times I talk about that I don't know if I believe in motivation, I believe in habits. And when you form these habits, you can create it again, again, again, right? But I think you, and we talked about it a little bit before the show, you in the dip actually, I think opened my eyes a little bit to say, yes, but what's on the other side of this habit that you're creating?
Is there something you know, a trajectory to something beautiful? Or are you full gas neutral going into this cul-de-sac dead end that is just getting you nowhere, which I found myself in my career as well. So how do you put all of these together as far as you're concerned?
Okay, so let's just talk through the dip. Now, far more than when I wrote it, there's a huge premium to go to the entity that wins, right? that if you type in best pizza in Cleveland, you're not gonna go to the fourth best pizza on Yelp, you're gonna go to the best pizza on Yelp. The idea that you can do very well coming in seventh place keeps fading away.
So what does it mean to be the best in the world? the best in the world at whatever world you define, for whatever customer you define, right? That if there are three gyms within driving distance of my house, the best in the world just means you're the best of those three gyms. Fine. What would it mean to be the best at that?
And it turns out that if we're trying to make change happen, to get from here to best, there's a dip. And the dip is the hard part. The dip is the part where all your competitors are going to quit because it's too hard. The dip is the thing that feels overwhelming, unreasonable to get through. And when the dip shows up, most people quit. That's why it's called the dip.
You should not be surprised if there is a dip because if it's worth doing, there's a dip. What you should do is when it shows up, welcome it and say, this is what I planned for. I planned for this extremely difficult slog because that's what's going to create value when I get to the other side. And if we see a platform like TikTok where anyone can be on it, because there's no dip really,
There's this huge long tail and no one is particularly happy unless they win the lottery. What you'd prefer is to find something that's actually difficult so that when you get to the other side, you're glad you did. But as you pointed out, sometimes there isn't a dip. Sometimes it's just a dead end. You cannot smoke enough cigarettes to get through lung cancer. It's a dead end.
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Chapter 7: How can you create value in niche markets?
Because they need to be organized. They need to be connected. They're disconnected now and they have money to spend to stay connected. So the hard work of strategy is to see where there is an actual problem and not just try to find a job without a boss, but to actually create value.
Right. And I think you talk a lot about creating value for a small group of people and then grow from there. So knowing that they're coming back to you again and again, they're coming not because you're soliciting them or because you're begging them, but because they're actually have value in what you're showing or giving or creating.
So how do you find that group for people who are listening to us? And how do you make sure that they're really coming back to you? Because that's the key to get started.
Well, the first thing I would say is that group is probably not a group you are a part of. That one of the challenges of do what you know is the things you know tend to be popular consumer things, and those things are crowded. What you want to start with is people who have a problem, who know they have a problem, and who have money to solve that problem.
So in my case, when I started the book packaging company, editors' only job is to acquire books. So it's not like I was hassling them. They were doing their job. They have a problem. They need a book tomorrow. They have money to spend to get one. Here I am. This is not true anymore. There aren't as many editors. They don't have as much money.
And there are more people pitching them than ever before. So that problem is solved. But it wasn't solved when I started. On the other hand, if you can find this group of people, you can try it out by having lunch with them, by being in the world that they are in. Before you open a bakery, work in a bakery.
and figure out what happens when a customer walks into the store and how do they behave and what do they ask for and what are they looking at? Because that's really practical empathy. Not saying, I dreamed of everything you want and now I'm going to make sure that you like what I did. No. Look to see what people like. Look to see where they have a problem. Where are they waiting in line?
What are they dreaming of, talking about? They're happy to tell you. And you can then say, well, the way they're trying to solve it might not be the best way. If I can solve their dreams in a different way, I can do that in my own unique way. And that's what Richard Saul Worman did when he started TED. And Chris Anderson multiplied it by a thousand.
And it also works in the nonprofit space to be able to say, I see the kind of donor that is looking for an effective way to make a donation. I see the kind of person that needs help. I can connect those people.
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Chapter 8: What strategies can help you rise above the noise in marketing?
What can I create with that? I mean, you're seeing many millions of people going through. You have huge keynotes, by the way, which are amazing. How do you see that, the shift in the difference today?
Well, if the world were fair, people would get fairly for the effort and risk they take. People wouldn't be judged by their appearance or their background. And we'd have this generative, resilient economy. None of those things are true.
So given that none of those things are true, what will help you be seen, treated with the dignity and respect you deserve, and earn the freedom that you're looking for? So this is back to the ideas in this strategy. The first one is, what do you own? What are the assets in your reputation, in your productivity, in your machinery, in your network that are worth paying for?
Because someone's not going to pay you because you want them to, they're going to pay you because they want to. So we get to build these assets. And if you are the most successful patent lawyer in the United States, you can charge $6,000 an hour. And it's not because you worked hard to do it. It's because someone who needs the best patent lawyer in the United States is happy to pay $6,000 for it.
So then the second part is find customers who have a problem they want to solve and money to solve it. And this seems trivially obvious, right? But people miss this all the time, right? So if you want to make money selling bean to bar chocolate, don't sell it to seven-year-olds. Because seven-year-olds just don't have a lot of disposable income. And they also have lousy taste.
So they just want to buy something that's big and sweet. They don't want to buy the thing you made. On the other hand, people spend $100, $200 for a bottle of wine. Not everybody, not somebody who's drunk on the corner, but some people.
So if you want to make money selling wine, probably you should find those people and sell them wine because it costs just as much to make a $200 bottle of wine as a $10 bottle of wine. If you're not going to make those choices at the beginning, you're probably going to be frustrated at the end, complaining that people are treating you like a cog. Here's what I would say to those people.
How come you didn't hire a $10,000 wedding photographer for your wedding and instead just gave everyone an Instamatic or told them to use their phones, right? There are photographers who worked really hard, but you didn't hire one because when you're the customer, you're saying, well, it wasn't worth the money. Well, the same thing is going to be true on the other side.
What I love about what you just said, which I think is just so, so important, I want to make sure our listeners understand this. I think from a certain age specifically or a certain stage in life, et cetera, people don't pay you per hour or for your time or even not for your expertise. They pay you for the outcome or the value of the outcome that you deliver, right?
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