All My Biggest Business Failures. All The Embarrassing Details.

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Yep.

2 sales. In fact, one of the sales was a chargeback, which was fraud basically. It wasn't actually a real sale. And the other sale was actually a sympathy sale from a friend, fellow entrepreneur friend, John Legdumis. Shout out to you, John Legdumis, for supporting and giving us that one sale. But I can't tell you how heartbreaking that was. 4 months of work, really believing this thing is going to be amazing, really believing this is valuable, and then launching out to the world and realizing, oh man, nobody wants this. I think it's important not to gloss over failures. You need to feel the pain of a failure so that you don't repeat it. And we need to sit with that pain for a moment. Like, for a moment, just think about it. 4 months of work. How many hours is that? That's like 40 hours a week. 5 days a week for 4 weeks every month for 4 months, making no money. And then at the end, getting 1 sale from a friend that doesn't even cover any of your costs. You're in the super negative here. Okay. So it's really deflating. It's good to feel the pain so that you could be like, hey, I got to learn something from this so I don't do this again. So what did I learn from this epic failure? Well, the first thing I learned is that people don't want to learn how to do something as technical, as complex as putting a webinar together. They want a tool. They want it done for them. They didn't want education. They wanted a solution to their existing problem. And I didn't understand that until I crashed and burned and failed with the DIY Webinar Guide. If I was going to really put this into one word, it's the word outcomes. People buy outcomes. They want an outcome. People don't buy a new jacket because they're cold. They buy a new jacket because they want to feel cool, right? They want to look cool. They want to be able to post it on Instagram and get compliments. They want to feel good about themselves. That's the outcome they're looking for. And with us, they want to run a smooth, easy-to-run webinar that makes them sales. That's the outcome they're looking for. So when I realized this, that is the birth of the idea of our software company, Webinar Ninja, which is a tool that puts all the technical pieces together, makes it easy for you to run a webinar and allows them to make money through a webinar, whether they're selling products and services. So the software did it for them rather than them having to learn and do it for themselves. So it's easy to get the outcome. And what I learned is that when you're selling a product and people can get an outcome quickly with very little effort, it's easy to sell that product. That product is super easy to sell because they see the pain being resolved quickly. And if you know anything about me and us and our whole story, Webinar Ninja was a business that we ran for 10 years. We got acquired in 2024, changed my life forever financially. That failure, that DIY webinar guide failure, helped me understand what I was doing wrong so I could do something right, built Webinar Ninja, that changed my life forever. So as much as I hated those 4 months of hard work and hitting that wall and having that horrible failure and feeling like a loser in that time, I'm so glad it happened because it gave me the tools and the understanding to know what to build. But that's the key. You have to be receptive to it. You can't just be like, oh, that sucks, I'm horrible, maybe business is not for me. So down on yourself that you blind yourself from the learnings. You gotta just be objective sometimes, be like, okay, that didn't work. Just like if you are going to play any kind of game or sport, let's say for example, you love to play basketball like me and you play a pickup game and you lose that game. It's not great to lose, but you can find out like what happened. Oh, maybe we didn't rebound. Maybe we didn't defend. Next time we play, we gotta do these things better. So hopefully we can win. You just keep playing. It's okay. Just learn and keep going on. Run your own business? The Total Solutions Advantage from Comcast Business does it all, just like you. The more you add, the more you save. Get started with a qualifying internet package for as low as $60 a month when you add an advanced solution. Plus, new customers, ask how you can get up to $1,500 in prepaid cards. Limited time offer. Prepaid card offers end 9/13/26. Restrictions apply. Call for details. Today's episode is supported by Upwork. Smart hiring begins with the right tools, not more work. Upwork makes it easy to hire specialized freelancers quickly so you can get the expertise you need now. How do I know? Well, I've been using Upwork for over a decade. I made some of the best hires in our company through Upwork, and it's for good reason. Upwork helps grow your business by giving you fast access to specialized talent across more than 125 categories. So you can fill in skill gaps, launch projects faster, and scale support up or down without committing to a full-time headcount. I absolutely love Upwork because it's a one-stop platform to find, hire, and pay expert freelancers across web and software development, data and analytics, marketing, business operations, and more. It's free to sign up and posting a job is easy. And with Business Plus, you can access the top 1% of talent on Upwork. And with AI-powered shortlisting, You get matched to the right freelancer in under 6 hours. No endless searching required. Visit upwork.com right now and post your job for free. That's upwork.com to connect with top talent ready to help your business grow. That's U-P-W-O-R-K.com, upwork.com. Failure number 2. My first podcast. This podcast, the $100 MBA Show, is not my first podcast. Our first podcast was called People Who Know Their Funny Name. Good name. Unfortunately, the podcast wasn't so good. Okay? It was one of my biggest failures. It was an interview podcast where we interviewed other entrepreneurs and we brought them on the show and we published these episodes just like everybody else. And that's the problem. It was just like everybody else. Same format as every other interview podcast out there. Now remember. This was 2014. Most podcasts, especially in the business space, were interview podcasts. So we were not really presenting anything exceptional or anything different or anything unique or any kind of unique value. We spent 6 months publishing this podcast week after week, and we published over 40 episodes in the process because we actually did some extra episodes as well. Our best episode ever was with Gary Vaynerchuk. We had Gary Vaynerchuk, who was a great guest, but that episode got 400 downloads.

Wow.

And just for context, so you can understand, you know, I was getting more views on my blog posts that time, and it was a lot of effort to put together a podcast and to get guests like Gary Vaynerchuk. This podcast, the $100 MBA Show, gets between 100,000 and 150,000 downloads an episode. So 400 downloads, not so impressive. So we really felt invisible. We felt like this podcast is a lot of effort and is not working. Why is it not working? Funny enough, us realizing that we're failing at this podcast came at a good time when we were about to go on a road trip. Nicole at the time was still doing video work as a videographer, and she had a gig in New York. And at the time we were living in San Diego, and we were trying to save some money, and we had the time on our hands kind of licking our wounds. So we thought, let's drive across country, do a road trip, have a discussion, and do some work at New York for the film work. And on that road trip, we had nothing but the open road. And our thoughts. And we had to ask ourselves some honest questions like, how are we going to compete with other podcasts, other interview podcasts that were out at the same time we were? People like Tim Ferriss, who has 4 New York Times bestselling books. OK, how am I going to compete with this guy? All this guy does is win. How am I going to compete with Dave Ramsey, who's been on radio since the beginning of time and now is running a podcast that's highly successful? How am I going to compete with Jordan Harbinger, Who was podcasting since 2006. That's before the iPhone. Like, how am I gonna compete if I'm just gonna be doing the same thing they're doing, interviewing other people in the space? So through that honest conversation and looking at our failure for what it is, we learned a few things. Here's what we learned from this failure. Number one, we realized that we can't win if we're playing their game. What does that mean? It means that we are not leveraging our own strengths. We don't want to compete with other people's strengths. We want to compete with our strengths. So if you look at my history or my career, I was a schoolteacher for over a decade and I have a master's in education and I taught 5 classes 5 days a week for over 12 years. So what can I do better than them? I can teach. I'm probably a better teacher than Tim Ferriss, despite the fact that he's a New York Times bestselling author or Jordan Harminger, who's been interviewing guests since 2006. I'm probably a better teacher than them because of my experience, because my unique experience. So we realized maybe we should be interviewing people and we should start teaching. And that was kind of the light bulb moment that we're not leveraging our strengths, leveraging our unique experiences. So that failure, that low moment of realizing, man, this podcast is not working. We're spending all this time and effort and looking like fools in front of our guests with Not that many downloads. That moment made us get real, get honest and say, hey, how are we going to compete with these people? What can I do that they can't do? So therefore I can compete in my own game. And one of the biggest takeaways I want you to take away from this is that don't try to leverage other people's advantages. Don't play other people's games. Don't try to hop on a trend just because there's a trend. Figure out what you can do better than most people. Figure out where your unique experiences, your unique talents, your unique passions can actually shine through. Play your game, not other people's games. And when we did that, when we decided, hey, we're gonna start teaching on this podcast instead of, you know, just interviewing guests. And that's when we launched the $100 MBA Show, which was a, at the time we published 5 days a week, short lessons. It was 15, 20 minutes, just like what you're used to right now. And it was just— Information, no fluff, no backstories. You know, while other people had these long interviews where maybe there was about 20 minutes of juice, of real good information, and the rest is a bunch of banter, we just condensed that 20 minutes into just like pure knowledge so that you can learn something, implement, come back for more tomorrow so that you can improve as an entrepreneur. And that changed everything for us. That podcast was an instant success. Like, we're nobodies, right? We have no audience. And then we launched this podcast with this new format. That no one had ever seen before in our space, in the business education space. And we automatically hit the top of the charts because people are like, this is new, this is different. I'm being served information in a format that I haven't seen before. So we're serving the underserved. The reason why I share this with you is that that failure was painful, but it led to a huge success for us. And in fact, that year we launched in 2014, the $100 MBA Show, 6 months later we won Best of Apple, which is awarded to like a dozen podcasts who won it during the same year as Serial and Startup and actually Tim Ferriss. And the funny thing is, I emailed Apple to ask them, why did we win this award? I was happy and surprised, but I wanted to know why. And the answer was, you added something new to the genre of the business podcast. And that is my lesson to you. My takeaway to you is that you can zig when other people are zagging. You can do something different and leverage your own strength So you can stand out and be successful in your own game. Hey, I'm hoping you're getting value from this honest version of my story, of my journey, giving you my embarrassing moments so that you can win. So hit subscribe if you are winning. I want you to subscribe because we have an upcoming episode I don't want you to miss. It's called How Do I Know If My Business Is Failing or If I Should Keep Going? Many people ask me this question. They ask me like, hey, how do I know if I should just persevere and just dig deep and keep grinding at my business, or should I just realize that, hey, it failed, I need to change, just like the failures I share with you today? Hit subscribe so you don't miss it. It's coming up soon. All right. Failure number 3. This is the weirdest failure of them all. This is a business I started in 2008. It was called Zenhom Designs. It was a success as a business, but a failure overall. And I'll explain. So what was Zenhom Designs? Well, it was an online custom tailored clothing line for Tall men like me. I used to get my clothes tailored when I was working in Dubai as a teacher because tailor shops were very normal there. And I would get them because I have long arms and I'm tall and I have a longer torso. And most clothes I would buy from a department store would never fit me. So I would get these clothes tailored and I would go back home to the States and visit family and friends. And people would compliment me on the shirts I would be wearing. Like, this looks great. This looks beautiful. Where'd you get the shirt? And I was like, oh, it's just something I tailored for myself. And they're like, oh, can you make me a shirt? I thought, hmm, okay. And there was this huge demand from my friends, my family, even my friends of my friends of getting them shirts tailored for them. So what I did is I created this short PDF measuring tape where they can cut out and measure themselves with the important measurements that the tailor would ask me, like your neck size, your arm size, you know, your torso, things like that. And they would send me their measurements and I would say, hey, I'll send you the shirt. Here are some shirts that I have. I just take pictures with my phone. And say, hey, tell me which ones you want and I'll make them for you. And then I just marked up the price a little bit so that it was worth my time and covered my costs of shipping. And they would get the shirt like 3 months later. This is like really low cost, very MVP. I didn't even see it as a business at the time. But what happened was that the demand for these shirts and these clothing was really starting to grow from my friends and family. I was getting like 10 a month, 20 a month. At one point it was like 30 people were asking me for a shirt a month. I was like, okay, this is— I got a full-time job. This is a lot of work. Maybe I should formalize this and make it a business, have a website. And that's exactly what I did. And something happened that I didn't expect. The business worked. I had so many customers, I had so many orders. The website was flooded with orders and we had backorder. We would sell out from all our special models and colors. There was some real demand that was happening because not a lot of people were doing custom tailored clothing at the time online. And I was able to like tap into a service like tailoring in Dubai that is not very common in the West, like in the US. And I ran this business just myself. I had some part-time help. I had 3 warehouses across the States because it was just cheaper to send the stuff in a warehouse and they would be able to ship it from the warehouse. We were selling in every major continent. I think at one point we were doing like something like 5,000 sales every quarter. So every 3 months we have 5,000 units sold. And it was successful and it was great. Problem is, I was miserable. I hated the business. Running the business drained me. I wasn't excited about it. My customers were more excited about the products than I was. There was things I had to do, like come up with new models, and I would have to actually hire physical models, real people, to wear the clothes and get photography done and post them on the website. All this stuff was boring to me. I was like, I don't want to do this. I'm, you know, I like to dress nicely. But fashion is not my passion. It's not something I want to do for the rest of my life. And what I learned in this process, which is why I'm sharing this failure, is sometimes you will start a business because you see an opportunity, because there's a demand. And it's like, wait, I want to win. This looks good. I want to make some money. And then what happens is that you do make some money, you do grow, the business starts going and the business starts owning you. And if you don't enjoy what you do every day in your business, it's going to be very hard to be sustainable. And I realized that I was cooked, right? I was really, really burnt out to the point where I actually just closed down the business. I just could not do it anymore. I couldn't take another order. I couldn't manage another thing. I was just so burnt out. And the biggest failure of all is that I was so like burnt out that it didn't even dawn on me that I could sell the business, right? I could just like sell it to my competitor or somebody that really loves the business. One of my customers. I was just so burnt out that I just like, I don't want to deal with this anymore. I just shut the website down. I sent an email to all my customers like, we're no longer taking orders. Game over. So here are the takeaways I learned from this failure. Market demand is not enough to justify starting a business, right? Why? Because business is a long road. It's consuming, it's taxing. It's going to cost you more than just time and money. It's going to cost you a part of your soul. It's going to take time away from your family, time away from the things that you love, your hobbies, the things that you enjoy. It's going to change who you are as a person. So you gotta choose wisely. And I learned a big lesson through that burnout, through like just shutting things down and not wanting to deal with this anymore, is that like, I never wanna get to that point again. And that's why when I started all my businesses after that, I was very deliberate about like, am I gonna enjoy what I'm doing? If I just make enough money to live and that's it, will I be a happy camper? And I'm happy to say that today, yes, I am super happy. I love doing what we do with the podcast. I love working with the smart people on my team. I enjoy it. I'm also very mindful of like not going too hard, like making sure that I don't get to that burnout stage. Or, you know, I will sometimes just push, push and want more growth and realize, oh no, weekends are a good idea. Holidays are a good idea to make sure burnout doesn't happen. So it was a huge lesson. It probably cost me a lot of money that I didn't sell the business or I didn't do anything with my inventory. I literally just gave all my clothes in the storage to Goodwill. I was just like, I gave it to like a charity. I just didn't want to deal with it. And that's how bad the burnout was. But I learned that if you don't monitor yourself, you don't realize what you're getting into. If you don't understand that joy and happiness and fulfillment through your business, that's one of the dividends. That's one of the things that you're supposed to get out of your business. And if you're not getting it, it's going to be very hard for you to sustain that business. So notice a pattern with all my 3 huge failures. The DIY Webinar Guide led to Webinar Ninja, which changed my life. People Who Know Their Shit, that podcast, right, that failed miserably, gave us the 100 OMR Show, which is the most successful thing I ever built. Zenhom Designs, my clothing line, failed miserably, but it gave me the filter I use for every business, for every project that I move into. It actually is a filter for everything I do, like even on a holiday, like, are we going to go on holiday to this place? Well, I'm actually going to enjoy it, or am I just doing it because that's what I'm supposed to do, or everybody's saying this is a great place to go? Do I enjoy the crowds? No, not really. Maybe I should go to like a, you know, a smaller city. This idea of like really imagine yourself in that situation, in that business in this case, and see if you're really going to enjoy it. None of those failures, as painful as they were, were a waste of time or a waste of money because I harvest the lesson. I took it on and I realized, okay, yes, this is horrible. I lost. It's not a good feeling. I feel bad. All that stuff is true and it's good to feel it so you don't do it again. But it's so important for you to say, okay, what can I learn from this? What can I take away from this? What am I gonna do differently next time? How is this gonna change me as a human being? That's really important. One of the things I remind myself always is your failures are not your record. They're your education. They're the way that you actually collect your diploma is these are the, the credits you need to have so that you can have successes. And the thing is, is that a lot of us, we're not willing to try because we're afraid to fail. And that's just not how it works in life or in business. You have to be willing to fail and be okay with losing, knowing that you can keep playing and you can have another chance at winning next time around. Guys and gals, I hope that this episode showed you what failure actually looks like and what it can actually do for you, right? It's actually not such a bad thing. Yeah, it's painful, but no pain, no gain. That's how it is. And you're going to learn a lot of lessons through the way and through the failure, and you're also going to Learn a little bit about yourself. It's going to allow you to fine-tune your selection process of what kind of businesses you want to start and how you want to run them. If you want to continue learning, there is a recent episode that we published called How Hard Is It Really to Start a Business? I go through all the excruciating details of the painful things you're going to have to go through, but also what the rewards look like and how it's all worth it. If you found today's episode helpful and you want more practical business lessons to help you start, grow, and scale your business, The best thing you could do is subscribe to this podcast. Hit subscribe or follow on your favorite podcast app, the one that you're using right now, whether it's Apple or Spotify or wherever you listen to podcasts. By hitting subscribe, you get our next episode automatically, and it's the best way to support the show. It's absolutely free and it's a way for you to commit to growing your business. And now that you've subscribed, I'll check you in the next episode.

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