All My Biggest Business Failures. All The Embarrassing Details.

You know those moments when you look at someone’s success and wonder what disasters they had to crawl through to get there? This episode is your reminder that you’re not the only one who’s stumbled. Omar gets brutally honest about the failures he usually keeps tucked away, the ones that shaped him far more than any win ever did.

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• 1:11Speaker 00

  I've built businesses for 20 years. I've sold a company that changed my life. This podcast, 300 million downloads and counting. I had a few wins, but today, I'm only sharing the failures. All the embarrassing details, all the real numbers, all the cringe moments. I'm feeling uncomfortable just talking about it. I'm sharing my failures today, as uncomfortable as it is, because most people don't. Most entrepreneurs, they just show you the highlight reel. They show you all the wins. But I believe that most successful people, most successful entrepreneurs, they have a graveyard of failures that they're just kind of hiding. They don't want to share it. They're a bit embarrassed. But I find that the failures are where all the learning happens. Here's the biggest takeaway of today's episode upfront. Failure is actually your friend. It's free tuition.

• 1:55Speaker 00

  You're going to learn a ton through each of your failures. In fact, each of the failures I'm going to be sharing with you today led to success, led to successes that were the best successes of my life. Because I treated failure as tuition, as a way to learn something and as a way to not do something. So that is the lesson upfront, but I'm going to give you the details and why and how you can approach your failures in a way that you can actually extract value and turn them into successes. And the last failure I'm going to be sharing you today is the strangest failure of all because the business was a success, but I still failed somehow.

• 2:35Speaker 00

  Welcome back to the $100 MBA Show. I'm your host, Omar Zenhome, where I deliver practical business lessons three times a week, Monday, Wednesday, and Friday, to help you start, grow, and scale your business.

• 2:49Speaker 00

  If this show has helped in any way, it would be amazing if you could drop us a quick review on whatever app you're using to listen to this podcast right now. It helps me and my team bring new episodes every week. And more importantly, more entrepreneurs will be able to discover our podcast, so you can help someone else start their journey. Thanks so much. The first failure happened in January of 2014. Nicole and I were running a lot of webinars to grow our community at the $100 MBA. And we realized it was a lot of work to put a webinar together, to put all the technical pieces together, but also it was a lot of work to put the slides together and to present. So we created a product called the DIY Webinar Guide.

• 3:32Speaker 00

  It was a PDF guide along with some online courses, some online videos that people could watch and learn how to do what we do. We put in four months of dedicated work building the DIY Webinar Guide and putting the offer together, writing the guide, shooting the course, building the sales page for this product, marketing, the launch, a ton of work. Nicole and I were so proud of the work we put into. We actually dedicated this guide to our mothers. We thought this is going to be so big and our mothers are going to be famous. We launched it and we got two sales. Yep, two 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 Lee Dumas.

• 4:14Speaker 00

  Shout out to you, John Lee Dumas, for supporting and giving us that one sale. But I can't tell you how heartbreaking that was. Four months of work, really believing this thing's 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. Four months of work? How many hours is that? That's like 40 hours a week, five days a week, for four weeks every month, for four months, making no money, and then at the end, getting one 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.

• 4:58Speaker 00

  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.

• 5:43Speaker 00

  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.

• 6:23Speaker 00

  That product is super easy to sell because they see the pain being resolved quickly. 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 four 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.

• 7:08Speaker 00

  You can't be so down on yourself that you blind yourself from the learnings. You've got to 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 got to do these things better, so hopefully we can win. You just keep playing. It's okay. Just learn and keep going on.

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• 9:38Speaker 00

  Failure number two, my first podcast. This podcast, $100 MBA Show, is not my first podcast. Our first podcast was called People Who Know Their [BLEEP]. 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.

• 10:21Speaker 00

  We spent six 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. And just for context, so you can understand, you know, I was getting more views on my blog posts that time. And there was a lot of effort to put together a podcast and to get guests like Gary Vaynerchuk. This podcast, $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?

• 11:05Speaker 00

  Funny enough, us realizing that we're failing at this podcast came at a good time when we're 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 four New York Times bestselling books. Okay, how am I going to compete with this guy?

• 11:49Speaker 00

  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 going to compete if I'm just going to 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.

• 12:33Speaker 00

  We want to compete with our strengths. So, if you look at my history or my career, I was a school teacher for over a decade. And I have a master's in education, and I taught five classes, five 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 Harbinger, who's been interviewing guests since 2006. I'm probably a better teacher than them because of my experience, because of my unique experience. So, we realized, maybe we should be interviewing people and we should start teaching. And that was kind of the lightbulb 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

• 13:18Speaker 00

  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 going to start teaching on this podcast

• 14:01Speaker 00

  instead of, you know, just interviewing guests, and that's when we launched the $100 MBA Show, which was, at the time, we published five 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 ever seen before

• 14:44Speaker 00

  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, six months later, we won Best of Apple, which is awarded to like a dozen podcasts. We 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.

• 15:28Speaker 00

  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?

• 16:12Speaker 00

  Hit subscribe so you don't miss it, it's coming up soon. All right, failure number three. This is the weirdest failure of them all. This is a business I started in 2008. It was called Zen Home Designs. It was a success as a business, but a failure overall, and I'll explain. So, what was Zen Home 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 wear. And they're like, this looks great, this looks beautiful.

• 16:57Speaker 00

  Where'd you get this shirt? And I was like, oh, it's just something I tailored for myself. 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'd 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 three months later.

• 17:39Speaker 00

  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, 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

• 18:22Speaker 00

  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 three warehouses across the States, because it was just cheaper to send the stuff in a warehouse, and they would, you know, 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 three 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.

• 19:05Speaker 00

  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, right? 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?

• 19:49Speaker 00

  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.

• 20:32Speaker 00

  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've got to 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 want to 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 going to 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 smart people in my team. I enjoy it. I'm also very mindful of like not going too hard,

• 21:17Speaker 00

  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 a 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. If you're not getting it, it's going to be very hard for you to sustain that business.

• 22:00Speaker 00

  So notice a pattern with all my three huge failures. The DIY webinar guide led to webinar ninja, which changed my life. People who know their [BLEEP]. That podcast, right? That failed miserably gave us the $100 MBA show, which is the most successful thing ever built. Zenith 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, 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.

• 22:45Speaker 00

  None of those failures, as painful as they were, were a waste of time or a waste of money. Because I harvested 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 going to do differently next time? How is this going to 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 credits you need to have so that you can have successes.

• 23:29Speaker 00

  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 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?"

• 24:14Speaker 00

  I go through all the excruciating details of the painful things we're going to have to go through, but also what the rewards look like and how it's all worth it.

• 24:24Speaker 00

  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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