MBA2543 Q&A Wednesday: I Failed in Business. I’m Afraid to Try Again. How Do I Not Fail Again?
2 Feb 2026 · 20 min
Omar Zenhom answers a listener who failed at business and fears trying again. His five-part framework: extract lessons from what went wrong, launch an MVP to test ideas, build mentors and cofounders around you, reframe fear through small bets, and track cash flow and runway obsessively.
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Hey everyone, welcome Back to the $100 MBA Show. I'm Omar Zenholm and welcome another Q and A Wednesday episode where we answer a question from one of you, one of our listeners, one of our community members. If you got a question you want to ask, go ahead and head on over to 100mba.netq. You could submit a question right there and it could be selected to be answered right here on Q and A Wednesday. Today's question is from Jamie, and Jamie asks, I failed in business. I'm afraid to try again. How do I make sure I don't fail again? This is a very powerful and important question. It's something that many entrepreneurs struggle with after facing like a big setback. And I thought it was interesting how the question is phrased. You know, I failed in business, I'm afraid to try again. How do I make sure I don't fail again? And this is kind of where the problem lies, where you're trying not to fail. And entrepreneurship doesn't favor people that come into the world of business with this mentality. In other words, you can't play this game of business trying not to lose. You gotta go in trying to win. And part of winning, part of succeeding in business is getting over this idea of being afraid to fail. You can't worry about failure so much that it impedes your progress. It impedes you from even trying to go for it. And listen, I totally get it. I failed so many times in business. Most of my successes actually started with a failure. So in today's lesson, you're gonna learn how to overcome this fear of failure. I'm gonna show you how I how to take some actual steps to move forward and start building your business, start building your legacy. Now, most of the time, I like to share some sort of interesting stat that supports today's episode, but instead, I'm gonna do something a little bit different. I wanna share with you an Egyptian proverb. Yep, an Egyptian proverb. My parents are Egyptian. They migrated from Egypt to the US and we heard this proverb a lot in my household. And I'm gonna share it with you. And it goes like this. Those who burn their mouth eating soup blow in their yogurt. So basically it means people that get burnt, you know, eating soup, in this case, they're over cautious and over worried and start blowing on their yogurt. Right. Worrying that they're going to burn their mouth on yogurt. Okay? So I love this proverb. And it comes to mind because a lot of us are trying so hard not to get burnt once. You get burnt once, and I get it, you know, once you get burnt in business and you fail, it hurts a lot. Right? And sometimes it takes a while to rebound from that, to come back from that. I know many people that start businesses that totally put them out of commission, put them in debt, they go back to a job, and it takes them years to recover from that loss. I get it. But you can't continue to blow on your yogurt. You can't continue to stop trying out soup.
Right.
And going for it. You have to learn from that experience and try to move forward. And I'm going to show you how to do that. And there's a few mental unlocks going to share with you that are going to help you along the way, but also some practical steps that you could take so that you can become successful in your next endeavor and the next endeavor and the next endeavor in business. The key that unlocks everything in today's episode is to understand it isn't about avoiding failure entirely. It's about learning how to minimize risk and maximize your chances of success. The second time around, third time around, fourth time around, at trying this thing called business. The first thing we want to do is if we failed before, we want to learn from that failure. We can't just forget about it and be like, that's too painful to think about. Failure isn't the end. It's actually feedback. And the more you see failure like this, the more likely you're going to be okay with trying things out and being okay with the possibility that failure might happen. Because if you fail, you learn. It's funny. Cause I speak on stages, at events, and people ask me on interviews, on other podcasts, hey, tell me about your successes and what you learned from it. And actually, I don't learn a lot from success. You learn a ton from failure. Success, kind of. You don't really understand how it works. It's almost like a culmination of enduring all the pain and learning along the way of what not to do. And you end up doing the right things because of that. So the most successful entrepreneurs I see in the world, the people that I know personally, they see failure as a learning opportunity. And Jamie, if you're watching right now, if you're listening right now, I want to send you a personal message here. The important question to ask yourself is, what did I learn from my last business venture? Okay. Don't frame it as failure. What did you learn from that experience? What did you learn from the ups and the downs? Okay. Reflect on that for a moment. What would you do differently if you would go back in time and. And try it again? Okay. Try to remove yourself from the equation. Try to imagine what happened didn't happen to you, happened to somebody else. Right? What can you learn from this situation? You know, early in my journey, I had my own share of failures. But those experiences were incredibly valuable. They taught me critical lessons about cash flow, about understanding my products and being a better champion of my products, understanding my customers, understanding the importance of systems in my business, the understanding of recruitment and how recruit great people so I can have a great team and a great product because of that or great business because of that. All those things that I screwed up allowed me to learn what not to do and basically do the opposite. And that shaped my success later. So action step I want you to take, write down the top three reasons why your last business, your last try at what you did, didn't succeed. Okay, where are the issues with your product market fit with your cash flow, with your marketing? Maybe your problem was you actually never launched it. You actually never put your product out there. You never actually saw to the the end, right? To seeing the product be out in the world and seeing customers enjoy it. Right? Identify the challenges you had. Write them down so they're in black and white so you don't do them the next time around. All right. This is a little bit of a painful process, but it's going to help you tremendously not make the same mistakes. One of the things I have as a rule in my business and with my teams, with the companies I've run is we're allowed to make mistakes. Mistakes are okay. Just can't make the same mistake twice. We have to learn from our mistakes so we don't repeat them. The next concept I want to share with you is the idea of starting small, testing and then iterating. Too many entrepreneurs work so hard on the product, on the service, on whatever they're about to release. They spend so much time, so much effort, so much money, and then they put out in the world and it doesn't work out. And they're so in the hole because they put so much time and effort and money into it that it has to work. If it doesn't work, then they fail and they can't continue and they can't try to make this business work out. Right. And this is a problem. I actually met an entrepreneur at an event who told me they've been working on their software solution. This product that they're releasing for three years and it won't be out for another year. So it's going to take four years and before even sees the light of day and gets to customers. And that's a problem because what you're creating, what you're putting out is not really timely. What customers needed four years ago are not the same thing, it's not the same thing now. So you want to get the most simplest version of your product or service out there as soon as possible. So you don't have such a high stakes situation where you've invested so much time and money and it's such a huge failure, Right? So if it fails, it's not a big deal. You've learned and you can pivot and you could change. You still have time, you still have capital, you still have effort, you still have a motivation to keep going. So what we want to do is we want to create an mvp, a minimal viable product. I talk about this all the time on the podcast and we want to put it out in the market as soon as possible so we can get some feedback. We don't want to use all our resources and all our money and all our energy building something that people don't want. You know, when I look at Webinar Ninja, the software company I built over 10 years and recently sold the first version that came out. It looks nothing like webinar ninja today because it was very minimal viable. It solved one major problem when it came to running webinars. It made it easy for people to run it by themselves. And it was just live webinars. It didn't have all the bells and whistles or all the features that it has today. I just wanted to make sure that what I was creating, the solution I was creating was something that people wanted. And once I got response from customers by the fact that they paid for it, okay, they like it. How can I improve it? I asked them, I got feedback, I iterated. And that was really good because I was bootstrapped. I didn't have any funding and I couldn't afford to recoup any loss financially if it didn't work out. So it's great for me to just put a little bit of money, a little bit of effort, testing things out, getting feedback. Improve iterate. Improve iterate. So, action step. You want to launch your next business after a failure? No problem. It's okay. But launch something small that you can pivot an MVP right? Get into hands of potential customers quickly and get their feedback to make improvements along the way.
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Number three, don't do it Alone. Build a support system for you and your business. Okay. It's very hard to build a business alone. And many solopreneurs fail because they're trying to just shoulder everything. Right? You need a support system, whether it's a team of people around you, whether it's a coach or a mentor, whether it's a network of entrepreneurs that I can offer advice and feedback and encouragement. This is why I created the Hundred Dollar B in the first place. Cause I know how lonely business could be. So the whole point I'm trying to convey with you here is that there's safety in numbers. When you build something with people, it's easier whether they're helping just by giving you encouragement or giving you advice or somebody who's coaching you. The point here is that if you try to do this alone, you're asking for trouble. Right. When I was starting out, I leaned heavily on mentors and fellow entrepreneurs who came with more experience than I did. Right. Their insights helped me tremendously. Right. And it was just not even. It wasn't like official coaching. It was just advice here and there. The things that I learned from them helped me avoid a lot of common pitfalls and gave me the confidence to keep moving forward, keep pushing, and feel like, hey, I can do this. There are other people that are doing this. They're where I want to go. They're where I want to be. So I highly encourage everybody who's watching to find your support system. That could be joining a mastermind group, hiring a coach or an advisor, finding a co founder. Don't be afraid to ask for help. We all need help. All right? No one does this alone. Every successful entrepreneur I know has a network of supportive people. Next, number four, manage your fear of failure. Okay. Fear of failure can be paralyzing, Right? It's important to remember that failure is just one outcome. It's not the end of the road. It's not game over. Okay? Failure is a learning, it's a setback. But then you learn from that failure, and then you go ahead and iterate, you improve. This podcast, right? This podcast, the Harlem Bio show, it's not my first podcast. I had a podcast before this, and it was a disaster. It didn't do well at all. And it was an interview podcast. I wasn't really good at interviewing back then, and I was really a teacher. That's where my training comes from. I used to be a high school university teacher. So when I realized this, I said, okay, I'm going to change my podcast. I'm going to start a new one called the $100 MBA Show. And I'm going to teach people business because I'm comfortable teaching, because that's where I have all my experience. I'm leveraging my experiences. So I learned what not to do, and I learned what to do based on my failure. So the goal isn't to avoid failure altogether, it's to manage it. It's to learn from it. It's to keep moving forward. You need to reframe your mindset. Don't see failure as this bad thing. It's part of the process. If you are falling down and, you know, scraping your knees, it's okay. We all go through this on the road to success. The difference, in my opinion, of people that ultimately succeed or fail are the people that continue to move forward despite failure. They learn from things, they calculate their risk. They see this as feedback, and they move forward. They keep going forward. A good action step here is to understand that failure might be a part of the process. But the way to mitigate the risk of failure so it doesn't like totally wipe you out is to break up what you're trying to do into smaller steps. Whether it's the product or the business or the service, break it into smaller steps. Get it out in the world as soon as possible so that you can minimize the risk along the way each step of the way so you can learn quickly and iterate and improve and and increase your likelihood of success. Number five. This may sound obvious at first, but it's actually a lot deeper than you might think. And that's focus on financial stability. One of the most common reasons businesses fail is poor financial management. Okay. The second time around, focus on creating a financially stable business model. Okay. This means managing cash flow carefully and keeping your overhead low while ensuring a clear path to profitability. Okay. This is really we're trying to do here. The more profitable you are, the more cash flow you have in your business, the more chances at bad, the more chances you will have to try things and learn and improve your business. But when things are so tight, your profit margins are so thin, it's really hard for you to absorb any kind of failure. Early on, I learned that cash flow management was crucial. How did I learn it? I didn't do well my first business because I had poor financial planning. And this leads to failure. It actually invites failure. Okay. So make sure you keep a close eye on your numbers. This is why I highly recommend you have your own P and L sheet profit loss sheet to monitor your cash flow. On a regular basis. If you don't have a profit loss sheet, don't worry, I got your back. I can give you my template, the same template I use with all the formulas for you. It's a Google sheet. Just go to 100mba.net templates and you can download our template pack. And you can use this template, this P and L sheet, to create a financial plan for your next venture even before you get started or even when you before you get the product out there. This way, you know your expenses going in, you know what your break even point will be. You know the cash flow projections that you might have. Right? Make sure you have enough money or Runway to keep the business going during tough times. Okay? This is why this sheet matters. Okay? So let's make sure that your company is set up to be financially healthy so it can absorb a few blows and not go out of business to wrap up. Failing in business is tough, but it doesn't mean you're not cut out for entrepreneurship or this is not for you. In fact, failure is part of the journey for many of the successful entrepreneurs I've met along the way. It's part of the reason why they're proud of their journey because they were able to keep on going despite the failures. Okay? That's what makes it so sweet, right? By reflecting on a failure, by thinking about your failures and figuring out what went wrong, you will learn something from it. You'll understand that you got to start smaller, you got to start building a support system, you got to start managing your fear and understand you got to take small bets, right? Over and over and over and break things into smaller chunks. And of course, focusing on financial stability like I mentioned, so you can absorb a few blows and not be totally wiped out. This will increase your chances of success. If you follow this template, you follow this kind of outline or advice that I'm trying to offer you because I wish somebody told me this when I got started because I was paralyzed with fear. And most people delay their entrepreneurship because they're afraid of failure and it cost them a lot of time. You know, I started my full time entrepreneurship career when I was 32. I had a lot of experience side hustling for 10 years before that. But I wish I took that leap earlier. I would be far ahead of where I am today because I didn't really spend much of my younger years putting into entrepreneurship and building businesses. I was teaching for a living and that was my career. But the point I'm making here is that what was stopping me from starting early. Fear of failure. And if you can get past that, you can get going and you can get successful sooner, right? You can start enjoying the fruits of your labor faster. And that's really my message to you, is that, you know, time is too precious. Don't let that fear of failure stop you. Thanks for tuning into the hundred dollar MBA show. I hope you found this episode valuable. I am encouraging you to take your failure, learn from it and give it another go. Right? Time is of the essence. Life is too short for you not to, you know, go after what you want out of life. And hopefully with what I shared with you today, it will give you the confidence to do so. So if you're looking for more insights, more resources, more templates like I mentioned, just go to100mba.net and you'll find it all there for free. I'm Omar Zinholm. Keep moving forward and I'll see you in the next episode.
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