MBA1960 Q&A Wednesday: My first 3 businesses failed. Is business right for me?
2 Feb 2026 · 14 min
This is a Q&A podcast episode of the $100 MBA Show (host Omar Zenholm) in which listener Andy asks whether to stop pursuing entrepreneurship after three failed businesses. The host answers that persistence depends on whether the listener truly wants entrepreneurship: if so, keep going and learn from failures; if unsure, pursue ventures part-time while maintaining financial runway. The episode includes practical tips (treat business as a learnable skill, keep stakes low, avoid repeating the same mistakes) and is interspersed with repeated commercial ad spots.
Chapters
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So Andy writes in asking the question on Q and A Wednesday. Hey, I failed in my first three businesses. Should I give up being an entrepreneur? Should I quit? Should I just say it isn't for me? And it's a solid question and it actually has a pretty simple answer. And the answer is really a question you ask yourself. Do you really want to be an entrepreneur? Do you really want to run your own business? Is this your dream? Is this your ambition? Is this something you really badly want? If your answer to this question is hell yes, then you shouldn't quit. Okay? Entrepreneurship and business and making money is a skill set. And you can learn this skill set over time, through experiences, through these failures. In my opinion, if you want something bad enough, you should just go after it. How long should you go after until you get it? Until you have a successful business on your hands? Like Mark Cuban says, one of the advantages of business is that you only need to be right once. Okay? You only need to have a successful venture once. And then you can just do that business for as long as you like. Now a few pointers though, and he mentions he had three businesses. All three, quote unquote, failed. Now I've had failed businesses in the past. I've built businesses that made some money, that were profitable, but I couldn't scale. I built businesses that I saw an opportunity in the market, but I really wasn't in love with the product and therefore it, it wasn't sustainable. I built businesses and products that nobody wanted and I spent a lot of time and effort creating it and realized, man, what a flop. Nobody wants this thing. The key to failures and by the way, in entrepreneurship, in business, in life, really, failure is a rite of passage. People that don't fail, don't try, or at least they're not stretching themselves to see what they're capable of. If you're always playing it safe and doing things you know for sure you'll be successful. You're not really stretching your abilities or shooting a little bit higher than you should. Now, that's not saying that you should not calculate your risk and make sure that you make the most sound decisions possible. But the key to failures is to learn from the mistakes, from the failure, from the loss. It's okay to make mistakes. It's not okay to make the same mistakes over and over. So if you failed, learn from this experience, but then you make the same mistakes in the next business, that's a problem. If you made new mistakes because it was a new experience, different things, and you can honestly say, man, that's a totally new thing that I goofed up on, that's okay. You're going to learn along the way with these new mistakes. And what these mistakes teach you is you need to understand what you're building, who you're building it for, and keep the stakes low at the start until you get traction. And I totally understand failing at anything. But a business particular where you're putting everything into this business can be disappointing, can be heartbreaking. It could be embarrassing, especially if you're building in public or even just amongst your friends and family. But no one said business is easy. Okay? This is why most people, you know, don't start a business, right, or don't have a business. Because you got to put yourself out there constantly as a business owner. You're taking risks, you're trading, you know, with your name, right? Your reputation. But like I mentioned at the start, if you want it bad enough, you're willing to do these things. This is why entrepreneurs do what they do. This is why they start businesses. This is why they continue to start businesses and pursue their dreams. Because they want it bad enough. Okay? If you want anything, you're going to keep doing it until you achieve it. My journey in entrepreneurship is not over, but if I look back, it was a series of struggles and small and big failures. It took me 12 years to quit my day job and stop doing business as a side hustle and start doing it as my full time thing. And when I went full time, it took me a solid three years of a lot of struggle and a lot of mistakes. Even with 12 years of side hustle experience. Those first three years of full time entrepreneurship were rough, were tough. A lot of sacrifices were made. I was 32 at the time, so my lifestyle was really, really affected because I had to not spend that much money to let my Runway last me as long as possible. I had to sacrifice some of the niceties I was used to and I had a full time job and on top of it I was falling on my face over and over learning the ropes of full time entrepreneurs. I could have easily quit anytime along that first 12 plus 3 years, 15 years. But I really wanted to be an entrepreneur full time. I really wanted to build a significant, important, fulfilling business. I really wanted to make an impact on the world in my own way. And that was the fuel for me to get up when I get knocked down, get up when I fail to say, okay, what happened here? What can I learn from this experience? What did I do wrong? What was something that I need to remember for next time around? What are the next steps I can take to turn things around to get better, to improve my situation? Entrepreneurs do a lot of self talk. They need to because they need to make sure that their mindset, their attitude, their emotional state is prepared, is ready, is equipped to take on the business world, is ready to take on what the world gives them and what challenges come their way. Now. If the answer to do you really want to be an entrepreneur? Is this something that you want to do more than anything in your life? If the answer to that question is no, or I'm not sure or not really, then my advice is continue on your journey. But in a part time capacity. You don't need to go all in. You can still have your full time job or career and learn as you go, or start working on business ventures or be part of business ventures or work for a startup on the side. The point here is that sometimes you just don't know. And if you don't know, my advice is don't throw your whole life into something you don't know. Only if you know 100% sure. Yes. That's when you go and throw all the chips in the middle of the table and say, you know what? This is where I want to spend all my time, all my energy, all my focus. That's my honest answer. Because otherwise you're investing way too much on shaky ground. You're investing way too much on something you are not sure that you really want. And there's nothing wrong with not knowing. This happens in life. But until you know for sure what you want to pursue in life, be safe financially and make sure that you continue to explore but in a part.
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To wrap up today's Q and A Wednesday's episode, Andy has asked, hey, I failed in my first three businesses. Should I stop pursuing being an entrepreneur? And like I mentioned in today's episode, it's all about if you really want it bad, listen, things are going to get challenging in business. Even when you find success, even when you have traction, even when you're four, five, six years into your business and things are going great, you're going to be thrown new challenges. Because the more you grow, the more you scale the different challenges you're going to face. I always give the analogy of climbing a mountain. When you climb a mountain, it's challenging all the way up to the top, every single step of the way. Just different kinds of challenges. And the thing that's going to get you through those challenges is your will and your wanting of the goal of being who you are. Being an entrepreneur. For me, it's more of an identity. It's more of a lifestyle than an actual job or career. Thanks so much for listening to the $100 MBA show. If you got a question you want to ask here on Q and A Wednesday, go ahead and email me over at Omar00MB. I love answering questions here on Q and A Wednesdays, so please don't be shy. Go ahead and email me and ask away. Before I go, I want to leave you with this. One of the things I had to learn very early on in my journey as an entrepreneur is that failure is going to happen, not may happen. You will fail. Okay? And the problem is that a lot of us are not used to this mentality. We hear this all the time. But, you know, we go through 12 years of schooling where failure equals a bad thing. You're not supposed to fail in school, right? And then all of a sudden you get into entrepreneurship and you might fail at something or you make a mistake or things don't go exactly as to plan and we're down on ourselves. We feel like we totally stink. But people that are successful, people that have made it, quote, unquote, they don't make it because they're lucky or they were born with these innate gifts or they somehow avoided the pitfalls you're going through, it's because they went through challenges, they became strong and were able to achieve the success you look at and admire. Thanks so much for listening and I'll check you in tomorrow's episode. I'll see you then. Take care. Gas, snacks, tolls. This trip is draining my wallet.
Yeah, but we'll be with family.
You're in a good mood.
What's your deal?
What's my deal? I saved at Metro with no activation fees and I got one line of 5G for just $25 per month. Kept the phone I love and a 5 year price guarantee on my top.
Text and data detour to Metro.
Get that more for your money feeling only at Metro by T Mobile. Just bring your number. $30 first month and $25 after with autopay not available if with Metro or T Mobile in the past 180 days.
