The Truth About Running Two Businesses At Once

For 10 years, I ran 2 multimillion-dollar businesses at the same time. And for most of those 10 years, I told myself I had it figured out. I didn't. The honest truth is I was a little delusional. The kind of delusion where you convince yourself that dividing your focus somehow is not costing you anything. It actually costs you more than you think. In this episode, I'm going to tell you what it was really like to run Webinar Ninja, my software company, and the $100 MBA program, and podcast and media company simultaneously for a decade. I'll be sharing the good, the hard, the things I would do differently, and the one lesson I didn't fully understand until I sold my software company, Webinar Ninja, and suddenly had nowhere to go other than just to focus on— From 2014 to 2024, I was building two very different businesses in parallel. On one side, Webinar Ninja, a software company, a product business. I had a huge team, a code base, a customer base, tens of thousands of people that relied on the software working. On the other side, I had the $100 MBA, a media and education company, a podcast, a program, a community built around my voice, my experience, my perspective. These are two different business models, two completely different revenue structures, two completely different teams. Needs, problems that show up every single day, no matter what you do. And there's only one of me and Nicole, who are the founders of these companies. And I want to be super clear about something before I go further. I'm not going to stand here and tell you running two businesses is impossible. It's not. Uh, I did it for 10 years, but I want to tell you what nobody told me before I tried, because knowing what I know now, I would have made some very different decisions. When you're running two businesses, you often will experience what I call the vampire effect. I coined this effect. I should trademark this, right? The vampire effect. What is it? When you're running two businesses, one of them will almost always be doing better than the other one at any given time. That's just the nature of business cycles, markets, product stages, team strengths. They never move in perfect lockstep across two separate companies. And here's what happens when one business starts pulling ahead. It becomes the vampire. It sucks your time. It takes your energy. It takes your attention. It takes your money. It takes your best ideas. At the other business, the one that's still steady, the one that's still ticking along but is becoming the blood donor, they're kind of giving up everything. It keeps everything alive but is doing it quietly without any glory, without much investment, just sustaining, just kind of trucking along. This happened to me. There were years where Webinar Ninja was in a crucial growth phase and I needed everything, everything I had, my attention, my energy, everything I had to make sure it was going to grow. I had to pour all my resources, all the customer service investments, all the strategic attention, everything. And the 100 LMBA, a business I genuinely love, really got my leftovers. And it's not because I didn't care about it. It's because there's only so many hours in the day. One business was bleeding and the other one was stable. And the bleeding one will always win your attention. And the blood donor can keep giving for a while, but not forever. And when your steady business starts to feel the effects of the strain and the neglect that is going on with it, you just gradually start to notice that it's slipping away. And it's a dangerous place to be at because it induces panic, induces you being reactionary, and you don't want to do that in business. Here's something that sounds obvious, but it is harder than it looks. 2 businesses needs 2 teams. Okay? Not 1 team stretched across 2 businesses. That generally does not work. You need separate teams and separate leadership and separate goals and separate incentives, all that kind of stuff. You got to set different priorities for each team. Sometimes you got to set different cultures as well, because each business will have its own problems to solve. And for a long time, I didn't fully have that. At the start, we kind of had overlapping resources, people trying to serve 2 masters, so to speak. And the problem with serving 2 masters is that you end up serving neither of them. You actually do a poor job with both. And if you haven't got it already, I'm talking about myself, right? I was serving two masters. I was serving the Webinar Ninja initiative and project and problems that I was trying to solve and the $100 MBA initiative and problems I was trying to solve. Every business needs and deserves someone who wakes up every single morning thinking only about that business. What are the numbers today? What's the team struggling with today? What does the customer need from me right now that I'm not giving them? What's the next thing I have to build for my business? When that person is also thinking about completely separate businesses with its own numbers, its own team problems, with its own customer needs, their attention is split before they even have the chance to have their first coffee, right? And a split attention at leadership level filters down to the rest of the team. It creates a sense of confusion about the priorities of the team. It creates decisions that are made a little bit too slowly, and it creates a culture where the vision's not super clear. What are we trying to do here? What's the North Star of our business, of our life here in this company? The lesson here is if you're going to run two businesses, treat them exactly that— two businesses, not one person with two projects. You need to assign a CEO for that business, and you need somebody to run that team, and maybe you'll be the chairman of that business, but You're not in the day-to-day operations. Now, I talked about delusion at the top of the episode. I want to talk about delusion for a second because it's real and I lived it. And I think a lot of you will start to recognize it in yourself if you haven't already. When you're running two businesses, there is a story you tell yourself to make it feel like it's okay. And the story goes like this, at least for me, this was my story that, you know, these two businesses, they feed each other. The podcast makes me better as an entrepreneur for Webinar Ninja, and Webinar Ninja gives me stories that are credible for the podcast. And the podcast helps grow Webinar Ninja because people are exposed to the brand. And this is actually a competitive advantage. The truth is, it's a story that I told myself. It's also like self-deception in some ways, because the part you leave out of the story is the cost. The cost of the meeting you rush through because you had another one immediately after that meeting that he had to get to because of the other business. The cost of the strategic initiatives that you are stalling because the leader who should have been driving this initiative is you, and you have other responsibilities with the other business. So you delay making decisions that are imperative for the business to grow, and the cost compounds over years. It's not just a once and done thing. Imagine you're running two businesses and you do the numbers, you know, it's not growing. Each of them are not growing at its full potential. You're growing maybe at 60 or 70% of your potential instead of 100% of your potential. So when I sold Webinar Ninja in 2024 and I put all of myself into the $100 MBA, something really shifted immediately. Everything changed. I'm talking about everything. The show found a whole new level. The program grew. The ideas came faster with more clarity. The decisions were much quicker. The team felt the difference. They felt like an energy that has been pumped into the room. There's something about undivided focus that just supercharges the business. I knew this intellectually for years and kind of just denied it. But I didn't fully feel it until I finally had it in my hands, until I actually was experiencing it with the $100 MBA. And here's something that a lot of people talk about. When you're running two businesses, you are giving at best 50% of yourself to each business. Now, each business is competing with other businesses in the marketplace. Those people are giving 100% of themselves. They're fully focused on their business. Are you going to beat them with just 50% effort? Get real. OK, it's tough out there. So you want to make sure you give yourself as much of a chance of succeeding and competing by giving 100% when you can. OK, I'm not saying that you have to, like, just shut down your second business or third business or sell it off right now. You got to be aware of the cost that you're copping right now by splitting your attention. Hey, if you're finding this episode helpful, subscribe to the show because I got another episode that I'm working on right now that's coming very soon. It's all about how to sell more of whatever you sell. It's the ultimate sales masterclass if you hate sales. This episode is actually quite personal because I learned a lot from my own father, who was a master salesperson. I kind of denied sales for a long time. That's why I was a teacher for a decade. But because I went to work with him every day, uh, because I used to wash cars at the dealership that he worked at, car dealership— my dad was a car salesman— uh, I learned a ton by just watching him in the showroom after my shift was up. but also share some of the modern sales techniques that have worked for me throughout the years with Webinar Ninja, with the 100MBA, with everything I've sold in the last 20 years. And you don't have to be pushy and you don't have to be aggressive. You just gotta have a plan and know what your objective is when you're selling to your customers. Hit subscribe so you don't miss it when it comes out. All right. I've been spending a lot of time talking about the hard parts about running two businesses, but I gotta be equally honest about the other side. Because running two businesses for 10 years wasn't just a lesson in what not to do. It was one of the most significant experiences of my life. In a lot of ways, I'm happy I had that experience and probably wouldn't trade it, at least for most of it, because I learned a ton. Building Webinar Ninja gave me something that no amount of podcasting or teaching could have given me. It gave me the experience of building something real, a tangible, real product that really served thousands and thousands, tens of thousands of people, a software product that was trusted by tens of thousands of businesses that their livelihood depended on it. Uh, a team of people who showed up every day to build something together. You know, that was a great feeling to be one of the industry leaders. One of the best softwares in my space was huge. And of course, an exit, selling the company that changed my life. I felt things building Webinar Ninja that I never felt before as an entrepreneur. The pride, the real pride of watching a product go from a clunky early version beta thing to something genuinely elegant and reliable and just gorgeous to use. That satisfaction of a customer telling you that your software helped them build their business, to help them make a million dollars in sales. The significance of that is not something small, and nobody could take that away from me. And here's the part that surprises people when I tell them Webinar Ninja made me a better teacher for the $100 MBA. It made me a better podcaster. Every difficult decision I made as the CEO of a software company became a lesson in the actual podcast. Some of these lessons I'm still teaching because they were so painful to learn at the time. I need some time to recover. Just like our previous episode where I'm giving you my advice on hiring. I share that I made a bad hire that cost me half a million dollars. Every mistake, whether it's hiring or pricing, uh, every customer service philosophy, every product launch that flopped and every one that actually did well. All of that went into the content of the show, not as some abstract advice or theory, as lived experience. I had some interesting experiences for 10 years building that business. And the $100 MBA program and the $100 MBA podcast and everything I do on social media is all better because of that 10-year experience with Webinar Ninja. Full stop. No questions about it. And the honest truth is, is that I was running two businesses because I wasn't ready to do the $100 MBA as a media company full-time yet. I wanted to prove to myself that I could build a wildly successful company business that I've never done before. I mean, there's no doubt that Webinar Ninja is my biggest success as an entrepreneur. In terms of building a business and being able to be valuable enough to be acquired. That's just something that I needed to prove to myself. And once I did that and we did get acquired in 2024, I was ready to go full on and give my full focus to the 100 All MBA media company and the podcast and everything that we do here. And to be completely honest with you, I felt like I was fully qualified to do what I'm doing here at the 100 All MBA. Unlike a lot of people that do these business podcasts and are on YouTube and are shouting from the rooftops on Instagram and TikTok. I've gone through it, you know, I'm a veteran. I've built a business, I've been acquired. I know what it's like to have a tough day as an entrepreneur. I know what it's like to barely make payroll. I know what it's like when it's going great and you're, you know, flying high. And that gave me the confidence to say that my next chapter now, focusing on the $100 MBA, is to give back, is to give back everything I learned through that process, through through those experiences. So should you run two businesses? Here's the honest answer: maybe. Maybe you should, but not the way most people do it. If you're gonna run two businesses, here are the rules I would give anyone based on what I learned in those 10 years. Rule number one is make sure both businesses can run without you, okay? You have management that is in place so that if anything happens, God forbid, health-wise, family-wise, they keep on running. They don't rely just on you. You should have at least a number 2 person that could step in and do what you do. Rule number 2, hire general managers before you start the second one. Right. Hire somebody that can run the day-to-day operations and you don't need to make every single decision before you start the second business. Don't hire them after things get overwhelming. Do it before. Rule number 3, watch for the vampire. Every quarter, look honestly at where your time and your energy and your money's going. Make sure if one business is consuming 80% and the other one is getting 20%, name it. Be honest. Don't let it become the default. Course correct. Either fix the imbalance or make a strategic decision about it. Don't just ignore it. Rule number 4: Know why you're running both. Have a compelling reason. This is probably the most important one for me. Are you running two businesses because they genuinely complement each other? Do they genuinely serve the same audience but in different ways? Or are you running two businesses because you're afraid to let one go? Because you love the idea of doing both and being like a serial entrepreneur? Be honest with yourself. Only you can answer those questions honestly. And you might be saying, well, Omar, what do you believe? Well, here's what I actually believe. For most entrepreneurs, for most of the time, one business done brilliantly is worth more than two businesses done adequately. Not because having two businesses is wrong. Because the compounding power of total focus is genuinely extraordinary. I've experienced this in the last couple of years. It's incredible when every decision you make, when every hire, when every product improvement, when every piece of content that goes out, when every customer interaction, when it's all pointed for one thing, that one thing moves faster, faster than you imagine. I know this now, and I felt it the moment I had it, and I wish I felt it earlier. But also know that the path I took, the 10 years of 2 businesses, of all the noise, of all the chaos, of all me being stretched too thin, and the reason why I have all these gray hairs, okay, it has a cost. And I'm hoping that some of that cost also came with some reward, meaning that I've learned a lot, allowed me to step into the 100 RMB and take it somewhere new with that experience. But it has a cost. Before I go, I want to leave you with this: 10 years 2 businesses, 1 exit that really changed everything for me. Here's what I would tell somebody who's just standing where I was in 2014, about to start their second business while the first one is still kind of finding its feet. Build systems before you scale. Hire leaders before you need them. Watch where your attention goes and not where you think it goes. Actually document it, write it down. And don't let one business quietly bleed the other one out. This is super important. Focus is not a limitation. It's a superpower. And the day I finally had full focus with The 100 All-NBA and nothing was competing for my attention, that was the day The 100 All-NBA really took another level, just skyrocketed. And the show started to grow. Our brand, our podcast, everything was just going to another place. Thanks so much for being part of this podcast, The 100 All-NBA. If this episode was helpful, insightful. I really recommend another episode that we published recently called 20 Not So Obvious Truths I Wish I Knew in My 20s. So if you like these kind of reflection, I know this in hindsight kind of episode that we just did today, you're going to love this episode. So check it out. 20 Not So Obvious Truths I Wish I Knew in My 20s. Even if you're not in your 20s, you're going to find some really good pieces of advice that I wish I knew when I was younger. Check it out. Thanks for listening today and watching if you're on YouTube. I'll see you in the next one.