How Do You Know When It’s Time to Sell Your Business?

How did you know it was time to sell your business? This is a great question from David and it's a deeply personal one for me because I had to answer this question after building and growing my software company with Nicole, my co founder and wife for 10 years. It's a question we both have to answer. A lot of people look at a business exit from the outside. They often think it's some sort of dramatic event. It's a exciting time. It's money, it's freedom, it's. But it's actually a very tumultuous emotional experience. And it starts with this question, is it time? Is it time for me to sell this business and let it go? Nicole and I started Webinar Ninja back in 2014 and at the time there was no grant exit plan. We just wanted to make sure that we built a great quality product that was a profitable business that made us money, that people actually wanted, that would allow us to live our life comfortably. We didn't have a pitch deck and a plan to sell in 10 years. We had no conversation about it in the first place. Our only focus was to create the best webinar software that we possibly could to serve our customers well, to really put everything we had inside of us into this product. And for the first several years we were completely in growth mode. We felt that we needed all the momentum and all the focus to be focused on that and not some 10 year plan. And we just really worked hard on making this product amazing with features and getting more customers to get us more feedback. We're learning more. We started to really refine the product and it was a very exciting time for us. It was very hard. We were working like 14, 15 hour days. I'm not exaggerating, but it was meaningful and I don't regret those moments. I don't regret those seasons in life. And honestly, I look back at those years with a lot of fond memories. You know, it was really magic to see a product be so well received and liked and used and consumed. And as a entrepreneur, it's like the best feeling in the world that people actually are finding value in what you're offering. And about five or six years in, something shifted inside of us. Not in a bad way, but in a more mature, realistic way. We started to, to entertain the idea that maybe we will sell this business one day we will sell this software and we will have an exit. And it wasn't a matter of like, should we sell it? It was more like I think we will sell it. And that's A very different mindset. We were still building the product to serve our customers, but now we're building our company to be viable as a sellable asset. And that's different. You're building now. We're going to build systems, you're going to build SOPs, you're going to build procedures. You're hiring with the idea in mind that one day somebody's going to take this over. So I must prepare for that. And that's a very important distinction. When you start building for an exit, you don't have a clear date or a clear buyer, but you have the idea in your head that, hey, this is probably going to happen. So I must prepare to make sure that my life is easier down the road. So what changed for me personally? What made me start to want to sell the business? Well, it was a moment of truth, you know, for a very long time. For years throughout our growth, we were being bombarded with emails and messages and introductions for people that want to acquire the business. And we would just say, no, we're in growth mode, not interested in selling right now. But something happened inside me that allowed me to start considering some of these offers. And what was that? And I can only speak for myself. This is me personally. I realized that I have taken the business as far as I personally could take it as the leader of this business. And that's a very humbling thing to admit to be honest. But it's an important one because I looked at the company and I asked myself a very important question. Are my skills, my energy, my strengths still what this business needs for the next chapter? And the answer was no, not because the business wasn't great. We were thriving. We had over 30,000 users use webinar Ninja. We were one of the top webinar platforms in the world. Millions of people were helped through our webinars and the software that empowered those webinars. Thousands of customers were building their livelihoods through selling products on webinars. So we were helping people pay their bills. It was an incredible, incredible experience to build something that significant and that impactful. But the next level required a different kind of leadership. A different system, a different scale, a different risk appetite, to be honest. And at that point, a of lot. I had two real options. I say I, but Nicole and I were co founders in this business. I was the CEO. I was a leader of this business. And my two options were either hire another CEO and I fully stepped back to replace me. I need somebody to replace me, or I sell the business to someone who could Take it to another level. What wasn't an option was staying in the middle, was just continuing to do what we're doing at the time. Because the status quo is dangerous in business. If you're not growing, if you're not innovating, if you're not improving, you're. You are asking for trouble. Your competition will eventually take you out. Real quick. If these episodes help you in any way, hit subscribe. It helps us keep bringing you practical business insights three times a week for free. Thanks. Then the truth just hit me like a ton of bricks. If I held out and kept the business going and didn't do anything out of ego, out of comfort, out of fear of change, out of, I'd be doing a disservice to so many people. I'd be doing a disservice to our customers. I'd be doing a disservice to our team and of course, to the product itself. The legacy of web intervention. And I had to get real. That's not real leadership. You got to do things even if it's not in your best personal interest as a leader. And honestly, you know, after pouring 10 years, 10 of my most energetic years, this is like my 30s and some of my 40s, you know, the prime of my career. I didn't want that go to waste. I wanted to make sure that I protect the legacy of this product. Webinar Ninja and let me be clear, by the way, you know, Nicole and I weren't always on the same page as co founders that we want to sell the business. There were times, I would say in year six or seven, I was ready to sell the business and Nicole wasn't. So we didn't do it. And then a couple years later, Nicole was ready to sell the business, but I wasn't. I wanted to continue to grow it. And, and then we eventually found a time and a place in our journey where we were both aligned. And we're like, okay, we both agree it's now the time to do it. And when we made that decision, there were two books that really helped us get some clarity. The first one is Built to Sell by John Warlow. It's a really, really strong book on how to prepare for a sale and how to make sure you build a product and business that is easy to sell. That book reframes your business not as something you're emotionally attached to, but as an asset, something that should be able to stand on its own without you being in every decision. The next book that helped us in this process was a Book called before the Exit by Dan Andrews. That book helped us think about timing, about the options that were in front of us. But most importantly, that book taught us what would happen if we didn't sell. Both books helped us tremendously and allowed us to zoom out a little bit. We actually listened to them in the car, on a road trip, on a little break, and that really allowed us to have, you know, some discussions. Some of those discussions were pretty lively. So if you got a co founder, I'd recommend doing the same. Here's another lesson that's important to understand. You never know what the future holds. This is something that I learned in hindsight. You might have a thriving, growing business today, but that's exactly when selling can make the most sense. When you're on the up. Selling when things are going up puts you in control. It puts you in a very strong bargaining and negotiation position. Selling when things are flat or even declining puts you in a corner, puts you in a position of weakness. Every year you stay in business, you're effectively pushing more chips onto the table. If we're going to use a poker example, and sometimes that's the right move. Most of the time it is. But sometimes it's an unnecessary risk. You're continuing to risk the chips that you've earned throughout the years. And when a strong buyer is interested in your business and your business is healthy and it's growing and it's valuable, that is often the best time to sell and not the worst. It's kind of the bird in the hand principle, and it's kind of counterintuitive because you don't want to sell, because you're growing, things are going up and you're making more and more profit. It feels wrong to sell, but it's actually the best time to sell. It's when you're going to get the most value. I have to say, honestly, we were very fortunate. We had interest from multiple parties over time, but when ProProfs came along, it felt right. They acquired us. They shared our values. They shared our values about customer service. They respected the product. They had a great vision for what was to come with the product. They had the resources and the experience to take Webinar Ninja to the next level. And that's exactly what we wanted. And most importantly, we trusted them to protect the legacy of what we built. And that, to us, was very important. Today, I can honestly say I have zero regrets about selling Webinar Ninja. Not because it was easy or that it wasn't. Wasn't an emotional decision. But because it was the right decision for me, for Nicole, for the customers, for the team. And that's how I know when you're at peace with the decision, even after the dust settles, you know you made the right decision. So, David and anyone else who's listening here is a real takeaway from today's lesson. You'll know it's time to sell your business. When you have taken it as far as you reasonably can and you feel you can no longer be the best person for the next chapter. When you can honestly say that to yourself, then you know it's time to sell. You're holding on more out of fear than conviction. That's when you know it's time to sell. And you also have to consider that, hey, if you don't feel fully committed anymore, if you are constantly looking at other ideas and wanting to kind of move on, it's not fair for your customers, for your company, for your legacy, for you to just hang on, just to hang on. If you want to compete, if you want to be the best of the best, if you want the best version of that business, then you need to be fully committed. And if you're not, don't fool yourself. At that point, it's better for you to give it up to somebody who can take it where it needs to go. I wish you the best, David. And remember that selling a business is not quitting. Sometimes it's actually the most responsible thing you can do as a leader. And if you are listening to this and you have a question just like David had a question, don't forget you could submit your questions straight to me. Just go to 100mba.net q Submit a question and I'll answer right here on Q and A Wednesday. If this episode has helped you and you thought of a friend or a colleague or somebody that you think would benefit from it, benefit from listening to this episode then and share with them. Go ahead and send them a message with the link and just use the share icon on whatever app you're using. And if you want to continue to learn from me, I encourage you to sign up for my weekly newsletter where I send you a short and sweet email to help you along your journey. Just go to 100mba.net newsletter and you'll get one in the coming days. Before I go, I want to leave you with this. The 10 year journey of building and growing and then selling webinar ninja was an incredible experience. And and I have to honestly say that yes, it was great to have a win and a great product and great customers and the money was great and all that stuff is fantastic. I'm very grateful for that. But the thing I'm most grateful for is what it made me right, what the business allowed me to become. It transformed who I became, and I've learned a ton in that experience. And I hope to share some of those lessons in the coming days and months and years here on the podcast. Thanks so much and I'll take you in the next one.