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How This Founder Sold His Ticketing Company Only to Buy It Back and Make It More Profitable Than Ever

Jonny White started his professional career as a freelance web developer. When a client tasked Jonny with finding a system to sell tickets online, he scoured the web for solutions. He knew he didn’t want to use a middleman because this was a “software problem” he could directly address. Jonny says, “I wanted to build a piece of software to do it myself.” Ticket Tailor was born out of Jonny’s diligent need to protect customer privacy and help clients save money in the process.

Ten years ago, the market for selling tickets was very different. Most websites either had a Paypal button, or they used an agency. Since Jonny’s background was in web development, he knew he could tackle the problem head-on. He could do all of this while saving his clients’ capital and simultaneously protecting their data. It was a lofty goal, but Jonny was confident he could do it.

If a Solution Doesn’t Exist, Build It

Jonny explains, “What event organizers need is a piece of software to help them sell tickets. I knew that I wouldn’t take data or hold onto funds. I wouldn’t even brand the process. I created a piece of software using PHP and MySql that was all about helping event organizers do their jobs rather than trying to be something in between a ticket buyer and an event organizer.”

Jonny spent three months and many long nights knee-deep in code building his first iteration of Ticket Tailor. He says, “I got stuck into doing the fun stuff first. I didn’t even have a finished product and I was already worried about getting the logo done. I left all of the boring stuff for last, you know, the really important things like managing billing, the password reset process, and the like. This was ten years ago, and the tools and frameworks that make this stuff much easier today didn’t exist.”

Imposter Syndrome Is Real

Jonny was in the weeds and losing motivation. He says, “I’m going through all of this boring stuff and I’m losing motivation right before launch.” At this point, he only invested fifty dollars on a logo but everything else was sweat equity. He doubted if it was worth it and began to get nervous about finding clients. This was a case of major Imposter Syndrome and it’s fairly common in the bootstrapping community. It’s always terrifying to go from idea to product because it makes everything real. The grind is far from sexy, and anxiety starts to set in.

As an in-demand freelance web developer Jonny was often busier than he had time for. When he built Ticket Tailor and it was ready for launch, Jonny began to second-guess himself. “I thought, ‘Do people actually want this?’ I was nervous about my own skills in acquiring customers. But I knew I had what it took, so I just jumped in.”

Jonny read his way through his anxiety. He bought a book on cold calling that he admittedly describes as “terrible,” but it was enough to “pump me up.” It gave him the courage to “not feel like a complete idiot, since it’s all about confidence.” On the third phone call, Jonny got a solid lead. It was a cabaret venue that set up a meeting. Jonny went to that meeting with a plan for a subscription model drawn out on a piece of paper. The client was impressed and told Jonny: “This is exactly what we want,” and signed up right there.

Retiring Cold Calling

Jonny knew he was onto something, and he could scale it. The best part was his one successful pitch gave him the confidence to retire cold calling for good. Jonny started to attend startup and technology events and put his feelers out. He met a lot of interesting people, and he showed them exactly what he built and how it worked. 

The Ticket Tailor network expanded exponentially after that. Jonny set a number in his mind, and once he reached it, he would devote all of his attention to Ticket Tailor. He says, “I had a goal in my mind that when I got to £1,000 a month, I would start to let go of my web development clients and move full time to Ticket Tailor.” After a short while, Jonny hit that mark and kept acquiring new clients.

Stepping Outside Your Comfort Zone

Jonny had to “get over a hump of fear” when he attended events, particularly as it applies to public speaking. He wasn’t a “natural” and he worked hard to hone his skills because it was a good opportunity to build brand awareness. But he was passionate: “There’s a natural energy that carries through the audience.” Jonny worked the crowds and enthralled his audience, proving that stepping outside of your comfort zone can pay off in dividends.

London was home and the cost of living high. Jonny needed to save every penny. On a whim, he put £50 into Google Ads – but nothing more. When people signed up for the top subscription plan, Jonny knew it was money well spent. Even so, he canceled the advertising immediately after conversion which was an admittedly “funny mindset.” 

Ticket Tailor wanted to build up a significant client roster through word of mouth and this is exactly what happened. It became a massive funnel for the business. Jonny likes it because each client has unique needs and working with them individually has allowed Ticket Tailor to become a flexible product. “We have grown a lot from word of mouth. We have a real mix of all kinds of different customers from all over the world.” 

Team Ticket Tailor working diligently

Jonny’s never bored because his customers work in lots of different industries and do various roles. It certainly keeps the work interesting. Jonny explains, “Whether they’re professional event organizers or just using a bit of online software for the first time – we have a real mix of offerings and we love the challenge of layering on a strategy.”

When Jonny doubled his initial income goal, he received a surprising and yet welcoming phone call. Time Out wanted to do personalized ticketing and Jonny thought this would be a great client to procure. He was slightly apprehensive since this was an enormous client and he was a one-man show: “The conversation turned from supplying services to Time Out to them acquiring the business.” After nerve-wracking negotiations, Jonny sold Ticket Tailor to Timeout (logo and all) and ended up working there for 18 months.

Jonny in the wild

Acquisition Isn’t Always the End of the Story

This is the part of the story that seems like a nice place to wrap up. Jonny built something from nothing, and then had the incredible fortitude to scale and sell. But, he wasn’t content. “I was just getting started and thinking of Ticket Tailor’s potential. I didn’t go into it wanting to sell, but it was a huge opportunity to work with a cool company and to work with other people.” (Jonny was used to flying solo up until this point.) Unfortunately, in practice, the integration of Jonny’s software to sell tickets for events on Time Out didn’t come to fruition. In other words, all of Jonny’s hard work was being underutilized and the initial strategy had changed

Jonny and Time Out came to a mutual agreement to part ways. Jonny, ever the optimist, looks back on the experience through rose-colored glasses. “It just wasn’t so interesting in terms of what I wanted to be doing, although I got a lot out of the initial experience. When it came time to leave, Jonny wanted to make a clean cut and asked to turn a three-month notice period into one month of wrapping up loose ends. Much to Jonny’s surprise, Time Out said no to the shorter period. “They said no, because ‘We’ve got your business and we’re not sure what to do with it.” The business was still running, but it hadn’t been integrated into Time Out in any way.

As it turned out, the business was a burden for Time Out. But Jonny wasn’t ready to walk away from all of his hard work. Jonny decided to delineate how Time Out and Jonny could extricate themselves. “I want to carry on. So, I proposed a few options to them. Here’s what it looks like to keep it running, here’s what it looks like to close it down, and here’s what it looks like to sell it back to me.” The most attractive option for Time Out was selling it back, and this was exactly what Jonny was hoping they would pick.

It was a strange time for Jonny because he had been so overwhelmed when he was first approached to sell and so frustrated that Ticket Tailor was underutilized. The whole experience was proving to be quite underwhelming. But Jonny didn’t know that was how he would feel until he lived through the days of entrepreneurship.

When Jonny was building Ticket Tailor, he was solely responsible for everything. When he sold, he was excited to step back and play a smaller role for once. But not being in complete control meant that Ticket Tailor was losing relevance and that destroyed Jonny even more. He stepped back into the spotlight with renewed vigor and energy and it paid off in spades. Jonny brought Ticket Tailor from about £2,000 MRR when it was first sold to £8,000 MRR after buying back the business.

A Community of Bootstrappers

Jonny attended an event comprised of a community of bootstrappers which was a new concept for him. Everyone around him was always touting the importance of raising funding. Jonny spent a lot of time creating pitch decks and putting in the time and effort to raise money. Jonny says, “I thought: I needed to get funding now. This is what I need to do, but I don’t really know why. It just seemed like what I should do.”

Thankfully, someone introduced Jonny to the world of bootstrapping. Up until this point, Jonny didn’t know that there was a community of bootstrappers who all supported one another. “It’s cool to be bootstrapped. This is an actual route that I can be confident in and forget about the funding because I don’t want what investors want.”

At the same time that Jonny was leaning into his self-funded entrepreneurship, he met the owner of a WordPress app development company who just happened to be a successful bootstrapper. They moved into the same co-working space and started to bounce ideas off of one another. “We were sharing loads of tactics.” One of them helped Jonny streamline his workflow. He outsourced customer support on Upwork. Up until that point, Jonny was spending half of his day on customer support alone.

Ticket Tailor’s co-working space

Geeking Out Over Growth Hacks

The two friends spent their lunches “geeking out over growth hacks.” Both of their businesses grew out of this friendship. Then more bootstrappers joined the coworking space and they would all share tips and hash out strategies.

Jonny was at the perfect place in his career. His business was netting upwards of £8,000 MRR and the only cost was his Upwork customer service freelancer. “It was the perfect lifestyle business. I’m going to work with my mates, my dog comes into the office, but after a year, I got bored. I wanted to take it to the next level.” Jonny wasn’t content just being successful; he wanted to go big.

He hired his first part-time employee, a designer, to help him elevate his game. The real challenge with bootstrapping, according to Jonny, is that “you’ve got some freedom to hire people and build a team and you have to be ready. You have to know that your job is going to change from creating things to managing people.” It isn’t all fun and games. But Jonny’s pivot to building a team has turned Ticket Tailor from a one-man-band to a proper company with ten employees in London, and another five remote employees.

Ticket Tailor team Zoom sans suit and tie

As Jonny continued to grow Ticket Tailor, he invested in a coach to help him make fast, confident decisions. He says “I stopped sweating every decision and worrying about every pound and instead started taking more risks, hiring people, and growing. It helped me to refine the vision of the company.”

Businesses Making a Difference

“The thing that gets me out of bed is that the world needs more examples of businesses that do good. We are a profitable company and we’re doing well. We’re growing, we don’t have any investors and we can do exactly what we want and there’s a lot of freedom in that. We ask ourselves, ‘How can we not only create a positive impact for ourselves but also as an example for other businesses?’ We are working on our B Corp now.”

Ticket Tailor is also donating a penny for every ticket sold. Currently, Ticket Tailor sells 6 million tickets a year, so the charitable aspect is no small feat. It’s an example of “growing better, not bigger.” Ticket Tailor averages £182,720 a month and currently works with over 10,000 event organizers across 183 countries.

Ticket Tailor living it up in Italy

If Jonny hadn’t sold Ticket Tailor so early on, he would’ve continued believing an acquisition was more glamorous and attractive than it was. But in reality, he signed the big deal alone in the lawyer’s office. The second iteration of Ticket Tailor is truly a family, and Jonny is celebrating his successes with a bevy of people who push him forward. It’s like the age-old adage – teamwork makes the… well, you know. But in this case, it’s absolute fact.

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Andrew Gazdecki
Andrew Gazdecki
Andrew is an award-winning serial entrepreneur with three exits. He’s the founder and CEO of MicroAcquire, the world’s most founder-friendly startup marketplace, and its rebellious child, Bootstrappers, which gives voice to the entrepreneurial underdog. When not building businesses, he writes for Forbes, Entrepreneur, and now, Bootstrappers.

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