Serial entrepreneurship can feel like a distant dream for many. The journey of starting, scaling, and selling one company is challenging enough. Now imagine doing that four times. George Burgess, founder of Modern Day Talent, has achieved just that, successfully building and exiting multiple startups. Today we sat down with George to discuss his entrepreneurial journey, from launching his first startup as a high school student to scaling businesses with innovative strategies. Below is an excerpt of our conversation:

Kajal: You’ve built and sold four companies. Your first business, Gojimo, gained traction with over 45% of secondary school students in the UK using your app. How did you achieve such widespread adoption early on?

George Burgess: I think the success of Gojimo was partly due to timing. When we were figuring out our user acquisition strategy, Instagram had just released video ads, which were very new at the time. This new format wasn’t widely adopted by advertisers yet because creating good video content was still costly and time-consuming.

Instagram had a lot of unused ad inventory, so the cost for video ads was much lower than other formats. We jumped on that opportunity, and it allowed us to acquire users affordably. Another key factor was product-market fit—students genuinely loved the product. We knew if we could get a significant number of students in each grade, they would spread the word and share it with their friends.

Kajal: You eventually sold Gojimo to a UK-based media group and worked there post-acquisition. How did it feel transitioning from being a founder and CEO to working in a corporate setting?

George: It was different—suddenly, I had a proper job with someone to report to, which was a huge change. In some ways, it was refreshing. I had spent six or seven years building Gojimo by myself, making all the decisions alone, so joining a large organization with 1,200 people was a welcome shift. There were senior management teams and smart people to collaborate with, which I initially enjoyed. But over time, I found the pace slower, especially in a well-established organization like the Telegraph. There was less willingness to take risks, which can be frustrating for a founder. After about two years, I realized I needed to return to the startup world.

Kajal: What were some key takeaways from working in a large organization that influenced how you approached your next startup?

George: Observing a big organization was invaluable. You get to see the good and the bad in management and operations. I learned a lot about what not to do—how not to manage teams, how not to handle communication. I also got to see effective management styles, which I adopted. When I started my next venture, I was more deliberate about how I wanted to lead and structure my team. My co-founder and I tried to take the best practices we’d seen and avoid the pitfalls.

Kajal: After leaving Gojimo, you co-founded a dating app. How did you differentiate yourself in such a crowded space, especially with giants like Tinder and Bumble?

George: The dating industry is tough because it’s all about marketing and brand appeal. You need to have exciting, attractive users, and your brand needs to stand out. We decided to differentiate with our product. Instead of allowing users to chat after matching, our app scheduled an in-person date automatically. It was bold—people couldn’t just text forever; they had to meet. It didn’t appeal to everyone, but for some, it was exciting.

However, we launched in October 2019, and then COVID-19 hit. Suddenly, meeting in person was illegal, and that posed a huge problem. We pivoted quickly to offer video dates, but that diluted our unique selling point since all the other dating apps introduced video features as well. It was a tough pivot, and ultimately we realized it wasn’t the right market for us. Thankfully, we were able to sell the company.

Kajal: That’s a challenging turn of events. You transitioned from the dating app to Basubu, a wellness-focused startup. Can you tell me about that shift?

George: After the dating app, we sold it and still had a significant amount of capital left. Our investors told us to take the time to come up with something new. That’s when we explored the wellness space. We saw a rise in wellness retreats—independent yoga instructors and teachers were hosting these experiences. We thought there was an opportunity to create a platform where instructors could organize and sell their retreats, kind of like a Booking.com for wellness retreats.

We launched a basic prototype within 30 days and spent a small amount on Google Ads. In the first month, we saw $13,000 in bookings, which validated our idea. It was exciting, but like every startup, it came with its challenges, especially balancing the two-sided marketplace between retreat organizers and customers.

Kajal: Running a two-sided marketplace can be tricky. How did you manage building trust on both sides of the platform?

George: The two-sided marketplace dynamic was really interesting. At first, we manually contacted retreat organizers, asking if we could list them. That worked, but it was time-consuming. Eventually, we just started listing retreats automatically. If someone wanted to book, we would then contact the organizers and let them know, “Hey, you’re on our website, and we have a customer ready to book.”

It was a bit of a cheeky growth hack. Most organizers were happy about it, but maybe one in five or one in ten would question us, and we’d take their listing down quickly. But that method solved the supply issue fast. On the customer side, we quickly realized it was going to be an SEO-driven business. We were ranking on Google and getting organic traffic, but we could tell that this model would only lead to a medium-sized business, not the massive returns venture capital investors expect. So, we decided to sell.

Kajal: You mentioned being proud of knowing when to exit, but how do you decide when it’s time to sell?

George: It’s definitely not an exact moment—it’s more of a gradual realization. As you go deeper into a business, you learn things that make you reassess. For example, with the wellness retreats, it became clear that the real growth would come from SEO. We were competing with others for top spots on Google, and there weren’t many other levers to pull. You start to think, “Is this still as exciting or as promising as I initially thought?” Every founder has an opportunity cost—spending five years on this business means I’m not spending five years on something else with more potential.

Another factor is having venture capital investors. VCs need huge outcomes to make their fund economics work. If your business is only going to be a medium-sized company, you’re probably not going to raise more money, and your investors might not even like the direction you’re headed. In both cases, with the wellness retreats and the dating business, we decided to move on because the upside was too limited compared to the opportunity cost.

Kajal: After that, did you jump straight into founding Modern Day Talent, or was there a break in between?

George: There was quite a bit of time in between. I was soul-searching for a while. My first three businesses were all tech and VC-backed, and after over 10 years of that, I realized I didn’t want to build another huge VC-backed company. I wanted to focus on building a healthy, profitable, medium-sized business—a lifestyle business, essentially. Something that didn’t need investors.

At the beginning of last year, I actually started three businesses: an email newsletter company, a TikTok agency, and Modern Day Talent, which is an offshore staffing agency. After six months, Modern Day Talent was clearly the winner—it was growing the fastest, already profitable, and had great potential. So, I shut down the other two and went full-time on Modern Day Talent.

Kajal: You said within six months you saw that Modern Day Talent was the clear winner. How did you scale it to that point?

George: We help companies hire remote staff in South Africa. I had experience with this model from my travel business, where we hired our whole team in South Africa and found great talent at a much lower cost than in London. That experience sparked the idea for Modern Day Talent.

When starting multiple businesses at once, you look for a “pull factor”—basically, product-market fit. With Modern Day Talent, I started seeing people approach me, not just those I had marketed to directly. That’s when you know there’s demand. We began to place staff for clients, and they were happy, which made it a no-brainer to go all-in on the business.

The business model was also appealing. Unlike my TikTok agency, which required constant content creation and management, once we placed someone with a client in the staffing agency, it became monthly recurring revenue with minimal extra work. That made the decision to focus on Modern Day Talent easy.

Kajal: Given your experience working with remote teams, would you advise startup founders to build their entire founding team remotely?

George: It depends on the business. Some businesses, especially in the early stages, benefit from having the entire team in one place. If you’re building a software product and iterating quickly based on customer feedback, being in a single office can speed things up.

But for other types of businesses, especially service-oriented ones, remote teams make sense. For example, in our travel business, the majority of our hires were in marketing, operations, and support, roles that didn’t need to be in London. We could hire three times as many people by outsourcing to South Africa. So, for some businesses, it’s fantastic to have a remote team, but for others, especially in the early days, you might want to wait before going fully remote.

Kajal: The first three startups you founded were VC-backed, while Modern Day Talent was bootstrapped. What advice would you give to first-time founders navigating the funding process? Should they pursue venture capital or bootstrap?

George: VC funding has become mainstream due to how often the media discusses it, but it doesn’t make sense for most businesses. Venture capitalists are looking for companies that can provide massive returns, typically aiming for a 100x outcome. Most businesses won’t achieve that, and many founders struggle to raise venture capital because their businesses don’t fit the profile.

The reality is that most businesses don’t need venture capital. However, if you’re building something high-growth, like tech or tech-enabled startups, VC funding could be an option. But for the vast majority, it’s not the right choice.

That leaves many founders in a difficult position. If you’re not aiming for the type of growth VCs want but still need funding, you’re in a tough spot. You might turn to friends and family or high-net-worth individuals, but they may take larger stakes due to the higher risk.

In the case of Modern Day Talent, I was fortunate. It didn’t require much upfront capital, so we were profitable from day one. But that’s rare. Most founders need to find creative ways to finance their businesses.

Kajal: Across all the ventures you’ve founded, what setback taught you the most?

George: I’m most proud of the decisions we made to sell some of our businesses. At the time, we knew we either had to sell them or shut them down. What I’m really proud of is our ability to recognize when an idea isn’t working and make the tough decision to move on.

In both cases, we built enough value for someone to pay for our tech and assets, which validated that we were good at what we were doing. Most founders wouldn’t admit defeat, especially if they had venture capital behind them. But we realized it wasn’t the right fit for us or the market, and that maturity allowed us to pivot and move forward.

Early in my career, I wouldn’t have had the confidence to admit defeat. I would have kept fighting for a project that wasn’t working. Knowing when to push forward and when to pivot is crucial.

Kajal: If you could change one thing from your entrepreneurial journey, what would that be?

George: In my earlier ventures, I didn’t invest enough time in becoming a better leader. I was just figuring things out as I went along. As CEO of a growing company, I had 16 or 20 employees, but I never stepped back to think about how I could lead more effectively.

Now, I spend a lot of time focusing on leadership and company values. In Gojimo, my first business, we didn’t talk about values for six or seven years. I thought it was a “wishy-washy” concept that didn’t matter. But now, in Modern Day Talent, we have clear values, and it’s a game-changer. Values guide hiring decisions, performance reviews, and everyday choices, helping the entire team work from the same framework.

Kajal: What are the three most important pieces of advice you would give to someone just starting out?

George:

1. Get started – The first step is often the hardest, but it’s critical. I see so many aspiring entrepreneurs who talk about ideas but never take action. Start by putting up a website, trying an ad, or selling your product. In Modern Day Talent, my first customer came from finding a virtual assistant for a friend. That was customer one, and we built from there.
2. Understand how hard it is – Building a business is tough, and it will affect every aspect of your life. If you don’t enjoy the process, it’s not worth it. A lot of people think being a founder is a path to wealth, but it’s incredibly risky, and the odds of massive success are low. If you don’t love the grind, you won’t last.
3. Hire slow, fire fast – You’ll know in your gut when someone isn’t working out. As a first-time founder, you might hesitate to let people go, hoping they’ll improve. But if you feel something isn’t right, trust your gut and act quickly. Keeping the wrong person on board impacts your entire team, and making tough decisions early will serve you better in the long run.