Interview with Craig Everett, Founder and CEO of Holibob

Our client Holibob have been on an incredible journey of growth over the last three years. They started out in May 2019 as a tech business providing an innovative and independent B2B marketplace for tours and experiences, helping consumer-facing travel brands to access safe and ethical tours and experiences via a best‐in‐class technology solution. Since then, they’ve completed several funding rounds and recently announced their first acquisition.

We spoke to Founder and CEO Craig Everett about starting and growing Holibob, and the challenges faced along the way.

  1. Can you start by telling us a bit about Holibob, how you came to have the idea for the business, and how you went about getting it off the ground?

It all started when we decided to take a group of 42 of our friends skiing to the South of France. It was intended to be an upmarket version of the traditional university ski trip – so whereas the university ski trip usually involved a 30-hour bus journey, tiny apartments shared with four other people and a microwave to cook all your food; we wanted to organize something more upmarket where we flew to France, stayed in a nice chalet hotel with a swimming pool, sauna, steam room, etc.

The winter after we did that initial holiday, we had friends and friends of friends coming and asking us if we could organize their ski trips. In the end we sold £400,000 worth of ski trips that year, having never previously sold a holiday in our lives – so it was a steep learning curve!

Following that, and on the basis that this was more money than we’d ever seen before in our lives, we decided to try something else entrepreneurial. So we moved into the summer holiday space and started a business called The Hundred Hour Holiday which was, as it says on the tin, holidays that fit into a hundred hours. These holidays were geared towards working men and women who want to get away for a hundred hours, as opposed to the more standard five days away from the office. Five days can be more stress inducing than stress relieving as we all know when you come back to a pile of work as tall as you are.

The problem we had with this venture was the fact that the suppliers we wanted to use for these holidays were mainly offline, instead using paper diaries and whiteboards to manage their availability. This meant a terrible customer experience because every time someone wanted to book, we then had to phone the supplier, leading to a clunky back and forth exchange.

So we decided we needed to automate that interaction with the supplier, and that led us to the idea for Holibob, the building a technology platform to facilitate this automated interaction. We got talking to the likes of Secret Escapes and other consumer-facing travel businesses and said “we’ve got these experiences, would you like to sell them on your website and we’ll split the commission” and they said yes.

The experiential economy is going through the roof just now. Wanderlust and the desire to travel doesn’t actually mean sitting in hotels, it’s about the things you actually do when you’re there. The consumer travel businesses we were speaking to were all quite interested in what we were saying so we ended up in more of a B2B space rather than the B2C space we thought we were entering initially, and that’s ultimately what Holibob is today – a B2B distribution platform for experiences and things to do. We’re basically harnessing new technology to connect people to an exciting new world of experiences and things to do.


  1. Did you find it difficult initially to get an investment in the business?

It’s always difficult to get investment in a business, that’s for sure. We did a couple of family and friends rounds raising around £200K prior to our more significant funding rounds. We then did a round of £800K led by an angel investor. After that we closed another £2.5M and we’ve just recently closed an £8M round. It was difficult – lots of door knocking and trying to make inroads, but that’s the start-up way in many respects. You’ve just got to keep persevering, believing in your idea and telling your story; trying to convince everyone that what you’re saying makes sense. We found it difficult there’s no doubt, but we got there in the end.


  1. What were the first challenges you ran into once Holibob was up and running?

We were incorporated in May 2019 and went live with Secret Escapes in February 2020, so our timing wasn’t great! The pandemic really a big challenge for us, but in hindsight, it actually enabled us to build out our technology at a slightly less aggressive rate than we may have had to otherwise. What we’re doing is trying to build an enterprise piece of technology which is used by very large travel businesses, therefore it’s important it doesn’t break, and building good, robust technology takes time. As well as building the tech we were also able to build out the supply, speak to partners and build relationships. Now we’re coming out of the pandemic we’re beginning to see an increase in bookings and an interest in what we’re doing which has been great.

As already touched on, finding investment was tough. You need the right investment to get the right people on board. Once you’ve got that investment, you move towards finding the right people, and once you’ve got the right people it’s about keeping those people motivated.

We also found that as the business changes from a 4-person start-up to 10 people then to 35 people, you need to be more organized and it’s a very different challenge in terms of managing people’s expectations etc. People are the key drivers to success, so if you can get your people motivated and aligned to your vision, then as long as your product or service is solid, everything else will follow on from here.


  1. Did you experience any people-related challenges?

As with any start-up business, there’s the immediate challenge of the need for things like contracts and handbooks etc. – the basics needed to give a bit of structure to what you’re doing and provide a bit of clarity for those joining. In the really early days some of that stuff doesn’t necessarily matter because people are joining you on a wing and a prayer and they’re willing to be more scrappy, as you are.

Building a starter pack of HR basics from the ground up is really difficult as you don’t know what these are, so that was definitely a big challenge.

We’re currently putting quite a bit of effort into tidying up the mess that we inadvertently created in the early days around how you hire people and how you engage with them, so that was another challenge too but thankfully most of that has been rectified now.

Another challenge we faced was around brand vision and cultural alignment. We understand culture is absolutely critical, but the problem is that it’s intangible and so difficult to quantify –there’s no practical way of simply “creating” it. In the end we realised it was something that we had to work on cultivating and it wasn’t something that was going to happen overnight. But with the right people on board who shared our values and were aligned to our vision we were on the right tracks towards this.


  1. At what point did you engage an HR/people person in the business, and what value did this bring?

We engaged Hunter Adams early on in our journey and they supported us with our contracts and handbook etc. The problem when starting out is that you don’t always know what you need, but Hunter Adams’ call-off service, Hunter 100, is a good model because it gives you flexibility and the ability to access advice when you need it on an ad-hoc basis.

The value Hunter Adams brought initially was the clarity around the things which were important for our new employees. They helped us to provide a framework which made our people feel comfortable, demonstrating that our business was robust and stable, and covering the key things that would impact them personally. Sometimes for founders and senior execs, the business is their whole life and they don’t necessarily think about things like maternity leave, or what happens if someone dies etc. Thinking more about HR allowed us to bring clarity to employees who may have been considering that and they knew there was mechanisms in place as and when they needed to access them.

From a management perspective, Hunter Adams ensured we had the information and tools we needed to make decisions, so that these were based on employment law and compliance as opposed to just opinion.

So with all this taken care of, we – the founders of the business – were able to focus on growing the business and developing the culture we wanted to create.


  1. In hindsight, is this something you wish you had done sooner?

In a start-up you need to move as quickly and with as few hurdles as possible. But as we know now, people and culture are critical to getting things right, and getting the fundamentals in place early on means you don’t need to think about it later.

But for every start-up there’s that consideration of risk vs reward; so if you spend £10K putting in the HR foundations, that’s £10K you can’t spend on something else, so it’s a constant balancing act. In every business there will be a right time to spend that £10K, and for every founder that’s a call they need to make.

But ultimately the key thing is that founders want to be spending as little time thinking about things like this as possible, as they have bigger things to focus on.


  1. How important do you think culture is within a start-up?

In many ways it’s the most important thing as it can make or break your business. Culture is such a subjective thing and it’s very difficult to put your finger on. The way you perceive your culture could be vastly different to the way your people experience it. You can have an idea of the culture you want to create, and you can employee people who you think are aligned to your values and overall vision, but you still need to get objective feedback from them, ideally using a third party, if you want to find out how people really feel about your company culture, they’re never going to give truthful feedback to the founding team.

Once you start measuring your culture you begin to see what an important tool it can be in convincing people to come and work for you. Talking about how it feels to work for Holibob is a persuasive tool when recruiting. And when you get great people in the business you want them to stay – and that’s down to culture again.

If you get the culture right, people will want to be part of it and you’re onto a winner.


  1. Reflecting back on almost 3 years of Holibob, what are you most proud of, and what would you have done differently if you knew then what you know now?

 Certainly the thing that fills me with most pride is the people we have in the business, the team that we don’t necessarily interact with on a day-to-day basis, but who work so well and enjoy being part of the Holibob journey. It’s fulfilling watching them grow and achieve their goals in a business that enables them to do that.

Thinking back to the early days, if I was giving advice to others I’d say surround yourself with as many good people as you can and accept you know very little. Once you accept this it’s so much easier to learn. Don’t think you know everything, as you definitely don’t. Be as much of a sponge for knowledge as you possibly can, and don’t hold your own opinions in too high regard otherwise you won’t get very far!