After taking Business Studies and French at the University of Edinburgh Jack had a successful career in commercial property investments. He started out as an Asset Manager at Land Securities for Trillium and then moving to Australia and to eventually become the Senior Manager, Capital Transactions for Dexus, one of Australia’s leading real estate groups. Today Jack is the Founder and CEO of Grapevine.

To find out more about Grapevine click here.

Why did you decide to work in Australia?
I spent my third year of university working and studying in Paris, so I guess that gave me the bug for living overseas.  After qualifying as a chartered surveyor in 2006, I considered New York but the American property market set up is different to the UK, so getting a job there would have been a challenge. A friend’s brother was a property recruiter in Sydney, and told me there were lots of job opportunities out there. It was 2007 and the property market in the UK was going gangbusters, so I decided to throw caution to the wind and quit my job to head out there to find work. Luckily, I landed a role before the end of 2007, as things went south soon afterwards with the global financial crash. I initially thought I might be there for a year or two, but I ended up there for 10 years!

At Dexus I worked my way up from an analyst to running core office and retail transactions, where I was involved in over $10bn AUD in office, retail and industrial deals. We had a smart CEO who recognised (in 2011) that the price of real estate would soon look cheap, so we went on a spending spree, building our ownership of A-grade and Premium CBD assets to over 25% in the major Australian cities. It was good fun and I thoroughly enjoyed it despite 5+ years of working 12-16 hour days, and often at the weekends too. It was a conscious decision to focus on my career and, I was happy to push myself. It was tiring but rewarding!

What would your advice be to anyone who is thinking of going abroad to work?
Once you’re there, to throw yourself in to everything, say yes to everything. You generally get out what you put in, so make the most of it. You never know who you will meet and what friends you will make.

The type of work you’re doing now would allow you to work anywhere in the world, do you think you would live abroad again?
I love travelling, but after having been away from the UK for so long it is nice to be back with family and friends. Maybe be one day if business required me to, but I’m in no rush.

You are now the Founder and CEO of Grapevine, please describe what Grapevine does.
Grapevine is an AI technology that helps Corporate Travel Agents increase bookings of ancillary products by sending right time, right channel messages to business travellers after their initial flight or rail purchase. Travel agents have historically been great at booking flights and rail, but they’re not so good at offering the extras. As a result, business travellers currently book 70%+ of ancillaries (hotels, car hire, airport parking, ground transportation etc) outside of approved tools, which not only means lost revenues for the travel agents, but also duty of care and productivity headache for corporates. In addition to the core ancillaries, our technology also makes contextual in-destination recommendations, such as restaurant suggestions, live events, guided tours and activities. For instance, if you arrived at the airport and your flight is delayed, our AI identifies this from the data and asks if you would like lounge access while you wait, which you can book instantly.

How did Grapevine start and when did you make the decision to leave your job to concentrate on it full time?
Grapevine actually started as a consumer facing friends’ recommendations platform. It was initially a side project which I worked on for 12 to 18 months on nights and on weekends while doing my day job. I would get back from work at 10pm then get on the phone to my developers in India – it took a lot of dedication!

In late 2016 I had made enough progress to quit my job at Dexus to focus on it full time.  It was a big risk to leave but a calculated one. I had no idea how to start up a business but decided to give it a go and it has been a steep learning curve since then! Having had some minor success as a b2c (business to consumer) platform, we were approached by several businesses in 2019 asking if we could do what we were doing for them. A pivot from b2c to b2b (business to business) is quite a well-trodden path in start-ups, as the prospect of people paying you for your service is quite appealing. So, we made the decision to pivot in late 2019, which was a decision I’m really pleased to have made.

Did you make any mistakes along the way?
I’m always making mistakes! In my previous career, one of my big learnings was that you don’t need to be an expert at everything, but that having good people around you is crucial. The challenge in starting a new business in an industry and skillset you have no experience in, is that you don’t know what you don’t know, so working out where to start is super hard.

So, it is natural that you can make the wrong hires and one of my early mistakes was keeping hold of people that weren’t right for the job. There is a saying in start-ups that you should hire slow and fire fast. I was good at the former but should have been better at the latter – not easy when the hiring process is so time consuming!

What impact has Covid had on your business?
Covid has obviously had a massive impact on the travel industry. We were fortunate to have just signed a contract with our first client, Gray Dawes Travel in March 2020. They were very supportive, stating that the pandemic actually reinforced our value proposition, as with travel volumes down, maximising revenues per trip was more important than ever.

After raising a ‘Covid-bridge’ investment round, mainly from existing investors, we were able to get our heads down in the second half of 2020 and build out the product which we eventually launched in Feb 2021. Whilst travel volumes were initially very low, they are now coming back and with the US opening in November, we should see some meaningful numbers in the coming months. Grapevine has been really well received in the market and we have won several awards recently, including at the Business Travel Show Europe and BTN Innovate in New York in late October.

Looking back over your career to date is there anything you wish you had done differently?
When I first started out in the property industry I worked on the client side, meaning I got less of a chance to get experience in different departments of the company compared to those who start in agency. I would encourage anyone new to any industry to move around and get a broad an experience as possible, to build a good foundation.

What job would you choose if you didn’t do what you are doing now?
Going back to property would be the easiest thing to do but I think maybe helping others with their start-up businesses would be fun. There are times when it can be overwhelming. You have to be resilient. It’s tough. It’s a misconception that being your own boss is easy. There is only you to get things done; staff and clients are relying on you. You have to be dedicated and informed of all that’s going on, and sometimes be a bit thick skinned and not take things personally. It is of course rewarding as well, to get your idea off the ground and to see it starting to go places.

Lastly, is there anything from Radley has stayed with you forever, any memories that come to mind?
I was lucky to have a great year group and came away with lots of good friends, many of whom I am still in regular touch with now. We actually have a WhatsApp group called ‘Thunder’, named after Richard Morgan, the then Warden, who would stand at the try line and shout “Thunder Radley, Thunder!”.

Embarrassingly, 23yrs since leaving, we still regale the same stories, so whilst we are amused, I think partners and spouses find them rather repetitive. An unlikely accolade I hold close to my heart was being named, alongside Dudley Heesom, as Patrick Derham’s (former housemaster) favourite ‘busting’ of all time in his departing C social speech. I definitely enjoyed the story more than the busting at the time!

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