'If you don't actually do it, it doesn't really count' - Caspar Woolley, Hailo

20 QUESTIONS: The co-founder of the e-hail app talks about selling timeshare to toadstools and why average just isn't enough.

by Adam Gale
Last Updated: 22 Dec 2014

1. IF YOU HAD DONE SOMETHING ELSE WHAT WOULD IT HAVE BEEN?

I started as an engineer and spent time in consumer goods and retail, so I’m pretty sure I’d have found another startup idea based on what I leaned from those. I always knew I was going to do my own startup at some stage.

2. WHAT ELSE WOULD YOU NAME YOUR BUSINESS?

Hailo was actually very nearly called RITA, which stood for Real-time Intelligent Traffic Algorithm. But then we realised that the Beatles’ famous metre maid might not be so popular with drivers, so we abandoned it and came up with the better option of Hailo.

3. IF YOU COULD BE BASED IN ANOTHER CITY WHERE WOULD IT BE?

I’d pick Barcelona because it’s got fantastic culture and wonderful people, but also because it’s a great tech city. Combined with the fact that two of my brothers live in the region, that makes it irresistible.

4. WHEN YOU STARTED, HOW DID YOU RAISE MONEY?

Unexpectedly. When we started, we were based on the HMS President, a First World War warship moored on the Thames, bootstrapping the business in the way that many startups do. Then we started looking for angel funding, and also talking to a couple of great VCs about our future plans.

We hadn’t expected them to be interested in what we were doing at that stage. Then, completely unexpectedly, they stepped in and provided our seed round of funding.

5. WHAT HAS BEEN YOUR MOST IMPORTANT DECISION SO FAR?

The most important decision was to have a brutal focus on beautiful simplicity from the beginning. Choosing to do lots of things is easy. Choosing not to do lots of things is much harder, but much more important.

6. WHAT HAS BEEN YOUR BIGGEST MISTAKE?

Our big mistake was not recognising soon enough how challenging it would be as a small organisation to make a team spread across three continents still feel in the loop. Because we expanded pretty quickly into both North America and Asia, we had to learn really fast to work at keeping those communication channels open. It probably took us a bit longer than it should have done to get ahead of that. 

7. WHAT IDEA DO YOU WISH YOU HAD COME UP WITH?

I always kick myself about uSwitch. In the early 90s, I did all the research around exactly that concept, allowing customers to compare which was the best telecoms provider based on their own usage. But I never got that idea off the ground and if you don’t actually do it, it doesn’t really count. 

8. HOW DO YOU HANDLE STRESS?

Like many men, I self-medicate. In my case that’s with as large a dose as I can manage of my long-suffering family and perhaps just a small amount of alcohol.  

9. WHAT WAS YOUR FIRST JOB?

Before I went to University, I was lucky enough to work for Arup, probably the world’s leading consulting engineering company. That taught me a huge amount about the built environment and why we should care about the spaces we inhabit.

10. WHAT WAS YOUR WORST JOB?

My worst job I hardly even like to admit to. One summer, I actually worked the streets of the West End for a week trying to persuade people to go and listen to a time share sales pitch. It turned out not to be my thing, but boy did I see some great selling going on.

When I went and told the boss, he had me turned around, enthused and ready to go within 20 minutes. He could have sold timeshare to a toadstool. It was amazing to feel that force.

11. WHAT WAS YOUR BEST JOB?

It has to be this one. Even when I arrive into work feeling tired and thinking of all the things I should’ve got done yesterday and need to get done today but probably won’t, I remind myself that I’m lucky enough to be living that dream of starting a great business and making a difference to lots of people’s lives.

12. IF YOU WERE ON THE APPRENTICE WOULD YOUR TEAM BE NAMED?

I think it would be ‘Average is Awful’, not just because we all want to be better than average, but because as a business and an operations person, I know how many important details and distinctions are completely hidden by averages. Averages just aren’t enough, you have to dig deeper, you have to understand each customer individually.

13. WHAT COMPANY WOULD YOU INVEST IN RIGHT NOW?

voXup. It’s a mobile technology startup here in London which aims to increase people’s engagement with their local communities. That use of technology to change the world for the better is really inspiring.

14. APART FROM PROPERTY, WHAT IS THE MOST EXPENSIVE THING YOU’VE BOUGHT?

My car. I have a family of five, and to get them around long distance, I own a people mover. It’s nothing special, but it’s amazing how much chunks of metal cost. It’s one of those things that still inspires me to extend the concept that over time fewer and fewer people will actually have to own a car like I do.

15. SUIT OR JEANS?

Definitely Jeans. I believe in that relaxed approach to the world.

16. FLEXIBLE WORKING OR OFFICE HOURS?

We’re a technology company – definitely flexible working! The kind of people we have working in this business give so much of themselves so much of the time. Flexible working is the way to get the most out of this kind of team.

17. WHAT IS YOUR FAVOURITE THING ABOUT THE OFFICE?

It has to be the people. They are so committed, they make me so excited about the business every day.

18. WHAT APP CAN’T YOU LIVE WITHOUT?

RunKeeper. It’s an activity app that tracks running, walking, cycling.  Life’s pretty busy – it’s great to have a little bit of help to keeping me on track with my exercise every week.

19. WHO IS YOUR BUSINESS IDOL?

One of my very first bosses, a guy called Jack Kennedy, was a former merchant seaman, working incredibly successfully in a buttoned up American corporation, Pepsico. He taught me that with the right attitude anyone, whatever their former history, could succeed anywhere. That was incredibly important to me.

20. IF YOU WERE PRIME MINSTER FOR THE DAY, WHAT WOULD YOU CHANGE?

My particular bugbear is uncoordinated road-works. Traffic congestion is an issue close to all our hearts and particularly close to my heart here at Hailo, because it not only drives incredible inefficiency but also stresses everyone and causes frustration. So I’d ensure that all road-works were coordinated and that no road could be shut for more than a particular length of time.

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