Hugo Woodhead

Always assume you know nothing rather than everything.


Hugo is a London born tech entrepreneur and the founder behind Pilcro, a UK based startup on a mission to help companies build sustainable, reputable brands. When Hugo was putting his team together at Pilcro he didn’t need to look further than family as his sister and two brothers quickly came on board. As a middle child Hugo clearly has a rebellious streak and this comes across both in person and through the disruptive nature of his businesses. With a history in Finance, Hugo says that the political and sclerotic nature of large businesses compelled him to go it alone and try and create something new. Hugo’s demeanour is informal but that does not disguise his serious and direct nature. It is easy to tell he is driven and motivated to succeed.

Where did the idea for your company come from?

At Pilcro, we were lucky. We were actually working on another product when we had the idea for Pilcro, something that’s fairly common among startups I guess. We started to have serious issues with storing and sharing creative assets. We never knew which versions to use. Managing brand assets and designs was becoming a job in itself. So we asked around. We work in a great shared space in London UK so it is easy for us to sound out ideas. We wanted to see if others were having the same issues. We got such an overwhelming response we had to make an MVP. It all just took off from there.

What does your typical day look like and how do you make it productive?

To be honest no two days are the same but there are some constants. I love to start out with a strong coffee and a quick chat with the team to set priorities. We have to be fairly reactive to the priorities of the day, such is the nature of a fast growing business. I try to limit the number of meetings I have and work on good internal communication across teams to get everyone pushing in the same direction. I don’t eat breakfast, and lunch is at midday, my colleagues will tell you that I can get moody quickly if anything delays lunch.

How do you bring ideas to life?

We are most skilled at web-development, so when we have ideas they tend to go down on real paper and then straight into a prototype. It’s quicker that way than progressing via a design tool like Sketch or Figma. Once we are happy with a concept, we will then go back into those design tools to refine our visual designs and UI.

What’s one trend that excites you?

We hate plastic waste at Pilcro. It is a massive problem for the environment and oceans. But as with any problem comes, there is opportunity for great innovation to solve it. We are seeing so many really exciting ideas trying to tackle this global, shared issue.

What is one habit of yours that makes you more productive as an entrepreneur?

Always assume you know nothing rather than everything.

What advice would you give your younger self?

Don’t be afraid to ask for help, even if you think it will make you look silly.

Tell us something that’s true that almost nobody agrees with you on.

Cricket (a sport played in the UK) is the best sport in the world! Period.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

My technical background has taught me that it is vital to double check (or get someone else to check) the work you do. At Pilcro we tend to work in pairs as that is a good way to keep tabs on the work being done – and that means everything gets two pairs of eyes on it. For me, I always make sure I take a break and then go back to my work to check it to make sure I haven’t missed anything. Making simple mistakes can be really damaging to your brand and is easily avoidable.

What is one strategy that has helped you grow your business?

Every time we do an experiment to grow the business, we set goals and make sure that we see the experiment right through to the end. This helps us to understand what works and what doesn’t. When you are in the fast-paced startup environment, it is easy to start experiments but not give it the time to see proper results.

What is one failure you had as an entrepreneur, and how did you overcome it?

The product that I was working on before Pilcro was not a success. It was overly complex and did not have a clear route to market. It was a hard pill to swallow but the key to overcoming failure was to dust myself off and start again. It was very important to recognise that failure is not always in your control and the best you can do is take away as much learning as possible.

What is one business idea that you’re willing to give away to our readers?

Suitcases as a service. Delivering the right sized suitcases to your door before travel. Living in London in a small flat, around 2-3% of my flat is taken up with suitcase storage. Wouldn’t it be great if you only had a suitcase, for exactly the correct size and shape only when travelling and not for the rest of the year? Who knows what you could use the space for.

What is the best $100 you recently spent? What and why?

My Bose QC35 headphone. I commute every day on the London Underground and they create a quite relaxed meditative environment for me before I start the day.

What is one piece of software or a web service that helps you be productive?

Asana. We use it for all our task and project management. It gives the team great transparency about who is working on what. It is perfect for tech projects but we’ve adapted our workflow to manage all teams through Asana.

What is the one book that you recommend our community should read and why?

I recommend reading Donut Economics, by Katie Raworth because it makes us rethink our basic understanding of the current models of enterprise and economy. It gives us a toolkit for entrepreneurship that contributes to our biosphere rather than depleting it.

What is your favorite quote?

“Your brand is what other people say about you when you’re not in the room” Jeff Bezos, Founder @ Amazon

Key Learnings:

  • Sometimes the best ideas are right in front of you
  • Failure is not always your fault, sometimes you can’t control it
  • Consistency is key to being successful when building a brand and a business
  • Don’t be afraid to ask for help, it can often yield the most unexpected results