Investing in Next-Gen Career Discovery: Phil Hewinson and Would You Rather Be

We’re thrilled to announce our £460k pre-seed investment into Phil Hewinson, and his mission to transform the end-to-end process of finding, and building a successful career. A seasoned operator himself, Phil’s mix of software, and sales skills has seen him drive incredible impact at Microsoft, Google, Facebook and Monzo - one of his many achievements include launching and growing Facebook’s Audience Network to a $Billion ARR in 18 months.

With no shortage of top-tier career capital in his pocket, the founder-market fit is undeniable. Phil was ultimately motivated by using software to drive large-scale social change. Upon his recognition that employment is one of the most powerful tools to alleviate poverty (and the realisation that most people are unhappy with their jobs), he set out to tackle the inefficient and fragmented process of career discovery and development by founding his startup, Would You Rather Be.

Phil approached us with 1 million data points on people’s career preferences, and an inspiring mix of integrity, tech know-how, and a deep understanding of his market. Our studio team is currently working with him to build out his product roadmap, and we’re excited to go on this journey with him.

Welcome to the portfolio, Phil!

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Talk to me about your journey to becoming a founder. Is this your first rodeo?

I came from a state school background, and grew up in North Wales. It was a bit of a bubble.

I studied computer science at Cambridge in 2001, and straight after graduating, ended up launching my first startup, making and selling computer games designed for youth groups with projectors. Unsurprisingly, it was called Projected Games.

The plan was to build and launch in 1 month. 1 month turned into 16 because of feature creep, and other things I had no idea about. When I finally launched...nothing happened. Classic, right? I was devastated. Eventually, I went to 10 conferences across the UK and US, sold about 400 licences, and broke-even ish.

More importantly, I caught the bug for building startups. I got a serious amount of energy from it. But I ran out of money, and recognised that I needed to learn from a bigger company. The plan was to go in-house for 3 years, and then return to founder life.

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How did the 3 years in-house go?

So, 3 years turned into 11. Which sounds extreme, but life happened. I met my wife, got married, we bought a house and started a family. But every day I worked during those 11 years, I was planning on going back and doing a startup again. Genuinely - every day I was thinking about what company I could start.

Remembering my ‘bubble’ of a childhood, and my zero-exposure to startup life, I also didn't know fundraising was a thing. So, the plan was to save enough money to last me 6 years. So for 11 years - before I eventually learned about VC and equity fundraising - I was also trying to save enough to have a 6 year runway. I didn’t quite make it there, but having a big bunch of savings is always helpful.

What was it about running Projected Games that made you so single-minded about launching a startup and essentially drove the rest of your professional career?

I love the freedom of being a founder. I get a huge buzz from building something from scratch. The excitement, the uncertainty, the freedom. Everyday I have 100x more freedom than I’ve ever had in a company, because you can literally do anything. I mean, of course, you stay on mission. That’s key. But there’s a surprising amount of leeway in terms of what you can actually do. That’s so empowering and energising to me.

And, I love software. I love the intellectual challenge and creativity. And I was also fascinated by business and trying to build something that can scale and have a big impact. And the leverage you accumulate when you’ve built something transformative - with the finance, the knowledge and the network you can scale your impact even further. That’s pretty fascinating.

The type of impact I’ve always been driven to have is social impact. I’ve always wanted to use my life to make a difference. It comes back to my faith.

Back to the 3-turned-11-year career. Microsoft, Google, Facebook, Monzo...that’s not a professional history for the faint-hearted. What did you do? What did you learn?

I joined the Microsoft grad programme in 2007. I was young, and mostly excited by the all-expenses paid travel that the programme offered. I mean that, and it was the hottest, coolest tech company that I knew of at the time. I assumed I’d be a software developer, but at the end of the application process was told that they don’t do software development in the UK, and I’d have to join the sales team.

Which I did...and the travel and the people were amazing, but I didn’t enjoy the role itself. Mainly because I was talking about the tech, and selling the tech, but not actually building it. I like the doing, and the building.

Funnily enough, starting my career in sales worked against my ambitions to write code. I tried to move into engineering at Google, but couldn’t crack it due to the sales background.

So my stint at Google was as a Technical Account Manager on the mobile team. I saw mobile as an exciting growth area, and it married well with my love for consumer technology. This was a transformational time in my career. Amongst other things, I was the lead for launching the Galaxy Nexus in Europe, which was the first Android device using Ice Cream Sandwich (a new version of Android).

Google is top-tier at retaining talent. Generous compensation, benefits coming out of your ears, etc. The only reason I left was because I was headhunted for Facebook. And Facebook was hot! But it was by no-means a no-brainer. An incredibly tough decision for a multitude of reasons.

So why did you leave?

Financially I would’ve been better off staying. However, my career philosophy has always been that the most valuable asset people can accrue is by far, what they can do. Some call it skills, others call it experiences. And, for me, changing companies would always significantly increase my learning, because I'm learning about new culture, new company, new business model, new product, new leader. New, everything.

At Facebook I was a partner engineer for 2 years. It was a blast. Travelling around Europe and working with games companies. And it was an unusually high-functioning, high calibre team, which was really cool to be a part of. We Incubated a new product called the Audience Network, which was Facebook’s third attempt at doing an ad network. (Think FB’s equivalent of Google’s AdSense).

It was possibly the hardest work I’ve ever done, and one of the most stretching experiences of my career. And we grew that to a billion dollar ARR in 18 months.

And then just when it may have been time to launch a startup...you joined Monzo.

I took 4 months off paternity leave, and didn’t think about my job at Facebook once. Which is how I knew it was time to leave. I woke up one morning and thought...it’s start-up time. I’ve been waiting 10 years, and now’s the time. But I felt like I needed a Plan B. Especially as I had a lot of career capital that I could leverage.

So, Monzo came to mind, and I successfully applied for a role as Head of Partnerships. My main goal with the role was to learn a lot about product leadership. I wasn’t necessarily in it for the mission, but the mission is brilliant. It aligned with my values.

Post-Monzo, I had 2 years of experimentation, essentially trying to combine software with social impact. I started a blog, to document my efforts. My hope was, although software can be expensive to build, it scales really well, and so can be used to solve problems for very big audiences. Such as extreme poverty, education, mental health and employment.

I worked on a project to raise money for a brilliant charity using a chatbot, but came to the conclusion that it’s really hard to persuade people to give up money for a charity. Which is more of a marketing problem than a software one. I also worked on projects in the areas of education and mental health.

OK, so is it finally time to launch the startup?

Yes. But it’s worth mentioning that 11 years is a long-time to plan to start a company. So I did a few other things during that time, including reading 200 business books. It all started with me reading ‘Entrepreneurship for Dummies’, developing a thirst for new knowledge, and then committing to read a book a week! And I did that for 4 and ½ years.

OK, talk to me about Would You Rather Be.

Going back to my thesis of software being able to solve big problems, employment was the problem that was on my mind the most. I watched a film called Poverty Inc that detailed all of the challenges with Foreign Aid, and realised that the best way to get people out of poverty is to give them jobs.

Inspired by Dave Evans’ book ‘Designing Your Life’, I built an app designed to help people prototype their careers. The app facilitated paid conversations between an operator, and an aspiring operator. But it turned out that getting people to pay for that is hard.

But through this I learnt that career discovery is a real issue. Most people are unhappy in their jobs, and 15% of people hate them. This isn’t a trivial percentage, considering we spend most of our life’s energy working. And it’s both a shame for the person, but also for the organisation they work for, because you’re not getting the best out of that person.

So, I stumbled on our mission: To help people discover, get into, and flourish in their dream career.

And when did you decide to raise investment?

Well by this point, I’d spent months thinking about the idea without committing to it. And that, in itself, is a strain, you know? But I was confident enough that I picked a target that had enough breadth. It’s a rule of business, that most things you try will fail. But I felt as if I’d picked a real problem, that’s broad enough that you could solve it in 100 different ways, and at least 1 of them will work.

I initially pitched Matt Bradley as a result of getting connected through a professional network we were both in. Next step was pitching both him, and Nic Brisbourne. This was the first pitch of my life, and I’d only spent two hours building a pitch deck, inspired by a YC podcast I’d listened to the day before.

To make the stakes even higher, at the start of the meeting Nic said he only had 5 minutes. So then I had to condense my first-ever pitch - where I was asking for half a million pounds - into 5 minutes.

I think I was visibly perspiring.

A big part of your pitch was that you had a million data points on what careers people wanted to go into. How did you collect that?

I built a model that was designed to help people come up with ideas for careers. There were 100 questions, and each question asked you to choose which of the two careers you would prefer to do. After 100 of these questions, the app shows the top qualities you look for in a career and the top careers that match those qualities. It then asks you if you would like to chat with someone doing one of your top careers to explore further.

It took around 3 months, and to my surprise, I managed to get some early traction off the back of a blog post I wrote. Within 24 hours, about 30 or 40 people had completed the survey. So that was my first bit of validation.

I ran a series of tests with paid ads to try and figure out monetisation. I’m still working through this, but what I did manage to crack was cheap acquisition. I think that’s because a lot of people have the problem of not knowing what career to pursue, so I was getting strong click-through rates on my ads. So I acquired 10,000 users to see both how low my acquisition costs would go, and to get a million data points (from each person answering 100 questions), that could later be used to train a machine learning algorithm.

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Why FP?

Well, I really enjoyed chatting to Matt. He got it. I also used to be a mentor for FP50, so there was a loose connection to Forward Partners and Nic. I loved what Dharmesh and J were doing with the Studio, and saw the obvious value that could drive. Up until this point, I’d been on my own! So, to have the money plus a team to support me and bounce ideas around with, sounded amazing.

Signing up for venture, of course, comes with certain parameters. But it aligned with my mission and the size of the opportunity. It is a go big or go home venture. It was also refreshing that FP was willing to back solo-founders, which isn’t the norm in the start-up ecosystem.

Lastly, what’s next for WYRB?

I’m in the middle of a huge learning phase and supported by the studio team, am conducting lots of user interviews as well as customer interviews with professionals, recruiters and training providers. After this, we’re going to start our first design sprint in order to figure out the product roadmap.

And, any advice for first-time founders?

There’s tremendous value in building something and seeing what people do with it. I’m an engineer, so that’s my natural inclination. If you don’t know how to code, you should learn, or persuade a friend or colleague to help you out. If you can’t do either of those two things, maybe you’re not as passionate about the idea as you thought.

Or maybe you’re just at the wrong stage of life. And that’s fine.

Also, remember - the toughest thing about this journey is the psychological aspect. All of the small failures you accumulate along the way take a toll. Especially when you’re alone, as a solo founder. Startup folklore says failure is learning, and failure is progress, but when you want to have an impact, and it’s not panning out the way you hoped, it’s tough.


Phil is hiring for Employee No. 1 - Apply here

www.wouldyouratherbe.com

Shope is a marketer, writer and headshot photographer. As Brand and Content Manager at Forward Partners, Shope executes on our content strategy and works to build our awareness with early-stage founders. Prior to joining Forward Partners she worked at e-commerce and marketplace startups, initially as a content creator at ASOS, before moving onto support Drover and Common Objective with their communications and content. She has a strong interest in consumer brands and sustainability.

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