Skip to main content

An Interview with The Portfolio Collective CEO Ben Legg

We caught up with Ben Legg, founder and CEO of The Portfolio Collective to get his thoughts on the future of portfolio careers;

Can you tell us about your career so far?

You can think about my career in a few different phases. I started my career as a Royal Engineer officer in the British Army for ten years. After that I moved into business, working as a strategy consultant for McKinsey. I then held various sales and marketing exec roles within Coca-Cola, before becoming COO of Google Europe. After Google I held  various tech CEO jobs around the world, before founding The Portfolio Collective in 2020.


What inspired you to found The Portfolio Collective?

In 2019, the year before Covid and lockdown, I quit my day job in favour of my side hustles – various consulting and advisory roles. I was effectively launching my portfolio career, working with a lot of early stage companies as an angel investor, mentor, board member or consultant. I was also working with investors – helping them with due diligence on their investments, helping US investors to find deal flow in Europe and so forth.

Then lockdown began and the great resignation kicked off. Soon my calendar became filled with career coaching Zoom calls with friends and family, as they were fed up with their senior corporate careers and itching for something better. I love helping people, but it was overwhelming my calendar. I then came up with an idea of running “portfolio career workshops”, where I could give people useful advice on how to start and manage a portfolio career. These workshops got bigger and bigger over time.

From there we just kept growing. We had such interesting and successful people in the workshops, they all started collaborating with each other, so there was a clear need for community. Then I realised that I needed to do more to help people overcome the complexity of launching a portfolio career. People would often ask me questions I didn’t know the answer to, like “how much should I charge for my services?”. I ended up with a list of 75 questions I didn’t know the answer to and Google wasn’t very helpful in helping to answer them. Running in the back of my head was a forecasts that I had read multiple times, from multiple sources – that by 2030, half of all workers won’t have a regular day job but rather have a portfolio of work. This was going to be big!

Over 70% of ambitious professionals want to be independent and not work for a big corporate. However, they’re worried about 1) continuity of earnings, 2) their inexperience around running their own business and 3) loneliness. The Portfolio Collective helps tackle all of these things.


How can The Portfolio Collective help portfolio professionals to win new customers?

If you look at most of the successful portfolio professionals, most of their work comes from ongoing relationships, referrals, or inbound leads through having built a personal brand. We help members with understanding the value of their knowledge, skills and network, then defining their offering, building their personal brand, growing their network, showcasing their portfolio and winning work. Some members keep their day jobs for a couple of years, whilst building up their side hustles and portfolio careers. Then over time they reduce their time commitment to their ‘main gig’ in favour of their side hustles.

We also help people looking for work – perhaps if they’ve been made redundant and need to find work quickly to pay the bills. We help them know where to look and how to optimise their chances of success. We also have many employers search the profiles of our members looking for talent.


Are platforms like LinkedIn and Upwork competitors to The Portfolio Collective? Or are you trying to offer something complementary to them?

I don’t think they are competitors – as our purpose is to help portfolio professionals in any way we can. If having a LinkedIn or Upwork profile is helpful to them then absolutely we recommend that they do it.

We are a community that wants to help people think through who they are and what they do, then help them to collaborate and learn together. We have a hugely diverse community on our platform and that’s something we’re very proud of. We find that the more you help people, the stronger that community becomes.


We are a community that wants to help people think through who they are and what they do, then help them to collaborate and learn together.


One of the criticisms of LinkedIn is that it has perhaps become too big and too noisy. How do you avoid losing that sense of community as you grow?

With 7,300 members globally, we are much smaller than LinkedIn, and we’re not trying to be the biggest platform. All of our members want to be part of the community, they’re not there to sell or show off. We shut down bad behaviour very quickly – if people are overly sales-y or otherwise dodgy, they get shut down fast. Absolutely you can sell on the platform but it must be done in a professional, helpful way.

Many people use the platform to ask important questions about their careers. You can always find articles, courses or experts that address your concerns. We’re starting to create specialist groups to make it even easier for members to find the right experts quickly.


Do you think that the Covid pandemic has made a lot of people re-think what they want to get out of their careers?

Definitely. During the pandemic when a lot of people were working remotely, they had a chance to re-evaluate what they wanted from their careers.  Work-life balance, spending more time with family, and having good health became priorities for many people. You could say that “life is a portfolio” – where you have to balance all of these important things.

During lockdown people realised the risk of working for just one company. They also became more entrepreneurial. Historically, working in one company for decades was the best way to get financial security and a pension, but now everyone is aware that even big companies lay off people and your skillsets might become useless if you spend too much time in one company. You need to hedge your bets by having multiple income sources and versatile, entrepreneurial skills.


As people increasingly pursue portfolio careers, does that mean we have to evaluate their skills in a different way? Historically we were told to avoid job-hoppers, and judge candidates by their tenure and achievements with prestigious companies – but this doesn’t feel like the right way to evaluate the skills of someone pursuing a portfolio career.

Indeed – let’s say that someone is an expert in product marketing and helping start-ups to find product-market fit. Listing a chronological career in a traditional CV/ LinkedIn type format doesn’t make sense for them. It would be better for them to say “Here are the 10 start-ups that I helped to reach Series A funding”.

It becomes more about your skills, your portfolio of work, your referrals, rather than how long you spent working for company X. I think one of the major benefits of our platform is that it makes it much easier to showcase your experience as a portfolio professional in the right way.


Do you think that it’s easier than ever before to start your own business?

Absolutely – you can set up a limited company online in 15 minutes at a total cost of £12. It’s easy to find website building or accounting software online and get up and running. At The Portfolio Collective, we focus on helping you build your business – helping you to find the best way to monetize your skills, helping you to network with others, discover how much to charge your services, learn how to win work and so forth.


What is your vision for The Portfolio Collective in the future?

We’re not aiming to be the biggest platform, but rather build an awesome network of people who are senior, diverse and collaborative. Between them our members can solve any problem. We want our community to be able to help all of the start-ups in the world with mentors, advisors, board members, functional leaders, consultants and so forth.  Our research suggests there are about 62,000 start-ups in the world between Seed and Series B funding, and I’d like to think that in the future we’d have a member of our community (or more) helping each one of them. We’d like to grow our user base, whilst ensuring that our members remain smart, collaborative and have low egos but high EQ. If start-ups need amazing talent, they should come to The Portfolio Collective.


“We’re not aiming to be the biggest platform, but rather build an awesome network of people who are senior, diverse and collaborative. Between them our members can solve any problem.”


To those who have never used The Portfolio Collective before, how easy is it to set up your profile?

You can set up a basic profile in about 15 minutes, or you could spend up to a couple of hours to really showcase your offering and experience. Our profiles aim to help people describe their portfolio careers. It’s less about the long list of jobs you’ve done and more about the skills and passions you bring to the table and the evidence of those skills and passions. It’s almost a one-page website that explains you a portfolio professional.


See other interviews with leading industry experts on our site, including;