Building a portfolio career: The story of how Ben Legg transitioned from his own corporate job to helping people like him find career freedom

Written by Tom Fairey

14 March, 2022

Ben Legg got his career start as a royal engineer at Sandhurst, traveling the world and building secure structures, before joining big business sales and marketing ventures globally, working for the likes of Coca-Cola and Google.

When he joined Google, the company was somewhere between a startup and an established venture. There were 1,000 employees based in Europe, and while the company had billions in operating capital, its core was in chaos, with the company still dealing with fine details like ad types, how to fit ads and maps together, how to handle different currencies, and how to handle different sized companies.

After three years, Legg left Google to serve as a tech CEO in places like Amsterdam, Kansas City, and New York, becoming an expert in advertising technology. But the industry was quickly becoming dominated by Google, and Legg realized he liked earlier-stage ventures. So he downsized and wrote strategy for Ola, a ride-hailing service based in India, and while Ola was successful, he eventually resigned.

“I had all these certain things spinning on the side taking up more and more of my time, and I enjoyed it,” he told me for a recent episode of my podcast, Back Yourself. “I wanted to help founders build great companies.”

Listen carefully to what Legg said.

Being successful in business to a large extent means pursuing your passion, not someone else’s.

This launched a new chapter in Legg’s life. He began angel investing, mentoring, and consulting — some of it paid, some of it not.

“My DNA is, I’m a builder,” he said. “That’s what I love to do.”

During the lockdown, Legg found that many family and friends came to him and asked for career advice — maybe they’d been laid off, maybe they had more time to think about their future and their goals. This turned into more than just a casual hobby — soon, he was getting four or five requests a week. He pivoted quickly, and soon, when anyone asked, he sent them a link, and instead of individual sessions conducted a once-a-week webinar.

People, Legg discovered, did not want a general chat, they wanted specific advice on how to replicate what he was doing, which he soon learned had a name: a portfolio career.

A portfolio career is a working style that combines multiple income streams, mixing full- and part-time employment as well as freelancing and consulting. As opposed to a gig career, where a worker will piece together bits of similar work to approximate a more flexible version of a full-time job, a portfolio career can be a lifestyle choice that takes the worker in several directions at once: for example, the portfolio careerist might consult, develop a product, and freelance write, all in different domains.

Legg launched the Portfolio Career Workshop and started charging attendants a small fee for the weekly Zoom classes (he sent the link for free to friends and family). The Portfolio Career Workshop was just one part of Legg’s own portfolio career until a webinar participant one day told him his message needed to be a full-time career. He slept on it and the next morning launched it as a business, bringing his portfolio career full circle into a startup. Legg proved himself to be a founder.

A founder is someone who finds a solution to a problem.

When it comes to creating a portfolio career, not everyone has an idea, but a lot of people have tons of great skills. Legg thinks of his company as doing what accelerators do for startups, but instead applying it to human potential and creating a life-long skill set.

Many members of his workshop are executives from huge corporations who hit a certain point in their career and realized corporate life was not for them. Others were C-level executives at startups who weren’t quite ready for retirement and liked the idea of working at not one but a number of startups. Still others are doctors, lawyers, and creative types who want to diversify.

“They come to us because they have hit a certain point in their career and said they don’t want this kind of corporate life, the one that I thought I wanted when I left university,” he said.

In all of his time with startups, Legg has come to see common problems which many face — and these by and large are easily addressable if identified on time:

  1. Not forecasting cash flow
  2. Hiring in a hurry — and too often hiring wrong
  3. Polishing plans without ever putting them in place
  4. Obsessing over contracts and legalese before winning any customers

Hiring in a hurry can cost startups a tremendous amount of capital — both time and money. Hire the wrong person and you could be set back six months or more. To get the right person, Legg counseled, you should write the job description thoroughly, get buy-in from the people who matter, post the job description in the right places, get a long list of people, whittle it down properly with surveys or questionnaires, and do rigorous case studies and culture fit for the final top candidates.

These are all solid observations. 

Legg uncovered the secrets to startup success:

  • The best teams build the best companies.
  • You have to experiment.
  • Hire the right people.
  • Don’t run out of money.

Legg gives one piece of advice to almost everyone: remain paranoid.

“The moment you think you’re doing fine is the moment you start slipping,” he said.

This thinking is key, he said, to remaining ahead of the competition. Be restless, be edgy, and don’t just think that because sales are going good this month they will go good next month.

The Takeaway

Legg has found success in business because followed his passions, did not accept off-the-shelf answers, and found ways to solve problems that no one else had. Along the way he happened into a career that he did not know had a name and helped hundreds of like-minded entrepreneurs break free from the daily grind to realize their full potential.

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