Xoogler.co: How to Launch your Portfolio Career with Ben Legg

James Cashen
Published in
3 min readAug 17, 2020


Ben Legg joined over forty Xooglers this week to speak on the growing solopreneur and freelancer community and how to capitalize on the movement. Thank you to Xoogler Alex Papageorgiou for organizing this community and hosting these events!

Ben’s Background

Ben has a career that is incredibly broad and diverse as he has explored new options every decade of his professional life. Ben was an army officer for the Royal Army in the 90’s, an analyst for McKinsey & Company in the 2000s, COO of Google Europe in the 2010s, and now Founder & CEO at Digital People International.

The 2020 Effect

The future has been brought forward by 5–10 years due to the Coronavirus Pandemic. We have quickly transitioned to working from home, remote education, and contactless payments among many other developments. How do we navigate this new reality? Ben points to portfolio work as the solution to this quickly shifting job market.

Why is portfolio work booming?

Permanent roles are reducing sharply due to a range of issues including high unemployment, likely bankruptcies, limited open positions, and overall lower odds of landing a permanent position. While permanent positions are declining, portfolio work is emerging as a promising alternative by enabling people to monetize their specialized skill sets. Specializing is key, for example copywriters make an average of $30 per hour while a more specialized position of ghostwriter for a CEO makes an average of $250 per hour. There is less competition for these positions, startups keep hiring part-timers, and temporary positions are much easier to land than permanent positions. A staggering 50% of all adults will be gig economy workers by 2030.

Three Steps to Start a Portfolio Career

  1. Define Your Value
  • Identify your monetizable skills, the more unique the better
  • Optimize your LinkedIn and connections. Maintain a competent profile, be active and interact with your connections, and make 30–50 new connections a week.
  • Brand yourself. Presenting a consistent brand across all your platforms can increase revenues by up to 23%.

2. Announce Your Arrival

  • Set up your company and business foundations. Create your company name, map out personal and business budgets, and outline your financial goals.
  • Launch your website as having a website increases trust and confidence from consumers.
  • Determine your digital marketing strategy

3. Generate Income

  • Identify the right platforms to find your first paid project. Platforms run by Xoogler CEOs include Scoodle (Ismail Jeilani), GLG (Paul Todd), and Worksome (Morten Peterson).
  • Manage your bookkeeping and taxes. Consider hiring an accountant to ensure that your filing goes smoothly and to minimize the time you spend on filing taxes.

Final thoughts

It makes sense to pursue a portfolio career even if you are currently a full-time employee as it can help you broaden your skills and learn how to market yourself. Portfolio careers offer flexible hours, time to learn and hone new skills, quick and easy money, and can eventually lead to full time offers. The ideal portfolio career is comprised of a mix of longer contracts with occasional short project work on the side. If you are interested in learning more about setting up your portfolio career through Ben’s expertise, visit www.portfolio-collective.com for more information on their next four week catapult course.