Late-Stage Career Strategies

How Darren Huston Picks New Projects

Experienced executive Darren Huston is no stranger to 60-hour work weeks or the grind of hustle culture. After an illustrious career as an executive at McKinsey & Company, Starbucks, Microsoft, and Booking.com, Huston took a step back from full-time operation to focus on a set of inspiriting and largely successful passion projects. “I actually thought I’d retire when I’m 55, and now I’m 57, and I could see going until I’m 70 just in what I do because it keeps me busy and I really, really enjoy helping others succeed in business as well,” he says.

In this tertiary span of his career, the business leader currently serves as CEO and founder of BlackPines Capital Partners; Executive Chairman of GameAddik and Operto; and Chairman of The Knot Worldwide, Allegro, and Skyscanner. Huston shares the principles of his current approach to his work and his criteria for selecting the right projects that intrigue and utilize his expertise.

Darren Huston’s Phased Approach to Leadership

Huston feels that his career is hardly ending, but rather transitioning into a new phase. “I think in your career, you have three phases,” he explains. “There’s the early networking and figuring out, ‘What am I really passionate about?’ And then there’s a second phase of taking it as far as you can take it, the passion that you’ve discovered. The third phase is sharing it with others, and that’s the phase I’m in now.”

Jargonistically enough, three would appear to be the charm for the busy executive. “I have sort of a plural career at this time,” Huston explains. “I’m Chairman of five companies right now. Three of them were more chairman-for-hire roles, so I was brought into private companies to have successful exits.  The other two I am the Chairman and majority investor.”

Darren Huston’s 3 Criteria for Selecting New Projects

Huston is extremely familiar with how much energy is required to grow and exit a business successfully. “I get a lot of joy out of what I’m doing now, which is winning with others, helping others,” he says. Not one to rest on his laurels, the executive pivoted into the venture of sharing his expertise with growing businesses — albeit with a strategic approach. Huston receives new business opportunities on a near-weekly basis; but cannot accept them all. Huston and his business partner, Alex, assess each proposal based on several criteria to perfectly suit their interests and endeavors.

“No. 1: Is it fun? Are the people around these interesting people? Are we going to personally get something out of this that makes our lives better and happier?” Darren Huston says. He can be picky about his projects, and he only accepts proposals that repose on the basic promise of fun. However, he avoids anything too frantic or with potential regulatory consequence. “Is it in a space that’s a vice? I don’t do booze or cannabis or gambling,” he adds.  “And, is the primary value driver digital?  This is where I would likely add the most value.”

If the opportunity advances through both the fun and digital interest criteria, he looks at whether his addition to the board would increase monetary value to the business. “I have one simple lens, which sounds a little greedy, but it’s not that. Could I, working with this leadership team, create $100 million worth of value? And that’s what convinced me that even doing the smaller businesses with big stakes for both myself and the business leaders, was still stuff worth my time,” he explains.  For instance–and it is this simple: If the leadership team owns 5% of a company and were to add $2 billion in value (possibly the upside that a private equity firm might share for an excellent outcome), it is comparable to owning 100% of a company where you added $100 million in value.  On a related note, both still take a tremendous amount of work, but illustrate that value creation in smaller private businesses can be just as lucrative as larger companies, especially when your heart is in it.

Of corresponding importance, Huston’s last criterion in project selection is a business’s potential for growth. If a business is only interested in cutting costs, it likely isn’t an apt object for Huston’s selective and passion-driven leadership style. “I love growth versus reengineering and cost cutting, so I generally tend to lean into that kind of thing,” he says.

Preserving Energy and Focus With the Four Islands Principle

While Darren Huston currently serves on five boards, he’s soon exiting Allegro to rationalize his portfolio to four projects. This isn’t by accident. “I can only have four seats around my table,” he explains. “I know when it’s five, it feels just too much, but my sweet spot is four. I call them islands. It’s an island that I believe in that has value, that is worth engaging in, but I can only do four of them. And if anyone presses me to do five, six, or seven, I know to say, ‘No, sorry. I just don’t have the capacity.’”

Huston’s ‘four islands’ principle is a prudent and intentional approach that allows him to give ardent focus and energy to a manageable handful of projects. While it is tempting for executives to take on every project that peaks their interest, Huston believes that knowing when to draw boundaries is an imperative characteristic of successful leadership.

He often looks to other entrepreneurs and business leaders who deliberately limit their potential ambitious endeavors. “With the help of my business partner, I looked at a few other people who do this kind of plural investing,”  he explains. “The best and most successful, for whatever bizarre reason, always have four things, and if they’re looking at a new thing, then they’ve got to exit an old thing. They all seem to max out at four.” Because of this, not only does this specification method ensure that each venture gets a practical amount of attention, but it also increases Darren Huston’s wholehearted enthusiasm for his projects. He’s in it for the long haul, and can delve more deeply into each of his desired projects.

Darren Huston’s Blueprint for Late-Career Success

After a career spanning over multiple countries and sectors, Darren Huston feels that a new phase of his career is just beginning. Instead of formidable 60-hour weeks, he spends 30-40 hours a week working on a digestible amount of fun, growth-ready projects that he holds great zeal for. Huston’s selection criteria ensures that he adds exceptional value wherever he goes — with plenty of room for personal growth and fulfillment along the way. “That’s part of the joy of it,” Huston says.  “I ask… what do I love to do, and why am I here on this planet?  And that thing is growing digital businesses.  That’s what I enjoy and I hope to pass whatever I can down to others!”