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, he took a step back from full-time work to focus on a set of exciting 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 the “third phase” 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 his current approach to work and his criteria for selecting the right projects for his expertise.
Darren Huston’s Phased Approach to Leadership
Huston feels his career isn’t 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.”
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 knows all too well 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 to sharing his expertise with growing businesses — albeit with a strategic approach. He receives new business opportunities on a near-weekly basis and can’t accept them all. Huston and his business partner, Alex, assess each project based on several criteria to find the right fit.
“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, so he only accepts invitations with the promise of fun. However, he avoids anything too wild or with potential regulatory issues. “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 passes the fun and digital criteria, he looks at whether his addition to the board would bring 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 where it added $2 billion in value (possibly the upside that a PE firm might share for an excellent outcome), that is like owning 100% of a company where you added $100 million in value. By the way, both still take a tremendous amount of work, but goes to show that value creation in smaller private businesses can be just as lucrative.
Darren Huston’s final criterion is a business’s growth potential. If a business is only interested in cutting costs, it likely isn’t a fit for Huston’s 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 return his portfolio to four projects. That 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 an intentional approach that allows him to give deep focus and energy to just a handful of projects. While it’s tempting for executives to take on every project that interests them, Huston believes knowing when to draw boundaries is the mark of a successful leader.
He often looks to other entrepreneurs and business leaders who intentionally limit their projects. “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 ensure each venture gets a decent amount of attention, but it also increases Darren Huston’s passion for the projects. He’s in it for the long haul and can dive more deeply into each project.
Darren Huston’s Blueprint for Late-Career Success
After a career spanning multiple countries and sectors, Darren Huston feels the new phase of his career is just beginning. Instead of 60-hour weeks, he spends 30-40 hours a week working on a handful of fun, growth-ready projects he loves. Huston’s selection criteria ensure he adds value wherever he goes — with plenty of room for personal growth 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!”