I recently read the latest autobiography of Richard Branson, Finding My Virginity. For those of you that don’t recognize his name, Richard is best known as the founder of the Virgin Group, a conglomerate of Virgin brands such as Virgin Records, Virgin Atlantic, Virgin Mobile, Virgin Galactic, and 400 other companies.

Sir Richard Branson is also a knight of the United Kingdom. In addition to being a billionaire entrepreneur, he’s an adventurer, philanthropist, and all-around troublemaker. I’m not as capable as Richard Branson, but I found myself aligned to his way of thinking more than I expected. As a reflection, I’d like to share the leadership lessons I learned.

Take calculated risks

Richard is an adventurer at heart. He kitesurfs, climbs mountains, flies hot air balloons around the world, skydives, and jumps off buildings, among other pursuits. I have similar passions and would love to do most of the things Richard has done. I wrote a blog article about my adventurous pursuits. Check it out here: Be a Hero: The GoPro Approach to Leadership.

Extreme sports aren’t the only outlet for Richard’s adventurous heart. He brings it to his job every day in the form of calculated risk-taking. Playing it safe leads to irrelevance and mediocrity. Being reckless leads to ruin. The secret is to live life just slightly on the safe-side of reckless. How do you know where that is? Richard has figured that out. He has cheated death in life and in business countless times. That’s not just luck. That’s good risk management. Richard has developed the skill for this judgment and knows how to use it.

As a technology leader, I need to push the limits of what technology can do for my business so we can achieve our mission. I also need to keep the lights on our operation and cannot put our business continuity in jeopardy. My love for adventure sports is congruent with my technology leadership style. Enjoy the thrill, push the limits, and get home safely.

Be irreverent

Richard Branson’s roots are about as irreverent as you could imagine. His first significant business was Virgin Records, which became a major success when it signed the Sex Pistols. By mainstream business standards, the music industry is irreverent all by itself. Within the music industry, punk rock is about as irreverent as you can get. Richard’s entrance into the business world couldn’t have come from a more counter-cultural place. Even the name Virgin was meant to imply that they were new entrants to the business, and not from the establishment.

The emphasis here isn’t the bad behavior, but more of being an outsider. Often this manifests as style more than substance. For example, Richard absolutely abhors wearing ties. Also, when it came to promoting his new business in public, he always took the approach of asking for forgiveness rather than permission. Establishment society doesn’t always like irreverence. But he didn’t let that bother him.

The world of enterprise technology has its own norms and establishment. We like waterfall development. We organize in silos. We’re comfortable with command and control management. We wear suits to important meetings. We stay quiet when we disagree with management. We give dry presentations with slides containing lots of bullets.

My irreverence looks a little bit different than Richard’s, but it’s still there. I’m a punk rock fan, but from a generation later than Richard’s. I let my geek flag fly in business settings. I give business presentations in-costume. I challenge traditional management thinking and practices at every opportunity. I break down functional silos and build DevOps.

Underserved markets are ripe for disruption

Richard Branson’s business strategy was to look for market opportunities where he was being underserved as a customer. He despised his airline experience, so he created an airline. He didn’t like his mobile phone experience, so he started a mobile phone company. He didn’t like riding commuter trains in England, so he created a train franchise. There are hundreds of additional examples of this.

The Virgin brand is a customer experience brand. It removes the inconveniences you hate, adds new experiences you love, and breeds intense loyalty across a variety of companies. This isn’t a genius business strategy. Anyone could have thought of this. In fact, companies that compete with Virgin, don’t exactly set out to be inconvenient and loathed brands. They just got that way over time. Virgin is a motivated and aggressive disruptor. Sure, anyone can do this, but it’s really hard. Virgin does it well, over and over again.

Enterprise technology is a market ripe for disruption. Enterprise businesses typically don’t love their IT department. They use it because they have to, sort of like going to the DMV to get your license renewed. Enterprise technology leaders have a real opportunity to turn that around. We have to learn to create the cloud experience inside the enterprise. We also need to be the digital entrepreneurs that attract investment from our business.

Build your team

Richard Branson doesn’t run his businesses, he recruits great people to do that for him. It takes discipline to stay high-level, and delegate to people you trust. This allows Richard to do only what he can do. Micromanagement doesn’t scale to 400 companies. Richard does this really well compared to another leader I profiled recently. Check out my blog on Elon Musk, for an example of what not to do.

As a technology leader, I love building a team. As a technologist, I love getting into the details to understand how things work. What made me successful as a technologist could sabotage me as a leader if I let it. I consciously and continuously let go of details and support my team through a servant leadership style.

Be generous and mission-oriented

It’s often the case that successful business people make a ton of money, and once they achieved their primary goals, they become philanthropic and give back to society. This is not the case for Richard Branson. He’s been very generous and focused on advancing world-changing ideas from on the onset. In fact, he sees his business as a means-to-an-end. He wants to change the world. Business is an excellent vehicle to achieve that in some cases, or generate the capital to do it, in other cases.

I try my best to lead a generous life both at home and at work. I try to be a servant leader. I write this blog as a gift to the community. I work hard to provide a positive work experience through the way I lead my team. I don’t know if I’m going to change the world, but I’m going to try my hardest to change the world around me for the better. I want to give more than I take.

Family comes first

For being such a wild adventurer, Richard Branson is pretty normal and boring when it comes to his family life. He’s been married to the same woman for a very long time. He is very close with his two children, which are both married, and his three grandchildren. He calls himself “grand-dude.” When he is on vacation with his family, he doesn’t take business calls.

Here’s one of his stories that impressed me: Once when Richard was giving a presentation, his phone rang. He picked it up because it was his daughter. She was calling him because she was accepted into university. He took the call right on the stage in front of everyone.

It’s pretty amazing to hear about a billionaire business tycoon that has a family life. It doesn’t seem possible to have it all. Most successful business persons sacrifice their family, but not Richard. While not common, it’s nice to know it’s possible.

This is certainly a good reminder. I’m not running 400 companies, but I often feel like my work is pretty important and it can be difficult to prioritize my family, especially if they were interrupting me in the middle of one of my presentations. I’ve gotten a lot better at unplugging during vacation time. Family is #1. It’s easy to say, but takes discipline to practice.

Those are my leadership lessons from Richard Branson. He’s achieved a lot in his 67 years and there’s a lot to be learned. He’s not just lucky, but chose to do things differently and challenge the norm. I’ll try to do likewise in my own way. How about you?