Mindfulness & Entrepreneurs: How Meditation Makes You a Better Leader

Research in entrepreneurship claims that mindfulness can boost innovation, enhance decision-making, and improve management skills. Some suggest that mindful meditation helps founders spot opportunity. Can regular meditation improve your leadership abilities and enhance your business acumen by making you more mindful? We sat down with Matthew Bellows, a serial entrepreneur who has been cultivating successful businesses and practicing mindful meditation for decades. In a conversation with Shikhar Ghosh, Bellows shares insightful takeaways about the benefits that mindfulness can have for entrepreneurs at any stage. And he offers some basic tips on how to start applying meditative techniques in your daily life. 

What is Mindfulness?

Practicing mindfulness helps you build or maintain a foundation. For Bellows, it provides, “a sense that you have a ground to come back to.”

Mindfulness is very simply the ability to hold your mind—your attention—on some particular problem or task or opportunity.

Matthew Bellows, Founder and CEO

Applying mindfulness techniques and meditating daily has helped Bellows weather the extreme highs and lows that all founders experience. “So much about the startup experience pulls you one way or the other,” he observes. Personal experience has led him to conclude, “everything having to do with the company can be informed or improved by being able to be more mindful about it.”

Mindfulness and  Entrepreneurs

How does mindfulness benefit entrepreneurs? Bellows learned that being fully present and focusing his attention on a particular problem, task, or opportunity enhanced his ability to lead. Practicing meditation or mindfulness regularly can improve your communication. It allows you to be more observant when engaging with customers. Mindfulness can aid you in designing products and pitching to investors. Being mindful can improve your hiring decisions and communications with your team. 

Everything having to do with the company can be informed or improved by being able to be more mindful about it.

Matthew Bellows

Mindfulness,  Innovation, and Entrepreneurial Success

How does it work? Bellows began practicing mindfulness meditation around the same time as he became an entrepreneur. Now on his third venture, BodesWell, a financial planning company, he credits his success to mindfulness. His first startup, WGR (Wireless Gaming Review) Media, Inc.—a pioneering company that provides gaming previews, editorial reviews, and insights for mobile gamers—was acquired by CNET. Under his guidance as CEO, Yesware—the second startup he co-founded—became a leading email productivity platform. It serves over 60,000 salespeople at companies like Box, Salesforce.com, Twilio, and Yelp.

Resilience and Insight

In 2018, after spending over eight years building Yesware, Bellows shocked many when he announced his decision to relinquish his role as CEO. He had built and grown Yesware impressively. But after years of practicing meditation and mindfulness, he began to realize that he was not the best person to lead the company through its next aggressive phase of growth. Armed with that insight, he transitioned to Chairman of Yesware’s board and supported hiring a professional CEO. Such gracious and amicable resignations rarely occur.

Research on founder-CEOs shows that, within three years of receiving investment, 50% of founders no longer held the role of CEO. In nearly 90% of the cases, the startup’s board of directors replaced the founder with a professional CEO. Typically against the founder’s wishes. Often, ego prevents founder-CEOs from seeing that requisite leadership skills change as companies rapidly scale. Practicing mindfulness gave Bellows insight to realize that the company needed a leader with a different skill set to grow exponentially. Instead of focusing on his personal position or ambition, he chose the best course of action for the company.

The ability to hold your attention on a particular problem is  helpful when talking to customers,  when planning a product, when talking to investors, and when hiring employees.

Matthew Bellows

Choose a Technique that Matches Your Personality

In what practical ways can someone begin to develop a practice of mindful meditation? Bellows recommends choosing something that feels natural and to start slowly. Not everyone will gravitate towards sitting meditation—what Bellows practices—right away.

Traditional Seated Meditation

Some people—especially high-performers—approach seated meditation skeptically. Dan Harris, award-winning co-anchor of ABC News’ “Nightline” and the weekend edition of “Good Morning America,” was intrigued by the anxiety-reducing benefits of meditation. But he feared that embracing a meditation practice would cause him to lose his competitive edge. After years of experimenting with various types of seated meditation, Harris wrote the best-selling book, 10% Happier: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge. He then founded a startup with a platform geared to teaching others how to incorporate meditation into their busy lives.

Meditative Activities That Enhance Mindfulness for Entrepreneurs

Many busy entrepreneurs, like Harris, don’t feel convinced that seated mindfulness meditations will work. You can practice mindfulness using other techniques. “Whether you choose a martial art or running or sitting meditation or yoga,” Bellows, believes that entrepreneurs can benefit routinely practicing mindfulness in a way “that is uniquely you.”

After finding an activity that resonates with you personally, he notes, you must practice consistently and incrementally build the skill. Then, “there’s a sense of, ‘Oh, I can actually do this.'” Once you embed the practice into your daily routine, he notes, “you start to feel this foundation to come back to” and apply at other times throughout the day.

Getting Started with Seated Meditation

If the results of meditation sound great, what’s the best way to start? Ghosh wonders, “should you go on a weekend retreat to get that first inertia out of the way?”

Bellows cautions that, for many, starting with an immersive approach, like a weekend retreat for seated meditation, might do more harm than good. Starting small—with a commitment to practicing for just five minutes a day and sticking to the commitment—yields better results for most people. He adds, “if a great friend says, ‘Let’s go on this retreat together.’ You don’t have much to lose. It’s not going to be terrible.” But he analogizes, “you wouldn’t want to go and run a marathon on your first day of jogging. Sitting meditation’s the same way.” It’s more effective—and you have a better chance of sticking with it—if you build up incrementally.

Using Technology to Start Incrementally

Today, thanks to technology, ways to try meditation proliferate. Apps like the one Harris’s company launched, 10% Happier, have created an online community in which expert teachers can walk members through the basics, “one breath at a time.”

Similarly, the app Headspace promotes “mindfulness for your everyday life” by offering guided meditations on a number of topics, including, enhancing creativity, optimizing performance, letting go of stress, sleeping better, and many others. Other popular apps, like Insight Timer provide free access to some guided meditations. They introduce people to different mindfulness practices five to ten minutes a day.

Commit to Mindfulness & Practice Regularly

One of the most important aspects of meditation is practicing consistently so that mindfulness becomes a habit. Bellows makes an analogy to running. “You get the shoes, you go for a run. You come back. You feel exhausted. You feel great. The next day, you have to do it again. And that’s often—for me—the hardest part.”

For Bellows, making the practice a habit—”getting the practice into your body” is essential. As with any practice, some days will seem easier than others. You need to commit to making mindful meditation a priority. Designating a specific time to practice each day can help you build that habit.

Consistency Yields Results

Bellows practices sitting meditation for about a half an hour a day, “either in the morning before work or in the evening before I go to sleep.” Depending on what’s happening on a particular day, he might meditate for a longer or shorter and, he confesses, “some days I don’t do it at all because things are just too crazy.” But typically he meditates at least five to six days a week for 30 minutes at a time. That way, each day he knows “I did one thing to help me ground myself and get back in touch with my core.”

Mindfulness Helps Entrepreneurs Withstand Extremes

The founder’s journey is riddled with unexpected challenges and prolonged stress. You will experience extreme emotional highs and lows as your business grows. Research shows that founders are twice as likely to struggle with depression and 3x to 10x more likely to experience other mental health disorders than the general population. “The ability to take care of yourself is a big success factor,” Bellows observes, “in making it for the five or ten or twenty years sometimes you need to build a big company.” While he admits that it would be challenging to start a sitting meditation while starting a company, he encourages all founders to find some practice to do for themselves.

Starting a business is very difficult,  so the ability to take care of yourself is a big success factor in making it for the five or ten or twenty years sometimes you need to build a big company.

Matthew Bellows

Regular Practice Can Temper Reactiveness

Why does practicing regularly matter so much? Ghosh presses, “What happens if, for an entire week, you stop meditating? Do you find that there’s actually a difference in who you are, how you relate to others, how you relate to the problems?”

Bellows reflects that, when he doesn’t meditate, he becomes more forgetful. Those around him recognize a change in his behavior as well. “My wife, particularly, is really tuned in now to the fact that I can miss stuff.” Primarily, he notices a large difference in how he responds to people. “I’m less mindful in my speech. I’m less aware of what I’m saying. I’m more reactive.”

He confesses to losing patience more easily. “Somebody’ll say something and I just lash right back.” In contrast, when he’s meditating regularly he feels “a little more space between the action and my reaction. And having that space then gives me the option to say, how do I want to respond to this person?”

Apply Mindfulness Techniques to Challenges in Your Daily Environment

What happens when you’re in the middle of a stress-provoking situation? Perhaps your startup is scaling at an unprecedented rate. You’ve become sleep-deprived and feel pressured to make critical decisions. But you lack time to consider all options.

Maybe you just ran a beta test and the results differed dramatically from your expectations. Or perhaps you dread an upcoming conversation with a difficult board member. What if you’re having a deep conflict with your co-founder and have to part ways?

Mindfulness Can Help  Entrepreneurs Prepare for Difficulties

At times when the stakes—and emotions—run high, it’s easy to lose perspective and become reactive. Mindfulness can help entrepreneurs in those situations by creating some mental distance between you and the challenge.

Bellows walks us through his process for preparing for an extremely challenging situation—firing a co-founder. Watch the video to do a three-minute guided meditation to prepare for a stressful situation. Or read the summary below the video.

Mindful Meditation Can Help You Stay Focused During Challenges

Many people prepare for stressful situations like that by rehearsing what they will say. “First I’m going to say X. Then, if he or she says Y, I will do Z.” Preparing with a short meditation does not entail mentally reviewing your conversation. Instead, it prepares you to listen to another’s perspective.

Bellows underscores that preparing with meditation doesn’t negate the traditional actions a founder would take before such a meeting. In the case of firing a co-founder, that would include long-term actions like talking to the board repeatedly over time. It would involve short-term action like reviewing the compensation package with HR and gathering forms they need to sign. But practicing a mindful meditation enables you to “have a genuine human interaction with the person, as a sign of respect for them and for your relationship.”

Mindfulness Can Improve  Communication

Often—especially if you’re busy building a company—you learn to be strategic. You plan what you’ll say or how you’ll respond to a request. Practicing mindfulness has helped Bellows communicate better by providing space to truly listen to the other person instead of sticking to a script he mentally prepared or reacting. He explains, “after the person speaks, I give them a moment—I let them finish speaking, and then reply.” He suggests that while someone else speaking, whether it’s via a webcam or in person, it helps to look at them in the eye and “sort of admire them—in the sense of appreciating them” as you would a film.

I give better answers if I let the person finish speaking than if I try to jump ahead with what I think they’re saying. As often as not, my guesses about what you mean are worse than giving you the chance to finish your sentence and pausing  to consider what you actually meant.

Matthew Bellows

He elaborates that, if you’re the CEO—or in any customer-facing role—being mindful can help you listen to your users. It can increase empathy and help you understand their perspective. Feeling truly heard is rare in our society and he notes, “it’s a differentiator to just listen to what they’re saying. It’s amazing how powerful that is.” For many of us, it takes a lifetime of practice, not to preplan conversations.

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