There Are Three Entrepreneur ‘Personas,’ But Only One Can Thrive


7 min read

Opinions expressed by Entrepreneur contributors are their own.


In the world today, there are over 500 million entrepreneurs, making up about eight percent of the global population. While some might view as a dream career full of excitement, it is not a road free from challenge. And yet, seldomly is light shed on a major hurdle many entrepreneurs encounter. This is the challenge of .

In fact, according to a study by Michael Freeman, entrepreneurs are 50 percent more likely to report having a mental health condition. And yet, we still struggle to talk about it.

Breaking down the mental health of entrepreneurs

Mental health is complex. It operates on a spectrum and it can change from day to day, or even in a moment’s notice. I have witnessed this throughout my experience in entrepreneurship, studying the science of brain health and mental wellbeing at Heights. I interviewed over 100 entrepreneurs on Secret Leaders, and have hosted dinners with over 500 founders. Through it all, I have identified what I would describe as three recurring “personas” among entrepreneurs. I’m not a mental health professional and these are not official diagnoses. But these are types that I have observed:

1. The “slaying it.” These entrepreneurs go around telling others that everything is awesome and that they are slaying/killing/smashing it.

2. The “Podoromo Timer.” These quieter entrepreneurs keep their heads down and focus on measuring their mental performance and productivity with apps and Pomodoro timers.

3. The “Open Ones.” Those brave few who are willing to open up and be honest that they are struggling inside. 

The truth is, in my experience, the third group represents most founders. Nevertheless, few are willing to admit that to themselves, let alone others. 

Why is this so? Well, first of all, there are great stigmas attached to confronting your mental fragility. The idea that any frailty will be interpreted as a sign of weakness by your team, investors, and fellow founders, is a story entrepreneurs tell themselves because it is so heavily perpetuated in the media. But the reality is that it makes you more human.

The ability to share with one another and be vulnerable with other humans is what connects us. It may also help us build stronger relationships with those we lead more than we realize.

That being said, let’s explore each of these mental health “personas.”

Related: Is Covid-19 a Mental Health Tipping Point?

The “I’m slaying it” founder

This person tends to feel the need to tell everyone about the awesome deals they are getting, the amazing progress they are making and the high profile investors they are turning down. It’s often the case that these are less experienced founders who believe they need to perpetuate this persona and project it into the ecosystem in order to be accepted by others. Of course, sometimes everything they claim to be true is indeed true and they are indeed “killing it.” However what this approach lacks, generally, is an awareness that enables other founders to have meaningful conversations with them, or even to help them if they are struggling.

The flipside, from a psychological point of view, is that they are manifesting the reality they want to create, and by reinforcing the story of success inside their brain they might well be creating the life they want to live. In my own experience, it’s totally possible to find a balance between doing this to yourself internally while externally making sure you are inviting welcome feedback, challenge, and encouraging help from your network.

The “pomodoro timer” founder

This type of founder tends to be obsessed with systems and habits. They are typically more introverted but ultimately they understand that future opportunities to be successful are predetermined by the decisions they make today. Moreover, they believe good practices compound to deliver exponential results. 

This is a highly logical and very practical attitude towards entrepreneurship and this kind of mental health profile requires a lot of discipline and sacrifice which means they can often miss out on having more balance.

As a result, they can be less sociable which might limit their opportunity to discuss how things are going even though they would like to. They are often objectively pretty successful because they have the maturity to take personal responsibility is using every possible moment in their day. But they can also lack emotional connection which can (though not always, of course) lead to a sense of  — a recurring problem in the entrepreneur’s mental health playbook.

Related: How to Support Employees’ Mental Health as You Return to the Office

The “open” founder

This type of founder is, in an ideal world, a version of the second founder, but more socially aware, community-driven, and interested in other people’s emotional and mental wellbeing. This helps pave the way for them to look in the mirror, shine a light on themselves, and lead from the front by asking: “If I am not brave enough to admit I am struggling, why would I expect someone else to?”

This founder picks their moments. I am not suggesting they should always confess when things are going well, and I’m not saying they should make a habit of complaining about their problems. Rather, they look for the right times to take the risk and admit that they’re not ok, what’s keeping them up at night, what challenges they are facing, and how they might need help.

Often this type of founder has failed before and learned that the facade they kept up was more of a hindrance. They learned that the emotional baggage that came from keeping the hard truth to themselves, in the end, was their undoing.

The reason why I think this persona is the future of entrepreneurship is that it builds human connection. It extends a hand to others who might be lost but unable to admit it openly, which can have dire consequences. 

The three personas in my own life

At one point, I pretended to be the “slaying it” founder with my last company, Grabble. We won a lot of awards (I won young entrepreneur of the year in the UK), I spoke on huge stages, we had millions of users and were the next big thing. What happened? I got so caught up in the PR that when we really needed help, it was too difficult to ask for it. Spoiler alert — Grabble failed. I ended up with acute mental health problems like and

Then came my shift toward the “pomodoro timer” founder. Investing in your health and wellness through optimized sleep, diet, supplements, with a focus on building systems and habits are likely to create successful outcomes. I’ve since used these tactics to build a high-performing podcast (Secret Leaders), an engaged community creating value for hundreds of entrepreneurs, and a new direct to consumer brain health and mental wellness company called Heights that is literally my dream job.

The persona I am most proud of wearing, however, is that of the “open” founder. I am now willing to speak up publicly and honestly about what I’m struggling with, both professionally and personally, including my mental health. I am a mental health advocate and think it is my duty to encourage an open conversation about both the highs and lows. This includes the human condition when stress catches up with me, the pressure is mounting, and I feel like I am just not good enough to meet the challenges I’ve set for myself. I am often my own worst critic.

Over the years, in society, we’ve learned to take an active interest in our physical wellness by committing to regular exercise and a better diet. But the new frontier for a happier and healthier entrepreneurial environment for all comes from taking an active interest in your mental wellbeing.

Related: These Strategies Help Entrepreneurs Combat Anxiety and Depression

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