Mentoring Entrepreneurs: Breathe through the Pain

I mentored a very compelling entrepreneur last night. She has a great background and has built a compelling v1 product in a massive market with little competition. In my view, she is on the precipice of greatness. She asked for mentoring time because she wanted to talk through a business challenge. The challenge was so vexing to her that she had lost sight of how much progress she has made and how close to success she was.

As she was explaining the details of her business challenge, I couldn’t stop looking at her eyes. I have seen those eyes before. I have had those eyes myself. There was pain in those eyes. There was sleeplessness in those eyes. There was fear in those eyes. There was exhaustion in those eyes. I could feel all that without her saying so because I have been exactly where she is currently.

One of my favorite entrepreneurs explained it this way:

“Being an entrepreneur is like eating glass and staring into the abyss of death.

— Elon Musk

As she ended the explanation of her business challenge, she asked for advice. My response surprised her. I said, “first, I can see pain in your eyes, let’s talk about that before we get to your business challenge.” [which is a very common business challenge, one that I have faced many times and is not as serious as she have made herself believe.]

In my view, creating a company is the single most challenging thing one can do in business. Being a Founder/CEO is a lonely, painful place which no one can understand unless you have been there. It is not a place that I recommend for anyone. But if you are brave enough to take the plunge, you have to be cognizant of the connection between your physical and mental health. If your body breaks down, your mind will too. And then you will make mistakes which will cause your worst fears to occur.


I relayed a story to this entrepreneur which I recently learned. I recently got into hot yoga. When I started, I thought it was a good way to sweat a lot and stretch my aging body. What I have come to learn is that yoga isn’t about stretching. Yoga, in my current understanding, is about holding a pose until the Lactic acid starts to burn in your muscles, and as your brain shifts focus to that pain, having the mental strength to remind yourself to breathe through the pain. To control your breath and focus on it. If you are a yogi, you know what I mean. What you find is that when you control your breath, the pain leaves your mind. After a few breaths, you might be reminded that your arms are supposed to hurt and then they start hurting again. But if you breathe again and focus on your breath, the pain goes away again. I find this phenomenon to be amazing. The Lactic acid build up will slow down with better breathing, but it doesn’t just go away because of breathing. On the contrary, as you hold the pose longer, it is building up more. However, if you control your mind, you can convince yourself that there is no pain.

As you start a company, you are going to be constantly faced with painful reminders of how far you need to go and how close you are to failure. The pain is going to be excruciating. You will feel like you are being punched in the stomach daily. If you are married and have children, the pain is going to be more excruciating. You will feel the weight of the world. My best advice: breathe through the pain and keep moving forward. Focus on what you can control and ignore things beyond your control.

Published by v1again

I try very hard to be a great father, husband and entrepreneur. Founded and sold 3 companies. is my 4th startup.

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