Startup Grind
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Startup Grind

The Conversation We Keep Avoiding

Mythologically within the world of successful entrepreneurs and business folks is this mirage that one must just muscle hard and power through the difficulties of starting a company as if it be purely a battle of physical measure. Of physical and mental willpower.

The Measuring Stick

Things become a game of physical measurements.

Who can stay awake the longest?

Who can eat the most fast food?

Coffee exists and so does Chipotle. So we are all good and even on this front.

In reality, this is only 10 percent of the battle.

The real combat takes place within the mind, intangible, hidden away and rarely talked about — like a founder who is flexing website views when the bounce rate is 95% and revenue at zero.

Startups are psychological warfare with yourself.

I’ve been following the tech industry for a few years drawing inspiration from Bill Gates who “never took a vacation in his 20s,” Steve Jobs who “was cutthroat and grinding til 3 in the morning,” and of course Elon Musk who “pulled 20 hour days at”

Three seemingly robotic master mind-minds who changed the direction of humanity by disregarding compassion and executing in robotic efficiency.

What a dream!

Yet it is just now, years later, I am seeing the true effects this inspiration has had in Silicon Valley and how these guys really “changed the world.”

It lies within armies of high achievers over-working themselves, facing depression and ill health — all because that’s how Elon did it.

Plenty good has come from the work of these three men. And you can’t knock them for doin’ it their way — but in their wake, a precedent has been set to slave away and be tough about it. Deal with no growth for three years? — be tough about it. Get rejected 250 times from investors? — be tough, wimp.

Silicon Valley is a breeding ground for the comparison of mental toughness.

I’ll totally agree, startups are tough. Toughness and grit are often talked about in partnership with startups and yet somehow it is still vastly underestimated by the thousands who seek quick success and Slack-like growth, just how hard it is going to be.

Startup Grind Global Conference

In February I attended the Startup Grind Global Conference in Redwood City. 5,000 of these lovely startup founders from all around the globe clamored into one spot to learn from the world’s best. Flipping through the event packet, I mapped out my conference agenda.

I spotted a unique session “Founder Mental Health: Staying Calm & Clear in Startup World.”

It seemed pretty cool. I circled it as my #1 must-attend session, even over the oogly and awe worthy names like Ben Horowitz and Safra Katz (who canceled for a Trump meeting, unfortunately).

Like Elon

I am 23 years old, nearing my prime for tech standards (kidding), and I run marketing at a startup in downtown San Francisco. This was a notable session for me as I have been busy working away like my idols ole’ Steve and Elon.

I am no exception to the self-inflicted pains of high standards and Slack-like dreams.

What’s interesting is that by most standards, I have it easy. My team has never taken on VC funding and our culture actually cares about balance. But actually. I know all teams push the balance, but that is only because it’s the cool thing to say nowadays.

This means I don’t have to be working at 11 p.m. on a Friday.

Keyword — “don’t have to.”

While I don’t have to be working on Friday nights, my mind runs quite quickly through what I know success to look like:

“But…. Bill Gates never took a day off…. and…. that guy I met last week is only 20 and already published in Forbes and working on asteroid mining… that is so cool….”

“My enjoyable Friday nights can wait a few years… once I am sat up on the TechCrunch stage speaking and telling great tales of hustle, then I can rest and enjoy Friday night.”

What Am I Thinking?

As you can imagine — this doesn’t lead to beautiful thoughts of purity, gentleness, courage, positivity and understanding, the type of selfless thoughts that lead to magnificent growth.

Instead, thoughts of competition, comparison, judgment and high expectation leads to a world of competitions. Winning is everything and today sucks because I need that benchmark I won’t get until tomorrow. Walking down the sidewalk all you experience is just a bunch of stupid people! No one works hard like me!

How poisonous are these thoughts?

As an old 96-year-old neighbor of mine used to say about people like this “oh isn’t he just a crab!”

Am I A Unique Case?

No! I am not a unique case. Young and ambitious, I joined the valley afflicted with a ship steered via comparison, expectation, and judgment. Despite being in the land of patience, meditation and mindfulness, it is an affliction that permeates so many of us.

For me, I am thankful that I realized I was being a big crab. Not only was I being a crab to others, but I was hurting myself, I wasn’t letting myself enjoy. If you’re reading this you might be in a similar spot as myself. It’s okay to lose direction a bit from beautiful thoughts. All things may be improved.

Since realizing this, I’ve been able to take the steps to be less crabby. And you can too.

The Session On Mental Health At Startup Grind

So I was really looking forward to the session on mental health for this very reason.

But… I still felt vulnerable circling this “overly sensitive topic.”

“Am I weak?… I am not even a founder… I don’t even have half the problems a founder has..”

Here I was still making comparisons. I had to remind myself to slowdown.

The session was placed on one of the side stages with limited seating.

I assumed I’d be one of a few in attendance to the discussion, being a sensitive topic and locked into a world of toughness, I figured everyone else would be off learning and growing their skills instead of working on something silly like sadness and depression!

As I made my way over to “VC Q+A Stage” I took note of something odd.

It Was Packed

It was packed. Like, packed, packed. The room was bursting at capacity and I just squeezed by the frazzled elderly gatekeeper, snagging a spot behind a wooden bar and coat rack in the back.

“I guess mental health is all the rage?”

The fireside chat was hosted by Khalid Halim of, a leadership coaching organization and Ben Huh, of YCombinator and founder of Cheezburger, a hot shot media company who lost a $30 million investment.


The chat was powerful in all of the ways you might imagine it. Khalid Halim was speaking softly and gently, guiding the conversation along as Ben Huh spoke of his experiences as a founder, the ups, and downs of growth. Getting an investment. Losing it. And still coming out alive.

A few notable points from the session:

  1. Apparently, this is statistic has been out for years, but I was just hearing it. I was stunned. 72% is an insanely high number for something so critical. That was an astounding number to hear. This truly highlighted three things for me.
  2. One, how universally high the expectations entrepreneurs clearly set for themselves. Two, how infrequent this topic is discussed given that I just heard the number and the date of the data. Three, how many people go through the same pains, yet feel completely isolated.
  1. Based on the above statistic and the jam packed side stage, this wasn’t so hard to believe. There was something comforting about many people struggling. Not that I want others to struggle, but that there is a united group to it now.
  2. It has a tribe appeal and almost normality. Ben Huh himself talked about a time when he seriously considered suicide. Ben writes about it here on his blog.
  1. Ben and Khalid spoke about the importance of identity. Much of the sadness and depression founders go through is because they do not allow their work and their own selves are separated. It is not Andrew is a person and that is his work, but instead founders view their work as a physical representation and extension of their cognition.
  2. For this, we perceive bad press articles as personal attacks. Loss of funding as personal incompetence and shattered trust. Constructive criticism hurts so bad even when we attempt to play coy like it doesn’t hurt because we know that’s what we are supposed to do.

It’s so hard. I am not even a founder and I can feel the pain and the struggles of these pivotal moments. I will have my day as an entrepreneur and I’ll bet my money it will be easy to become forgetful of these lessons and to overwhelm myself with anxiety.

I sure hope I don’t, but entrepreneurs bet big. They go all-in. It seems fully identifying with your work and being so deeply and passionately embedded into is the only way.

I can’t tell you what is right or wrong, but is a $100m valuation worth it if you hate yourself and you broke off all of your closest friendships and haven’t seen your family in two years?

That is a personal choice.

Improving Your Mental Foundation

On my end, I have been working diligently for months to improve my mental foundation. There are a few things I have personally picked up on my journey and resources I would like to share that may help and have helped me view this topic not as weak but courageous.

These are resources that have helped me love working a balanced week and become impassioned with life. The life of today. Not tomorrow.

I didn’t lose my drive, either.

I was scared to better myself thinking that if I became happy and fulfilled with today, on my mind, what then does that leave for tomorrow’s ambitions?

I am hungry for tomorrow but happy with today.

Author’s suggestions

  1. I have struggled for so long aiming to be perfect. I had once heard a quote “it is not that we must be perfect, but that we must put forth perfect effort.” I really took it to heart. And it’s ripped me to shreds. I agree high-quality work is important in your job.
  2. But there is a difference between good work and over optimizing your life. I personally had scheduled out my days Sunday — Saturday, by the minute. I would put in headphones to avoid my roommates’ attempts at conversation to stay on schedule.
  3. In my mind, it was the only way to maximize my day. I don’t know about you but this sounds crabby and unpleasant. I have actively worked on being imperfect. As Tim Ferriss says; “let small bad things happen.”
  1. The topic of meditation is a well-beaten horse. But if you aren’t doing it, it could really help. I am as A.D.D. as they can be. I used Headspace to learn the patterns and habits of meditation.
  2. The founder Andy talks you through noticing and enjoying small things while you meditate, like the sounds of your house utilities running and the feeling of the shirt on your back. I have applied this idea of intense, intimate focus to all things I do now.
  3. One example is by stepping away from my work at lunch and really enjoying my meals. No phone, no computer, just me and my lunch getting intimate. Food is so good, don’t let yourself miss out on food.
  1. As I shared above, I have been massively afflicted with comparison which hamstrung my happiness and made me crabby. Whether it be Bill Gates or the kid across the street, someone was doing it better. And this wasn’t just a game of comparisons upwards… to feel better, I would reflect on people I was doing better than. This is so poisonous.
  2. I’ve had to admit life is a journey. After reaching so many accomplishments, I have had to train myself to love the difficulty of training and just being the best version of me. A powerful book for this is Mindset by Carol Dweck. I know you are thinking… “a whole book? Can’t it just be a blog?”…. This book frequently makes it on top 10 lists for most likely to change your life forever.
  3. This is the mental foundation that will bring a fruitful life for you as long as you live. 300 pages. Worth it.
  1. In the book, Man’s Search for Meaning, Viktor Frankl, a Jewish psychiatrist who literally lived through the concentration camps, emphasizes a life of meaning, not happiness. He suggests that pursuing a life of endless happiness is not appropriate. Happiness is an emotion and full of movement. It will never be infinite. By expecting this, we actually compound the difficulty of the hard times because we expect ourselves to be happy. Instead, he suggests, seek fulfillment and purpose.
  2. A cause or a thing in life that brings you meaning to your suffering. Don’t suffer until 11 p.m. on Friday because Bill Gates did it, suffer instead because of your belief that the world needs what you are making. Nothing is wrong with suffering and working hard. Just do it for the right reasons.

I am not here to be the expert with all of the answers. I am the last person I ever thought would be excited to attend a session at a conference on the topic of mental health. I am, however, someone actively in the process of rewiring 23 years of cognitive hardware.

So while I can’t give you all of the answers, I can say I have been in similar spots. You may be in a much darker place than I have been. I haven’t lost loved ones, been betrayed, lost money, missed out on a big opportunity, been fired or any of the things that generally ignite a depressive spout, but, I have been working hard on improving myself and to get to a better state of mind.

Whatever the reason is, you have my vote of confidence on these resources.


If you’re looking for experts or other resources try out these items I have collected below.

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Andrew Frawley

Advocating for well-being and mental health through politics ~~~ Past: #2 hire/Director of MKTG Andrew Yang 2020 Presidential