If you ever feel alone in this…

“I missed your talk, but caught the end… You’re doing like suicide prevention for startup founders? Keep up the good work!” That wasn’t what I intended when I spoke recently at FounderFables, an off the record event aimed at founders sharing stories in a private environment, but I took the feedback as validation that I should be talking about what I was sharing and not just to an off the record group.

What I was talking about isn’t spoken about in our industry enough and it affects all of us deeply. Perhaps I’m willing to speak about this because I have a unique background.

I grew up as a rich kid, going to private schools, living in the only mansion in my town… I wore a non-rented Armani suit to my senior prom, and if that sounds pretentious, it’s because I was. But under the veneer of the rich kid popular jock, I was self conscious, depressed and a little lost.

I was the youngest kid in a loving but busy home where I felt forgotten. I needed the approval of my father and he wasn’t around. I wasn’t a fat kid, but I was the fattest in my neighborhood and that was enough to leave me with body issues that I still deal with today. I cried in private, hoping that my cries might just be loud enough for somebody to hear. I hit myself, to create physical pain that might distract from the emotional. My mom was thankfully listening and I was taken to a therapist when I was around 10. Into high school, I still had way more going on internally then I would ever let out, but who wants to hear the popular jock complain about his life? Who’d believe that the kid who has everything is empty where it matters most. So at a young age I learned to bear a heavy burden, alone.

As I grew older, the large trust fund that was waiting for me in my twenties was traded in for a failed political campaign & restaurant by my father. I grew up tasting every meal from the end of a silver spoon and then when I turned 18 and went off on my own I was handed a plastic spork. Honestly though, I’m very appreciative of this and wouldn’t have wanted it any other way. I tasted what life could be like and then was given the chance to make it for myself.

With the aftertaste of a life that could be, I’ve always been deeply driven to achieve success and wealth again. That drive has taken me across the US, to many cities, exploring offline & online businesses… that were largely met with failure. But I’ve also enjoyed incredible success. And now, I’m one of the happiest and most satisfied people I know, and that’s largely because of how I think about and see wealth.

Classes of Wealth

The above graph has done a lot to frame my thinking about personal wealth and it was shared with me by Chris Sacca. I need this framing because in our dreams of becoming Zuck rich, few of us really talk about what it means to have material wealth and the kind that 99.9% of us as entrepreneurs are ever likely to achieve. What this image is showing is the quality of life people have at different levels of financial security.

A person who is $50k in debt has a very hard life. They have no budget for luxuries or means to try and improve their life. They eat the cheapest foods and aren’t able to travel. A person with $0 debt, but $0 savings has a quality of life worlds different. They may not have luxuries, but they have way more comfort and abilities to improve their life. Somebody with $50k in the bank is again dramatically better off than somebody with $0… And the quality of life dramatically increases again when you have something like $500k in the bank. That person is able to enjoy high quality foods, travel, live in luxurious comfort and use their capital to try and make their and those close to them lives better. A person with $5M does enjoy a higher quality of life, but not as dramatically better… they might fly in chartered planes vs first class, or drive a $120k car instead of a $70k car, but overall their quality of life is similar. And the increase in quality of life dramatically tapers off as you get to somewhere like $50M. I’ve personally experienced most of these levels of wealth, and while I haven’t yet experienced the very top levels I’ve spoken to friends that are there and generally they agree.

So why is it important to talk about net worths? Because we never do. We report on acquisitions, successful founders exiting big… But never what that really means for their finances. We’ve put so much glory on the billionaires that we’ve made people with $1M in the bank feel self conscious about their “limited success.” We keep numbers quiet and hope people think our $50k is really $500k and our $5M is $50M. But it’s not and its absolutely ridiculous to feel bad about any of these levels of wealth.

I’ve been rich. I’ve also been totally broke. My personal bank account & business accounts both overdrawn, tens of thousands of dollars in debt to family members and my credit cards maxed out or closed. I’ve had no cash in my pocket and a dwindling supply of food in the cabinet. I’ve seen both sides of the coin and through years of suffering as a struggling entrepreneur I’ve grown comfortable living small. Finding wealth in my relationships, in my good health, in the abilities I have… And now the the success of not being in either of the bottom two wealth classes.

With that all being said, I’m not out at $5M. My ambitions aren’t pinned to where the marked improvement in quality of life starts to taper off… Because I’m not working this hard for myself. I’m the youngest of 7. I have an amazing wife and daughter… I don’t view success as improving the quality of life for just myself, but for my family, my community and as much of the world as I can.

Even when we enjoy outward appearances of success, we can still bear heavy internal burdens. I probably have an unhealthy deep desire to make my father proud and to achieve accolades and success in his name. I know he loves me and I know he is proud, but the kid who wanted his dad to be at his soccer game is still watching the sidelines hoping he’ll show up. I can’t even write the last few sentences without stopping to cry.

We all have our internal struggles and in an industry driven by perception, struggles are a black cloud that no investor, partner or acquirer wants to stand under. So we’re forced to weather our storms alone.

The truth is EVERYBODY is struggling. Even “successful” founders with millions in the bank are worried… about keeping their companies alive, finding an exit, not just being a lucky one hit wonder, keeping what wealth they’ve built up, etc.

When we all say we’re killing it and everything is awesome. We make it that much harder for anybody to honestly say they’re having a hard time. When a founder tweets that he’s struggling to raise a round, or that he’s worried about mistakes he’s making, he might as well brand himself with the mark of the beast.

When I was raising my first round, it fell apart because an A-list investor who had given us a verbal commitment backed out. He did this because he had heard from his friend, who I went out for beers with, said that we were struggling and unsure of what we were doing. I don’t blame the investor for backing out and I don’t blame his friend for relating his honest opinion he took away from our conversation. But I will tell you that I now never share my struggles with anybody I think might be even remotely close to affecting my future opportunities. And in San Francisco, that pretty much means everybody.

As a founder, with a massive burden, and nobody to turn to it can be incredibly lonely. The truth is, you can’t talk to normal people about your trouble. It’s like how I felt as the depressed popular kid, it’s really hard for a normal person to empathize with somebody who has a million dollars in their company bank account… Regardless if it’s really theirs or not. We just operate in an alternate universe than the one most of the rest of the country lives in.

It’s hard to talk to the people that love and care about you most, cause you’d scare the shit out of them. If they knew every up & down you went through, they’d probably hold an intervention to get you to switch careers. They don’t want to see you suffer, and rare is the founder who hasn’t suffered.

So most of us keep these struggles private, some of us are lucky to count fellow founders as close friends who we can confide in. Who we can talk to candidly in a circle of founder trust. If you’re a founder and don’t have this, make these friendships. They can save your life.

If you could have an honest conversation with every founder, you’d probably find that they either are or were very depressed at some point. Maybe there is some predisposition for emotionally unstable people to want to be founders, but most likely the high rate of depression is because this is fucking hard, it’s stressful and there are huge risks.

I’ve also seen what life is like outside of the bubble in which our weird little tech world lives. During my quarter life crisis and while feeling lost in my ambitions smacked in the face with my first entrepreneurial failures. I ended up in Thailand a few weeks after the Asian Tsunami took the lives of thousands of people. I went there on a pilgrimage to help others and to find myself. That short trip turned into cofounding Hands.org and the next 2 years of working and living in disasters areas around the world… Thailand, Biloxi MS, Philippines & Peru. And spending time in places like a war torn Kabul, Afghanistan.

I left my problems behind and helped other people rebuild their lives, literally brick by brick. I met the families of hundreds of people who had long to do lists and plans for a tomorrow they never got to see. I came to appreciate every day I have in this life on a much deeper level and made a promise to never take it for granted. While I was in Thailand I got a dotted line tattooed across my wrist as a reminder of all those who didn’t get another day, who all would I’m sure do anything to have just a little more time. I got the cut here line tattooed on my wrist to remind myself that if I ever don’t fully appreciate the opportunity that I have and the life ahead of me, then I don’t deserve it and it can easily be taken away. To me it’s a very positive reminder, with a dark but real truth behind it.

Two very well known, respected and assumed “successful” founders took their own lives recently. I don’t know what burden it was exactly that they felt was unbearable, but they felt something was impassable and that they were alone in carrying that burden. Nobody should ever feel that and nobody has ever truly been alone in that struggle, they just didn’t feel like they could share it with anybody.

I haven’t thought about killing myself in 20 years, but I’ve been there. So if you’re ever so depressed and stressed out, and you think you’re alone. You’re not. I’ve been there. It can get better and i’ll bear that burden with you. Send me an email with the subject, “I feel alone in this” and you’ll be the next email I write or the call I make.


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