I've not had any kind of big success or built a business but I think I can relate to this being perhaps "successful enough" relative to people I know / my own expectations.

I think you can pour so much of your energy and focus into this vision of the goal you need to complete to feel fulfilment/happiness that it blocks out the depression, you're too busy to feel down and it will fuck up your plans and your goal to give into it, that's for other, less successful people (not my view, just what one tells oneself).

Then you get to that goal or aim and realise it doesn't make you feel the way you told yourself it would at all, maybe you feel a moment of satisfaction but it's probably very brief. Then you realise the beast of financial insecurity and social failure has stopped chasing you and that drive to override your mental state disipates, then you're alone with the underlying problem, the lack of any meaning to it all.

Sorry if that's not the way you experienced it but I thought I'd bounce the idea around. I hope you find a way to work to some peace with it.

People with money seem so happy. I had a lot of cognitive dissonance when money didn't make me happy. The lifestyle I obtained felt like a gilded cage with no way out. The wife certainly wasn't buying my unhappiness and wouldn't consider that we should go back to what we were. If you didn't grow up with money, then I strongly recommend people get themselves a wealth counselor. I'm not even sure they exist, but didn't find anyone who could discuss with me my feelings about money and what it meant for my identity.

> The wife certainly wasn't buying my unhappiness and wouldn't consider that we should go back to what we were

Probably because your wife wasn't there in the trenches like you were. You created the wealth, she just benefitted from it.

Please note that I'm not ragging on women. Children of rich families would also probably have the same attitude, regardless of gender.

I don't know about a wealth counselor, but get a therapist. So many people, especially founders, would benefit from talking to a professional.

Honestly, I'm surprised that there aren't a few therapists who work exclusively with founders - I'd honestly love to see a VC firm with a therapist on staff for its founders.

If investors offered me counseling services, I don't see how I'd feel comfortable taking them. Not because I have anything against therapy (I used to regularly see a CBTist, and still employ the techniques personally all the time), but because I would have an incredibly hard time believing in both the VCs' wherewithal to hire such a person on more than their perceived celebrity within their professional/social circle and also I'd struggle in fundamentally trusting that mine and the therapist's incentives were properly aligned.

It seems like it couldn't possibly produce a dynamic that's much different than say corporate HR. Wherein the helping hand extended to the employee is always beneath that of the one that's protecting the company.

But, maybe that's just me exposing my rank cynicism, which by some measures is a personality flaw in its own right.

I recently spoke with someone from Alpha Bridge Ventures (https://www.alphabridge.vc) after writing a book about entrepreneur mental health. They provide mental health services to their founders, and my understanding is that they have a firewall between the investors and a separate entity that provides mental health services. A menu of mental health services is available to founders but the investors never know which founders are using them. Although they emphasize the intrinsic humanitarian value in helping their founders, they also rationalize their approach by noting that providing mental health services is good business; founder burnout is a leading risk factor for startup failure. I was impressed by their approach, which seems to mitigate the incentive problem.

Yeah, that's fair. I don't think it's quite like HR because it's a situation where your interests and your VCs' are better aligned, but that's not always the case.

Maybe better if they could just refer some independent therapists who have experience with founders.

That all makes a lot of sense. I wonder if those issues could be alleviated by contracting a sufficiently large outside firm to manage therapy services, thus at least creating some separation and objectivity for individual therapists.

My wife has been using an approach called "Design Therapy" (www.designtherapy.org) that uses design thinking methods for self/couples development. This allows mental health challenges to be approached outside of a "disease treatment" frame. I appreciate the approach.

It’s becoming increasingly popular, at least in NYC, for VCs to promote their mental healthcare perks. Some have coaches, some even have psychologists as GPs. We are making progress.

‘I think everybody should get rich and famous and do everything they ever dreamed of so they can see that it's not the answer.’ Jim Carrey

I really resonated with this when I first heard it. Like Carrey, I've also found happiness in meditation and some aspects of Eastern philosophy

My cursory view of your personality is that you would feel the same misery if you had spent all your time with your kids and none of your time chasing your dream to build a company. Many people find peace with meditation, therapy, exposure to nature, exercise, limiting caffeine / alcohol, natural medicines etc.

I would have had the same hole inside, but I have found since that the love of my children goes a long way towards helping that. I am saying that I denied myself this for 9 years because I was busy, and I denied them a father who was present and paying attention. With a lot of work, together we have figured it out. The funny thing is they grew up with a lot of money and now there is none, but neither one of them has said a single word about the money being gone. They are happy I am back.

Glad you are in a good place now. Try not to be so hard on yourself.

I wager you don’t have kids yourself. Anyway, missing your kids growing up is a forever lost opportunity. Starting a company is not. Very much not comparable

True but some people just don't chase sharing moments with kids that much. Whilst most people seem to want kids, not all of them want to spend all their time with them at the expense of their own personal dreams.

We're perhaps still under the influence of some older generations' way of living...

I don't disagree. My point is many people think if they'd done this or that they'd be happier. I completely disagree with this premise.

Man this comment is scary af for me. I mean I don't know you from adam but getting to the success at the end of the rainbow is what makes me jump out of bed each morning and not want to go to bed each night.

It's my dream that consumes me and keeps me happy more than anything else. But I too sometimes feel that "what happens after it's done" and it is not everything I imagine it to be. What if the bag of dreams we're all chasing is just empty like this Alan watts video(1).

Call it denial but I just try not to think about it a lot as I don't know what the future holds and it's pointless to speculate right now as every person is different. But reading your comment did scare me a little tbh!

(1) https://www.youtube.com/watch?v=ERbvKrH-GC4

Founder depression is extremely common: https://blog.asmartbear.com/startup-identity-selling-sadness...

If success is the only thing that drives you it's inevitable that you'll be depressed when you become successful because you've just lost the one thing that keeps you going.

Can you expand on your experience? any particular lessons you learned? Seems like you had all the conventional marks of success, I find it hard to believe that that was all for naught.

It wasn't all for naught, but success is not going to completely fill the hole inside. Lesson? It's simple, don't work all the time and neglect your family. I cringe everytime I hear Musk talking about working 100 hours a week. He has kids by previous marriages afaik, but it sounds to me like he's not much more than a sperm donor. He's a terrible role model for fathers. I worked probably 70 to 80 hours a week for 9 years. My son has a lot of complaints about me not being there and he's right. The only thing I can say to him is that I'm here now.

I've found lots of founders either become 1) big time family people, or 2) small grocery store operators, or 3) heavily radicalized leftists.

One of these is not like the others.

It sounds a bit like you personally reached high status, then discovered that status is hollow. Was that a big part of it?

Do you think you would have been as disappointed if you had ignored your goals and settled for a more “normal” life?

>personally reached high status

when 'high status' is the benchmark, there's going to be an element of let-down & disgust with one's self on arriving.

i'm seeing less and less smart people think in terms of status.

I'm confident you will be there for him in the future too.

Maybe it was whose definition of “success” the person was pursuing…conventional definitions are conventional because people accept them without deep reflection on whether they are right for them. They are easier to adopt than to question.

Or a problem with winning the rat race is you have to be a rat.

Unhappiness is worse than for naught.

If you've seen Breaking Bad (if not, I'm not spoiling much) there is a scene where he tells his wife "I did it all for the family" and she disgustingly turns her head away and says something like "You did it for your own ego. You didn't care about us." It's kind of like that.

I apologize for mischaracterizing your experience. I am sorry.

I hope you are healing.

There is always another adventure beyond the horizon, as they say. I just wish there was more time.

I've seen this only among founders who's product/business didn't reflect their authentic, deepest values.