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What Are The Worst Mistakes You've Done In Your Entrepreneurial Journey?

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CrimsonNight

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I am currently on the journey so it might not be worth much in value or wisdom compared to those with more experiences.

The number one mistake anyone can make is to be complacent in their current situation.

You will not give your best because there’s no reason to.

Just like a tiger in the zoo. Sure it has no freedom but at the very least it will be fed. This tiger won’t even bat an eye if there is a delicious prey in FRONT of its cage. Why?

Cause feeding time is just around the corner. (Or it has just been fed)

Why risk or try anything with its best efforts if the outcome is the same. (Well, almost)

I am currently in this situation and I am sure there are many more who‘s in the same position as me. Even those with five or six figures monthly income.

We are complacent and satisfied with our current lifestyle.

(Trying to change this but it is definitely hard)
 

VicFountain

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I'll tell myself to travel the world & don't worry about business until my 30's.
I'm telling myself the opposite story. I'm spending my teens grinding and trying to reach my goals. It's literally my life mission. An obsession.

But how'd you travel without money? And would you be actually motivated to start working in your 30's when you have traveled the world already? What would you be fighting for?

One reason I never ask my parents money is because it's as if I'm using cheats on a videogame. Where's the fun? When you have something to fight for, you have fire inside.

One mistake I'm doing, though, is that I'm taking action, but is it the right action? I have no way but to fail over and over again and see for myself.
 
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VicFountain

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I am currently on the journey so it might not be worth much in value or wisdom compared to those with more experiences.

The number one mistake anyone can make is to be complacent in their current situation.

You will not give your best because there’s no reason to.

Just like a tiger in the zoo. Sure it has no freedom but at the very least it will be fed. This tiger won’t even bat an eye if there is a delicious prey in FRONT of its cage. Why?

Cause feeding time is just around the corner. (Or it has just been fed)

Why risk or try anything with its best efforts if the outcome is the same. (Well, almost)

I am currently in this situation and I am sure there are many more who‘s in the same position as me. Even those with five or six figures monthly income.

We are complacent and satisfied with our current lifestyle.

(Trying to change this but it is definitely hard)
One thing I've learned from Sam Ovens is that we live our life according to our lowest standards. We accept our life as it is when we are aligned with our standards.

If the lowest standard you accept is to have "a decent pay" and be able to travel 7 days a year, then you'll never get out of your way to take risks and start a business.

If the lowest standard you accept, on the other hand, is to live in a huge mansion, free from 9-5 slavery, able to travel whenever you want with no restraints, you'll do anything it takes to get there.

Humans live and act according to their life standards. A guy born rich, with parents giving him everything without him having to work for anything, will probably never achieve anything worthwhile by himself. What did he failed at? What did he learn?
 

sparechange

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  1. Learn to love rejection
  2. Get out there and fail alot
  3. Focus on a single business and revolve your entire life around it
  4. Hustle like a madman, then hire people to do the work for you
My failures are a combination of action faking, lack of work ethic and not executing the proper strategies, focusing on building social media pages (doing give aways and posting content) And of course money chasing, not having a good product and not having marketing skills.
 

LordGanon

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Partnering up.

The whole "you need a great team" narrative is a lie. You need great employees at some point, yes. But you should keep 100% ownership of the business for as long as possible, maybe even forever.

First of all, when it comes to startups, statistics show very clearly that single founders are far more likely to succeed, to get funding and make the bigger exits (everyone is going for, for whatever reason).

Second of all: Business is easy. People are hard. (!!!!!!!!!!!!! I can't stress this enough !!!!!!!!!!!)


My own story with that: I partnered up for my third business. My partner had a lot of debt from a former business. It made him jump onto and suck up to anyone who had money. My uncle, who has been an accountant for decades, told me that every team he worked with eventually one day came to the conclusion that one has to lead and the rest has to follow, our they bought each other out. I first didn't want to believe it, then the problems came.

His marriage was strained because of his debt and infidelity. When divorce came onto the table, it would effectively have made his ex-wife a shareholder. No thanks.

Then, our business plan more or less developed into an investment scheme. Up until the point when I said: "That's it. We're going to the notary and delete my name as CEO. I'm not taking legal responsibility for this."
 
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LordGanon

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Also, taking investors. Do not go with investors for as long as you possibly can.

It's no myth that as soon as they have anything to say in your business, they'll try to commandeer the whole thing. Maybe that sometimes is helpful, but most times it is absolutely not. Did you want to be your own boss? You can now effectively forget about that.

I've met about 50 investors. They mostly come in two categories:

1) Sharks meticulously looking for return on investment. While that is their good right, they tend to be like banks (which at least don't interfere with your business). They offer you an umbrella when the sun is shining and will take your pants when it is raining. They do not - I repeat, no matter how nice they may treat you, they do not - care about you in any way. Be extremely cautious of people who tell you they care about people and often stress it. Those - and I do not dramatize - tend to be psychopaths (opposed to popular culture, most psychopaths are all too perfectly integrated into society, but they just imitate feeling and acting like a normal human being, which is why their manners are often perfect [I've seen a lot of those while working in psychiatry]). You're an investment. Often people who have an industry career behind them. Which can be helpful. But since they've been work animals, they now are bored. Which means they have a lot of time (and maybe even rights) to interfere with your business.

2) The man who somehow ran into money and now has no idea how to spend it. Sometimes he'll not be interested in what he put his money in (good for you!), or suddenly you have to deal with someone who swings by the office every other day to hang out with you, maybe even accompanied by his "crew" and puts his snake leather boots on your table. I don't mean that figuratively. This scenario happened exactly like that to a client.
 

Sandy Dives

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I had a job before I traveled.
In 1989 I started with £1500, a one way ticket to Bangkok & a one year working visa for Australia.
I backpacked through Asia first & I started freelancing in Singapore, never used that visa to Oz. I wanted to stay in Asia so I researched where I could base myself for travel & work. I suppose that would've been my "why" at the time.
In 1992 I built my first business in Hong Kong & didn't return to the UK until 2017.

Awesome!
 

Andy Black

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One mistake I'm doing, though, is that I'm taking action, but is it the right action? I have no way but to fail over and over again and see for myself.
I don’t see this as a mistake. Sure, we can be busy folks, but if you’re taking action, learning, and adjusting then that’s perfect imo.

“You can’t steer a parked car.” (James Schramko)
 
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Hadrian

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Was wondering, what are the worst mistakes you've done during your journey as entrepreneurs?
What would you tell your 20 year old selves?

Honestly if I could talk to my younger employee self I’d say embrace the book “How to win friends and influence people” and learn the art of office politics (social/sexual networking) to perfection. I’ve always had a Star Trek (Picard) level of integrity and have never been able to suck up to anyone, and my excessive honesty gets me in trouble constantly. It’s made my life far more difficult!

If I could talk to my younger entrepreneur self I’d have advised learning how to code myself. Relying on others is a minefield in more ways than I can explain here. And key Point: Never trust anyone you haven't known for at least ten years, and known extremely well! A good friend does not mean a good busiess partner.

Stay safe out there!
 
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Knugs

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Strangely mistakes are the ones which teach you the most and shape you as a person. Retrospectively I feel they are not mistakes but lessons in life; they are rather experiences that are extremely valuable. As we are coming to an end with our business I made a list of mistakes/advice I wished I had at the beginning of the journey.

-Partnering up with family is one of the most riskiest and craziest things to do. It might make sense but the risks and downsides when things go sour are far too great. I pulled in a close family member. I feel I cant talk truly with them and need to avoid tough conversations to maintain the relationship. Standing between 2 founders put me in an awkward position. Keep business away from family.

-Partnering up with friends destroyed my friendship. The experience of losing a business are aggrevated with losing what was known as a life long friend. Usually when a business fails people start to look at others for the reason of the failure. Its a defensive method you do to avoid critiquing yourself and protecting your mental health. Pointing fingers at others is easier and distracts from yourself. You see that in all aspects of life but when it comes to something like a business things can go really ugly. Some founders dont understand that everyone is responsible equally.

-Dealing with people is the most complicated part in business by any means. Especially with partners you will discover their true self and really get to know their bad sides. But also employees and freelancers can become a pain in the arse. We blew money on devs that didnt perform, wasted time on underqualified devs who couldnt handle the task and worked with people that just didnt have it. I havent worked this out but it had been incredibly difficult.

-Dont hype. Hype makes you jump into the waters without asking the difficult questions. The questions that are essential for the business progression. You need to be tough on your own concept/idea and your aim should be to try to destroy it as well as you could. If you feel that you can still make it succesful than go for it but I wished we did that properly. In another thread I explained how we made some silly but significant assumptions that killed our business model instantly the minute we found out (1.5 years too late).

-The above transitions to our next mistake: not validating all assumptions properly. We didnt really validate the need/ problem/ solution with customers. We made assumptions on cost and timelines that turned out to be completely wrong. Our assumptions were based on reasoning and public data but we lacked key information that would change that assumption. Its interesting how a simple assumption that is essential in the progression can throw the entire concept off.

-We took on dumb VC money. Most startups (preseed/seed) will take everything they can put their hands on and sometimes there is no alternative but: Dumb money (investor without expertise) are dead shares that will direct your business in the wrong direction. Combine Dumb money with VC money it becomes a toxic cocktail of investors who just want one thing: Profit. We took VC money from a Berlin investor which wanted to have the next investment round ASAP. Our business aims changed to get the things done that would make ourselves an interesting investment case.

Shit loads of workshops on pitching, raising rounds and preparation of documents for the next round. Anyone who is raising a round will tell you how much time and energy it cost and what bs it really is. All the core business became secondary and all timelines and deadlines were based on that next round. Losing focus on the core service/product had cost us a lot of time and ultimately was a major factor in the failure of the startup. Taking the investment also resulted in loss of control and I felt having a parent above me watching every decision I take.
They made me move to Berlin, made me attend compulsory meetings and forced me to work in their coworking space. I felt as if I was an employee again.

-My business partner had a tendency to really manipulate and deceive investors and clients about our progress and data. It was so bad that he started to believe his own lies as time went on. It reached a stage where he didnt even know what was correct and not. A lot of our "progress" was based on our lies and I HAD to play along. But you can only lie to get so far. One day it hit us straight in the face. When evidence of real traction was asked for he got angry and anxious that we needed traction now. It was horrible.

-There is also another thread about on here which asks when you should stop the business. This is a tough one and more difficult with multiple founders. When you poured in so much of your soul you start to ignore red flag as you dont want your baby to get hurt.
 

Knugs

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I have more experiences I could list but I want to finish this off with the most important mistake that seems to overfly everyones mind as they think it would never affect them. Do not ignore your own mental health.

Mental health is a serious issue amongst entrepreneurs. You are most likely transitioning into entrepreneurship because you are unhappy with your current situation. You quit your job and career and you consciously move into complete uncertainty about your future. You think entrepreneurship will make you happy and succesful because you are creating something yourself and that you will be defining your own future.

The reality is that everyone has a limit of how much shit they can take. As soon as you make the transition from your shitty but emotionally stable job, time starts running. You will be depleting your savings slowly, your parents and family will doubt you and critize you. Your spouse will most likely hate that idea but they will support you initially. It will strain your relationship with her/him.

You will be on a rollercoaster of emotions. Many highs and many lows. You think you have to persist and work ungodly hours as everyone tells you that THATS exactly what you need to do to be succesful. You will face many rejections from clients and others. People will call you names and disrespect you. You will fail a lot of the times and doubt yourself. There are more shitty days than good days. You tell yourself this is part of the game and grind through it.

Initially you will not notice how this affects you as a person. Your closest ones will notice how you "change" and appear more "stressed". Then it will start to affect you emotionally and physically pretty quickly. Most likely you subconsciously adapt your behaviour to deal with these issues one way. It could be eating more junk, doing drugs or drinking. A degree of generalised anxiety disorder and depression could be observed among many founders in the co-working space with the naked eye.

In my case I was getting far more anxious and my mood became more unstable. My physical health deterioriated significantly. Gained 30 pounds, backpain, neckpain and developed sleep disturbances. Became far more tired in the day and started to neglect my appearance. Drinking helped. Benzos, Propranolol and CBD helped too. I was SO close to losing my gf. I'm a clinician and it took me awhile to see these things creep on me like that. Closing the failing business has solved almost all of the above issues. Still fat.

Sometimes the biggest mistake is to go into entrepreneurship in the first place. Its not meant to be for everyone. And the ones that go into it make the mistake of ignoring their mental health.
 
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VicFountain

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I have more experiences I could list but I want to finish this off with the most important mistake that seems to overfly everyones mind as they think it would never affect them. Do not ignore your own mental health.

Mental health is a serious issue amongst entrepreneurs. You are most likely transitioning into entrepreneurship because you are unhappy with your current situation. You quit your job and career and you consciously move into complete uncertainty about your future. You think entrepreneurship will make you happy and succesful because you are creating something yourself and that you will be defining your own future.

The reality is that everyone has a limit of how much shit they can take. As soon as you make the transition from your shitty but emotionally stable job, time starts running. You will be depleting your savings slowly, your parents and family will doubt you and critize you. Your spouse will most likely hate that idea but they will support you initially. It will strain your relationship with her/him.

You will be on a rollercoaster of emotions. Many highs and many lows. You think you have to persist and work ungodly hours as everyone tells you that THATS exactly what you need to do to be succesful. You will face many rejections from clients and others. People will call you names and disrespect you. You will fail a lot of the times and doubt yourself. There are more shitty days than good days. You tell yourself this is part of the game and grind through it.

Initially you will not notice how this affects you as a person. Your closest ones will notice how you "change" and appear more "stressed". Then it will start to affect you emotionally and physically pretty quickly. Most likely you subconsciously adapt your behaviour to deal with these issues one way. It could be eating more junk, doing drugs or drinking. A degree of generalised anxiety disorder and depression could be observed among many founders in the co-working space with the naked eye.

In my case I was getting far more anxious and my mood became more unstable. My physical health deterioriated significantly. Gained 30 pounds, backpain, neckpain and developed sleep disturbances. Became far more tired in the day and started to neglect my appearance. Drinking helped. Benzos, Propranolol and CBD helped too. I was SO close to losing my gf. I'm a clinician and it took me awhile to see these things creep on me like that. Closing the failing business has solved almost all of the above issues. Still fat.

Sometimes the biggest mistake is to go into entrepreneurship in the first place. Its not meant to be for everyone. And the ones that go into it make the mistake of ignoring their mental health.
Damn man seems like you are talking to me lol

I've had insomnia for the last 1-2 years and been taking benzos to sleep. It all started with excessive weight lifting, which led to a shitty, endless cycles of high cortisol and stress (which I haven't sorted out yet).

Now, I still lift heavy and sleep like shit, and I've also been working on "businesses" (I hate calling them businesses cause I feel more like a kid playing with the Monopoly game), first with a blog and now with a YouTube channel and I'm spending at least 10-12 hours a day working on it.

The lack of positive feedback from my grind is also impacting my mental health negatively. It's hard to work hard for months without seeing any reward.
 

MJ DeMarco

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What would you tell your 20 year old selves?

Everything I wrote about in TMF and Unscripted ... that's why I wrote them ... a message to 22 year old me.

Some quick things that come to mind...
  1. Following passion with no consideration for market needs...
  2. Partnering with people who had other priorities and commitments, "our' business being 5th or 6th on their list...
  3. Putting too much thought into business plans...
  4. Following, not leading... (control issues)
  5. Engaging in commoditized markets, or markets with scale issues...
  6. Businesses that had nothing unique, nothing different ... chasing money.
  7. If you're not searching for the truth, you're not getting the truth.
 
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Hadrian

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I have more experiences I could list but I want to finish this off with the most important mistake that seems to overfly everyones mind as they think it would never affect them. Do not ignore your own mental health.

Terrific Post. I will confess I started my journey 5 years ago with just enough money to fund an MVP for my first app, a tourist networking app for AirBnB users, and buy an engagement ring.

A year later I was living alone in a tiny studio with no money, no app and no fiancée and in very poor shape indeed. The gory details are outlined in my original intro.

The desert of desertion since has seen me pivot my ideas into three fantasy themed mental health style apps. One for "Meditation/Spirituality", One for "Productivity/Accountability", and one for "balanced living and guild based social networking".

Ironically its been this crushing Entrepreneurial journey that has inpired my biggest ideas... but has anyone else felt like the've become narcissistic and/or Bi-Polar? I just hope its temporary!

Emotionally the lack of support from family has been the most difficult where they were all supportive in the beginning but once you fail the first time they say "Oh well at least you tried" and anything after that is discouragement all the way... I think Mj's numerous references to: "Get a Job Baby" may be understated to put it mildly!

Yes the Mental Health aspect of this is for me by far the most difficult!
 
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sparechange

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One of the bigger mistakes I made was doing things that other people wanted me to do vs doing what I wanted to do. It set me back a lot and hindered my growth in the first few years. Business is/was all consuming and when you're in the thick of it, everything else falls to the wayside. You could potentially lose friends, family, or your spouse and harm these relationships; I know because it happened to me. I don't regret it, I just wish I had been more present as the past few years have been a blur.
 

Knugs

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Damn man seems like you are talking to me lol

I've had insomnia for the last 1-2 years and been taking benzos to sleep. It all started with excessive weight lifting, which led to a shitty, endless cycles of high cortisol and stress (which I haven't sorted out yet).

Just need to be careful about benzos as they are incredibly addictive. I use them sparingly now, because I noticed how effective CBD has become for me. You can try it, its generally safe and is pretty good post-exercise. I think that since I removed the external factors (the business) my mental health is slowly recovering. Initially my orthopedic colleague prescribed me benzos based on my morning neck and backpain that would only resolve with ibuprofen. He suggested I might have a sleep disturbance which I followed up with a sleep study. It turns out that I have no issues falling asleep but that I dont have quality sleep (stress). I apparently wake up dozens of times without realising and would be checking my surroundings. My body was so tensed up that I would wake up with pains and I would just be tired all day. First night benzo and I woke up euphoric. No pains and full of energy until 8pm. Now no benzos and no pains. Energy levels are ok.

My orthopedic colleague also suggested a visit with the psychologist to work out the underlying issues but I feel that the business is caused a lot of that.

Terrific Post. I will confess I started my journey 5 years ago with just enough money to fund an MVP for my first app, a tourist networking app for AirBnB users, and buy an engagement ring.

A year later I living alone in a tiny studio with no money, no app and no fiancée and in very poor shape indeed. The gory details are outlined in my original intro.

The desert of desertion since has seen me pivot my ideas into three fantasy themed mental health style apps. One for "Meditation/Spirituality", One for "Productivity/Accountability", and one for "balanced living and social networking".

Ironically its been this crushing Entrepreneurial journey that has inpired my biggest ideas... but has anyone else felt like the've become narcissistic and/or Bi-Polar? I just hope its temporary!

Emotionally the lack of support from family has been the most difficult where they were all supportive in the beginning but once you fail the first time they say "Oh well at least you tried" and anything after that is discouragement all the way... I think Mj's numerous references to: "Get a Job Baby" may be understated to put it mildly!

Yes the Mental Health aspect of this is for me by far the most difficult!

The untold story of entrpreneurship. You are hitting it on the head. I might think the idea of the bipolar-like behaviour stems from the rollercoaster of emotions (the many highs and lows).
 

strobe

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I would say the biggest mistakes are not doubling down on whats working for you, if it is working well do not stop it.

The other would be to not lose momentum and venture away from entrepreneurship, it is like going to the gym and being fit and healthy, you need to stay consistent every day. If you fall off the bandwagon, get back on it the next day.

I think that if you are stressed out and upset with ups and downs from your current or previous job then moving over to entrepreneurship is not really much different,you have less to lose than if you are happy and content with your current job.

You can also mitigate and lower your risk of failure and stress by lowering your expenses and obligations, it is hard/impossible to be truly all in if you are trying to keep up a social life/image.
 

LordGanon

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The untold story of entrpreneurship. You are hitting it on the head. I might think the idea of the bipolar-like behaviour stems from the rollercoaster of emotions (the many highs and lows).

I don't know about this "bipolar" issue, @Hadrian. "Bipolar-like" is a good term, here. Bipolar disorder stems from physiological issues.

I had a lot of diagnoses, and one of them was bipolar disorder (these days, all everyone will attest to is severe ADHD).

Sure, entrepreneurs exhibit (hopefully) signs that come with (hypo)mania. Inhuman amounts of energy and motivation, self-confidence, risk-taking behaviour.

The question is at what point this becomes unhealthy. And I've seen a lot of manic patients. At some point, you can point your finger on it. It also comes with a lack of realism that goes far beyond the belief "My business will make me a millionaire". It also makes you unbearable for your surroundings.

The problem with bipolar disorder is that depression and mania can (!) switch so quickly and without any external causes you could attribute the switch to. During switching, patients with bipolar disorder are most likely to kill themselves, which a whopping third of them will do at some point. Even when your loved ones die, you can still be manic as hell.

Also, the depression they get and full-blown mania are such extremes of mood that no healthy individual will ever experience. And it comes with extreme strain to know both and constantly travel between them.

Bipolar disorder can be treated to the point of being seemingly nonexistent. But that demands compliance of the patient. And life is bo-ring for someone who knows its absolute extremes and suddenly goes on mood stabilizers. Every bipolar individual wants the one drug that just cuts the depression, not the mania. It doesn't exist. And mania at some point - no matter how good it makes you feel, will ruin you. Financially, socially, mentally, physically.
 

Jasper S

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The whole "you need a great team" narrative is a lie. You need great employees at some point, yes. But you should keep 100% ownership of the business for as long as possible, maybe even forever.
Seems to be what David MacNeil, founder of WeatherTech did. It's now a huge company and he still owns 100%.

Who owns WeatherTech?
 
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ElleMg

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Uhhh, invested ALL my money in buying a house outright when I was 19. So I'd tell 20yo Elle, "GET OUT OF THERE NOW, DON'T WAIT". :rofl:

It's only been a few years since but besides that, I'd tell my younger self that it's fine to be different and do your own thing. When you embrace what makes you unique, it becomes your biggest strength.
 
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Terrific Post. I will confess I started my journey 5 years ago with just enough money to fund an MVP for my first app, a tourist networking app for AirBnB users, and buy an engagement ring.

A year later I was living alone in a tiny studio with no money, no app and no fiancée and in very poor shape indeed. The gory details are outlined in my original intro.

The desert of desertion since has seen me pivot my ideas into three fantasy themed mental health style apps. One for "Meditation/Spirituality", One for "Productivity/Accountability", and one for "balanced living and guild based social networking".

Ironically its been this crushing Entrepreneurial journey that has inpired my biggest ideas... but has anyone else felt like the've become narcissistic and/or Bi-Polar? I just hope its temporary!

Emotionally the lack of support from family has been the most difficult where they were all supportive in the beginning but once you fail the first time they say "Oh well at least you tried" and anything after that is discouragement all the way... I think Mj's numerous references to: "Get a Job Baby" may be understated to put it mildly!

Yes the Mental Health aspect of this is for me by far the most difficult!
I can get where you're coming from with the narcissism. I became particularly dickish as a 21 year old to the point where no one wanted to be around me.

For me, I believe that narcissism is the result of when you focus way too much on your needs against others. Especially when you view it as a 0 sum game which it doesn't have to be.

I could be wrong, I'm not an expert, just sharing my story with you.

I wish you the best in getting better and I'm sure you're gonna smash the millionaire boundary!
 

Ing

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I had some good businesses, while I was getting my degree.
My biggest mistake was, that I finished these businesses, when I began working my (dream)job.

Otherwise maybe I had steered my businesses to a bigger thing.
Honestly if I could talk to my younger employee self I’d say embrace the book “How to win friends and influence people” and learn the art of office politics (social/sexual networking) to perfection.
That was the first and most important psychological book I read, when I was about 15 years old
 

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