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What are the WORST decisions you've made in your entrepreneurial journey?

TreyAllDay

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Lately I've been reaping the sow of some poor choices I made last year in my entrepreneurial journey. I thought it might be interesting to hear from some people what the worst decisions they made were in their entrepreneurial journey, maybe we can help others from making the same choices.

Why did you make the choice and how did it affect you?
 
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TreyAllDay

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For me - it's getting involved in pointless side projects.

Last year my business was growing VERY fast but my devs who I consider close friends were looking for more work, at the same time a close colleagues agency was looking for designers. To give my devs some hours in the meantime, I allowed the agency to hire us to do their web design thinking I would have zero involvement, the work would just go through my LTD company. It turned into a big cluster-F that is still taking up hours upon hours, has likely cost me $25,000. Stupidest decision ever.

Don't get involved in pointless side quests to please people.
 

GoodluckChuck

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Didn't account for the lack of daily structure of being an entrepreneur switching gears from 9-5 life.

Spent a year wondering why consistency was an issue. Finally developed a daily routine and it all became clear.
 
D

DeletedUser0287

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Listening to self-proclaimed experts on here and not doing by due diligence that there is a lot of bias in who endorses who.

Learned to ask myself, if they selling an business course they most likely a scammer. Them providing so called free value is just them attempting to position themselves as an expert, even if they are not. Just part of their inbound marketing game.

Biggest one is realizing that the intuition of others are also not very good in judging who actually knows their stuff. Aka, regular people saying “But how can you not listen X person? He knows so much about X topic” These are the people that completely fell for the scammers inbound and expert positioning scam I described above.

Solution? I do my own thing and think for myself even if it goes against the so called “expert’s advice” everyone else is following.
 

dropservicers

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Took on almost anyone that was interested in my service. Hired an agency to help offload some of the work. Agency had amazing reviews online and passed my very "loose" interview.

One month later, two chargebacks and an entire month's worth of wage to the agency was coming out of my pocket. This was months ago and I've since hired some absolute rockstars but it has taken awhile to get out of the cash flow mess I was left in. Lesson learned? Interview like the CIA. High quality won't be afraid to prove it.
 
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MoneyDoc

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Took money out of the business for other investments when the company was beginning to grow.

Used personal credit cards to finance inventory.

Bought a Rolex. Sold it at a loss of $8k.

Lack of clarity and consistency (still deal with this today).

Told family/friends I have a business. Now they won't stop leaving me alone to the point I ignore phone calls and texts. Been asked for money a lot as well.
 
D

Deleted78083

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Listening to self-proclaimed experts on here and not doing by due diligence that there is a lot of bias in who endorses who.

Learned to ask myself, if they selling an business course they most likely a scammer. Them providing so called free value is just them attempting to position themselves as an expert, even if they are not. Just part of their inbound marketing game.

Biggest one is realizing that the intuition of others are also not very good in judging who actually knows their stuff. Aka, regular people saying “But how can you not listen X person? He knows so much about X topic” These are the people that completely fell for the scammers inbound and expert positioning scam I described above.

Solution? I do my own thing and think for myself even if it goes against the so called “expert’s advice” everyone else is following.

Amen
 

DonJuan

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Taking too long to kill a weak idea, product or business venture.

If you don't, you end up burning cash & ultimately getting nowhere.

I've found it essential to quickly recognize when something just won't work out.

Lesson learned the hard way.
 

Paul David

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Can you still use the money left from the loan to build another business?

Unfortunately not, there's none left now. I have however started an ads agency which I don't need any capital to get off the ground!
 
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socaldude

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-trusting the wrong people and not knowing how to read people.

-thinking that having six figs in cash makes you a baller, it doesn’t.

-not being able to identify and correct emotional and behavioral flaws.

-not overcoming depression and low self esteem quick enough. Huge mistake. Very poor decisions and motivations to learn new things or to invent new ideas.

BTW

look into metacognition, it’s the study of analyzing your thinking. Also look into heuristics, the study and science of decision theory.
 

100ToOne

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Told myself:

"No need to keep progressing and learning and improving, it's time for the business to go steady and fulfill the needs and generate the current profit /imtired"

1 year later:

Everyone else improved and my business profits died and I ended up closing it down.

Moral of the story, if you want to be passive robot, get a job, if you want to open a business, it develops as long as you stay actively developing.
 
D

Deleted78083

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-trusting the wrong people and not knowing how to read people.

-thinking that having six figs in cash makes you a baller, it doesn’t.

-not being able to identify and correct emotional and behavioral flaws.

-not overcoming depression and low self esteem quick enough. Huge mistake. Very poor decisions and motivations to learn new things or to invent new ideas.

BTW

look into metacognition, it’s the study of analyzing your thinking. Also look into heuristics, the study and science of decision theory.

Thinking fast and slow is a must read for anyone who has a tendency at being "their worst enemy".
 
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D

Deleted78083

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Taking too long to kill a weak idea, product or business venture.

If you don't, you end up burning cash & ultimately getting nowhere.

I've found it essential to quickly recognize when something just won't work out.

Lesson learned the hard way.

Could you expand on that?
 
D

Deleted74396

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Buying and renovating a house. The stress made me suicidal and when I took an income hit I couldn't invest in business cuz all my capital was tied up in the house which made me more depressed. Now I'm selling just as a recession is starting so I could end up coming out after 3 years with LESS than I started with, even after renovating from top to bottom. Don't buy a house if you're under 25/don't have double the cash!
 

MoreVolume

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Decided to become a wine tester (aka bought new bottles of wine frequently) with my new found personal spending budget
I stopped taking my health seriously, and as a result, became lazy in my daily routine

It wasnt until I looked at myself in the mirror and felt disgusted, that I did anything to change it
When my health improved (stopped drinking, started working out) my productivity improved. I was able to develop new innovative campaigns, which lead to a trend upwards in sales

Listening to self-proclaimed experts on here and not doing by due diligence that there is a lot of bias in who endorses who.

Learned to ask myself, if they selling an business course they most likely a scammer. Them providing so called free value is just them attempting to position themselves as an expert, even if they are not. Just part of their inbound marketing game.

Biggest one is realizing that the intuition of others are also not very good in judging who actually knows their stuff. Aka, regular people saying “But how can you not listen X person? He knows so much about X topic” These are the people that completely fell for the scammers inbound and expert positioning scam I described above.

Solution? I do my own thing and think for myself even if it goes against the so called “expert’s advice” everyone else is following.
Aren't you the guy who's sold 0 products so far?:)
 
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Last edited:

BizyDad

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VentureVoyager

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-Sideprojects and not fully focusing on a SINGLE project, chasing shiny objects. Firmly believing that I need 3459 different sources of income, because somebody wrote so in their book or said so on their YT channel.

-Not taking care of my health and diet, quitting gym to be able to "grind and hustle" more. It was effective for my business, for some time, but destroyed my mental and physical health. So it was totaly counterproductive in a long run.

-Not listening to my body and my needs and my own deep desires: Not taking care of proper life-work balance (e.g taking proper vacation frequently enough, or doing digital detox once in a while), which finally resulted in serious burnout.

-Becoming complacent: not actively investing in learning more, e.g. concrete marketing skills like copywriting etc.
 

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I don't really have regrets except for ONE thing... Not moving to somewhere like PR that has a much smaller tax burden before I made money. I always thought to myself that I would do it once I saved up or had resources to make the move without a financial burden. Well that day has come, and now I just wished I had done it back when it was easy and wasn't such a big deal to leave. I am sure this only gets harder so, we are definitely making this a priority now.

Beyond that, I have made TONS of mistakes over the years. Sucks, but GOD HELP the entrepreneur that hasn't screwed up yet. Because people like us, in this thread, are a hell of a lot smarter for our mistakes.

I am a better leader and a better businessman because of the difficulties I have had to deal with and I wouldn't change anything else.
 
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luniac

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neglecting my health and burning out, which destroyed my productivity for several critical years.

you are not indestructible, take care of your health please.
 

Bearcorp

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Decided to become a wine tester (aka bought new bottles of wine frequently)

can relate to being a wine tester in the past :rofl:

I’ve made heaps of mistakes along the way but the worst decision was not creating my company structure sooner, I got sued a few years ago and I was exposed personally as well as my company. It wasn’t a huge deal for me because I didn’t have anything but my business partner had a house with his wife that was at stake if things went bad. It had a bearing on how we handled it over the journey, but that’s over now, so lesson learned and we move forward. Making more little mistakes along the way :rofl:
 

AFMKelvin

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Took money out of the business for other investments when the company was beginning to grow.

Used personal credit cards to finance inventory.

Bought a Rolex. Sold it at a loss of $8k.

Lack of clarity and consistency (still deal with this today).

Told family/friends I have a business. Now they won't stop leaving me alone to the point I ignore phone calls and texts. Been asked for money a lot as well.
What do families and friends call you for other than money?
 

Entre Eyes

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Took money out of the business for other investments when the company was beginning to grow.

Used personal credit cards to finance inventory.

Bought a Rolex. Sold it at a loss of $8k.

Lack of clarity and consistency (still deal with this today).

Told family/friends I have a business. Now they won't stop leaving me alone to the point I ignore phone calls and texts. Been asked for money a lot as well.

There was someone I really respected who owned a "rolly" and I had to get one.
But once I got it I noticed it was always one minute off an that pissed me off! :)

Then I researched that it can be common with Rolex. What a let down.

This is a great topic others can learn and leverage from. Props to the Op.

I almost wrote a book called The Broke Genius. I love double meanings.

It meant you can be a genius and be broke in the pockets and also have a broken mentality.

For example, making great money and not a good money manager. Blood type energy drinks. Not sleeping. Not enjoying life.

But I think if I could go back to my first big success online and give myself advice it would be to build my own email list first and foremost.

It keeps your business in business. It is social proof, google proof, economy proof.
 
Last edited:

MoneyDoc

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What do families and friends call you for other than money?
Family; unfortunately, nothing else. But, I’ve learned to ignore. My cousins still owe me thousands. As cliche as it may sound, I had some calls from uncles I didn’t know existed, lmao. Ahhh life.

Friends; cut off the ones that were leeching as I couldn’t take it anymore. The few friends I do have are all entrepreneurs and all my age. So we get along perfectly.
 
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MoneyDoc

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There was someone I really respected who owned a "rolly" and I had to get one.
But once I got it I noticed it was always one minute off an that pissed me off! :)

Then I researched that it can be common with Rolex. What a let down.


This is a great topic others can learn and leverage from. Props to the Op.

I almost wrote a book called The Broke Genius. I love double meanings.

It meant you can be a genius and be broke in the pockets and also have a broken mentality.

For example, making great money and not a good money manager. Blood type energy drinks. Not sleeping. Not enjoying life.

But I think if I could go back to my first big success online and give myself advice it would be to build my own email list first and foremost.

It keeps your business in business. It is social proof, google proof, economy proof.
For me, I just needed the money. So I'm kinda glad I did buy it then. Paid like $18k with taxes (brand new). Sold it for $10k. It was my first ever watch, so it held some sentimental value but I had no choice. I know I could've sold it for $14-15k, but I didn't have time to wait. Needed the $10k ASAP.

Live and learn.
 

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