I asked 54 brilliant entrepreneurs and business professionals:
"What's the biggest, most expensive mistake you've ever made?"
In this thread, you can find their answers 🧵
"What's the biggest, most expensive mistake you've ever made?"
In this thread, you can find their answers 🧵
1. Andrew Gazdecki — @agazdecki
I'd say not hiring people smarter than me sooner at my 1st startup.
It takes a team to win.
I'd say not hiring people smarter than me sooner at my 1st startup.
It takes a team to win.
@agazdecki 2. Jesse Pujji — @jspujji
Not selling my company because I got hung up on valuation.
I was mentally ready to make a change. yet got caught up in a 10-15% price difference and didn't do the deal.
Self-awareness, knowing what you truly want and acting on it is so important.
Not selling my company because I got hung up on valuation.
I was mentally ready to make a change. yet got caught up in a 10-15% price difference and didn't do the deal.
Self-awareness, knowing what you truly want and acting on it is so important.
@agazdecki @jspujji 3. Sam Parr — @thesamparr
Being too generous with equity early on.
Employee equity pools rarely are very big.
Wish I saved it for the real needle movers and instead paid higher in cash salary.
Being too generous with equity early on.
Employee equity pools rarely are very big.
Wish I saved it for the real needle movers and instead paid higher in cash salary.
@agazdecki @jspujji @thesamparr 4. Justin Welsh — @JustinSaaS
I spent $3,000+ on software I didn't need.
I hadn't validated that I'd need the platform's features.
After 2 months, I gave up and moved to a $19/month solution that powered my business for the next 2 years.
When just starting, keep it simple
I spent $3,000+ on software I didn't need.
I hadn't validated that I'd need the platform's features.
After 2 months, I gave up and moved to a $19/month solution that powered my business for the next 2 years.
When just starting, keep it simple
@agazdecki @jspujji @thesamparr @JustinSaaS 5. Dan Go — @FitFounder
Not getting coaching soon enough.
Coaching speeds attainment by learning from other people's mistakes & being held accountable to your goals.
Not getting coaching soon enough.
Coaching speeds attainment by learning from other people's mistakes & being held accountable to your goals.
@agazdecki @jspujji @thesamparr @JustinSaaS @FitFounder 6. Ross Simmonds — @TheCoolestCool
Taking on clients that weren't aligned with our vision because they paid well.
The distraction of working with a brand that didn't align with our goals set us back months.
The lesson?
Stay focused.
Taking on clients that weren't aligned with our vision because they paid well.
The distraction of working with a brand that didn't align with our goals set us back months.
The lesson?
Stay focused.
@agazdecki @jspujji @thesamparr @JustinSaaS @FitFounder @TheCoolestCool 7. 𝐓𝐡𝐞 𝐀𝐫𝐭 𝐨𝐟 𝐏𝐮𝐫𝐩𝐨𝐬𝐞 — @creation247
NOT betting on myself sooner.
I played it safe for too long because it was comfortable.
That held my personal growth back.
Once I made the jump, I tapped into my potential and I never looked back.
NOT betting on myself sooner.
I played it safe for too long because it was comfortable.
That held my personal growth back.
Once I made the jump, I tapped into my potential and I never looked back.
@agazdecki @jspujji @thesamparr @JustinSaaS @FitFounder @TheCoolestCool @creation247 8. Noel Dávila — @NoelDavila
In 2015, I took a job based solely on salary.
Something felt off, but I ignored my instinct.
This resulted in a professional crisis that lasted over 3 years and cost me a lot.
The lesson:
Always consider the full picture.
In 2015, I took a job based solely on salary.
Something felt off, but I ignored my instinct.
This resulted in a professional crisis that lasted over 3 years and cost me a lot.
The lesson:
Always consider the full picture.
@agazdecki @jspujji @thesamparr @JustinSaaS @FitFounder @TheCoolestCool @creation247 @NoelDavila 9. Taylor Welch — @taylorawelch
Creating short term incentives & expecting long term decisions.
It's difficult to get a man to understand something, when his salary depends upon his not understanding it. - Upton Sinclair
I wrote more about it here: shorturl.at/fjmJ1
Creating short term incentives & expecting long term decisions.
It's difficult to get a man to understand something, when his salary depends upon his not understanding it. - Upton Sinclair
I wrote more about it here: shorturl.at/fjmJ1
10. Coach Timothy Reigle — @TimothyReigle
Being cheap.
I tried to do everything myself just to save money.
When I put out the money to get real help...
...I made more money from using their quality work than I ever would have saved doing it all myself.
Being cheap.
I tried to do everything myself just to save money.
When I put out the money to get real help...
...I made more money from using their quality work than I ever would have saved doing it all myself.
11. Simmo — @iamsimm0
Biggest mistake I made was to always think I needed to rush & force things.
The irony being, because I didn’t take my time & wasn’t more methodical, it took me MUCH longer.
Slow & steady wins the race.
Biggest mistake I made was to always think I needed to rush & force things.
The irony being, because I didn’t take my time & wasn’t more methodical, it took me MUCH longer.
Slow & steady wins the race.
12. Steve · Millionaire Habits — @SteveOnSpeed
Thinking I could do it alone.
Rookie mistake.
Today, I belong to a couple mastermind groups where we all help each other out.
It's made a big difference for me and others in the group.
Thinking I could do it alone.
Rookie mistake.
Today, I belong to a couple mastermind groups where we all help each other out.
It's made a big difference for me and others in the group.
13. Dagobert Renouf — @dagorenouf
Bringing in a co-founder I had never worked with before.
I learned that you can't know how someone will react under pressure ahead of time.
So it's better to partner with people you already trust.
Bringing in a co-founder I had never worked with before.
I learned that you can't know how someone will react under pressure ahead of time.
So it's better to partner with people you already trust.
14. Austin Belcak — @austinbelcak
Trying too many channels at once.
Early on, I was doing Twitter, LinkedIn, IG, YouTube, etc.
But nothing was happening.
Then I cut them all out except for LinkedIn.
The result?
I grew from 3k to 100k+ followers in 12 months.
Trying too many channels at once.
Early on, I was doing Twitter, LinkedIn, IG, YouTube, etc.
But nothing was happening.
Then I cut them all out except for LinkedIn.
The result?
I grew from 3k to 100k+ followers in 12 months.
15. Kyle Prinsloo — @kylepdotco
Going into partnership.
Having expectations on how you think things will work out.
My advice: stay solo.
Rather outsource tasks.
A successful business doesn’t need a partnership.
Most don’t work out.
Going into partnership.
Having expectations on how you think things will work out.
My advice: stay solo.
Rather outsource tasks.
A successful business doesn’t need a partnership.
Most don’t work out.
16. Chase Dimond — @ecomchasedimond
Hiring cheap is actually more expensive.
The cost of doing it wrong or slow, ends up costing you more in the long run.
Better to do it once, right.
And ideally quickly.
Hiring cheap is actually more expensive.
The cost of doing it wrong or slow, ends up costing you more in the long run.
Better to do it once, right.
And ideally quickly.
17. Steph Smith — @stephsmithio
I spent far too long working for a terrible boss.
I lasted in that role for nearly a year, despite knowing the problem was bad in month 1.
There are so many opportunities out there!
Don't waste your life trying to change someone else.
I spent far too long working for a terrible boss.
I lasted in that role for nearly a year, despite knowing the problem was bad in month 1.
There are so many opportunities out there!
Don't waste your life trying to change someone else.
18. David Mendes — @YouActualized
Many times I stress myself out over bad outcomes.
I let them demoralize me, impacting my results negatively.
On a long enough timeline, these outcomes don't matter much.
Time in the game, volume, and constant iteration > everything else.
Many times I stress myself out over bad outcomes.
I let them demoralize me, impacting my results negatively.
On a long enough timeline, these outcomes don't matter much.
Time in the game, volume, and constant iteration > everything else.
19. Margaret Molloy — @MargaretMolloy
In business in general, I think the biggest makes are around hiring.
Talent and culture are everything.
Hard to fix anything else if the wrong people are on the train!
In business in general, I think the biggest makes are around hiring.
Talent and culture are everything.
Hard to fix anything else if the wrong people are on the train!
20. Kent Stuver — @KentStuver
Invested in an education company that couldn't deliver.
Always trust the executive team.
Invested in an education company that couldn't deliver.
Always trust the executive team.
21. Hustle 4 Freedom — @HustlingForever
Trying too many things at once instead of fully focusing on one thing.
That made me lose a lot of money and time.
Trying too many things at once instead of fully focusing on one thing.
That made me lose a lot of money and time.
22. Real Estate Hacker — @rehacks_
I had a rigid vision.
Entrepreneurship is a jamming session with users; an iterative approach with a #failfast mentality.
Validate everything and be ready to pivot.
Most entrepreneurs end up doing something different than they intended.
I had a rigid vision.
Entrepreneurship is a jamming session with users; an iterative approach with a #failfast mentality.
Validate everything and be ready to pivot.
Most entrepreneurs end up doing something different than they intended.
23. Jose R. Rosado — @joserosado
Getting comfortable when I tasted success for the first time.
I made as much money in one month as I did in a year.
The result?
My income dropped.
When you're winning, don't slow down.
Instead, double down on what’s working.
Getting comfortable when I tasted success for the first time.
I made as much money in one month as I did in a year.
The result?
My income dropped.
When you're winning, don't slow down.
Instead, double down on what’s working.
24. Jeremy Moser — @jmoserr
Diversifying too soon.
Getting a win in business.
Then trying to start multiple ventures too fast instead of tripling down on what was already booming.
When you think you’ve hit the ceiling of growth in a venture, you probably haven’t.
Diversifying too soon.
Getting a win in business.
Then trying to start multiple ventures too fast instead of tripling down on what was already booming.
When you think you’ve hit the ceiling of growth in a venture, you probably haven’t.
25. Lucian Tartea — @luciantartea
Not building my own templates shop and audience sooner.
I relied for too long on marketplaces.
Not building my own templates shop and audience sooner.
I relied for too long on marketplaces.
26. Swyx — @swyx
Not intervening quickly enough when it’s clear a project or team is starting to go in the wrong direction.
Micromanaging sucks.
But mistakes also compound.
Need to constantly align on goals or we spend a year winding up in a place nobody is happy in.
Not intervening quickly enough when it’s clear a project or team is starting to go in the wrong direction.
Micromanaging sucks.
But mistakes also compound.
Need to constantly align on goals or we spend a year winding up in a place nobody is happy in.
27. Dakota Robertson — @WrongsToWrite
Partnering in business needlessly.
We both had similar skills. It didn't make sense.
The workload was lighter, but profits were cut by 50%.
I should’ve hired contractors instead.
Fortunately, I could cut ties before my business scaled.
Partnering in business needlessly.
We both had similar skills. It didn't make sense.
The workload was lighter, but profits were cut by 50%.
I should’ve hired contractors instead.
Fortunately, I could cut ties before my business scaled.
28. Tyler Todt — @tyromper
Not to trust myself sooner.
Not to hire coaching sooner to help me avoid some of those mistakes.
Not to trust myself sooner.
Not to hire coaching sooner to help me avoid some of those mistakes.
29. HUSTLE & CONQUER — @hustlenconquer
The biggest mistake I made was:
"Trying to create a market for my products."
I lost a ton of money & time doing that.
The right way is to find where the buyers are and solve problems for them.
The biggest mistake I made was:
"Trying to create a market for my products."
I lost a ton of money & time doing that.
The right way is to find where the buyers are and solve problems for them.
30. Brittany Berger — @thatbberg
Trying to get professional branding done before my business was ready for it.
I didn’t know how to properly vet collaborators.
I ended up spending $4k on someone who had horrible processes & ended up ghosting me before anything was done.
Trying to get professional branding done before my business was ready for it.
I didn’t know how to properly vet collaborators.
I ended up spending $4k on someone who had horrible processes & ended up ghosting me before anything was done.
31. Andrea Bosoni — @theandreboso
The biggest mistake I've ever made was building a product without validating my idea first.
The biggest mistake I've ever made was building a product without validating my idea first.
32. Joey Justice — @heyjoeyjustice
Not staying consistent.
In both business and content creation, consistency is key.
Without it, you'll lose momentum and get stuck in a rut.
Not staying consistent.
In both business and content creation, consistency is key.
Without it, you'll lose momentum and get stuck in a rut.
33. Midnight Underdog — @MidnightUDog
The biggest mistake I’ve made is investing too much into a business too early.
Proof of concept is essential when starting out.
That one failure taught me to be more patient and find the right opportunity.
The biggest mistake I’ve made is investing too much into a business too early.
Proof of concept is essential when starting out.
That one failure taught me to be more patient and find the right opportunity.
34. Mat De Sousa — @DsMatie
Starting a new business without validating it.
Validate the problem and the need.
Never assume you know what people want.
If I properly validate an idea, I can't fail.
I mean, I can still fail, but it won't be because nobody wants it.
Starting a new business without validating it.
Validate the problem and the need.
Never assume you know what people want.
If I properly validate an idea, I can't fail.
I mean, I can still fail, but it won't be because nobody wants it.
35. Feldon Richards — @nycphonebuyer
Wallowing in self-pity over mistakes I've made.
I learned that trying to avoid mistakes is like trying to drive 70 MPH in New York City traffic.
It's impossible.
You have to embrace mistakes if you want to grow.
Wallowing in self-pity over mistakes I've made.
I learned that trying to avoid mistakes is like trying to drive 70 MPH in New York City traffic.
It's impossible.
You have to embrace mistakes if you want to grow.
36. Tibo - 6/100 — @tibo_maker
Thinking a big team will make things easier.
I hired 10 young interns for my first startup.
I was spending my days managing, not building.
It can work when you’ve got proof of concept. It's a nightmare when you're still exploring an industry.
Thinking a big team will make things easier.
I hired 10 young interns for my first startup.
I was spending my days managing, not building.
It can work when you’ve got proof of concept. It's a nightmare when you're still exploring an industry.
37. Julie Joyce — @JulieJoyce
Building a business on one large client.
They were around 75% of our total client load.
When it worked, it was great.
But when they pulled out, it was carnage.
I now prefer to keep a more balanced roster of clients.
Building a business on one large client.
They were around 75% of our total client load.
When it worked, it was great.
But when they pulled out, it was carnage.
I now prefer to keep a more balanced roster of clients.
38. Simon Høiberg — @SimonHoiberg
Thinking that I didn't need an audience.
Expecting that recruiting other influential people would have as big of an impact as if I did it myself.
Building a brand as an entrepreneur is one of the most valuable decisions you can make.
Thinking that I didn't need an audience.
Expecting that recruiting other influential people would have as big of an impact as if I did it myself.
Building a brand as an entrepreneur is one of the most valuable decisions you can make.
39. JK MOLINA — @OneJKMolina
Thinking when it's time to not think.
Not thinking when it's time to think.
High performance is only possible with your full mental capacity or none.
It's not possible if you're half-thinking.
Thinking when it's time to not think.
Not thinking when it's time to think.
High performance is only possible with your full mental capacity or none.
It's not possible if you're half-thinking.
40. Tim Hughes — @Timothy_Hughes
Don't let toxicity get into your business.
There may be times when you think due to lack of resources, a given hire will work.
Don’t do it; you will always regret it.
If you think a person is toxic, don’t go near them and don’t hire them.
Don't let toxicity get into your business.
There may be times when you think due to lack of resources, a given hire will work.
Don’t do it; you will always regret it.
If you think a person is toxic, don’t go near them and don’t hire them.
41. ROGUEWEALTH 🔱 SALES — @ROGUEWEALTH
Went crazy with spending.
Don't go crazy with spending when your income might be variable still.
Went crazy with spending.
Don't go crazy with spending when your income might be variable still.
42. Arvid Kahl — @arvidkahl
When growing FeedbackPanda, I overestimated my bandwidth and resisted hiring for help.
It caused me to spiral into burnout.
This turned out to be very costly for me.
We can delude ourselves into a "hustle mindset," neglecting our mental health.
When growing FeedbackPanda, I overestimated my bandwidth and resisted hiring for help.
It caused me to spiral into burnout.
This turned out to be very costly for me.
We can delude ourselves into a "hustle mindset," neglecting our mental health.
43. Michael Lisovetsky — @_Liso_
As a venture-backed CEO, I thought my job was to have our runway be as long as possible, rather than achieve venture-scale outcomes in the shortest amount of time.
We made our runway last a long time, losing a lot of progress in the process.
As a venture-backed CEO, I thought my job was to have our runway be as long as possible, rather than achieve venture-scale outcomes in the shortest amount of time.
We made our runway last a long time, losing a lot of progress in the process.
44. Harry Dry — @harrydry
Spending 4 months in a basement building a website to sell “custom Twitter prints” without talking to any customers.
We sold about 4.
Lesson — Build something people want.
Spending 4 months in a basement building a website to sell “custom Twitter prints” without talking to any customers.
We sold about 4.
Lesson — Build something people want.
45. Guillaume Moubeche — @GuillaumeMbh
Hiring a developer who stole our code when we fired him.
Even if you have really good lawyers and contracts, your power is still fairly limited when you work internationally.
Hiring a developer who stole our code when we fired him.
Even if you have really good lawyers and contracts, your power is still fairly limited when you work internationally.
46. Elizabeth Yin — @dunkhippo33
Not validating customer demand with pre-sales before building the product.
We spent a lot of time building out something no one wanted at all.
Not validating customer demand with pre-sales before building the product.
We spent a lot of time building out something no one wanted at all.
47. Tom Hirst — @tom_hirst
Overwhelming myself.
The temptation to do too much when you’re capable of doing a lot is high.
It’s better to pick off 1 or 2 pursuits to give your all and bring on people to help with the things you’re not an expert at.
Overwhelming myself.
The temptation to do too much when you’re capable of doing a lot is high.
It’s better to pick off 1 or 2 pursuits to give your all and bring on people to help with the things you’re not an expert at.
48. Aaron Williams — @IAmAaronWill
Not sticking to one thing.
Buying course after course, instead of buying into one thing.
Would’ve saved thousands of dollars if I just bought one course, studied it, and then began implementing.
Pick one thing and give it 101%.
Not sticking to one thing.
Buying course after course, instead of buying into one thing.
Would’ve saved thousands of dollars if I just bought one course, studied it, and then began implementing.
Pick one thing and give it 101%.
49. Chantelle — @ccmarce_writes
I've learned to be more firm and confident in my communication.
I've waffled on decisions when I wanted to avoid uncomfortable conversations or conflict.
In the end, I only prolonged issues instead of avoiding them.
I've learned to be more firm and confident in my communication.
I've waffled on decisions when I wanted to avoid uncomfortable conversations or conflict.
In the end, I only prolonged issues instead of avoiding them.
50. Devin McDermott — @devinmcdermot
Taking my foot off the gas after seeing some great results, which killed my momentum and cost LOTS of potential growth.
Taking my foot off the gas after seeing some great results, which killed my momentum and cost LOTS of potential growth.
51. Dashiell Bark-Huss — @DashBarkHuss
I spent $2k on a 3D body scan business for events.
I never validated it.
I was afraid of failing, yet over excited.
Be patient and recognize the commitment and steps required to see an idea through before spending money.
I spent $2k on a 3D body scan business for events.
I never validated it.
I was afraid of failing, yet over excited.
Be patient and recognize the commitment and steps required to see an idea through before spending money.
52. Shama Hyder — @Shama
Not asking is the biggest mistake.
If you never ask, the answer is always no.
I wanted to acquire a newsletter I admired, but didn't think the editor would ever sell.
Two months later, they announced they'd sold.
Not asking is the biggest mistake.
If you never ask, the answer is always no.
I wanted to acquire a newsletter I admired, but didn't think the editor would ever sell.
Two months later, they announced they'd sold.
53. Brian Casel — @CasJam
Back when I was unable to build the back-end for my product ideas, I spent tens of thousands of dollars (and way too much time) shipping early SaaS ideas.
Back when I was unable to build the back-end for my product ideas, I spent tens of thousands of dollars (and way too much time) shipping early SaaS ideas.
https://twitter.com/CasJam/status/1509898292058075138
54. Dickie Bush — @dickiebush
Thinking I needed to have everything figured out to get started.
This led to extended periods of "planning" that were really procrastination in disguise.
The time will never be right to start something.
Everyone is figuring it out as they go.
Thinking I needed to have everything figured out to get started.
This led to extended periods of "planning" that were really procrastination in disguise.
The time will never be right to start something.
Everyone is figuring it out as they go.
Neville Medhora — @nevmed
"Playing business" for too long.
Before you have a product that's selling, you setup an LLC, make business cards, design a website, etc.
All before making sales!
This is not a great way to start a business. Start small and get sales. Then build up.
"Playing business" for too long.
Before you have a product that's selling, you setup an LLC, make business cards, design a website, etc.
All before making sales!
This is not a great way to start a business. Start small and get sales. Then build up.
56. Adrienne Barnes — @AdrienneNakohl
The most expensive mistake I've made, is not listening to my instincts when I knew a client wasn't a good fit.
It filled up my time, made my days challenging, and always felt like a struggle.
The most expensive mistake I've made, is not listening to my instincts when I knew a client wasn't a good fit.
It filled up my time, made my days challenging, and always felt like a struggle.
57. Ryan Stephens — @ryanstephens
My biggest, most expensive mistakes were mistakes of inaction, not things I tried and messed up.
Everyone's still figuring it out.
There's countless ways to add value.
Jump in and get started.
If you mess up, learn from it and pivot.
My biggest, most expensive mistakes were mistakes of inaction, not things I tried and messed up.
Everyone's still figuring it out.
There's countless ways to add value.
Jump in and get started.
If you mess up, learn from it and pivot.
58. Gal Shapira — @galjudo
Not believing in myself.
Thinking too small, being afraid to promote myself or charge for the service I provide. Letting fear get in the way of opportunities, keeping ideas in my head.
If you have an idea, act on it.
Speed is what matters.
Not believing in myself.
Thinking too small, being afraid to promote myself or charge for the service I provide. Letting fear get in the way of opportunities, keeping ideas in my head.
If you have an idea, act on it.
Speed is what matters.
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