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INTRO $30m business and I'm just a bitch

FIFL

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I come here to seek advice, admonishment and like-minded souls.

I am 3yrs in as 2nd-in-command (non founder) of an emerging tech startup. Roughly a $30m business that's just hit Series B. I have equity in the business (around 3-4%) that's illiquid until exit (goal would be $100m+). I look after the revenue/commercial operations of our business, basically everything aside from building the product. I've had a role in most of our ~$3m / year of recurring revenue. Pay is around $300k/year and will grow. Some days I like what I do. Many days I can't stand it and feel a FTE is extremely close. I fantasize regularly about building my own company. Oh and the CEO is a narcissistic pathological liar. It's objectively an incredibly difficult environment to succeed in, with very little empowerment, recognition or support. Kind of sounds like running your own company to me :)

To me I'm in the slowlane. I feel like I am failing @MJ DeMarco 's commandments. Like an employee with a little tiny bit of cream. This makes me incredibly anxious to do something else with my time.

Circumstantially I have done fairly well. Perhaps too well and the comfort prevents a complete FTE meltdown. From $0 in my pocket 10 years ago, I now have a house, investment property, stock portfolio, crypto investments, etc. and have been a well paid slowlaner for those years. I still for the most part live the same way I always have and tend to save and invest my money. I guess you'd call me a savings rat. I have a well-paid wife and two children under 3.

I am not risk averse, and I have progressively worked for riskier and riskier businesses. This company was absolutely fledgling with shitty, unknown customers when I joined and I have helped grow it from a nothing to where we now have major utilities, telcos and 100's of customers.

Recently I've been thinking it's really time to pull the rip cord. I want control of my own destiny. If I leave, I'll lose some of my unvested equity (probably $1m worth over 4-5 years), but my already vested equity will still be worth a couple of $mil, and I don't have a slog my guts out on something I have no control over working for a maniac.

I'm a little lost on what to do. It is a bit to walk away from. It's really not a topic I have anyone I can talk to about with and none of my friends are in similar situations nor do they have aspirations to build businesses from scratch.

I believe I have plenty to offer and have the chops to work through failure and struggle, but the pace and intensity of the shit I deal with daily leaves barely a moment to stop and think and plan for what next. I feel like I need to just jump.

I would greatly appreciate practical advice on what to do or criticism of my thought process or mindset. Don't hold back now.
 

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alexkuzmov

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I now have a house, investment property, stock portfolio, crypto investments, etc.
but my already vested equity will still be worth a couple of $mil, and I don't have a slog my guts out on something I have no control over working for a maniac.

You can always make more money, but you can never get back time.

So what are you waiting for?
What else do you need to quit and start your own journey?
What is stopping you?
 

WillHurtDontCare

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Quit being dramatic. You make $300K a year and you have investment expertise - just start buying your own assets and build your own portfolio.
 

MTF

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To me, if you're smart about your investments, it looks like you're on track to be retired within a few years at most.

If you start a new business now, it'll be starting from zero, with no guarantee it'll work anytime soon. It'll most likely take more than 5 years. Is this worth it?

I'd probably figure out a way to make your job more enjoyable and follow @WillHurtDontCare's advice.
 

Antifragile

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@FIFL

these decisions are highly personal. It’s easy to “give advice” on a public forum, and most of that advice is useless.

What I can tell you is that when I was in a situation similar to yours (but worse), my mentor who is in his 70s told me “you don’t need my advice, in your heart you already made a decision, follow it.”
Since then, I make my decisions with a simple test, I imagine I’m on my death bed (yes, morbid but useful) and I look back at this point of my life, what decision or lack of decisions will I regret? Don’t do things you’ll regret on your death bed.

good luck!
 

humananalytics

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If you're in an expensive area like SF/NYC, 300k/year in income is not enough to be baller or retire that quickly.

In terms of your equity, do you know if how much you will be diluted if you leave now? Do you have an opportunity at the next round of fundraising to offload your equity? Also, if the CEO is THAT bad, is there an opportunity for you to take over the CEOs role?

I've had friends that have left behind equity to start their own thing, and it has often worked out for them. If you have a high profile role in a well funded start-up, you'll have some options to raise quite a bit if you venture off solo.
 

MJ DeMarco

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Where do you see your life in 5 or 10 years? Your job might be able to play a role in those visions -- it pays well and has an opportunity for asymmetric returns, which can be a conduit to your longer term goals.

Your path depends on that outlook.
 

FIFL

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You can always make more money, but you can never get back time.

So what are you waiting for?
What else do you need to quit and start your own journey?
What is stopping you?
Good question. I'm indecisive as it's a lot to walk away from.

What's stopping me, to be honest, is that I don't know what I'd do otherwise yet.

Quit being dramatic. You make $300K a year and you have investment expertise - just start buying your own assets and build your own portfolio.
Good advice. I am doing that (not active investments mind you). I have been thinking about buying symbiotic businesses and building other revenue streams.

To me, if you're smart about your investments, it looks like you're on track to be retired within a few years at most.

If you start a new business now, it'll be starting from zero, with no guarantee it'll work anytime soon. It'll most likely take more than 5 years. Is this worth it?

I'd probably figure out a way to make your job more enjoyable and follow @WillHurtDontCare's advice.
I'm pretty close yeah - around 5 years.
 

FIFL

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@FIFL

these decisions are highly personal. It’s easy to “give advice” on a public forum, and most of that advice is useless.

What I can tell you is that when I was in a situation similar to yours (but worse), my mentor who is in his 70s told me “you don’t need my advice, in your heart you already made a decision, follow it.”
Since then, I make my decisions with a simple test, I imagine I’m on my death bed (yes, morbid but useful) and I look back at this point of my life, what decision or lack of decisions will I regret? Don’t do things you’ll regret on your death bed.

good luck!
I appreciate this post, thanks.

Regrets would include the "what if I had seen this through to exit". From that perspective I err on the side of going hell for leather where I am and jumping into another endeavor when I've cashed out.
 

FIFL

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If you're in an expensive area like SF/NYC, 300k/year in income is not enough to be baller or retire that quickly.

In terms of your equity, do you know if how much you will be diluted if you leave now? Do you have an opportunity at the next round of fundraising to offload your equity? Also, if the CEO is THAT bad, is there an opportunity for you to take over the CEOs role?

I've had friends that have left behind equity to start their own thing, and it has often worked out for them. If you have a high profile role in a well funded start-up, you'll have some options to raise quite a bit if you venture off solo.
I could offload equity though it is likely to 3-4x from here in the next couple of years.

Displacing the CEO is difficult as they're a founder. The VC's coming in and taking board seats as well as the necessary change in the business due to the phases we are to pass through are likely to positively influence his behaviour, or so I hope.
 

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Antifragile

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Keep us posted here on what you do and how we can support you. Consider Insiders side of the forum if you ever wanted to get deeper into a conversation that’s not for full public consumption.
 

FIFL

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Where do you see your life in 5 or 10 years? Your job might be able to play a role in those visions -- it pays well and has an opportunity for asymmetric returns, which can be a conduit to your longer term goals.

Your path depends on that outlook.
Ultimately I think this is key. With those timeframes I genuinely see myself taking the direct time to build something else when I have the focus - but with a significant safety net and asset base.

What I am learning doing what I do daily is very valuable. I'm exposed to so much that I haven't had the opportunity to see, and wouldn't be likely to otherwise. I'm grateful for that.

It feels as though continuing to focus on what I'm doing can be a path to a fantastic result, but some solid investing on the side would be wise to start to diversify my income (but ideally not my focus).
 

FIFL

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why the hell is a 3m revenue business worth 30 million?

MJ is right, what are your goals mid-long term? The answer to that entirely changes what the next logical steps would be.
Typical valuation multiples in my industry are 8-12x of recurring revenue (subscriptions).
 

FIFL

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Keep us posted here on what you do and how we can support you. Consider Insiders side of the forum if you ever wanted to get deeper into a conversation that’s not for full public consumption.
I will, thank you.
 

alexkuzmov

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Good question. I'm indecisive as it's a lot to walk away from.

What's stopping me, to be honest, is that I don't know what I'd do otherwise yet.
So the first reason is no good.
Indecisiveness is not a good trait.

The second one I can understand.
Say that you`ve quit and pulled the max money amount you could, all stock liquidated, best case scenario.
What would your day look like?
 

Knugs

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I come here to seek advice, admonishment and like-minded souls.

I am 3yrs in as 2nd-in-command (non founder) of an emerging tech startup. Roughly a $30m business that's just hit Series B. I have equity in the business (around 3-4%) that's illiquid until exit (goal would be $100m+). I look after the revenue/commercial operations of our business, basically everything aside from building the product. I've had a role in most of our ~$3m / year of recurring revenue. Pay is around $300k/year and will grow. Some days I like what I do. Many days I can't stand it and feel a FTE is extremely close. I fantasize regularly about building my own company. Oh and the CEO is a narcissistic pathological liar. It's objectively an incredibly difficult environment to succeed in, with very little empowerment, recognition or support. Kind of sounds like running your own company to me :)

To me I'm in the slowlane. I feel like I am failing @MJ DeMarco 's commandments. Like an employee with a little tiny bit of cream. This makes me incredibly anxious to do something else with my time.

Circumstantially I have done fairly well. Perhaps too well and the comfort prevents a complete FTE meltdown. From $0 in my pocket 10 years ago, I now have a house, investment property, stock portfolio, crypto investments, etc. and have been a well paid slowlaner for those years. I still for the most part live the same way I always have and tend to save and invest my money. I guess you'd call me a savings rat. I have a well-paid wife and two children under 3.

I am not risk averse, and I have progressively worked for riskier and riskier businesses. This company was absolutely fledgling with shitty, unknown customers when I joined and I have helped grow it from a nothing to where we now have major utilities, telcos and 100's of customers.

Recently I've been thinking it's really time to pull the rip cord. I want control of my own destiny. If I leave, I'll lose some of my unvested equity (probably $1m worth over 4-5 years), but my already vested equity will still be worth a couple of $mil, and I don't have a slog my guts out on something I have no control over working for a maniac.

I'm a little lost on what to do. It is a bit to walk away from. It's really not a topic I have anyone I can talk to about with and none of my friends are in similar situations nor do they have aspirations to build businesses from scratch.

I believe I have plenty to offer and have the chops to work through failure and struggle, but the pace and intensity of the shit I deal with daily leaves barely a moment to stop and think and plan for what next. I feel like I need to just jump.

I would greatly appreciate practical advice on what to do or criticism of my thought process or mindset. Don't hold back now.

I was also living the startup life but without the success that you enjoy. I think you are currently experiencing a "grass is greener on the other side" syndrom. You have seen all the success literally next to you and believe it should be you (forgetting that most dont even get to a Seed investment). Meanwhile you stop to appreciate what you have: A house, investment portfolios, vested equity and a 300k salary with NO financial risk. Say. This. Out. Loud.

You need to realise that you are part of a succesful venue and that you havent seen first hand the other 90% that failed. Just like me who has worked more than 1.5 years with VC investments and blew it all. The opportunistic cost is far too great for you.

I do understand that tingling sensation and the realisation of "hey, I'm the one who made this succesful so it should be me" and the dream of being an entrepreneur yourself. I really do, thats what happened to me too. Are you perhaps burned out after the last round? They are super tiring. Maybe a long holiday would do.

I think what is really important in your case is to understand how your vested equity agreement looks like. Are we talking about a 1 year cliff (that you already passed) with another 3 years left to go; How much time is left. Btw, you will be in a great negotiation position when you have vested all your equity and when you are about to go into the next financial round. (Just imagine the no 2 leaving before the next round = Red flag for all investors).

Also another important point is that you need to have some sort of plan ready. Just jumping is not good enough.
 

AceVentures

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You call yourself a bitch in the title of the thread.

Pretty obvious from what I can read that you're wanting to challenge yourself but you're too scared to take a risk.

Should you take a risk? Not something anybody here can tell you. Not even something a thicker portfolio would help with.

You've got a house, a stock and crypto portfolio, and a 300k/year salary. In your own description, this has likely made you too comfortable. In your own description, you're a "bitch".

Consider 5-10 years from now -- what does the dream life look like and importantly, what does hell look like? What's the absolute most nightmare outcome for you - keep that in mind as well as your ideal future.

You may realize you already have what you want, or it may become evident to you that no amount of money could thwart the feelings of guilt and shame you may feel about staying comfortable. But only you would know that.
 

Mike_Espo

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I come here to seek advice, admonishment and like-minded souls.

I am 3yrs in as 2nd-in-command (non founder) of an emerging tech startup. Roughly a $30m business that's just hit Series B. I have equity in the business (around 3-4%) that's illiquid until exit (goal would be $100m+). I look after the revenue/commercial operations of our business, basically everything aside from building the product. I've had a role in most of our ~$3m / year of recurring revenue. Pay is around $300k/year and will grow. Some days I like what I do. Many days I can't stand it and feel a FTE is extremely close. I fantasize regularly about building my own company. Oh and the CEO is a narcissistic pathological liar. It's objectively an incredibly difficult environment to succeed in, with very little empowerment, recognition or support. Kind of sounds like running your own company to me :)

To me I'm in the slowlane. I feel like I am failing @MJ DeMarco 's commandments. Like an employee with a little tiny bit of cream. This makes me incredibly anxious to do something else with my time.

Circumstantially I have done fairly well. Perhaps too well and the comfort prevents a complete FTE meltdown. From $0 in my pocket 10 years ago, I now have a house, investment property, stock portfolio, crypto investments, etc. and have been a well paid slowlaner for those years. I still for the most part live the same way I always have and tend to save and invest my money. I guess you'd call me a savings rat. I have a well-paid wife and two children under 3.

I am not risk averse, and I have progressively worked for riskier and riskier businesses. This company was absolutely fledgling with shitty, unknown customers when I joined and I have helped grow it from a nothing to where we now have major utilities, telcos and 100's of customers.

Recently I've been thinking it's really time to pull the rip cord. I want control of my own destiny. If I leave, I'll lose some of my unvested equity (probably $1m worth over 4-5 years), but my already vested equity will still be worth a couple of $mil, and I don't have a slog my guts out on something I have no control over working for a maniac.

I'm a little lost on what to do. It is a bit to walk away from. It's really not a topic I have anyone I can talk to about with and none of my friends are in similar situations nor do they have aspirations to build businesses from scratch.

I believe I have plenty to offer and have the chops to work through failure and struggle, but the pace and intensity of the shit I deal with daily leaves barely a moment to stop and think and plan for what next. I feel like I need to just jump.

I would greatly appreciate practical advice on what to do or criticism of my thought process or mindset. Don't hold back now.
It sounds like you aren’t happy with your current role because of CEO of the company and your current compensation structure. If you truly believe it’s time to jump ship because of these issues why not sit down with the CEO and give him some hard truths with how you’re feeling. Maybe he listens and things become better, maybe you can even negotiate more equity or a higher salary. If things don’t go well and he tells you to f*ck off then you now have your definite reason to leave and pursue new endeavors.
 

Flint

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Feelings are a strange thing, aren't they.

Take "fairness". What an emotional and messy dynamic it can be.

View: https://www.youtube.com/watch?v=meiU6TxysCg


As Chris Voss said: "Most people make an irrational choice to let the dollar slip through their fingers rather than accept a derisory offer, because the negative emotional value of unfairness outweighs the positive rational value of the money".

Take another one: analysis paralysis. Hilarious. Why on earth would my mind throw a spanner in the works and lead me into inaction. This is pretty fascinating when you think about it: there's this 3 lb brain redirecting all resource to figuring out the puzzle of an uncharted territory... while simultaneously blocking potentially harmful "just jump" behaviours (because "unfairness" lol).

@FIFL

I second previous opinions that the long-term big picture is very important here. Remove "unfairness", "slowlane vs fastlane" and other comparative labels. When it all goes away, trust your feelings. What is it that makes you tick? What life do you want to live? What is the lifestyle of your choice, down to "a day in a life"?

You're stuck in the moment of struggle. With 4 underlying forces at work. You can feel them, but the vector of change isn't strong enough to make you step up and resolve it. Good. It's a signal you haven't figured out what really bothers you, what you really want, how you'll get there and what you're ready to give up. Four forces.

1623449184177.png


I've been in a similar situation many times. I've tried to resolve it by "dramatic analysis" as well as "just jumping". Mathematical inaction vs brute force. Neither is ideal. But as much as the latter got me burned and set me back a bit, it also showed me that I can handle it. I've also learned I enjoy the process more than the result. And that a team makes or breaks the journey.

I work with big clients in B2B and I deal with multiple teams. I always tell them the same thing. It'll be a bumpy ride, it's just the nature of it. There'll be a lot of stress, uncertainty, unplanned sh*t going our way. And we can do it either the easy way or the hard way. We'll achieve 80% of perfection, undermine our relationship with the client, frustrate each other and won't want to work as a team anymore. Or we'll achieve the same 80% perfection, make the client excited about it and end up wanting to work together as a team again despite the delays, uncertainties and stress. Same results, different outcomes.

Soooo.... is it the amount of money that bothers you? People you deal with? Level of control you have over your life? Routine? Uncertainty? Unfairness? Lack of recognition?

With more clarity, it's much easier to engineer a path to daylight.

Good luck!
 

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Wow, so you're getting FREE mentorship in how to build a successful company and take it public, not only that but they are paying you $300k per year to learn on the job, not only that but they're also giving you 4% equity.

Yep, you are a dumb bitch and an ungrateful one too. Quit you SOB and let someone less entitled take the position.
 

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Kolslaw

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Good question. I'm indecisive as it's a lot to walk away from.

What's stopping me, to be honest, is that I don't know what I'd do otherwise yet.


Good advice. I am doing that (not active investments mind you). I have been thinking about buying symbiotic businesses and building other revenue streams.


I'm pretty close yeah - around 5 years.
I think you answered it right there, "I don't know what I'd do otherwise yet." I think you should stay where you are until you have at least an idea to build on. Then take your money and build it. Good Luck!
 

Kolslaw

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I was also living the startup life but without the success that you enjoy. I think you are currently experiencing a "grass is greener on the other side" syndrom. You have seen all the success literally next to you and believe it should be you (forgetting that most dont even get to a Seed investment). Meanwhile you stop to appreciate what you have: A house, investment portfolios, vested equity and a 300k salary with NO financial risk. Say. This. Out. Loud.

You need to realise that you are part of a succesful venue and that you havent seen first hand the other 90% that failed. Just like me who has worked more than 1.5 years with VC investments and blew it all. The opportunistic cost is far too great for you.

I do understand that tingling sensation and the realisation of "hey, I'm the one who made this succesful so it should be me" and the dream of being an entrepreneur yourself. I really do, thats what happened to me too. Are you perhaps burned out after the last round? They are super tiring. Maybe a long holiday would do.

I think what is really important in your case is to understand how your vested equity agreement looks like. Are we talking about a 1 year cliff (that you already passed) with another 3 years left to go; How much time is left. Btw, you will be in a great negotiation position when you have vested all your equity and when you are about to go into the next financial round. (Just imagine the no 2 leaving before the next round = Red flag for all investors).

Also another important point is that you need to have some sort of plan ready. Just jumping is not good enough.
Good point on the negotiating position once he's vested. Red Flag indeed.
 

srodrigo

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I think you answered it right there, "I don't know what I'd do otherwise yet." I think you should stay where you are until you have at least an idea to build on. Then take your money and build it. Good Luck!
+100
 

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I think you answered it right there, "I don't know what I'd do otherwise yet." I think you should stay where you are until you have at least an idea to build on. Then take your money and build it. Good Luck!

On that, another good video from Noah:
View: https://www.youtube.com/watch?v=k9CoZCDl51Q


Nothing generates more opportunities, smashes more sticking points and those pesky "what should I do" questions than putting yourself out there and experimenting with what happens, what works and what sticks. For me it's the playfulness of testing the truth of the situation: whatever the outcome, you gather valuable reference experiences.

Just quitting a day job may be more Hollywood-like. But making little jumps at the opportunities that present themselves each day to see how you can help or collaborate with one person at a time has its compounding power of a positive mindset change.
 

Antifragile

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I’ve been asked many times a different question “should I start my own business?” And every time my answer is the same “no”. Inevitably the person asking is surprised and follows up with “why not? I’m good at bla bla bla”.
The truth is, if you have to ask, you shouldn’t. It’s a hard road, a lot harder than you theoretically can imagine. And yes, many make a lot of money and gain independence (especially on this forum). Partly because @MJ DeMarco is like a coach that helped score better. Partly because of being lucky. And partly because of having grit to continue when the going got hard. The hard kept going.

And this is how I view business, if you ask, means you are trying to be “rational” about it. Logic says you’ll fail. Odds aren’t that great. But for some of us, we can’t imagine any other way. It’s like a hungry wolf out there who must find pray to eat. It’ll do anything and succeed. And when you want it that bad, you aren’t being logical. It’s something you must do.

Oh and last thing, before taking advice from internet strangers remember to check with your doctor if the advice is safe for you. Don’t take it if you have high blood pressure!
 

Private Witt

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10x revenue? That’s retarded. You sure it’s not 10x EBITDA? Maybe I should whip up an app for my service company and call it a tech company. It would make us worth 3 mil then lol

If you were to sell Johnny Boy Lawn Service tomorrow how much would be the asking price?
 

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If you were to sell Johnny Boy Lawn Service tomorrow how much would be the asking price?
I'd sell it for 2x earnings. 150k profit = 300k asking, cash only. Note this is 150k profit with employees doing everything and just managing.

Then I would immediately start another one with so much more free cash flow and be 3 times as big the following year.

But nobody would buy it. I will just keep doubling in size each year. We should be at 30k/mo profit next year anyways.

I would much rather just take out a loan to leverage growth.

I laugh when I see these companies like Lawn Starter try to be the uber of lawn care and raise 17 million by calling themselves a tech company when they bring in 2.5m in sales after 8 years and being in 120 cities. What a stupid business model. Subbing out work = low customer retention. Being a middleman = lower margins. Their profit will be squeezed into nothing if advertising costs rise at all. We make a thousand per customer per year and we keep them. They make a hundred bucks per customer and lose them. It's easy to see who will be able to compete long term. Their tiny 2.5m in revenue will be us in 1 single city and only 35 employees bringing us nearly a mil in profit. I wonder what they are profiting on that 2.5m :rofl: . We might be making more than them now. And we'll be there in less time than them too. Whatever happened to the scalability of tech companies?
 
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