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Considering to work for a startup vs entrepreneurship

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Read Millionaire Fastlane
Aug 12, 2020
United States
I am thinking that I should work for a startup first rather than take the full leap of entrepreneurship as an alternative. Because truthfully the odds are stacked against me. This whole idea of postponing college to save up money to buy some random business I have no skills or industry knowledge in is flawed and will lead me to miserable failure. It would be worse than starting a business because it would take me a lot longer and more sacrifice to realize I don't have what it takes to make it work. So my plan is to study software development at this college that will leave me with a degree in 2 1/2 years. And no it's not computer science it's more of a computer and information science degree with a concentration on software development. Effectively a bachelor's in less time than what most people would go through. And also way less money too. Then after working as a software developer for a few years I then proceed to work for a startup. Because I know it's going to take me at least 20 years of trial and error for me to truly succeed in business. Because the people that do have fast lane success tend to be people in their thirties and beyond. I personally do not want to wait to achieve fast lane success at 35 or 40. It's a lot of sacrifices I'd have to make that would leave me with only half of my life left to live. I don't want to spend too much of my youth building my life for me to only enjoy it being middle aged. Considering that the average age of an entrepreneur is 40, it would make sense their success rates are higher than young entrepreneurs. And the ones that succeed weather young or middle aged have some sort of industry knowledge or skill set. Which will take me some time to get. So the chances of me acheiving fastlane won't be until I'm 40 if I were to pursue entrepreneurship so I think I'll take the middle ground option. It seems easier and less risky than doing it all by myself. I'd learn from the entrepreneur and if I feel confident I can start my own thing than I'll do it. If not I'll stay with the startup. And yes I know that startups fail. But I'd rather do that than start my own thing without an ounce of experience or knowledge (Which will take forever to get anyway).

Note: The following disclaimer is only for middle aged people reading this. Otherwise ignore it.

Before anyone decides to talk shit that boils down to me being young, stupid, and ignorant. Yes. It's unfortunately what comes with youth, that is why I'm here asking the more wise about whether what I think could work for me has merit. There's a difference between being blunt (constructively) and just coming off as condescending (arrogance and belittlement). We were all young once so please don't pretend like you didn't have the same youthful struggles, ignorance, and stupidity that me and other people like my go through. Anyway I digress.

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Platinum Contributor
Speedway Pass
Aug 27, 2017
Desert of Desertion
There's nothing wrong with joining a startup first. It will teach you how to solve hard problems. You would learn that pursuing entrepreneurship, also, but why not be paid to learn? You can craft your business concurrently. Start by helping one person - prove to yourself you can add value. You wont get anywhere trying to eat a pie without taking a bite first.


Gold Contributor
Read Millionaire Fastlane
Speedway Pass
Aug 17, 2016
Sahuarita AZ
Effectively a bachelor's in less time than what most people would go through
You should look into degree hacking , enterpise Saas salespeople make a quarter million + base (thats 4 or 5 years into a sales career if you play your cards right) , the bigger companies (microsoft, oracle etc) won't even see a resume without a bachelors but it can be in literally anything.

Now another angle to "learn stuff" and not go the degree

This is "startup" startups but you can find jobs where part of the benefits is a small slice of the pie (0.05% up to 2% although with no skills I don't think you'll find a 2% job, thats like for the CMO's and VP's) , anyway neat thing here is, chances are the company you work for will fold but if it doesn't you could "accidentally" yourself wealth (think about if you had signed on as some low level schmuck for facebook or some unicorn way back when and gotten 0.05% of the initial shares)

More importantly , even if it fails you're going to be neck deep in the real deal. Like , they aren't gonna share tons of details with someone low on the totem pole but if you hustle and network and act curious you'll learn TONS.

Also PLENTY of remote opportunity post COVID (and I don't think its going to go back quite to "normal" post vaccine) , Those high paid enterprise salesmen I was talking about? not just guys in the bay area - you take a paycut to work remote but these companies aren't gauging it by actual cost of living (one guy on reddit with a 350k base 500k OTE is taking a 37k hit to his base and moving to flyover country, so his cost of living is essentially 1/3rd of what it was but he's only taking a 10% haircut off the top)

If I were young and had no kids and mortgage and all that (in your shoes?) , i'd degree hack the software development degree (you're a smart fella right?) and simultaneously work some schlub job for a startup to make ends meet.


Silver Contributor
Read Millionaire Fastlane
Speedway Pass
Jan 20, 2008
Currently Traveling

With kindness, I read your post and just .... *shrugged*

Lots of:
'I know this or that would fail'
'I want this'
'this is how it is'
'this will surely happen'
'I don't want that'

Maybe you've got a crystal ball I didn't get but, basically everything you wrote, I think an experienced business person, would roll their eyes at.

Things aren't going to go perfectly man.
You aren't going to nail it on your first try.
You aren't going to win, by being anxious that you might not win.

I started my first business at, god, as a teenager?
But my first real business at 22. After 15 years, I don't work now.
Did I fail, as I'm late 30s?
If you look at it a certain way, sure, I guess...'s been the most magical ride ever.

I didn't get a map of where to go.
No one assured me of success.
I almost ruined it a bunch of times.

I didn't start out trying to win big on my first at bat.
I just started.

One step in front of the other.

I long ago stopped worrying that life was some perfect destination.
For me, it's an epic journey, and I've had so much fun, so many memories of building my business.

It's a riot, and a roller coaster.
But you've got to get on to ride.
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Silver Contributor
Read Millionaire Fastlane
Summit Attendee
Speedway Pass
Jan 8, 2018
I've been working in start-ups for years as a bill paying day job whilst I work on my own projects. It's been great getting paid to learn, getting to leapfrog up the ladder (there's no way I'd've been in charge of what I've been in charge of at a larger organisation given my limited experience prior to being in charge of it), & of course a smattering of equity never hurt. Sound great, right?

But, the risks of entrepreneurship are still there - even if it is someone else's entrepreneurship. The more early-stage the start-up you join the more great opportunities for everything I mentioned above, but also the greater chance it could all fall over. Even without falling over, being paid on time could be subject to the changing tides of cashflow (& I'm talking more than a few days late - the latest I've been paid is 6 months, but it wasn't my only source of income).
Company culture is also heavily dependant on the personalities of the few people you work with. I've typically been in companies of between 2 & 7 people. Super early stage.

I'm completely fine with the risks I'm taking with this job, & if you are too, then yes it could be a great path for learning from & building entrepreneurial confidence. If you're already like "whoah, nope, was thinking of something far bigger with more secure funding" then you probably need it even more if you hope to become an entrepreneur yourself. Along with addressing the many limiting beliefs you displayed in your post.

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