Lifestyle business VS C-suite at a startup

[firstbornunicorn]

tl;dr; I'm a founder/CTO at a startup. We have a half a million bucks in the bank which will last us about a year, but we will get more investment in the meantime, and also start to turn a profit.

My vesting period is 4 years for no less than 12% (30.3% now, but it will dilute with more investment). In 5 years our valuation could be at $300M US.

12% of that is 36 million dollars.

There is of course a lot of risk. My salary is 50% of what I can get in already established companies, and in the meantime the market could change and I make nothing/way less than expected.

Hours are also insane.

I'm considering leaving this and going for a "lifestyle" business that simply earns me like $10,000/month but allows for the freedom to not be "on" all the time.

Would you choose a guaranteed $10,000/month with not much increase, or a $36M payout in 5 years with a big chance that it doesn't happen? My salary is about $3600/month right now. Rent is $1200. It's still not a bad spot to be, but I could earn $7000-$8000 after tax already if I'm a consultant. The **** hits the fan if we don't grow as expected. I could always leave, but then I leave my cofounders high and dry.

Opinions from people who know what they're talking about?

 

[oOh Nasty]

What exactly do you mean by "lifestyle" business? If you mean that your quality of life seemingly increases and you have more direct control over your own results and expectations, then personally, that would seem like the better for choice.

Kudos on being a CTO. From the other side of the fence, lots of people would wish they were in your position. That being said, as you get into your 30s, you start to realize that time is the most important asset. If your startup was able to raise half a million, then there's little reason why you wouldn't be able to do it again once you need to with the added benefit of having more time and freedom the next time around.

The 5 year payout sounds really good also, granted you had the power and confidence to steer the ship in that direction. But it's only worth it if you actually believe and have faith in your partners and company. You could be holding yourself back by not wanting to leave your partners high and dry.

The "hours are insane" part that you wrote is the highlight for me. While it's expected that working should take long and hard hours, it doesn't mean that you shouldn't be enjoying your work. Don't mean to be speaking in cliches, but a relaxed 10k a month is better than a stressful "maybe" 36m in 5 years.

 

[BackInTheGame78]

Depends on how much you believe in what you are doing. If you believe in it then it's a no brainer to stay.

 

[2Rocky]

I'm going to guess you could pickup that Life Balance job any time in the next 5 years if you had to. If your High Reward-High Stress job is covering your costs now with a much bigger upside, Don't say WHOA in a Horse race. Instead figure out how to depressurize yourself daily weekly and monthly through meditation, exercise and mental rest exercises. Schedule in Self Care. make it a daIly time on your dayplanner.

Just like fueling during a marathon, you gotta fuel your motivation.

 

[jaygreenb]

tl;dr; I'm a founder/CTO at a startup. We have a half a million bucks in the bank which will last us about a year, but we will get more investment in the meantime, and also start to turn a profit.

My vesting period is 4 years for no less than 12% (30.3% now, but it will dilute with more investment). In 5 years our valuation could be at $300M US.

12% of that is 36 million dollars.

There is of course a lot of risk. My salary is 50% of what I can get in already established companies, and in the meantime the market could change and I make nothing/way less than expected.

Hours are also insane.

I'm considering leaving this and going for a "lifestyle" business that simply earns me like $10,000/month but allows for the freedom to not be "on" all the time.

Would you choose a guaranteed $10,000/month with not much increase, or a $36M payout in 5 years with a big chance that it doesn't happen? My salary is about $3600/month right now. Rent is $1200. It's still not a bad spot to be, but I could earn $7000-$8000 after tax already if I'm a consultant. The **** hits the fan if we don't grow as expected. I could always leave, but then I leave my cofounders high and dry.

Opinions from people who know what they're talking about?

Take the upfront pain for the equity if you think there is a good shot at it being successful. You will learn a lot and get out of the wage mindset. You are young enough that you can recover if it doesn't work out. Take advantage of the energy you have being young. You can take your foot of the gas when you are older after you hit some financial milestones. I started a business 11yrs ago at 30, first 3 years were brutal and lived like a college kid to get things off the ground and pay down my debts. By year 5 started doing really well and now could retire if I really wanted too.

 

[Modern Man Advice]

tl;dr; I'm a founder/CTO at a startup. We have a half a million bucks in the bank which will last us about a year, but we will get more investment in the meantime, and also start to turn a profit.

My vesting period is 4 years for no less than 12% (30.3% now, but it will dilute with more investment). In 5 years our valuation could be at $300M US.

12% of that is 36 million dollars.

There is of course a lot of risk. My salary is 50% of what I can get in already established companies, and in the meantime the market could change and I make nothing/way less than expected.

Hours are also insane.

I'm considering leaving this and going for a "lifestyle" business that simply earns me like $10,000/month but allows for the freedom to not be "on" all the time.

Would you choose a guaranteed $10,000/month with not much increase, or a $36M payout in 5 years with a big chance that it doesn't happen? My salary is about $3600/month right now. Rent is $1200. It's still not a bad spot to be, but I could earn $7000-$8000 after tax already if I'm a consultant. The **** hits the fan if we don't grow as expected. I could always leave, but then I leave my cofounders high and dry.

Opinions from people who know what they're talking about?

Freedom and security (especially nowadays) would be big incentives. Don't think you can go wrong with choosing a "lifestyle" business (whatever that means).

I am a consultant/small business owner myself, and I do enjoy the freedom. I mean sure, it'd be nice to get more money in the door but money comes and goes. Just like women.

I chose freedom and mental health over anything else, women and money included.

Ultimately, it is such a personal decision based on your own values and principles. We are unique in that regard, each of us have a unique "soul-print".

I would say a little more context about this "lifestyle" business would help me, and others, provide better perspective/advice.

Hope this helps.


Modern Man Advice