Startups Are Hard. So Work More, Cry Less, And Quit All The Whining

Watching the founders leave was the hardest because you could watch them slowly come to terms over the first couple of years that:

a) this actually is harder work than what we left

b) it's not just somebody tossing money at you to go work on your pet projects and screw around, treating the expense account like a personal luxury account

c) there is a reasonable expectation by the investors at the end of all of this that they will make their money back off of your work

Surprisingly, making the transition to a professional management team was easier than working with the original founders. During the tenure with the founders they made all of the mistakes above, plus acted like petulant children when they ran into each of these problems. Whining, foot stomping (literally), crying, flying cross-country to be away from the team and showing up unannounced at a satellite office. Bizarre behavior.

I guess what I'm saying is that it's not just the work that's hard. It's the intestinal fortitude to deal with technology, business and people, day in and day out -- especially when all three of those things are often acting at odds with each other that makes startup life hard, and being small, with startups those things can be magnified out of all proportion. Minor office quibbles turn into nuclear explosions, a broken technology stack a looming iceberg, lack of sales ability into a waiting sink hole.

People often remark about the perks of working at a startup, but it's those perks that make the often miserable part of the work tolerable. Or at least act as transparent incentives to work more, cry less and quit all the whining -- because at least you get three free meals a day!

Your a low number employee and your company goes public, woohoo you are rich, but people who work with you and came later and are doing the same job as you are not. The cognitive dissonance is huge, people sometimes feel guilty that they are rich and their co-workers aren't, sometimes they feel like they 'must be smarter' because they are rich and their co-workers aren't. Newly rich people want to marvel in it, and share how amazing it is that they can spend 10K on a watch if they feel like it, and the people around them, doing the same work and not rich, well they often aren't all that appreciative of what it must be like.

Those relationships get awkward quickly. And people separate so that they can be with other people where their lifestyle (or lack of it) won't be a source of awkwardness.

Not a lot of people talk about the side effects of 'success' but they should think about it.

The point of the OP's post is that huge sacrifices are necessary for great rewards. I think the truth is more like, your huge sacrifices are necessary so that our investment strategy works.

Meanwhile, guys like patio11 and the 37 Signals team have shown there's plenty of different paths to success. And if you think about what people like Jimmy Wales or Tim Berners-Lee have done, there's lots of ways to "make a dent in the universe" without even forming a traditional company. I know this is crazy talk, but not all roads to greatness involve making a VC rich.

But you know, now that I think about it, I think people are going to read what I just posted and only zero in on the "dozens of instant millionaires" sentence and ask how can I get in on that?

Alternatively, you can raise (or save) a moderate amount of cash, work comfortably at whatever pace you choose, and build something scalable and sellable. If you're making quality software, it's not difficult to generate enough passive income to support the lifestyle you want to live.