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I've been working on startups more or less for most of my 20s (both as a founder and an employee at a venture-backed startup), I've learned a great deal from it, lost a lot from it and endured a lot of hardship, but I think the journey also transformed me and cut me out of wood (http://max.levch.in/post/36289276742/strengthen-your-startup...). So no regrets, I'm really excited about the future and I'm thinking long-term.

I disagree with this post though, if I had to start all over again out of college... my recommendation would be to start a profitable, bootstrapped business. Build that up to 7-figures and be financially independent. You'll earn your first stripes way earlier than most, at much lower risk, and once you attain that black belt, then you'll be ready to consider swinging for the fences with a startup. And people around you will want to bet on you too with your track record.

I'm 28yrs old now and that's my gameplan for the next few years. I'm tired of being poor.

Worth reading: http://www.gabrielweinberg.com/blog/2010/06/paths-to-5m-for-...

Hmm, start a profitable bootstrapped business with 7 figures of revenue right out of college? And it's much lower risk. Why didn't I think of that?

Because you're too busy reading TechCrunch...

I'll throw my hat in the ring. I started an eCommerce enterprise SaaS focused business in high school as a hobby, sold it for $4M at age 21, bought it back for $32k, built it again into a $6M/year revenue (profitable) business, and sold it again in 2012 to Answers.com. All of this was 100% bootstrapped with revenue, no debt, no outside funding. In neither case, round one or round two, did I self-fund it, other than the $32k -- the revenues from the business funded the business, it wasn't me funding anything. Sure, it was a long slog, but worth it.

I really admire that... props to your success and track record, thanks for chiming in. If I was an investor, sounds like you would make a good bet and someone to keep an eye on.

Starting out, the best way to learn entrepreneurship IMO is to just do it and build it organically like you did.

what kind of business specifically was it if you don't mind me asking? Are there still low hanging fruit like that around?

You make it sound like bootstrapping a business to 7 figures is a walk in the park.

Obviously not, but there are plenty of success stories out there on the internet. It's far much more of a walk in the park than making it with a venture-backed startup first time around. If you don't have what it takes to make it with a "lifestyle business", then there's no way you have what it takes to make it as a startup founder.

Also, sorry don't mean to sound cocky. I'm still a failed entrepreneur, just speaking from lessons I've learned from scars of failure. I'm not giving up on the startup game, just thinking long-term about it and my development as an entrepreneur.

I'd add an important lesson that I have learned: it takes money to make money.

A ton (perhaps most) failed businesses fail because they're undercapitalized. Even if your costs are low you can only go so long without eating, and if you're worrying about how your life savings is going to run out in 4 months I guarantee that you won't be as effective at building your business.

Your chances of bootstrapping a successful business are much much higher when you have money.

The best thing you can do is not start up a different kind of company (bootstrap vs. VC) but build up your bank account. In this market there are a lot of opportunities to earn good money, particularly if you're a developer. Save, save, save and in a few years, you should have enough to start a business from a credible, realistic cash position.

"I'd add an important lesson that I have learned: it takes money to make money."

Amen. Although, my approach is to be working full-time making a good salary, but spend my nights/weekends working on my business and investing my savings into it. I'm not going to do it full-time until I start making good $ with it.

I don't know how well the night/weekend ventures actually work out but if you're not willing to wait to start a business, I'd bet on a night/weekend venture over a full-time one where the founder thinks $10,000 in savings is going to take him to break even.

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