You make it sound like an either-or (income or shot at $10M-100M exit), but it's not.

I was pulling a 500k per year in income from a web business I founded AND got a $10M+ exit. It depends a lot on the business model and multiples.

My advice would be to continue to build the business and balance income and reinvestment until someone makes you an offer that allows you to retire.

Btw, my definition of "allows you to retire" is $250k/yr after tax, drawing no more than 2% of your portfolio indefinitely with a 95% chance of portfolio survival at age 95 assuming below avg market return of 4% and above avg volatility of 10%. If you're in your 30's, that's probably going to be around $20M. It goes down as you get older.

You could easily reach that definition of "retire" with a very part-time effort on a small biz product, instead of a huge liquidity event, too. Not a huge fan of Tim Ferris' whole schtick, but the idea of semi-retirement is a very good one.

What I really appreciate about your approach is that you are willing to identify and stick to specific dollar amounts. Hell, the name of your course is two numbers multiplied! Nice work, really. In SV entrepreneurship circles, I rarely hear people talk about what specific numbers they have in mind as an outcome, I think because the numbers are so big, so rare and so far away that it sounds silly to discuss them with any sort of specificity.

Thanks! You're right, in SV, people rarely talk about real numbers… even to the point of never discussing how much money a founder actually makes from an $x mil exit. Which, to me, is astonishing, since on the other hand all people talk about is numbers (exit numbers)… but not the ones that count for most people.

If you look at the amount of yearly income you want/need, and then look at products vs built-to-sell startups, it's pretty clear how easy it is to achieve that income on a paid product and how hard it is to achieve it from a liquidity event.

Hey! I just checked out your profile... I ran across your 30x500 site a while back. Looks really cool. Keep up the good work.

After selling my last company, I'm back looking to create another business in the same vein as what you guys teach people to create.

I absolutely agree with you -- the fact that he's a VC has a lot of bearing on what he writes. Ditto for many of the other people whose posts often end up on the front page of HN. Which goes largely without remark!

And you summarized my approach pretty well -- that it's a lot better to have $500k/yr nice and steady and 'easy' than a tiny sliver of the tiniest chance at a $10-100M payout.

There's just one thing which you missed about that: in most cases, a Liquidity Event doesn't lead to $500k/yr for more than a few years, much less freedom, because of lock-in, and dilution, and taxation. A $100m sale is vanishingly unlikely, and most importantly, to get there you will have to have taken on lots of funding, so it's not like that's your $100m sale.

Then what? You have to start over again.

What I really promote is also an investment model, an self-investment in yourself instead of hoping to receive investment from someone else. Assets are the gift that keep on giving. In the long run, most talented people can make far more from my kind of business than they could from an exit (even assuming they could have a fairly good-sized exit!).

Re: "it should be noted that you have an interest in forwarding this kind of a story as a valuable model of entrepreneurship…"

A lot less financially vested than you might think. My class always sells out, with barely lifting a finger… I don't have to be here to stump for the traditional way of doing business in order to make my living. Emotionally, I'm very vested, because I'm tired of watching people suffer simply because they didn't know there was a viable alternative (because the folks who write about entrepreneurship almost all come from the same exact root stock).