What is the Third Road?

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Here’s something I wish I had learned 15 years ago.

The vast majority of advice when it comes to building software companies and selling ‘stuff’ is fake. Earth-shattering? No. But that’s not the surprising part.

What struck me most over the years is the astounding level of fraud, of charlattans selling their courses on how to make money (when their only way to make money is through selling courses).

I could always see how that would work (publish a lot of great free stuff, build up a trusting audience, sell them your ‘knowledge’), but I never could figure out why it didn’t sit quite right.

The movement towards ‘legit’.

There are a few people out there in teh world who are truly ‘legit’. These are the people that have nothing to sell you, and have done so well in their respective fields that they give out advice because they like to, not because they need the cash to pay their rent.

I guess I always envied those guys and gals. Masters of their craft to such a high level that they’d never have to worry about making money again. And not even necessarily because they sold a company for 100 million bucks in cash, but because whatever thing they mastered would always be in demand. Thus, they would always be in demand and able to charge the highest prices.

I think it’s much easier to start with what I don’t want.

  • I don’t want a job that tells me when to show up and where (even if it’s just online meetings)

  • I don’t want to be afraid all the time that it’s all ‘gonna come crashing down’ and I won’t have any money to take care of my family.

  • I don’t want to ‘fake it till i make it’ and sell nonsense info-products that play off other people’s same insecurities about financial independence.

  • I don’t want to spend 10 years chained to a desk trying to figure out the venture capital/startup game. Working like crazy chasing metrics to be able to raise the next round to fund a massive hole in our income statement.

Hmmm, well that seems like I don’t want to do pretty much every available option to people when it comes to earning a living in this world.

What about waht I do want?

  • I want to be so good at something, that I’ll always be able to make money at the highest level with it (hundreds of dollars per hour, if not more)

  • I want to build stuff (software) I’m proud of that has a real impact on real businesses, not just ephemeral information based business.

  • I want to work at a reasonable pace, and be able to live a lifestyle full of long-term travel and adventure with my wife.

  • I want to forget about my day to day/monthly expenses because we have such a cushion of wealth saved up we can weather any economic storm.

Sounds good right? Here’s the problem.

There’s no current ‘path’ for achieving all my wants without sacrificing some of my don’t wants. There are two major paths:

Path 1 - The Job- Hacker

This is the person that climbs the job market ladder, and saves well. The FIRE movement fits nicely here. These are folks that get good jobs, and have better budgets. They save a huge % of their incomes and eventually hit a poitn where their investments are big enough to pay their relatively small expenses.

Path 2 - The Modern Entrepreneur

Two ways to become a modern entrepreneur and hit the financial goals I mentioned (I lump them together as the Modern Entrepreneur becuase neither choice looks good to me).

The Startup Game

This is the game of investment, of hype, of spending your time building something to convince investors it’s great, not necessarily your customers. Companies can play this game and play it well for years without actually building anything useful or turning a profit (See WeWork). This path works to get rich, no doubt. But not on my terms.

The Lifestyle Entrepreneur

The second option for a Modern Entrepreneur is closer, but still no cigar. Enter the now famed by Tim Ferriss the ‘Lifestyle Business’. These are micro-businesses that usually have one very slim ‘edge’ they exploit to make small revenues with the tiniest expenses possible. These give their owners lots of flexibility in work, and often enough cash to live well without trading all of their free time. These folks put ‘their lives first’, and would rather make 3k and have loads of free time than make 15k and have to ‘work for it’ on a daily basis. Th e pipe dream of ‘passive income’ is prevalent in this community.

So we' have two roads, the job-hacker and the modern entrepreneur. And you’ve probably guessed by now we aren’t choosing either ot hit our want/don’t want list. We need something new. Something that lets us work towards mastery, and big wealth upsides without completely sacrificing the adventure potentials of today.

We still want to ‘get rich’, but we don’t need to do it this year. As long as we are building towards it, with every year better than the next it can take 5 years, or 10 years to get there. What’s the rush if life’s so great right now?

Who is this newsletter for?

If you're interested in maximizing your experiences and relationships without opting out of the game of money/financial independence, then you’ll find this interesting.

If you want the freedom to live where and how you want.

If you want to live through incredible adventures, and share them with the people you love most.


Core Tenants of Third Road

  • Not trying to work insanely hard at the expense of all else (health, friendhships, relationships, fun)

  • Not reliant on a salaried job (owning assets, your own business and more)

  • Striking the balance between living now, and building for tomorrow.

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Essays on creating software products, getting people to buy them, and enjoying the weird and wild ride along the way.

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