Why and How to Start Your Career in Sales at a Startup

Startups are great and full of career opportunity.

Sales is valuable and transferable anywhere.

Entry level sales at a startup is an excellent way to begin your career.

It's not glamorous.

It's hard.

Most are scared of it.

It's way more valuable than you think.

It's not like stereotypes of used car salesmen.

Here's the definitive guide.


The Universe is a Shit Test

From the day you're born, the entire world is telling you what to do, what to think, and who to be.

That's the test. The secret is that all of it is bullshit. None of it should be followed. You've got to find a way to create and maintain your own identity in the face of a universe that screams, "Conform!"

Once you become you, a lot of the stuff the world offers becomes useful and valuable. But not because everyone tells you it is. Because you decide it is. And only after you've learned to ignore the demands to heed it.

Isaac Morehouse

Isaac Morehouse is the CEO of Crash, the career launch platform, and the founder of Praxis, a startup apprenticeship program. Isaac is dedicated to the relentless pursuit of freedom. He’s written some books, done some podcasting, and is always experimenting with self-directed living and learning.

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Crazy People Work on the Most Interesting Stuff

Think of the most exciting possible inventions and discoveries you can imagine.

Deep space travel. Telepathy. Wireless electricity. Anti-gravity. Cold fusion. Terraforming. etc.

If you poke around YouTube or podcasts or badly designed websites, you'll find people working on them. Devoting years to research and experimentation. You'll notice their passion and conviction. But you'll also notice something else: most of them are kinda crazy. Whether or not they are discovering anything true, you suspect they would be the last people on earth capable of bringing their idea to market or even credibly explaining it outside their niche circles.

But if you poke around places full of high achieving people with sharp minds, big vision, and lots of ability, you won't hear them say stuff like, "I'm working on faster than light travel. I think the current model of physics is all wrong, and I suspect it's possible so I want to prove it."

Most of the best, most respected minds seem to be employed on the more mundane stuff. Sure, they're doing cool valuable stuff (except when they go into politics), but how often does it question the most fundemental assumptions?

We know so very little about reality. We don't even know what we don't know, or whether what we know is actually true. And the most fundamental stuff - the nature and origin of the universe, our planet, our species, the basic rules of the physical strata, consciousness, death and beyond - is the stuff most of us spend the least time on.

Except the crazy people. They live there.

Part of the crazy label comes because they are working on this stuff. To examine widely accepted beliefs is often considered crazy. Part of the label is because most of the time these people are crazy. So it feeds itself. People who don't know how to be normal are more likely to go into crazy stuff because they have less to lose. The more they do, the more the belief that "only crazy people study that" is re-enforced and better minds are repelled.

I'm not trying to place blame or cast judgement. I'm trying to understand this phenomenon. It's the same thing that causes most conversations with neighbors and acquaintances to be so boring. Most of us - myself included - are not willing to dive into crazy stuff most of the time. If your reputation is shot, say, because you're crazy, it's easier.

Conformity is a powerful force. I try to do a little something every day to combat it. A world of crazy questions is much more interesting than a world of probably wrong answers no one wants to talk about.

I Dream of Anarchy


Last night I dreamt (whoa, spellcheck doesn't like "dreamt". This prompted Googling. Apparently some do not accept this spelling. Weird.) that I was at some event somewhere, and some guy showed up. He was there either as a maintenance man to fix some kind of large trailer, or he was there to interview the attendees. It was a dream, so maybe he shifted between both roles.

Anyway, he made some comment about libertarians being recalcitrant. I asked what he meant. The rest of the dream was a discussion between us. I told him the classical liberal tradition is long and broad. You might begin at Hesiod, then Aristotle. You might include interesting figures most have never heard of, like Auberon Herbert, as well as luminaries like Adam Smith and Milton Friedman.

As any good conversation about liberty ought to, it turned to the question of anarchy. Not in the positive, bomb-throwing sense. Anarchy simply meaning society without a political ruler, or without the initiation of violence. I shared with him a deep and rich body of thought, from Linda and Morris Tannehill, to Lysander Spooner, to Frank Chodorov, to Roy Childs, to David Friedman (Milton's son), to Spencer Heath MacCollum, to Murray Rothbard, to Leo Tolstoy, to Leonard Read, to Randy Barnett, to John Hasnas, to Bruce Benson, to Robert Higgs, to Edward Stringham, to Peter Leeson, to Jeffrey Tucker and more.

Then we discussed the lived experience of a great many societies at a great many periods in history - some long, some short. We talked about the Hanseatic League. We talked about free market money in Scotland. We talked about the not so wild, wild West in the U.S. before government and military arrived to "civilize" it with violence. We talked about the nearly three-hundred years of peaceful anarchy in Iceland.

We talked about every major function of the current government - from police, to courts, to rule-making, to defense, to infrastructure, to money, to education, to health care - and discovered how every one of them emerged as a market function that was only co-opted by violent monopolists late in the game, and that the monopolized version is in every way morally and practically inferior to its voluntary foundation.

I haven't had an ideological debate or attempt to persuade anyone in years. I've moved into the world of action through entrepreneurship, trying to build a freer, better, more peaceful world through voluntary exchange instead of arguments. But this dream was a ton of fun. I woke up with my mind reeling through all the other stuff we didn't even touch on. My intellectual and experiential journey to anarchism took nearly a decade and thousands such arguments, books, lectures, observations, points, and counterpoints. It felt like I crammed a few years worth into a single conversation in a dream. It was kind of a rush!

Oh, and then I was suddenly in a large apartment/warehouse trying to stop a flooding bathtub, flood a large kitchen, and pull a houseplant out of a different flooded room before rescuing an old refrigerator from the driveway. Dreams are so strange.

Turn Any Blog Into a Unique Book

Build your own book.

I've had this idea for a few years, and I'd love to see it happen (though apparently not enough to make it happen yet). I'd start with my blog as a guinea pig and play around with it.

The basic idea is to have the reader be able to select posts to add to their table of contents. Then they could arrange their preferred order and it would generate a formatted book with a TOC, chapters, etc, all ready to upload to Kindle Direct Publishing for paperback and ebook.

It would be a completely one of a kind book curated by the reader. The reader could choose the title, cover design, select the essays, sections and order, write an introduction (or dedication to make it a very personal gift to someone), even section or chapter intros. This makes the author the provider of the raw material, but allows the reader to re-arrange the content into any combination they want.

Now imagine it's beyond just this website or any one blog. Imagine a browser plugin that lets you tag any blog post or article and it automatically adds it to your book. To avoid legal issues, it would probably only allow public, non-paywalled articles and blog posts, and would have to add attribution to author and source for each chapter.

You could have an entire new expertise in democratized book curators, just like Amazon reviews spawned a new expertise in book reviews. Like your friend who used to make the best mix tapes, you'd have people with a keen sense of what essays by what authors make a great book combo. If resale created too many legal issues, you could at least have a great new way to personally consume content or give very cool gifts. Imagine a chronological sampling of the blog posts that impacted you most?

I may try to make this happen someday. Or you can try it and let me know.

Matter Before Mind Moves to Mind Before Matter

My two year old loves talking about "working mans".

Any kind of construction, excavation, or manual labor he sees gets him excited. I told him I used to build houses, so now he says I used to be a working man, and now I'm a business man.

I always assumed this kind of professional sequence, but never thought about it explicitly. When I was a kid, I had lawn jobs and paper routes, then worked in retail, etc. I knew this wasn't what I'd do forever. I figured I'd work with my hands until I was valuable enough to work with my mind. It seemed a natural progression.

In a way, this progression is an embodiment of a philosophical shift over the course of individual human life. We begin in a matter before mind sort of world. We're bumping into everything, grabbing everything, trying to understand the world with physical apparatus. Mental patterns begin to form based on the physical experience. Over time, the mental side becomes deeper, more complex, and more useful than the material side. We can envision a lot more than we can experience.

At some point, all the cliches about "Believe and you can achieve" start to make sense. We understand that belief is a precondition for action, and ideas are the birthplace of man-made objects. We move into a mind before matter world. The further along I've gotten in life, the more in this direction I've shifted. Nearly every issue has at its core something that begins in the mind. Most unhappiness isn't rooted in or fixed by material conditions. Or if it is, the material changes necessary must first begin in the mind.

Perhaps humanity as a whole has moved along this continuum as well. Once matter has been molded in an instinct-for-survival sort of way, mind becomes more dominant. Consider speaking, writing, and coding. Things that reshape the material world by transforming thoughts into something that alters the thoughts of others, then actions, then material outcomes.

Bahm-Bawerk referred to economic progress as the deepening of the production process; an increase in roundaboutness that resulted in greater wealth. Material experience is direct and instant. Mental work is indirect and through time via long causal chains.

The working man becomes the thinking man, which is to say his work becomes less direct and also gains leverage.

The challenge with this shift is maintaining sufficient connection to the outcome that you don't lose motivation. Seeing bricklaying as cathedral building is easy compared to seeing designing the dashboard for the software tool that the chemist will use to measure the additives going into the bricks that will get shipped to a contractor who will hire bricklayers as cathedral building.

Why Does Everyone Want to Be a Coach?

This seems like a new phenomenon.

I have encountered a surprising number of young people who are trying to become "coaches". I don't mean in sports. They want to be a life coach of some kind. Why did this start?

It doesn't seem to be in response to demand. I don't see anyone knocking down their doors begging to be coached. It's the other way around. They are all over social media, begging to coach. It usually takes the form of proclamations about professional decisions, peppered in with a lot of, "I tell my coaching clients", or, "Clients ask me all the time".

Are they really being asked these things? Do they really have clients?

I'm trying to understand what change has occurred in the world to make this such a common desire. I'm not talking about people who've had a long career and experience a late-stage desire to work with younger people. That's always been around. I'm talking about early twentysomethings who seem to skip right over direct experience and just want to come out the gate coaching people.

Potential theories:

Social Media Mimesis - Many popular accounts are "coachy". Perhaps young people see this, want the kind of likes and follows these people have, and try to mimic the style.

A Big Safety Net - This country at this time in history is absurdly wealthy. Young people are rarely in danger of losing material comforts. They've got little need for survival, so instead they play around with what looks to them like "higher" things.

Maslow's All Filled Up - Expanding on the above. Perhaps the first several sections of Maslow's hierarchy are covered, so young people start out immediately trying to wrestle with self-actualization.

If any of these have a grain of truth, I wonder what the outcome will be for these young aspiring coaches. I don't think you can skip steps on the journey to create a meaningful life. If you haven't learned how to earn a buck and survive at the basic level without attention or credit, no way you'll have developed enough mental muscle to find true meaning, let alone coach others on how.

I want to guard against crotchety old man syndrome, but I suspect more independence (and not just upside independence, but the kind of independence that means you own the wins and the losses), less of a safety net, and higher real-world expectations (not academic expectations, which are all about envy, ranking, rules, and status) would be a good thing for most young people. It'd probably eliminate this drive to be (or more accurately I suspect, be seen as) a coach.

Or maybe I'm wrong and this isn't silly at all. Maybe this is a wonderful development in human society, and some day we'll all spend our time coaching each other on morning power routines and how to project confidence while software and robots do all the other stuff.

God, I hope not.

Isaac Morehouse

Isaac Morehouse is the founder and CEO of Praxis, a startup apprenticeship program making degrees irrelevant for careers. Isaac is dedicated to the relentless pursuit of freedom. He’s written some books, done some podcasting, and is always experimenting with self-directed living and learning.

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