How to Money — A Guide to Feeling Better About Creating Wealth.

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Most of my ideas and feeling towards money, I got from my grandpa.

Despite years and years of hard work and essentially no longer needing to worry about money upon his retirement after running a successful radio-repair business for years — a self-proclaimed, poor boy from The Bronx — seemed to never take his mind off of it.

He was the type of person who’d always worried that he was one missed payment away from bankruptcy.

Any minor expense or luxury always felt excessive to him and, as a result, he rarely ever enjoyed everything.

Except for one thing: charity.

About the only thing that he ever really freely spent money on was in supporting and donating to charities.

If anyone had asked him for money, he willingly gave it away.

He always told me that most of his donations were repaid back ten-fold.

After a while, I started to believe that — that if I donated towards a good cause or an interesting charity, that money would flow back to me later-on in life in some way or another.

Kinda like I was generating karma through my charity-giving activities.

And as a result, that’s generally been true — over the years, I’ve donated thousands upon thousands of dollars to various different causes, charities, friends, and other organizations, and often those things come back ten-fold in the form of gratitude or opportunities or otherwise.

I might not have the same penchant for frugality as him, but I’ve certainly learned how to value money and power it wields through him.

Being raised in a Jewish family, we often spoke about money a lot — how much are you making?

Are you saving anything?

What about investments?

Are you planning on buying a house?

Where are you planning on buying?

It’s a topic of conversation that we bring up with about the same levity as somebody might mention what they ate for breakfast or what they did that week, except we apply that same casual nature towards money.

And I think how you talk about money and whether or not you actually do it can have sweeping ramifications on how you build wealth throughout life: a recent Pew study found that 44% of Jews earn more than $100,000 a year, the highest of any religious group in the world.

A big part of that — beyond the obvious cyclical effects of being part of an economically well-off group that’s relatively tight-knit — is that we simply talked about money more.

Something that, depending on who you ask (or what study you refer to), can be quite uncommon in households.

Over the last few months, my perspective on money has shifted rather dramatically — instead of viewing it as something taboo or evil, I’ve spent a lot of time talking about it with friends, colleagues, acquaintances, and so on.

I’m rather open about it — what I’m investing in, things I’m exploring, what I spend my money on, and so on.

Money doesn’t have to feel like this painful, uncomfortable, and confusing thing — with the right mindset and approach towards it, and a fundamental understanding of how it works and how to fully leverage it, you can use your skills for good.

In this article, I’d like to explore that in detail — removing the shame around openly discussing money, a more empowering view on making money, and how to start becoming somebody who is exceptional by being seen as an expert.

This article is mostly centered around developing a money-making mentality — future articles will explore different ways that you can make money, including selling products and services, investments, etc.

Let’s dig in.

Why we feel the way we do about money.

Even though my parents and my grandparents often spoke about money, I never really had a clear understanding of just where we stood on the socioeconomic ladder.

My parents were never ones to show off, so we always had cars that were several years used, my dad always stored way too much old, used crap in the basement, and my mom would often scoff when I asked her for a birthday present that seemed a bit absurd or out of reach for her.

And so, my parents never discussed things like budgeting, how much income they were making, where their money was coming from, taxes, how much they paid in taxes, how much their house cost, and so on and so forth.

My mom was always talking about investments and I always knew that she was smart and seemed to be rather successful with a number of her investments, but she rarely ever did anything gaudy with it.

We always seemed to live far below our means, and for a while I viewed that as shameful — why not have a nicer house or a fast car or the newest cell phone?!

But my parents were content with never trying to keep up with the Joneses.

We were never forced to reckon with and really talk about the specific details of money — how much we had, and so on — until my grandparents died.

With that came a litany of different estate arrangements, distributions, and lots of conversations around money.

At the time, it felt like such a massive weight but in hindsight I’m glad I got to experience those conversations.

I’ve never viewed money the same since.

It wasn’t until college, in which I took a class with a dopey-eared former CEO that I started to become more fascinated by and curious about money — how to earn it, where I should be investing it, and so on.

I remember, many years ago, telling my teacher that I thought Amazon was a good buy at $200 and that I was thinking about investing some money in it.

“It’s overvalued,” he said.

He was wrong.

(It’s now worth 15x that.)

I learned to never trust just one opinion about an investment after that.

America has an interesting, complex relationship with money — if you’re poor, you talk about money a lot, but since you haven’t had the good fortune of getting access to a lot of the economic opportunities that a wealthy person has had, it’s harder to empower other people to make money with those conversations.

On the other hand, if you’re wealthy — you often don’t talk about money with your family and loved ones.


It’s a curious taboo — when you’re poor, you’re forced to think about money and where it’s coming from because it’s always a burden.

But when you’re wealthy, it suddenly becomes an evil, taboo thing that you feel like you’re shoving in someone’s face, or worried that if you tell someone that you have money they’ll take advantage of you.

I encourage another approach — a willingness to talk openly and honestly about money, and to be conscious of the fact that, Hey, this is a little weird!

Not in a shitty, “Look at me, I’m so broke,” or, “Look at me, I’m so rich,” kinda way, but, rather, “What’s your view on money?”

“What steps are you taking to get out of your current situation, or to grow your wealth?”

“How much do you want to making, or how much does your business generate?”

And so on.

As Brene Brown has discovered through years and years of research on shame, generally when we don’t talk about something, our shame towards that thing only grows.

Money is the greatest example of this — when we don’t talk about money, we don’t educate ourselves on it, and then we continue to become increasingly more and more shameful and disappointed when things don’t work out the way we’d like them to.

The Artisan’s Approach: An empowering view on money.

Over the last few years, I’ve often had an incredibly shame-focused view of money: I am bad with money, and eventually I will be broke.

So, as a result, I would often find myself going months without paying myself from my business, overextending myself in terms of my expenses and springing for things I didn’t need, and generally being relatively laissez-faire around money.

Recently, my perspective on money has started to shift rather dramatically: instead of feeling shameful towards my good luck and fortune, I’ve started to find an immense amount of empowerment in it.

I’ve started to donate more towards causes that I love, hire and work with people who I want to support, freely spend money at businesses that I want to see succeed, and so on.

I refer to this as The Artisan’s Approach towards money.

To me, an artisan is somebody who has become a master at wielding their tools.

I imagine somebody — probably a sweaty old dude or woman, covered in dirt, with a mustache, in a dank toolshed, who’s been working on a wooden bench for a decade. Decades, even.

This person is a master at utilizing their tools.

In this case, that tool is money.

The typical laymen isn’t all that adept at wielding money: they spend it when they have it, and scrounge it when they don’t; they don’t often take risks that might result in serious returns because they are crippled by fear; they fail to educate themselves on money and investing and wealth-building because, to them, it feels so out-of-reach.

What if, instead of floating through life just hoping that money might find its way towards you, you spent time and energy on actually educating yourself on it?

Learning how to effectively wield it, like a true artisan?

For example, you might…

As a result, you’ll likely start to make some significant changes — instead of letting the world of finance just wash over you like a dirty mop, you’ll start to actively curate the resources, connections, and opportunities necessary for you to learn how to really manage your wealth like a true artisan.

That’s The Artisan’s Approach.

And a critical step in actually believing that, Hey! I can build wealth, too!

Finally, becoming an expert at selling You.

Since I’ve been a kid, I’ve always been good at figuring out ways to stand out — at school, that was by being The Class Clown.

I was always someone who’d go out of his way to disturb the classroom by shouting some stupid shit from the back of the room and then everyone would laugh.

At home, that was a little different — my sister was always the more exceptional student, so in order for me to stand out with my parents, humor alone wouldn’t work.

So I learned how to sell.

First, stuff. Like radios I’d buy from my grandpa, or video games I bought from strangers on the Internet.

And then as that grew less and less interesting, ideas.

I started to become a master at getting people to buy-in to some of my absurd ideas.

Most of the time, that was simply letting me sleep over at my friend’s house around the corner, or letting me go into the city to hang out with my friends, or letting me borrow the car to visit my other friends.

But sometimes, it was absurd shit like letting me invest $1,000 of their money into my own ETrade account, quickly realizing how little I knew about the world of stocks.

That money quickly got cut in half, and before I knew it, I was freaking out in my room trying to come up with ways that I’d never have to tell my mom about how incompetent my trading skills were.

I held onto that money for years, and watched it grow before I had to use a significant chunk of it to pay for a bunch of pipes that burst over the winter break in our college house.

(It was self-inflicted, and insurance didn’t cover it.)

Over the last few years, the one thing that I’ve invested a disproportionate amount of my time and energy on becoming exceptional in is marketing and sales.

In marketing, depending on the day, I’m MEH — in sales, I feel pretty confident.

And so, those are the two major skills that I spend an inordinate amount of my time and energy in continuing to grow in — if you suck at sales and marketing, even the best products in the world will likely fall flat.

(With several notable exceptions, including the likes of Tesla — they’ve invested $0 in advertising, though I’d argue that Elon Musk is a genius marketer and salesman even though he often stumbles his way through presentations.)

So, here’s how I’d recommend developing the skillsets in order to be seen as an expert in any given field, that I’ve curated over the years:

Step 1. Identify a niche you love sharing about.

For me, recently, that’s been productivity, and more specifically, how do you spend as minimal time as possible on the things you don’t want to do, so you can maximize your time living a fulfilling life.

Realizing how short life is, how I might die tomorrow, and how I couldn’t give a f**k less about helping other people create distractions, I’ve focused all of my time and energy in recent months on answering that question.

And it seems to already be picking up a decent amount of steam — in the last month or so, my website traffic has doubled, I’ve been invited to speak on webinars with hundreds of attendees, and I’m often finding that a lot of my outreach is being met with, “Hells yes!” instead of the normal tepid, luke-warm, “followup with me, later!” message I used to get.

This process might take a long, long time — you’ll start writing about something, only to later realize that you don’t particularly care or that it’s not all that interesting to talk about.

Then it’ll change, again and again.


You’ll find that you’ve found the sweet-spot between things that you care about, and things that people out there in the real-world actually want to read or listen to or watch from you.

Step 2. Start building an email list.

After you’ve started to resonate with an audience — that could be through writing, video, or, podcasting…

… at some point, you’ll start to find a few topics that really seem to be sucking people in.

The next step is to come up with means of actually capturing those people — for as much as emails get shit on for being annoying, it’s still easily one of the most effective channels for reaching people at scale.

(And, in case you’re skeptical, here’s some research that backs that.)

One of the simplest ways to do this is to create a package of old content — maybe resources, guides that you’ve created, or simple lists.

For example, here’s a page that I’ve started attaching to a Quora answer that gets 10,000s of thousands of views every month, that’s resulted in a decent chunk of emails:

A simple, free tool that you can use to create these is called

(Though I use Leadpages, in this case.)

Embed that PDF into a landing page-like tool using (also free), and voila!

You’ve got yourself a landing page that can attract emails.

Step 3. Ask people what they might be interested in buying from you.

Once you’ve started collecting emails and growing your email list — even at just a few dozen, or even a hundred people, you can start asking people, what are they interested in buying from you?

I explore this topic in a lot more in-depth, step-by-step, in my How to Launch a $1k/Month Product, which you can read here, but here are just a few examples of questions you might want to ask:

  1. What are you struggling with in your business or personal life that you think I might be able to help you solve?
  2. What challenges are you running into related to developing your own [solution to the thing you’d like to help them solve]?
  3. How are you trying to solve that challenge right now?
  4. If you could wave a magic wand — what might that solution look like?
  5. Do you feel confident in your ability to solve those challenges right now?
  6. And how critical is it for you to be able to develop a solution to this right now?

The simplest thing to do, might be to send an email to your list with just one of these questions, and find out, how can I help people?!

Then start with that.

The goal through all of this is to not only redefine how you feel about money and growing wealth, but to also turn you into somebody who is good at seeking out opportunity.

The only way to do that is to become active in identifying opportunities, and the only way to really be active in that is to become an expert in a field.

The latter part takes years — the first part of this process can take as little as a few months, but, to be honest, it’s probably taken me the better part of the last 5 years.

None of this is easy.

And it’s not supposed to be.

I remember the one moment, later on in my grandpa’s life, when his sheer disdain for any sorta luxury seemed to disappear, if not for a brief moment.

Every night, we ate as a family in the cruise’s main dining room and I always eagerly anticipated whatever it is might arrive on my plate from the kitchen.

I loved fancy food and seemed to always enjoy it, no matter how strange it was.

The first time I ate escargots, I was 12, and I’ve never enjoyed anything more since.

My grandpa had ordered the Duck a L’orange and, after quickly scarfing it down, I later asked him how it was.

Now, I must remind you that before this moment I’d never before heard him say that anything was good.

Everything was always Eh! or Garbage!

Nothing was ever Good.

And so, I’ll never forget the words that left his mouth: “It was pretty good!”

I remember, even as a kid, that absolutely blew me away.

Wow! I thought. That must’ve been one amazing duck!

I always try to live my life through the lens of, pretty good!

Which isn’t to say that I aim to have amazing, luxurious meals every day.

Rather, I try to eke enjoyment out of everything I do, even if it isn’t the most fun or exotic thing I’m doing that day.

Wealth can sour you to the joys of the world, if you want it to.

I’d often run into people down in Wall Street in New York who had true Fuck You money, but wore their misery on their sleeve.

No amount of money would have made them happy even though they continued to chase it.

For me, wealth enables me to live the life I want, to freely give to the amazing friends who I make along the way, and to live generally free of any

That might change, at some point — at some point, my luck might turn and I’ll be forced to make significant cutbacks and to live a radically different life than what I’ve had the good fortune of living these past few years.

And I’ll try to be feel just as fortunate then as I do now.

Remembering, as much as I can, those specific moments when my life was, “pretty good!”

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