Decision Making

Everything is Made Up By People

The other day I Tweeted this.

It’s something I’ve been exploring for the past few years.

It started with an exploration of my emotions. When I was running my business, Jakt, I had massive swings in my emotional state. I worked with a coach that helped me explore these emotions and the stories I told myself.

It took many, many months of working together to really understand that the world is entirely made up. The stories we tell ourselves, the meaning we assign to things, etc. It’s all made up.

So how did I go from that to the Tweet above?

Well, over the past few months I’ve been diving into financial history to try and understand the world better and how we got here.

I still have much to learn, but one thing that has come to light for me is that the financial and social systems we have in place are also all made up.

Yet, when we are young we grow up with these systems, indoctrinated in them, and oftentimes don’t question them.

But if we look at history, these systems were not always there. Perhaps they have always been around in our lifetime, but not always. So while for us –in our lifetime– it may seem like they are normal or guaranteed to last, if we take a longer view of history, they are not.

New systems are created over time. And they are implemented to make people act a certain way and maintained to keep them acting a certain way. 

And who puts these systems in place? Those in power. Those with financial, economic, and political power.

We have to look at the motives of people and why they are doing things.

And we must question things.

  • Why does the prison system exist?
  • Why do children have to be in school from 8-3 pm every day?
  • Why do we have “weekdays” and “weekends”?
  • Why do we have a pension system?
  • Why do we have a “retirement” age?

Even something as simple as going to the grocery store. That is man-made. 

It’s something we created. 

Sure there are “reasons” why they were created, but the underlying truth: they were all made up.

By people.

Yes, people made all these things up.

And then push them out to society and make everyone believe it’s what is best for them.

But, is it really?

If you view the world from this lens, it starts opening up your mind and you might just notice virtually everything in our society is made up by people.

And because it’s all made up, it means we don’t HAVE to follow it.

Unfortunately, because we do live with some of these systems, we have to follow them to an extent. Unless we go totally off-grid, we’ll never really be free from them. And even then, are we? I’m not sure.

But given that we can’t get away from them, perhaps by opening up our eyes to it, we’ll realize we can change it. That said, the forces at play to keep systems in place are large. And powerful.

So maybe it’s not always about changing the system, but just playing a different game within it?

Entrepreneurs are one group that goes against the system in a way.

School teaches us to become good workers, not entrepreneurs. This is by design. 

Go to school, get a job, work for 30-40 years, retire, die.

That. Sounds. Awful. To me at least.

But it’s what is ingrained in us. Too many people going against this and perhaps systems would break.

But that’s just scratching the surface. Next time you do something, take a step back, and think about the systems in place that are completely man-made. 

I’ve found it to be quite powerful. 

Because once we realize it’s all made up, we can create and live in a different way. 

Sure, some systems are there, and we have to follow them. Because they are too strong and engrained. For example, in the past (and still in some states today), if we broke the “law” and had weed on us, we could go to jail for many, many years. It’s hard to go against that when you have an entire legal system that opposes this.

But here’s the twist — now it’s legal in many states. 

How is that possible? 

Simple. It was a completely made-up rule. 

Put in place to “protect” us, or whatever other excuse given to convince us it’s best for us, but what was the real motive? 

More often than not, with most systems, it’s to make us act, or not act, in a certain way. To benefit those creating the systems. 

That’s it. 

It’s not because it is “right” or “wrong” or what is truly best for us, yet that is what those in power will want you to believe.

Now, here’s the cool part. Once we start realizing that everything is man-made, it also means WE can question everything and be the creators ourselves.

We may have to play within the constraints of certain systems because they are so large and powerful, but within those, there’s a lot of room to be and act differently.

We don’t just have to follow everyone else’s creations.

I leave you with these questions:

  • What systems are you living in that you have never stopped to question? Why do they exist? Have you been blindly following them? Are they really what is “best” for you?
  • Given that it’s all made up and you can be a creator yourself, what will you create?
  • Will you forever be used by the systems created by others or will you try to understand how these systems and people work and create your own reality?

P.S. With this lens, I’ll throw this at you. Many people think Donald Trump is crazy. I actually think he just understands how the systems and people work, extremely well. More than people realize. He’s using the system and creating his own reality. Note, this is not an endorsement of him. Just an observation.

P.P.S This doesn’t just apply to systems, but also things like diamonds, wedding rings, etc. Marketing to influence behavior and actions is a related topic. Marketing is used to push ideas and systems out to people. Or to make you buy things. Or…. But I’ll leave that discussion for another day.

P.P.P.S As I finish writing this piece, I realize I’m still grappling with many unanswered questions myself. I’m on Step 1 — understanding (or, at least, trying to understand). Step 2 is what to do with that understanding. I’m still mulling it over myself, but I’ll keep reading, writing, thinking, and studying about it. 


Decision Making

The Time I Made $100k by Answering an Email at 10:30pm

On February 23, 2015, I received the following email at 10:30 pm:

“Hey A.T.,

I am consulting for a hedge fund, [redacted], and they have a time-sensitive project that they need help on. It is a website for one of its portfolio companies.

It is a pretty standard site: overview, mission statement, management, board members, investors, products. There might be design work for logos. However, no eCommerce or other functionality.

Since the project is on an expedited timeline, they are willing to pay for that consideration.

If you are interested, can you come tomorrow and meet with members of the fund? Please let me know as soon as you can.



There are a number of factors at play here that can be uncovered from this email.

First, the project and decision timeline was clearly time-sensitive. The email clearly says this.

They also wanted to know if I could meet with the members of the fund (i.e. the decision-makers) tomorrow. My read on this was that it was indeed a serious project and given they were emailing me at 10:30 pm and wanting me to meet with the decision-makers (members of the fund) the next day.

Because of the email at 10:30 pm and wanting a meeting the next day, my guess was also that they weren’t really evaluating any other options. Another point in my favor.

Also, if you notice the intro it says “Hey A.T.” 

A.T. is a nickname that only people who know me would say. The person who emailed me was someone I knew and therefore was effectively my “champion” here. He was the one bringing me into this opportunity. And a referral means a lot when trying to close a deal. 

After reading this email, I immediately knew this was:

  • A real, serious project
  • A project with budget (the client was a hedge fund – hedge funds have money)
  • A good chance of me winning it if I showed up the next day because of the time-sensitive nature and the personal referral

I responded 13 minutes later:

Yes, definitely interested. I’m free from 11-1 pm and anytime after 4:30 pm tomorrow. What time should I come?”

If you notice in my reply, I gave concrete time slots that were big enough such that at least one time would probably work and asked: “what time should I come?”

I always like to make it easy for someone to reply and limit the unnecessary back and forth.

I used the word “should” on purpose to highlight that I was coming in tomorrow, you just name the time and I’m there.

I heard back that the meeting would be at noon.

I then back-channeled with my contact to try and get a bit more context around pricing. I specifically wanted to know if they had any expectations around rates. I told him since it was a rush job we’d charge more and he replied “That works. Go with the higher figure. They will most likely go with you bc I recommended you.”

Ok, awesome. I’m feeling great before the meeting. 

So I show up at noon.

I met with some of the members of the fund. Note: My contact is not there at the meeting. But he has teed it up great. He must have pre-sold me very well because the meeting couldn’t have lasted more than 30 minutes. It wasn’t a typical sales meeting where you have to win over the client. It was really more of a “let’s just meet in person, make sure he’s a real person, ask him the rate, and get this started” type of meeting.

I left the meeting having a verbal “yes” and just needed to send over the engagement letter.

We ended up signing and over the next couple of months it resulted in over $100k in billable work.

So why am I telling this story? 

Well, there are a few key takeaways I want to highlight:

  • Speed can be KEY in sales.
    If I didn’t reply until the next morning, I may not have closed the deal. I don’t know that for sure, but I didn’t want to take that risk. I will say that I have had similar cases of time sensitivity and when I have replied quickly, it was a stated factor by the client that our response time helped close the deal. I have also had the reverse where being a bit too slow on reply has resulted in the Client moving forward with someone else.
  • Language in email matters.
    Every interaction you have with someone matters. You can learn a lot from emails. You don’t want to overthink or overanalyze things, but I do believe there is an insight to be gained from the language used in emails. And conversely, the words you write to someone in an email can move things one direction or another. I am constantly refining my email skills because of how important I believe it to be.
  • Having an internal champion is very helpful.
    People trust referrals much more than a random person. If they do much of the selling for you, you may find yourself in a position to just have to show up and not screw it up. The above is not a one-off case; this has happened to me a number of times over the years.

I feel it’s also important to address the fact that I was emailing at very late hours of the night. This was one time when being “on” and working all day/night turned out to be positive. Now, I want to be clear that this article isn’t meant to say working 80+ hours a week is what you must do to succeed. This is just one data point that I found interesting to share. I also have other times where being “on” all day/night ended up being detrimental — particularly to my physical, mental and emotional health. But those are stories for another time.


Decision Making Self Care

Something Is Missing

Six months ago I sold my business. 

I started the business when I was 22 and sold it 7 years later, a couple of months before turning 30.

Running the business was pretty much all I knew in my 20s.

It’s where I spent virtually all of my time. Days, nights, weekends. I was obsessed. I cared for it more than anything. Perhaps too much. 

At times, my identity was so tied to the success of the business that it became unhealthy. If the business had a bad period, I would feel awful — at one point falling into a deep depression for many months.

In the last couple of years, I tried to move my identity away from the business.

I would be “Anthony the CEO” not “Anthony the founder”.

I was playing a role in the company now, not the parent.

And this definitely helped.

It took time for my identity to slowly shift. And in the months leading up to the sale, I was pretty removed from the day to day operations of the business. This was by design — we had set up the company so that it could run without me — but also because internally I felt I needed to separate myself.

When the opportunity was there to sell, I took it.

I felt that this chapter of my life had run its course, I’d learned everything I wanted from it, and it was time to move on. Selling the business would be the final chapter and I’d be able to close the book on “Anthony, the founder”.

For the first few months, I felt amazing. I was able to walk away from the business right away, and I moved from New York City to Miami.

I rented a beachfront apartment and woke up to the sounds of waves hitting the sand each day.

I had zero responsibilities — no employees, no business, nothing.

And I had enough money now to not need to work for at least a decade.

Sounds like a dream right?

Well, it’s been about six months now.

And something I didn’t expect started to happen.

I started getting a bit depressed. But I had no idea why. 

I have zero responsibilities and zero money issues. 

When I was a kid, I thought these would make me the happiest person around.

So then I got to thinking and really started to examine why I was feeling this way because it didn’t make any sense.

And I started doing some research.

What I found was fascinating.

One article I came across was called “Dealing with the Emotional Fallout of Selling Your Business” by Jeff Giesea, published in the Harvard Business Review.

The article starts like this ‘“Congrats on selling your business,” a longtime mentor said the day after I signed the paperwork. “Now get ready for a depression.”’

He goes on to say how entrepreneurs who have sold their businesses often feel “isolation, a lack of purpose, a sense of drift. It seems obvious in retrospect. When you spend years architecting your life around business and suddenly it’s gone, you’re probably going to have an identity crisis and some post-partum depression.

Then there’s the issue of purpose and motivation. Without the constraints of money and responsibilities of your business, what will be your ‘reasons to keep trying’…The freedom of being unanchored sounds great, but it comes with the potential of drift and lack of motivation.”

This was speaking to me.

Without the responsibilities of the business or any real worry for money, I was lacking any motivation to really do anything. 

I no longer had a reason or purpose to do anything.

So I started spending hours and hours watching TV. Which is something I pretty much never did when I had the business. But I needed to fill time, so that’s what I did.

The article goes on to say “When selling your business, it’s natural to think of other major life changes to make — like moving to Montana or buying a new home. Selling and leaving your company is enough to change to handle at once.”


This was literally what I did.

Turns out I’m not alone, which is nice.

In retrospect, I might have rushed all these changes. I shifted my identity so quickly and drastically, I’m not sure I was able to fully process it.

And 6 months later, it hit me.

That feeling of “something is missing” started to make sense.

A report called “Life After an Exit: How Entrepreneurs Transition to the Next Stage” summed it up well “the reality of selling a venture often represents a loss of identity and community.”

I started to miss the team and leading people. I missed the day to day interactions. I missed the challenges, the problem-solving. I missed having a company. I missed having a purpose that drove me every day for years.

And so now I realize and admit, something is missing.

It seems obvious now that I’m writing this. 

Something that made up such a part of my life for 7 years was gone. 

And without anything to take up its place, it makes sense that something is missing.

I’m missing a greater purpose, meaning, and community that I had with my last business.

I’m not sure what I’m going to do moving forward, but I think this is a step in the right direction.

Before you can make a change, you must identify the problem. 

So, this is me identifying the problem.

And now I’m going to work towards solving it.

Decision Making

When (and Why) Should You Fire Someone?

Firing someone for the first time is to this day one of the hardest things I’ve ever had to do. 

It’s one of those things that every agency owner has to go through at one point or another. 

And it’s never easy. 

The way I see it, there are two reasons to fire an employee:

One is performance-related. 

To be honest, this one can get complicated to work through. While it’s out of the scope for this article, I recorded a podcast with more thoughts and details that you can listen to here:

And the other reason to fire someone is based on culture.

Your company’s culture is a critical factor in scaling an agency that can stand the test of time.

And you are its guardian. 

That doesn’t mean going for drinks after work or playing table tennis at the office.

It means that it’s your job and your responsibility as the founder/CEO to foster, protect and maintain it as you grow.

And, like a king that oversees the borders of its kingdom, the first step to guard it is to decide who enters and who doesn’t.

What you can do to prevent having to fire employees:

Ideally, every individual that comes into your organization should embrace and add to your company’s culture.

You know… ideally. But you and I know that won’t happen.

There are a couple of things you can to filter people out during the hiring process, but it’s no guarantee you’ll get it right 100% of the time.

What’s worked for us:

Again, when I say this is what’s worked for us, I don’t mean we’ve found “the perfect solution.” 

There still had been (and will be) situations where we face this issue. But it has helped minimize the number of times this happens. 


What should you do when an employee doesn’t fit your culture?

I get it…

I get it can be tempting to keep an employee that just KILLS it in their role, no matter if they don’t fit the culture or even if they negatively impact it.

But after seven years of running a business (plus dozens of experiences with firing people), I’m telling you, it’s NEVER worth it.

In fact, you will actually lose more money in the long term by keeping them.

When someone repeatedly does not live up to the company’s values, and you don’t do something about it, you are thus tolerating AND accepting that behavior.

You’re telling the rest of the team that it’s okay to be toxic.

You’re telling them that short term revenue is more important. 

In short, it means your values don’t matter at all; they are just something you wrote on a piece of paper and forgot about.

When that happens, toxicity will begin to slowly spread to the rest of your company like a virus — from that one person to the rest. 

Look, I don’t like telling people what they should or shouldn’t do. You’re ultimately the one who makes the decision.

But I’m making an exception here: 

Don’t do it. 

Don’t put an employee’s performance above your company’s core values.

I did it many times. And it slowed us down a ton long-term. 

Now, maybe you tell yourself things like:

“But they bring us so much revenue.”

“But we will lose clients if they leave.”

“But we can’t find someone as good as them.”

“But, but, but…”

Look, I’ve told myself all the excuses in the book. And what I’ve found is this:

The stories we tell ourselves about what will happen if they leave or why we are justified in keeping them are just that, stories.

You can and you will find a replacement.

When should you fire someone?

Look, I’m not saying you should go and fire someone the moment they do one little thing that’s not aligned with your business’ culture.

Everyone makes mistakes. Have a conversation with them about it. Give your employees the opportunity to learn from them.

Hell, I know that even I’m not perfect…

There have been times when I didn’t live up to Jakt’s core values.

That’s why it’s not just you who was to keep everyone accountable as the owner. All members of the team also need to play that role too.

But accountability starts at the top.

So you have to be the one setting the example.

If someone’s repeatedly offending your culture, and it’s clear it’s negatively affecting people, then you know what’s your role as the guardian.

But firing based on culture should not be rocket science.

If you implement clear expectations for culture from day one and have regular check-ins and reviews to give feedback, there shouldn’t be much of a problem.

And if someone fails to live up to the company’s core values, you can talk with them and keep an eye on their progress.

Even more, ask yourself if they have the potential to change.

If you believe that’s not going to happen, well, then they don’t fit in the business.

And that’s not to say they are bad people.

It might just be that the rules you established were not the right fit for them. 

You’re actually doing them a disservice by keeping them.

Because if it’s not working for the company, it’s probably not working for them either.

You see…

The more time you debate on the decision, the longer your business suffers and the longer they are not taking an opportunity elsewhere where they do FIT in with the culture.

So you’re screwing your team, your business, and even yourself in the process.

As the founder/CEO, you get to dictate the rules of the game.

I don’t want to compare it to a dictatorship. It isn’t.

But the thing is, you are the one who has the final say on whether someone gets to stay or not.

If you believe someone in your team is negatively impacting your culture, you decide if they stay or not.

And so… you’re the one who decides if the ship pivots and corrects course or sinks.

3 Takeaways on firing when there’s no culture fit:

  • As the CEO, you have to be the guardian of the culture. It falls on you to monitor your employees, see how they perform, and watch if they are a negative influence on the company.
  • Don’t put an employee’s performance above your company’s core values. Toxicity will spread to the rest of the team. 
  • The stories you tell yourself are just that, stories. If an employee’s not the right fit, you’re not doing them a favor by keeping them. If it’s not working for the company, it’s probably also not working for them either.

Decision Making

Why I Negotiate Everything But NOT With Service Businesses

When it comes to negotiating, it’s easy to fall on either side of the spectrum. I know some people who try and negotiate everything they buy. And I know others that just the thought of it makes them cringe. In my opinion, negotiation is part of the game. I like doing it –but I don’t blindly do it at all times. It depends on the circumstances.

(I wasn’t always this way – I used to negotiate absolutely everything – but that has changed over time. I’ll explain why.)

Here’s when I think you should negotiate and when you shouldn’t:

Why I negotiate all products I buy:

Products are inanimate objects and a change in price doesn’t correlate to a change in value. Here’s what I mean by that:

Let’s say I’m looking to buy a purse for my girlfriend. If the original price is $1,300 and I negotiate it down to $1,100 — what’s changed?

Other than how thick my wallet is, nothing, really. It’s still the same purse. It’s not a worse purse just because I paid less for it. The product itself doesn’t have a direct relationship with the price it’s sold at.

In the end, I’m negotiating for a thing. If I pay less, I’m still leaving with the same exact “thing” everyone else leaves with.

Let me give you another example:

I just moved to Miami from NYC and I’m currently apartment shopping here. When I go tour this place tomorrow, the real estate agent will give me a monthly rent of $4,000, for example.

Again, if I am able to reduce it to $3,000/month after negotiating with them — I will have saved $12,000 for the year. But, most importantly, it won’t come with any attached negative repercussions.

The apartment is still the same apartment whether I pay 3 or 4 grand. It will have the same bedrooms. The same kitchen. It will be on the same floor… I will just pay less for it.

And that’s why I negotiate as much as I can when it comes to products.

Is negotiating… good and fair?

I honestly love to negotiate. It’s really not even about the money that I save –even tho it’s obviously an added benefit.

I just have a passion for it –and I’ve seen that many entrepreneurs do too. I just enjoy the thrill of the hunt, the mental debate, the persuasion, even the emotional battle.

For example, I’ve always thought of a price tag as a “starting point” of a negotiation. It’s what the other part wants for it, not what they’ll accept for it. Big difference.

It’s a game. Can I go outside of my comfort zone, ask for a better price, and get away with it?

But… And this is a big but… 

I only do this with products and objects. I do not negotiate services (although I used to).

Why I do NOT negotiate with service businesses, anymore:

When it comes to services, this is a completely different story.


When you are paying someone to perform a service, you are not buying an inanimate product. You’re partnering with someone –a human being–and things get more complex. 

If you negotiate to pay less for a service, something has to give. Something else will be reduced along with the price.

It’s usually the quality of the service you get in return. But it also can be the speed of delivery or even the customer service and how responsive they are.

Just last year I commissioned a painting for my place in NYC. When the artist quoted me a price, I could’ve negotiated. And sure, I probably would’ve saved a few hundred bucks. But the result would not have been anywhere close to what it was.

Another negotiation example:

Let’s say you need to hire an accountant to file your taxes. His rate is $10,000 for this particular project, but you offer him $5,000.

For whatever reason, he decides to take it and you leave his office with a huge smile on your face. You just saved $5,000 –cool, right?

More than likely, however, he won’t go the extra mile for you. He’ll take longer to finish the project. He won’t respond quickly when you email him. And he won’t be there when you need to make a last minute change.

Maybe that even makes your tax savings smaller — so how much did you really save here?

Put yourself in their perspective:

If you run a service-based business, think about how you deal with people trying to negotiate your prices.

Where will you invest more of your time: on the client who’s paying you $100 or the one paying you $50…for the same service?

It’s human nature (and makes business sense) to make sure the largest sources of revenue are taken care of first.

So I apply that to myself as well. If I’m doing business with someone for a particular service, I don’t negotiate. If I don’t think it’s worth the value I’ll get, I don’t take it. And if I do, I move forward with it.

At the same time, if I accepted your price, I now can hold you to a higher standard. There’s no excuse to provide the value we agreed on.

You set the price. I didn’t. So I can expect the quality, customer service, speed and all these other elements to be at the level we agreed upon.

Negotiate for certain things, but not everything

  1. I try to get a better deal when it comes to products because the price I pay doesn’t affect the value of what I get. The object –an iPhone, an apartment, a TV– is still the same. All that changed was how much it cost me.
  2. But services are a different story. If you push for a price reduction, you’ll more than likely receive less of another variable –quality, customer service, speed, etc. Take the deal or don’t, but be very mindful when you negotiate.