Over the weekend, I met up with a few guys from my marketing and hustle group here in São Paulo. We started at a wine event and, as usually happens, ended up at an after-hours bar where the conversations got a little more interesting as the night went on.

One of the guys is in the early stages of starting a new business, and from everything he was telling us, he's actually making great progress. But as we started talking through it, almost every part of the conversation came back to another question: What if this happens? What if I do this? Will this become a problem later? What about this scenario?

It turned into one of those productive arguments between entrepreneurs where nobody is really wrong, but everyone has a completely different way of looking at the same situation. Eventually I just told him, "Man, you think way too much. Just go do it. Make the mistake."

And that conversation got me thinking about the difference between overthinkers and doers.

I have always found there are generally two types of entrepreneurs when it comes to making decisions. There are the people who want to think through every possible scenario before they make a move, and then there are the people who would rather make the move and figure out the problems as they come. I have definitely spent more of my career in the second group.

There is obviously value in both. The overthinker can usually see problems coming that the doer completely ignores, while the doer has the advantage of actually getting something into the market instead of spending months trying to predict what the market is going to do. The problem is that neither approach works perfectly on its own.

I've always liked the mentality of just doing something and apologizing later if you have to. You see this mentality with a lot of entrepreneurs, and even watching shows like Shark Tank, you can see how often somebody simply started without having every part of the business figured out. They got customers, created a problem for themselves, figured out that problem, and then moved to the next one.

The older I get, though, the more I realize there is a difference between moving fast and moving blindly.

The Thinking Before Doing Problem

An overthinker wants to know what can go wrong before it happens. They want to talk to somebody who has already done it, research the business model, understand the legal problems, understand the operational problems, calculate the downside and probably create several different scenarios for what happens if things don't go according to plan.

There is nothing wrong with that. Actually, I probably should have done more of it throughout my entrepreneurial career.

The problem starts when all of that research delays the actual decision. There will always be another person you can ask, another article you can read, another lawyer you can talk to and another possible problem you can imagine. Eventually you can spend so much time trying to avoid mistakes that you never put yourself in a position to make progress either.

The doer looks at the same situation differently. Instead of asking what happens if everything goes wrong, the mentality is usually that we'll deal with it if it happens. That approach has created some headaches for me over the years, but it has also allowed me to move into businesses and opportunities much faster than if I had waited until I understood everything.

One of the best examples was when we decided to get into the Nutra business.

When an Affiliate Becomes the Actual Business

I came into Nutra from the affiliate marketing side, so naturally my understanding of the business was heavily focused on traffic and customer acquisition. My world was running media through Facebook, Google and whatever other traffic source we could make work. I understood offers, funnels, landing pages, conversion rates, media buying and scaling campaigns.

When you are an affiliate, your main responsibility is usually getting the customer to convert. Somebody else has already manufactured the product, negotiated the fulfillment, stocked the warehouse and figured out how many bottles need to be sitting somewhere waiting to ship.

Then we became the advertiser and suddenly all of those things became our problem.

We launched, traffic started coming in and customers started buying. From the marketing side, that was exactly what we wanted. The part we didn't think through enough was what happens after you become successful at acquiring those customers.

We needed inventory. We literally ran out! Traffic was rushing in!

Not just inventory today, but inventory weeks and months from now. We had to understand when another order needed to be placed, how much product we needed, how long manufacturing would take and what happened if our campaigns suddenly produced more customers than we expected.

These sound like obvious questions now. They weren't obvious to me when most of my experience was based around sending traffic to somebody else's offer.

We essentially created the demand first and then learned how to manage the operational side while the business was already moving. It created stress and problems that probably could have been avoided if we had sat down beforehand and really mapped out everything that could happen after the sale.

An overthinker would probably look at that situation and say we should have figured all of that out before we ever bought the first click. They wouldn't necessarily be wrong.

At the same time, I also wonder how long we could have spent preparing for a business we didn't even know would work yet. We could have spent months studying inventory management, talking to manufacturers, modeling sales volumes and trying to predict every possible situation. Eventually somebody still has to turn the traffic on and find out if anyone actually wants the product.

We chose to find out first and solve the problems as they arrived.

That experience cost us some headaches, but I also never forgot the lesson. If I get involved with another physical product business, one of the first things I am going to think about is inventory and what happens operationally when the marketing actually works. Nobody needs to teach me that lesson anymore because I already went through it.

I Made the Same Mistake With Company Structure

Another example happened as we started expanding businesses and creating LLCs and different corporate structures. This was an area where I didn't have much expertise, so I did what most entrepreneurs would probably do and hired a lawyer.

My thinking was that this is exactly why you hire professionals. I know marketing and business, the lawyer knows corporate structures, so let the lawyer handle the legal side while I continue focusing on growing the company.

That works until you realize that hiring an expert doesn't mean you should completely remove yourself from understanding what that expert is doing.

Looking back, I should have spent more time understanding why something should be an LLC, why something might be structured another way, when a C-Corp makes sense, how ownership should be divided and what happens to these structures as companies and partnerships change.

I didn't need to become a corporate attorney, but I needed enough knowledge to ask better questions.

Instead, I depended heavily on somebody else knowing what was best for us. Later on, we had to deal with headaches around structures that I probably would have looked at differently had I understood more when everything was originally being created.

That was another expensive way of learning something.

Would I do it the same way today? No. Today I would still hire the lawyer, but I would understand just enough about the subject to challenge things, ask what happens in different scenarios and probably get another opinion when something didn't make sense.

But I only think that way now because I already made the mistake.

Learning From Other People's Mistakes Only Gets You So Far

There is a saying that you should learn from people who have already made the mistakes. I believe in that heavily. If somebody has already lost money, wasted years or created a massive headache doing something and they are willing to explain it to you, it would be pretty stupid not to listen.

A mentor can save you from a lot of unnecessary mistakes.

What I don't believe is that a mentor can save you from making mistakes altogether.

There are things people have told me throughout my career that I understood logically at the time but didn't fully understand until I experienced the situation myself. Once it happens to you, the advice suddenly has context. You understand why that person was warning you and why they were so specific about it.

That is one of the weird parts about experience. Sometimes somebody can give you the correct answer before you are ready to understand why it is the correct answer.

You still need mentors. You still need smart people around you and you should absolutely ask people who are ahead of you what they think. But there eventually comes a point where you have enough information and continuing to ask questions is really just another way of delaying the decision.

At some point you have to make the move.

The Risk of Becoming Too Experienced

Something else I've noticed as I've gotten more experienced is that experience itself can start turning you into an overthinker.

When you are starting out, you don't know enough to understand everything that can go wrong. There is actually a little bit of an advantage to that. You are naive enough to try things that somebody with twenty reasons not to do it might avoid.

After you've been through enough businesses, partnerships, campaigns and mistakes, you start seeing problems everywhere. You remember the campaign that blew up, the partner situation that became complicated, the legal headache, the cash-flow problem or the operational issue nobody predicted.

Experience gives you pattern recognition, which is incredibly valuable. But experience can also make you hesitant if you allow every previous mistake to become a reason not to take the next risk.

I don't want that.

The lesson I took away from the nutra supplment business isn't that I should spend six months building the perfect operation model before launching another product. The lesson is that if I launch another product, inventory needs to be part of the conversation from the beginning.

The lesson from the LLC situation isn't that I need to research corporate law for three months before starting another company. It is that I need to understand what is being created well enough to ask intelligent questions and not blindly depend on somebody else simply because they have a professional title.

Those mistakes didn't teach me to move slower. They taught me what I need to pay attention to while I am moving.

Think Ahead, but Keep Moving

I think that is probably where the real balance between overthinkers and doers exists.

You should foreshadow problems. You should ask what could go wrong. You should listen to mentors, lawyers, partners and people who have already been where you are trying to go. There is no reason to intentionally repeat somebody else's expensive mistake when they are standing right in front of you explaining exactly what happened.

But you also have to accept that you are never going to predict everything.

Some problems only appear after customers arrive, the actual data. Some questions only make sense after money starts moving. Some weaknesses in a partnership don't become obvious until there is pressure. Some operational problems aren't really problems until the business reaches a certain size.

You cannot research your way out of every mistake in entrepreneurship.

What you can do is make better mistakes.

You can use the experience of other people to avoid the obvious ones, use your own previous experience to recognize patterns earlier and then still be willing to move before everything is perfectly figured out.

I would rather have to solve a problem created because something I launched is working than spend forever preparing for a problem in a business I never launched.

There will always be something that needs to be fixed.

The inventory will run low. The corporate structure might need to change. The campaign will break. The employee you thought was perfect might not work out. The strategy that made complete sense on paper might completely fail once real people interact with it.

That is part of doing business.

Overthinkers are good at asking, "What if this happens?"

Doers tend to say, "If it happens, we'll figure it out."

I think after enough years doing this, I've landed somewhere in the middle. I want to ask more of the "what if" questions than I did when I was younger, but I never want those questions to prevent me from doing.

Learn from the people who screwed up before you. Ask them why. Take their advice seriously and try not to step on the exact same landmines.

Then make the decision and move.

You are going to make mistakes anyway. Just make sure you learn enough from them that you don't have to pay for the same lesson twice.