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Entrepreneurial Journey: Key Lessons Learned for Achieving Success

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14 min read

I’ve been an entrepreneur ever since I can remember, driven by a mindset that later I would understand as part of professional development.

In the second grade, I started collecting Pokemon cards.

I’d sell them to kids after school, and it was a fun way for me to keep building my collection.

When I moved in the fourth grade, the kids at my new school didn’t share the same enthusiasm for Pokemon.

So naturally...

I started selling candy out of my backpack.

Initiating my journey in small business.

I’d buy what the Snack Shack didn’t have and charge fair prices.

I kept things on the down low for a long time.

I was afraid to get caught.

Mainly because the demand was getting so high and I was already taking two backpacks to school each day.

I was racking in that 5th grader cash.

I had my eyes on the prize.

I wanted that new Razor phone.

So here I went.

Sour Nerd Ropes, Skittles, Laffy Taffy’s, and my personal favorite:


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When kids found out about the hookup…

I got detention, flunked 5th-grade history, and couldn’t go with everyone to my school trip to the San Diego Zoo.

They never said entrepreneurship was going to be easy.

What did I do?

I doubled down.

My efforts were working.

I just needed to change my approach.

If you do what you've always done, you'll get what you've always gotten. If you want to change your results, change your approach. When you change your approach, you will change your results.

So I set up a table in my garage.

I saved enough money to buy a popcorn machine.

I stocked up on candy.


I let everyone know that I was selling the best of the best AFTER school.

Lucky me, I lived right by the school, and all my friends would pass my house on the way to the park.

So when the final bell rang…

I’d run home as fast as I could.

I'd pull out the table I set up the night before.

Turn on the popcorn machine.

Put up my signs.

And watch as all the kids flooded to my new pop-up.

I was amazed.

What a thrill!

For every birthday?

If I was asked what I wanted.

I would say, “investment money.”

I’d get a giggle followed by an envelope with $100 and a sweet note about having good luck with my investments.

I loved birthdays.


In middle school, I started selling technology.

I got Rock Band for Christmas once.

I sold it on Craigslist for $400 plus a Sidekick.

Yes... I'm talking about the T-mobile sidekick.

Those things were the jam.

Until the iPhone came out of course.

There was nothing like the iPhone.

(How far we've come.)

Which led me to sell my Sidekick for iPhone money.

That kicked off a whole slew of iPhone trades, sells, and upgrades.

I was able to buy and sell iPhones up until I found myself working for Apple when I was 16.

At Apple, I got professional skills I never had access to.

I was being trained and guided by some of the most talented people in the world.


I was a die hard.

(There's a picture of me waiting in line for the first iPad floating around on the web somewhere. It's okay if you don't go looking for it.)

I loved everything about Apple.

It was everything I could ever ask for at the time.

Apple taught me a lot about business, core values, and developing a vision that every employee could believe in.

Every day, I was inspired when I went to work at Apple.

I felt like I was growing both personally and professionally.

I was challenged.

I had to practice patience.

I dealt with a lot of ambiguity.

I took the leadership skills I was learning and applied them directly to my role as drum major in my high school marching band.

I served incredible customers.

Most importantly, I was a part of a fantastic team.

Little did I know…

A couple of years go by…

I have one more semester in high school.

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My dad pulls me aside and asks me if I would like to be a partner in his HVAC company.

Not what I had planned.

I thought I was going to graduate, continue to work for Apple, move to the east coast and enjoy a typical college experience.

My parents were serious.

They really wanted me to be a part of the family business.

My parents are immigrants from Brazil and I really wanted to help them.

It was a hard decision, but I said “Yes.”

They've taught me so much about working hard and working to get one day better every day.

I’m proud of our little American dream. 

Working with family can be one of the most difficult and rewarding things that anyone can ever experience.

If you've been there, you understand exactly what I am talking about.

I am proud of all the lessons I can take with me from that experience.

Now, fast forward a few years.

Here I am.

I run one of the most epic digital creative agency’s I could ever ask for.

I help businesses grow better by helping them align their sales, marketing, and customer service efforts through effective collaboration.

I work with some of the most talented people in the world.

I create and share a vision with people who are really committed to changing the world for the better.

It's wild.

I am so in love with every bit of it.

I do my best to lead with an open heart.

I want to remain authentic in everything that I do.

It blows my mind how we are all moving along this continuum of time.

If I were to ask that little candy hustler where’d, he'd be in 15 years...

What do you think he would say?

I’m not quite sure, but I have learned quite a few things about what it means to be an entrepreneur since then.

Here are the top ones I'd like to share:

1. Listen.

If you want to develop great relationships, take time to listen to others.

I really believe that deep down, we all just want to be heard and understood.

I saw this cheesy, but oh so true, quote on Instagram once:

"Spend more time listening instead of talking. You'll be amazed at what you learn."

You can only learn what you want and are willing to listen to.

2. Gratitude.

I love being reminded to zoom out.

Take a moment.

To take a solid look at my life.

From a different point of me.

It’s challenging to take a 3rd person look at yourself.

Realize that you, at this moment, are all that you need to be.

I find that to be one of the most reassuring blessings I get each day.

Every time I open my eyes I get to celebrate the opportunity to play the game of life one more time.

How dope.

Don't short change yourself by not living a life filled with an attitude of gratitude.

It's much better that way.

3. Create.

If all else fails.


Think of where this world was 100 years ago.

It's mind-boggling to think that we've experienced so much innovation as a human species.

Who knows how much we still get to accomplish?

The creator of Rick and Morty, Dan Harmon once said, "Output is magical."

Whatever you're feeling.

Put it out in the world.

Chances are other people are feeling what you're feeling too.

Create what makes you feel good and you’ll probably help others feel good too.

Giver’s gain.

4. Action

It’s one thing to think.

Or as many like to call: manifest.

It’s another thing to take action.

I love those people who talk about manifesting.

Don't get me wrong...

I believe we are still far from understanding the world as it is.

I also believe that if you really want something.

You must do more than just think about it.

Whatever it is that will produce the result you want:

Just do it.


Go for it.

Take action that drives you towards your goals.

Turn your positive thoughts into action.

Allow yourself to get out of your own way.

You'd be surprised at what you can accomplish.

5. Trust

Have you heard of that trust exercise?

The one where you fall back into a group of arms...

What happens if you fall?

Hit the ground?

Hurt yourself?

You get back up.

One of the best things you get to realize is that life is filled with times where you fall.

Things aren’t always going to work out the way you think.

You are not your mistakes.

It's okay to fail.

Trust in yourself.

Trust in others.

Trust the process.


I'd be lying if I said that I don't learn something new every day as an entrepreneur.

It's the best part of my "job."

I get to learn, absorb and question everything around me.

I guess that's the thing about entrepreneurs...

This sincere desire for constant improvement.

We've all heard it before.

“Those crazy enough to think they can change the world are the ones who do.” - Steve Jobs

I love meeting with entrepreneurs who feel they are hitting a wall and can’t seem to get to the next level.

It’s easier than ever before to get in front of one another face to face.

Why are authentic connections so difficult in such a social age?

I guess that's a question for another post.

Chances are that if you’re reading this right now, you are in the range of Wifi and most likely we could hop on a Zoom call together.

So I dare you.

Let’s get together.

Let’s chat.

This is an open invitation for you to step out of your comfort zone.

I’d love to learn about what’s working for you.

I’d also love to understand what the next level looks like for you, in your life and in your business.

I hope that I was able to give you some lessons of entrepreneurship to think about to start thinking about how to grow your business.

Talk to you soon,

- Tiago

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