Why I Became an Entrepreneur… and what I think of Side Hustles…

A Rude Awakening

In college, I had a family friend, that was 29 years old at the time. He was extremely successful – he had started several businesses and was definitely a figure that I looked up to.

We were chatting one day – he was just asking what I had going on in my life. I was in college then and had a couple of ‘side hustles’ going on. I was dabbling with a few ideas that I was telling him about and he stops me mid sentence and says,

“Bridger, when do you think the best time in your life is to start a business?”

I think about it for a second, and I’m like – well probably in my mid 30’s sometime? I’ll have experience and some cash in the…

“Wrong”. (He cut me off again)

He kept going with –

“The best time to go all out and start a business is in your early 20’s, so right now for you…”

After acknowledging the confused look on my face with a laugh, he continued by saying that some people need the track record and to learn about life before starting a business, but for the vast majority, the early 20’s is the best time to start because you have a stress free life no obligations.

Group Of Coworkers Discussing In Conference Room

You don’t have a mortgage.

You don’t have any kids.

And as a college student, you have access to a stupid amount of mentors! Everyone wants to help a college kid!

Also, your body is in the best possible condition to take on large amounts of stress that comes with starting business.

I said, “What about School?”

“His response,

“Do you think that school will still be waiting for you if you fail in a few years?”

That hit home pretty hard. Here I was thinking that I was on this strict timeline- needing to be married at this age, graduated at that age, buy my first home at that age and then I’m free to do what I want.

That conversation really rocked my world.

Now What?

Right now, amid the Corona Virus pandemic, unemployment is at an all time high – the crazy thing is that just 6 months ago, unemployment was at an all time low! What a crazy world right?!

Jeff Bezos has this theory that he calls, the ‘Regret Minimization Theory‘. Basically, he trys to live his life in a way where he will have the least amount of regret later on.

“I want to have minimized the number of regrets I have…I knew that when I was 80 I was not going to regret having tried this.”

If you got blind sided by this recession, then my sincerest apologies. But I encourage you to think about all of the different opportunities you have right now.

If you just got bucked off the horse (lost your job) – do you really want to go and get back on that same horse??? I know I wouldn’t!!!

That is what you are basically doing if you go and try and get a similar job to the one you had before! You probably thought your former job was safe and steady… which is awful because it wasn’t. It just appeared safe. How could starting your own business be any riskier?

Fortunately, there were people in my life that encouraged me and supported me in taking the leap to go all in. It was a combination of subtle, yet inspiring nudges, that led me to where I am today. It took a lot of hope and determination to jump 2 feet … but I am so happy I did!

I had started about 7 businesses throughout my undergraduate degree- they were okay… none of them were home runs… they were good… but never great!

I was always leaning more into school then I was my businesses- and because of that, my businesses suffered. But it wasn’t until I really went all in and started a fund till I saw success. I regret nothing.

My grades suffered at the time- but who cares?! I’ve now launched two successful funds and a successful business to help others people start their first fund.

Think about it…

I have been on the sidelines eating popcorn and sipping on a soda my entire life. I’d go to the games and I talk to the players, trying to talk the talk and walk the walk.

Going half way into your own business is like going to a professional baseball game, watching the players super intently, and then going up to the pros afterwords and saying something like…

“Man, you should have seen me the other night. Me and my 8 year old were playing t-ball in the neighbors yard- and I just crushed one. You

should have seen it man – it was wild.”

T-BALL | Dawson County, Georgia

Sounds ridiculous right?

I’ve learned that is basically what you are saying the next time you go up to a successful business owner and say.. “Yea so this side hustle I’ve go going right now..”

I hope that he stops you mid sentence saying,



Starting a business is a lot of work…if you are one of those individuals that want to start a business… and you haven’t… it’s 99% of the time, entirely your fault.

I have a family friend where two of his sibling are homeless. I recognize that there are a lot of people that have mental or physical obstacles that make it difficult to function…. But my family friend’s siblings do not struggle with either of those – My family friend and his parents have offered several times to help out… but the siblings won’t accept the offer.

It just makes me really sad.

In the United States, there are even systems in place to keep people off of the street, but for whatever reason- some individuals think the world is out to get them and won’t let their family or the Government help them.

There are also Government systems in place to make it easier to start a business- in the form of tax incentives. Ask your family or friends if you can work out of their garage or somethings, because I think for the most part, that people are good and want to help you succeed!

I’ll get off of my soap box in just a sec… but don’t get back on that horse that is just going to buck you off again. Please stop playing T-ball in your neighbors yard and step on to the field and take a couple swings!

Even if you aren’t in your early 20’s… live life like Jeff Bezos and live your life in a way where you don’t have regrets!

Now- What do you think of side hustles?

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