Why Every Sales Rep Should Start Their Own Business

I’ve always been someone who has enjoyed dabbling in the business world outside of work. I guess you could call it a hobby. Personally, I just enjoy being productive.

Even in my younger days, I was always launching some website, radio show, or random venture in my free time. Fast forward to present day, and I’ve got multiple real estate projects to go along with a blogging side-hustle on top of a full-time job for the NFL.

I can’t really explain why – I’ve just always sort of had that entrepreneurial itch. Hobbies are great, and I have quite a few of my own, but a good, old fashioned, side-hustle? Now that’s the good stuff. Find me a hobby that I can throw some passion behind and turn into a money-maker, and I’m all about that life, baby.

So here’s the real reason for this article:

I’ve learned more about sales through my side hustles than anywhere else in my career.

Seriously. Side-hustles have been incredibly influential on my sports sales career, and I recommend them to anyone that will listen.  Every business venture I launch (even the ones I fail at) make me that much better at my real job: sales.

I know entrepreneurship isn’t for everyone. I get it. It’s hard work and there’s risk involved – but in my opinion, every sales rep should start their own side-business at some point during their career.

Here’s why:

1. Grow Your Business Brain

I talk about it all the time: sales skills are life skills, and visa-versa. Communication. Negotiation. Organization. These are all pretty important life skills that are absolutely crucial if you want to be a top seller in your field.

But one that is often left out in sales discussions is business acumen. And it’s arguably the most important of all.

If you’ve ever read any of my posts or heard me talk about premium sales, you know I’m a sucker for a big business brain. Business acumen is absolutely essential if you want to be able to sell in the premium landscape. I’ve never met a good B2B seller who didn’t have robust business knowledge, and the very best reps I know are overflowing with it.

I’m not saying you have to be an expert on the stock market, or a real estate mogul – but business knowledge is incredibly important, and the more you have, the better off you’ll be.

Obviously, you can sharpen your business brain through all the normal channels – reading business journals, subscribing to newsletters and attending networking events. But in my opinion, the best way to build your business acumen is by starting your own.

There is no better way to learn what the CEOs you’re pitching deal with on a day-to-day basis. Risk analysis. ROI. Opportunity valuation. These are terms we talk about a lot in sales – but have any of us actually lived them? Do we actually know what they really mean?

Trust me when I say launching your own business – however small – gives you a real taste of the business world. And if your venture actually turns out to be a successful one, having some skin in the business game will make you that much more dangerous as a seller.

2. It’s Easier Than You Think

I want to clear up a few misconceptions before I keep going.

• You do not need a ton of money to start your own business. I’m not asking anyone to launch a Fortune-500 company out of their garage. Very few of us have that ability. Trust me – there are plenty of low/no-cost business opportunities out there if you do your research. AirBNB is probably my favorite, but I know people who have had success with E-Commerce, retail, blogging, among others; all requiring super low start up investment. Don’t let this be an excuse.

• You do not need a ton of free time to do it. We are all busy. I get it. Nobody believes more in working your tail off at your real job than I do. But for all my long days working in sports, I always found time to sharpen my skills outside of work. Starting a side-hustle is no different. Obviously getting anything off the ground will take a donation of some precious free time, but the best businesses I have started were super low maintenance once they got going. We all make time in our busy schedules to watch football, grab drinks with friends, etc. If being successful is a hobby, you’ll find time for it.

• There isn’t as much risk as you think. Fear can be a big deterrent when it comes to starting your own business – and I get it. That’s why it’s important to start small. Don’t invest a bunch of money if you don’t want to. Don’t take on more stress than you can. That’s the beauty of a side-hustle – it can start small, and in most cases, free. Are you big into fitness? Put together a workout program and sell it online. Do you like watching NETFLIX? Start a website that ranks the top NETFLIX shows. And make it good, seriously. If I spent as much time actually watching NETFLIX as I do googling what I should watch on NETFLIX – I’d be finished with the app. Seriously though – in 2020 there are thousands of teenagers making millions of dollars a year on Youtube. I remember what I was like as a teenager, and I’m sure you do too – so don’t tell me it’s too scary or too hard.

3. Passion Projects are Healthy

Stop me if you’ve heard me say this before: work-life balance is the most important thing they’ll never tell you about.

Look – I’ve worked alongside plenty of people who love their work life more than their personal life, but that’s just never been me. I find I am way more successful when I’m passionate about something both inside and outside of work.

Let’s call a spade a spade: our job is incredibly difficult. There can be a lot of stress, expectations, and competition. Those things aren’t actually bad – in fact, they can be great motivators. But too much of them can weigh down even the best of sellers.

Think of it this way: when you put too many eggs in one basket, it’s easy to get out of balance and become frustrated in a job like sales. If your whole life revolves around work, and you have a bad day with a bunch of poor calls and a big sale that fell through, it can ruin your week. And sometimes your month. And guess what that does to your sales numbers?

Conversely, when you leave work and have other things going on that you enjoy and are passionate about, it’s a heck of a lot easier to wake up the next day and get right back up on the horse.

We talk a lot about not getting too emotional in sales, and a great way to buoy that is by having other stuff to tether yourself too.

Obviously, none of this is breaking news, but it is important to consider. Having hobbies you are passionate about can really help you become a better seller. The happier you are at home, the happier you’ll be at work, and the more you’ll sell. Simple as that.

4. Business Experience is Life Experience

Do you remember my article about “sink guys?”

If not, the gist is this – experts respect other experts. And the CEOs you’re pitching are all experts in their field. Sometimes, as sales reps, we can come off immature and quite frankly, not worth their time.

A great way to get on their level is to actually experience what they experience. Become your own CEO. Get a sense for what real business failure is like, and how success truly feels. Personally, the failures can sometimes be more important in the grand scheme of things. One of the best parts about side-hustles is that even when you fall on your face – and you will – what you learn from that is worth every second you spent on it.

Again – we’re not talking about launching a $500M business in your basement. We’re just dabbling with passion projects – but the result is the same. The confidence and intelligence you gain from these experiences will make you that much more dangerous in your sales meetings.

5. Generate Some Extra Capital

This is an easy one. Who doesn’t like extra money?

I don’t want everyone to think launching some NETFLIX website is going to miraculously make you thousands of dollars. That’s probably not realistic. But many of us, who have failed countless times at starting their own side-hustles, still enjoy the spoils of their few successes.

As someone with absolutely no experience in real estate, I can’t tell you how thankful I am that I randomly decided to take the plunge into something I was curious about all those years ago. I currently run multiple AirBNB’s and real estate ventures that are literally paying my bills during these crazy times, as the sports sales industry struggles to find its way.

My point is not to brag, but rather to put everything in perspective. I’m just some guy with a journalism degree who sells tickets as a job. And if I can do it, anyone can. Seriously. And some of these side-hustles can really blossom into money-making factories for you.

After all, the new American dream is to make money while you sleep, isn’t it? Passive income is the new white picket fence.

Don’t limit your own potential before you even try. Find something you’re passionate about and see what you can do with it. Your failures and successes will teach you more about yourself than you ever knew before. And as you work through the obstacles of launching your own tiny business, your sales skills will be the biggest beneficiaries. Things that your clients wrestle with every day, you’ll be getting a hands-on experience with.

Before you tell me no and that I’m crazy, just try it out. And let me know how it goes.

As I said before, hobbies are healthy. I have a few of them. Fantasy football. I’m a sucker for a good Marvel movie. I even dabble in FIFA occasionally. And while hobbies are great, to me they’re just more enjoyable when they pay me back for the time I invest.

All I ask is that when you’re accepting the Nobel Peace Prize in 10-years for growing your side-hustle into a $6B company, don’t forget to tag this blog on Linkedin.