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From Start-Up to Success: 15 Years and 3 Businesses Later, My Top Tips for First-Time Entrepreneurs

Entrepreneurship is a path deeper within yourself.

Saving for that $30,000 tax bill is one of many tips I have from building 3 businesses over 15 years.

But Pathfinders, I'm getting ahead of myself...

I'm going to share my top tips for first-time entrepreneurs with you so you can be successful sooner, but first, a little background on me.

I built 3 businesses over 15 years. They were in Information Technology (IT), software development, and online marketing. The first was a huge failure, the second did very well, and the third did pretty well.

When I started my first business I didn't have:

  • Business experience

  • A college degree (more on this later)

  • More than a year of experience with computers

Adding to that I was recently married, and 23.

Not exactly what some would call a "winning combination" of traits.

I let none of that hold me back from starting a business.


Because I knew deep within myself that I could build a business. If I'm completely honest, I also did it to show my parents I could do it my way. (The number of entrepreneurs that start businesses out of spite would shock you.)

At first I didn't consider myself an entrepreneur. I'm not sure I even knew what one was. But I knew I wanted to work for myself and be in control of my life.

Now here's a question for you - do you think you're an entrepreneur?

You ARE An Entrepreneur

When you hear the word entrepreneur, who comes to mind? Elon Musk? Oprah Winfrey? Jeff Bezos? Rihanna? Steve Jobs?

Everyone on that list are entrepreneurs. And guess what - you are too!

Being an entrepreneur doesn't always mean:

  • Quitting your job to start a company

  • Getting venture capital (VC) funding to "go big or go home"

  • Hiring a ton of people

You have a product or service idea that may benefit others. If you start a business based on it, you're an entrepreneur.

Full stop.

Don't let the word or what you think it means hold you back from going for it!

You Don't Need a College Degree

I'm a fan of formal education as it can improve your quality of thinking. Also, the more you know, the more dots you can connect. More knowledge is always good.

Some people say you should have a degree before you start a business. I call shenanigans!

You don't have to have a college degree to start a business. I got mine while growing my businesses.

Having a degree will give you a fallback though if you find yourself back into the workforce.

Entrepreneur's Aren't Born

To be a successful entrepreneur, you must have great and innovative products.

Bill Aulet

When we hear tales of famous companies and the people who started them, we tend to put them on very high pedestals.

But guess what - entrepreneurs aren't born. They aren't magical creatures endowed with powers others don't have.

Are some people less risk averse? Sure.

Do some people seem to have more drive than others? Sure.

But you can mitigate risk and learn to be more disciplined.

At the end of the day, you have what it takes to be an entrepreneur.

Here's how.

Tip 1: Do Something You're Passionate About

You may have heard this advice, a lot. That's because it's true. So very true.

Building a business can be a lot of work. And if you're doing it while working a full-time job - which I have - you'll be pulling some serious hours.

Your passion for what you're doing is the fuel that will get you through.

As you grow your business, passion is what gets you through the tough times that will happen.

Don't complicate this - it doesn't have to be "change the world" level stuff.

It could be as simple as:

  • I want to prove to myself that I can do this

  • I love programming and want to create a cool app other people will use

  • I want to create the type of company I'd want to work for

There are many passions. Figure out yours, determine if it'll be enough to get you through, and go from there.

Tip 2: Remove Failure From Your Vocabulary

We have an incorrect view of failure. Because failure is a necessary part. And the thing is you learn from failure, and so it's either you win or you learn.

Alex Hormozi

I love this quote.

Where others see failure, you and I see learning.

Did my first business fail?

I wasn't able to keep it going.

Did I learn a TON about building a business? Did I find out what worked, what didn't work, what other skills I need, and much more?

You bet your sweet potatoes I did!

I then took that knowledge to my second business and made it a roaring success.

Starting today, "failure" is no longer a part of your vocabulary.

Tip 3: Always Keep Cash on Hand

Remember that $30,000 tax bill I told you about before?

It's insane to write a check that's the amount of someone's yearly salary.

With that said, I was lucky I had the money in the bank to cover it. The government does not like it when you don't pay the tax bill. So pay we must!

Having cash on hand can help you pay the IRS, but more important is it can help you get through lean times. And like tough times, lean times happen too.

One of the best ways I've found is to keep cash in the bank. That's great personal advice too.

Tip 4: Create Plan B's

Following on from the "lean and tough times" happen above, you need to expect that shit you don't like will happen. Plan for it.

Some of the things that happened to me are:

  • Huge tax bill

  • A very bad hire

  • Increased competition in my space

  • Advertising costs going through the roof

  • The U.S. economy sinking like the Titanic

Some things are within your control, like who you hire and saving money for taxes. Other things like the economy and ad costs not so much.

Take off your rose-colored glasses, consider what might go wrong, and come up with ways to handle them.

Tip 5: Tell A Good Story

Since people started talking they were telling stories. For millennia it was how knowledge passed generation to generation.

We love a good story.

Your story is what gets people to "buy in" - it's the why they buy from you and not your competitor.

Your product/service is the what - it's the logic, the "what's in it for me", the "thing I need."

Your story is the why - it's the emotion, the thing that drives a customer to action.

A good story can help sell almost anything.

Tip 6: Become a Master of Time Management

Mastering time management helped me balance things. I ran a growing company and attended business school. I also spent time with my family.

There are tons of time management techniques. Here are 5:

  1. Pomodoro Technique: Work in 25-minute intervals (pomodoros) separated by 5-minute breaks. After four pomodoros, take a longer break of about 20 minutes.

  2. SMART Goals: Create goal that are Specific, Measurable, Attainable, Relevant, and Time-bound.

  3. Eisenhower Matrix: Prioritize tasks by urgency and importance.

  4. Rapid Planning Method (RPM): Envision the result you want and understand its purpose. Then, create a massive plan to achieve it.

  5. Plan Your Day in Advance: Take time to plan your daily, weekly, or monthly tasks.

I tried these and more. At the end of the day I had to find what worked best for me, and so you do. Try different things! Also keep in mind that what works now may not work later, so be bold and switch it up.

Tip 7: Hire Amazing People

A company is a collection of people coming together to create a product or provide a service. How well that collection does comes down to the people who compose it.

I mentioned before that I made one very bad hire. Making up for that person's mistakes cost me tens of thousands of dollars. That's a hard lesson learned.

I also made a lot of great hires. Clients loved my employees, I treated them well, and they did incredible work. They thrived, and so did my business.

A big mistake though was not hiring "non-production" employees.

As your business grows and you become more successful, you need to focus on what you're best at. For me, that was being the public face of the company and bringing in more clients. But if you're out getting clients and others do the work, who's doing the rest? What about the marketing, finances, operations?

Non-production employees and managers, that's who.

Continued growth is awesome. Unsustainable growth will kill your company.

As soon as you're able, start hiring for non-production skillsets.

For businesses between 5-10 employees, I generally suggest hiring in the following order:

  1. Sales (unless this is your jam and you love it) - to land the work

  2. Marketing - to bring in work

  3. Project Management - ensure products and/or services are being delivered well

You can outsource certain functions like accounting.

As soon as you can, surround yourself with skilled people.

Tip 8: Don't Go It Alone

With each business I did and the more I learned, the faster I could do the initial set up. If you can, find a co-founder.

There are a lot of benefits to having a co-founder:

  • Better brainstorming sessions: not only are they more fun, you can come up with more ideas.

  • Joint decision making: a pro and a con, joint decision making can help relieve some of the pressure.

  • Risk sharing: sharing risk can lessen some financial and emotional pressures.

  • Workload distribution: this can be more efficient and reduce your potential for burnout.

  • Diverse expertise: individual experience and knowledge improves problem solving

  • Accountability: co-founders can hold each other accountable for their actions and decisions.

If you're super driven, okay with less sleep, and have a passion for learning, starting solo can be awesome. In the beginning there were so many things I wanted to learn, so I did them all. Over time that changed.

If you don't know any potential co-founders or don't want one, that's okay. Starting is the most important thing.

Tip 9: Start Today!

Newton's first law of motion is that an object in motion tends to stay in motion. The trick is starting that body moving!

There's a lot of inertia to getting going:

  • Beliefs that say you can't be successful

  • Thinking the business you want to start has to be "the one"

  • Settling for the illusion that a paycheck is security

  • Family and friends not believing in you

  • Having no role model entrepreneurs in your life

Each of these is an anchor holding you back.

The best way I've found to release them is to get into action. Nothing beats fear like action and experience.

No matter the outcome, you're not worse off for trying. In fact, you'll be a hell of a lot better off.

So how exactly do you get started?

5 Steps for Starting Your Business

There are 5 steps to starting your business:

  1. Determine if you're going to create a product or provide a service.

  2. Think up a name and incorporate online.

  3. Open a bank account in the name of the business.

  4. Connect a payment processor to the account so you can take money (may be optional).

  5. Start providing value to someone else.

That's it!

In a few hours you can be in business.

Make The Decision, Then Act

Starting your business is as easy as deciding to do it. It's also one of the most fulfilling things you can do.

Entrepreneurship is about more than growing a business - it's about growing as a person.

To be successful you need to learn to sell your ideas. To sell your ideas you need to gain clarity on those ideas. You need to be brave and try new things, sometimes a lot of new things.

You need to get clear on why you're starting a business. It is to prove others wrong? Is it to show yourself that you can? Is it to feel more in control of your life and destiny? Take a few moments to think on your why. It's your fuel.

Take that fuel, and make it happen Pathfinder.

Do it now.

Then let me know what you're starting. I can't wait to hear about it.