I had always loved the idea of starting my own business but never really went after it. I dabbled here and there but never fully committed. There were many reasons for my hesitation—fear of failing, lack of an idea worth committing to, not having a partner crazy enough to help me, and just complacency. 

But once I got a taste of what it could be like, I was hooked.

Over a decade ago my brother and I started a learning solutions company, eLearning Brothers, in our basements. Today, I’m the CEO of a company with over a hundred employees. It was hard. It was scary. It was worth it.

How did I know it was the right time to take the leap, leave a great job with good benefits, and step into the unknown? The truth is—there is no right time to start your own company. There will never be a right time. But I realized I didn’t want to be left wondering “what if” for the rest of my life, so I reframed the question. “What if…?” became “Why not? What’s stopping me?”

“Why not start a business?” As I thought about it and started to list my reasons, none of the “why nots” were outright show-stoppers. For example, one of my initial “why nots” was that I would have to quit my nice, cushy job. So what? If things didn’t work out I could always go get another job, right? Right. Another “why not” was the potential failure of the business. But businesses go under all the time, I thought. There wasn’t any way to know what would happen unless we tried. 

I didn’t have a business degree but I did have years of experience in the industry I wanted to start a business in and that gave me confidence. As business leaders, most of us are making it up as we go. To be clear, we’re not closing our eyes and throwing darts, but we often must step into the unknown. For example, my company’s initial product was eLearning templates. As the only two people in the company at the beginning, my brother and I had to set the price for these templates. 

There’s no science to pricing new products or services, no mathematical formula or scientific chart that could tell us exactly how much to charge. We had to make that decision. Of course, if we had a physical product, we could have known our materials costs and manufacturing estimates, done some competitive research, and created spreadsheets to get some approximations. But at the end of the day we had none of that and we had to decide what the price would be and adjust later. 

Despite all of the unknowns we faced (like pricing) when we started our business, I soon realized, that there were only three things I truly needed to start my own business: A good idea in a familiar space, a financial plan, and a supportive partner. Here’s how I went about doing each of these things as I started my own business.

Choosing my focus

For me, it was an easy transition to go from working as an employee in corporate learning to running a business targeting corporate learning professionals. This is a space that I know and where I’m comfortable. 

Before I jumped off the deep end, I needed to vet my idea. So I asked myself these questions:

• “What problem am I trying to solve?” For me, it was BORING eLearning. I knew there had to be a better way to create training courses that rocked!
• “Who is my target customer?” It was me in my employee role.
• “What similar products or services already exist?” I was using the competitors’ tools already. 
• “What resources (capital, experience, partners) do I have?”
• “What are my goals?” Over ten years later, our mission is still the same: helping everyone become an eLearning rockstar! 

Having a clear focus in the beginning helped me build a strong foundation. This doesn’t mean that I couldn’t change my focus later, but at least it gave me a strong starting point. 

Of course, I didn’t do all the vetting on my own. Having my brother working with me and other trusted professionals as sounding boards was essential. Vetting my idea with others provided valuable insight into the bigger picture. The process was scary, but I wouldn’t get anywhere if I didn’t start, and now I was determined. 

Making a financial plan

There’s an art to running a business because an idea also needs to be revolutionary and financially viable. This means that before I could take that exciting leap, I had to crunch some numbers. I’m no accountant, but I started by asking myself these questions:

• What is the income potential of my business idea? 
• How long will it take to start making a profit? 
• How much money does my family need to survive while trying to get this new business off the ground? 
• Do I have the startup money needed or will I need initial investors? 

It’s been interesting to look back at these questions over time and see where my predictions were and weren’t accurate! Luckily, it was pretty inexpensive to start my business idea—I just needed two computers and a basement. I’ve learned a lot since then, but I’ve also brought in some great finance professionals who are essential to keeping things running smoothly. 

Building my support system

I’m going to be blunt—business is hard. There are good days and bad days. There are thousands of right ways to do things, and that’s scary as a founder. Especially because as the business grows, more people depend on you to make decisions and have answers. 

Since making the leap to be a founder, I’ve learned that I can’t do it alone.  A successful business leader needs a team in their corner, whether that’s a business partner, a mentor, or a significant other cheering them on from behind the scenes. 

Just look at 2020. My company was in the midst of finalizing a major acquisition when the COVID-19 hit and we had to transition to working from home. I had all these grand plans for revealing the news of the acquisition and welcoming the new companies into the eLearning Brothers family. We were going to fly out, paint office walls orange (our brand color), and have big celebrations on-site at the new companies.  

Instead, I closed the deal on a Zoom call in my son’s bedroom, with my wife at my side for support.

I’ve been incredibly lucky to build a strong, supportive team—both professionally and personally. Having that support has helped me through the ups and downs of running a business. Because I have people I can turn to for support and advice, I’ve been able to pivot when needed, take risks, and make strategic decisions to grow my company—even during a pandemic.

All because I dared to ask myself, “why not?”