I Started 6 Businesses in 12 Years. Here are the 10 Hard Lessons I Learned

Cover Photo by Loe Moshkovska from Pexels

Over the past 12 years, I’ve started 6 businesses. The first one was when I was 19 years old and still in college. I was programming software for other businesses to help them manage many aspects of their operations. I made enough money to survive for a few years but never grew the company to have any employees.

I went on to start another business with three friends a couple years later. Then again a couple years later. And guess what? I did that again a couple years after!

I was hooked.

Being an entrepreneur is at the very core of my personality. As such, I never feel like I’m a very good employee because all I can think of is starting my own thing all the time.

Now, I’m certainly no Jeff Bezos. But I’ve learned valuable lessons that will benefit any new (and old) entrepreneurs and I want to share them with you now.

1. It’s not about what you know, it’s about who you know.

All of my clients for my first business happened through word-of-mouth. By discussing with other entrepreneurs, I’ve observed this to be a trend amongst early stage startups. There’s nothing more powerful than a satisfied customer talking positively about your products or services.

Also, by growing your own network of professionals, you never know what important person you’ll end up connecting with who will help expand your business in ways you could never imagine. My mentors are experts in their respective industry and they’ve given me the best tips to grow my business and have connected me with other important people who also helped me grow my business.

Basically, the more connected you are, the easier it is to find clients, improve your business, and hire the right people.

2. Being able to sell is as important as being able to build.

This is where I fall short. Every time. Of all the skills that I’ve learned and of all the hats I’ve worn, marketing just hasn’t sunk in (yet) for me. This is likely the number one cause for the downfall of all my businesses. I couldn’t get my products and services into the customers’ hands.

I’d argue that to be successful in business, you need to know how to sell first, then be able to build a product. If you can manage to sell a subpar product or service, imagine how easy it would be to sell something great. And in this day and age, there is so much competition and “pollution” that it’s more important than ever to be able to make your offering visible to the world.

3. You don’t have to register a business until later in the process.

Technically, a business’ goal is to generate income. Until you’re at that stage (or close to it), you’re free to start whatever you want. If it doesn’t work, you’ll have saved yourself both time and money. I have it easy here in Canada where I can do it all electronically for $60 and have it ready within a few minutes, but I know it’s not that easy everywhere.

And if you’re thinking about the expenses, in some countries, you can claim them up to 7 years after.

If you have a great idea that you want to explore, just do it and don’t worry about that aspect of the business until later in the process. You have much to think about before then.

4. You can create Minimum Viable Products in less than a week.

I realized this to be true after doing it myself multiples times, but also by chatting with other entrepreneurs who were clever about how they built their MVPs.

Viking Boutique was technically all built on a single Friday. I wrote all the stories, had my assistant find all the items, went to Fiverr for a logo, and I used Shopify’s incredible tools to put it all together.

My accountability program was somewhat built in a day too. Add one or two days for the reflection on what it would feel like and how to implement it. The implementation is, basically, just a weekly email and a Google Form.

That’s the beauty of an MVP. You don’t need much. Think email + communication tool + spreadsheets & forms + your best feature.

5. Finding the right co-founder is hard.

Starting a business venture on your own is hard. Think about all the hats you need to wear! Not even the most well-versed polymath truly has all the skills required to run a startup on their own. That’s why most people turn to finding a co-founder. And it’s not as easy as it seems. It is, after all, not that different from marriage.

In all my years as an entrepreneur, I still haven’t found the perfect co-founder for any of my startups. And I like to think that I’m not that picky. Even though I appreciate having learned many business skills, it sure would have been nice to have someone with more experience make better-informed decisions than I have. And nothing beats bouncing off ideas with someone who cares just as much as you do. And that can only be done with a true co-founder.

6. Growing the right team is hard.

A motto I really like in theory is “hire slowly, fire quickly.” Sounds brutal, but when you realize that what makes or breaks a startup is the people there, you soon realize that it’s the wise thing to do.

When you get people who share the same values in your team, yet come from different backgrounds, you get the most productive outcomes. Collaboration flows naturally and quality products or services are getting built.

But it’s hard. I’ve actually never hired slowly, and very rarely let someone go. “Good enough” is so easy. And while it works early on, you start to realize that, for longer projects, “good enough” may not have been good enough.

7. Saturday and Sunday will become just another day.

And you know, it’s not all bad. When I speak to my friends working 9–5, they think I’m crazy. When it’s your business, you WANT TO work on Saturday and Sunday (in fact, I’m finishing this article on a Saturday at 5:30am). If you don’t, then maybe you’re not working on the right business.

If you ask me any day of the week what day it is, chances are I won’t be able to answer you. And there’s something beautiful about that. When you have something important to do on a weekday during the day or something you really want to do, well, why not do it? After all, you know you can work on weekends too!

Truth is, you’ll rarely HAVE TO work on weekends, but it’s a good sign when you find yourself working then without realizing it because it proves you’re working on something you’re truly passionate about. And that’s very important for motivation.

8. You’ll have freedom but you’ll realize it’s a double-edged sword.

Even though having freedom with your time seems like an absolute blessing, for most people it’s actually a curse. Mastering your own time is not a skill we’ve practiced much in our lives and first-time entrepreneurs struggle a lot with this. It turns out, self-discipline is a skill you’ll never truly master, but with practice, a healthy lifestyle, a good routine, you get much better at it.

But on the plus side, it’s true that you get to choose where you spend your time, and when you do it right, you can accomplish so much more and improve your life so many ways. There’s (almost) no way I could be a nomad, write every day, practice 3 skills per day, workout, meditate, read and hang out with friends on a daily basis if I didn’t have that freedom.

9. You’ll get addicted to success, for better or worse.

Being an entrepreneur, your success really is your success. It’s your hard work and decisions that made you successful. And that is a powerful feeling. The rush you get will make you think bigger and reach higher. You’ll be hooked like I was. That’s when most people start losing sight of the big picture. That’s when you start saying “yes” to too many opportunities.

Back in January, my success in writing made me want to only write and expand my personal brand. The problem was that I was already running my own video game company, I was about to launch an online store, I had just partnered up with a friend to work on a SaaS company. I took on too much but still managed. The problem is, when the momentum goes away, it’s hard to keep up with success.

I can stress that enough: “The main thing is to keep the main thing the main thing.”

10. It takes years of hard work to become an overnight success

An overnight success hardly exists. Sure, some people get lucky and their work was recognized faster than most, but the truth is, rare are the people who become a success who are clueless about what they’re doing. These people worked at least as hard as you and I did to get to where they are.

And that’s one thing to be successful, but that’s another to maintain it. Those with great habits, skills and personality tend to remain successful. Others are considered “one hit wonders”.

People are looking for shortcuts to become successful, well, these people rarely become successful. Work hard on yourself — your health, your skills, your personality, your habits — that’s where the real success lies.


Conclusion

I hope you’ve learned something! If you’re an entrepreneur yourself:

  • Which ones resonated with you most?

  • What would you add to or remove from the list?

  • What’s your own experience as an entrepreneur?

Share with everyone in the comments!

If you’re not an entrepreneur yet and are thinking about becoming one, I hope this paints the right picture for you. I made sure to include both the good and the bad because truthfully, it’s not always the easiest road. But with expectations set right, you might just find it easier than you’d expect.

You can do this!