Four Hard-Won Lessons From My Early Years As An Entrepreneur

Use this serial entrepreneur’s four biggest mistakes to help you up the learning curve as a first-time startup founder.

Four Hard-Won Lessons From My Early Years As An Entrepreneur
[Photo: Flickr user Heisenberg Media]

When I started out as an entrepreneur, I made plenty of decisions without knowing what the outcome might be. I still do. But back then, I didn’t have the same level of experience to guide me. Looking back, these were four of the toughest but most critical lessons I learned during those first few years when the learning curve was the steepest.


1. Winning A Large Sum Of Money Doesn’t Guarantee Success

A huge chunk of change can actually put you right down at the bottom again if you don’t manage it properly.

When I sold my first company, I made what I thought to be a small fortune. True success, it seemed, had finally arrived. Little did I know that this money would actually be the start of a string of problems that led me to end up with less cash than I’d had before I even started the business. Because I misunderstood what had led to those initial earnings, I wasn’t able to manage them appropriately. That meant I didn’t put them into a new business that I could actually go on to grow.

Looking back now, I should’ve worked with a mentor or money manager to determine how best to save and use that revenue as a springboard to make even more. Sometimes you’ve got to lose what you’ve got in order to know what it was really worth.

2. Never Fear Asking For Help

Being new to internet marketing, I was afraid to ask anyone for assistance because I saw it as a sign of weakness or worried it might compromise the personal brand I was trying to build.

This was a mistake. I realized only much later that it took me a lot longer to get up and running because I didn’t go out and get the contacts that could help me make short work of some key steps. Instead, I chose to reinvent the wheel–and paid the price. It would’ve saved money and ramped up profitability more quickly had I just reached out for help.

Many entrepreneurs know they should find mentors or advisers that can guide them, but they’re too slow to do it. There are lots of experienced people who can help walk you through the process of navigating a new industry and building a business from the ground up.


3. It Doesn’t Have To Be Perfect Before You Release It

Like many startup founders, I’ve always been a perfectionist, so I spent way too much time on my first product than I needed to. Later on, I realized I’d wasted a lot of time and money again, plus lost the opportunity to start making money sooner. I had no idea that people don’t mind if a product isn’t perfect–or that getting their feedback is how you learn how to make it better.

In reality, you only need to have enough of the product available to help your customers with a problem or issue they’re having. That’s a lower bar to clear than many entrepreneurs set themselves for a product launch. Ideally, when you get the product or service out there, you can beat any possible competitors to market, and that’s ultimately much more valuable than a “perfect” release.

With my subsequent startups, I’ve rolled out my product and then tweaked it later–after hooking customers with the initial product that gave them just enough to start seeing benefits. Later on, the other enhancements were just the cherry on top, but by that point we’d already figured out we could give our customers something they really wanted and turn our attention to doing it even better. Listening to their needs actually cemented those relationships and helped attract new users.

4. Don’t Stay In A Business Niche Because It’s What You Know

Early on, it felt easy to stay just in internet marketing because it’s where I got my start and had become my comfort zone. The only problem was that it only would only take me so far as an entrepreneur.

When I realized that there was limited growth, it dawned on me that I could take what I knew from that field and apply it to any other industry that interested me. Once I did that, I really started making money–because I’d taken away the barriers I’d set up for myself by thinking I should just stick with what was familiar.

There’s something to be said for domain expertise, but it can limit you, especially as startup founder. I didn’t know much about online invoicing and business payments before I started exploring that space, but I studied the industry and looked for where I could make a difference. Then, I started using everything I knew about internet marketing to grow my business in that industry.


It doesn’t require glossing over their differences to realize that in most industries, the same fundamental rules apply for growing and running a business. It hit me much later that I’d stayed too long in my comfort zone and could have launched into multiple industries sooner if I had just known that was possible. The truth is that you can probably bridge business niches even if you start out with a limited knowledge of those areas.

In hindsight, there were more than just these four things I could’ve done differently, but I learned the most from these experiences–enough to implement these lessons in all the ventures I’ve pursued since my first startup. And hopefully, they can help you save a ton of money up front and start succeeding much sooner than I did.