The 5 Biggest Mistakes I Made as an Entrepreneur and How You Can Avoid Making Them Too

If I could look back and apply my new found love for the saying “fail fast,” life would look a lot different right now.

If you’ve got an online startup, save yourself from my top five mistakes:


I needed a sophisticated platform because of where I was trying to go, or so I thought. Reality check—you’re a programmer or you’re not, and I’m the latter. It only took three years to come to the realization that I had bitten off way more than I could chew and I’d been oversold.

I fumbled my way through the set-up of not one but three platforms, paid developers to program them, brought more technology savvy types onto my team to manage the build-outs and got so frustrated that I even pitched development shops to partner with or better yet outsource to. No matter which path I went down, one thing rang true:  I was beyond disappointed!

And being the typical female, I inadvertently cared way more about how it looked and less about how it would function.  It wasn’t until the most frank of my advisors pointed out that I needed to put my “guy” glasses on and use the simplest of tools that would easily integrate with the other cloud based programs I used religiously and allow me to do what I wanted—today.

I went right back to basics and what a difference it has made. It won’t be forever but having the data from 300 different furniture manufacturers at my fingertips has dropped the average time we spend per client from 20-plus hours to just one; talk about increasing efficiencies.


When the bottom line is everything, of course you’ll jump at deals. It’s so easy to get enticed by paying upfront for a year’s worth of this service/platform/software to cut your costs , but let me be the first to tell you month-to-month is where it’s at when you’re building an online company.

Why? One reason: your needs change faster than you’ll ever expect. Like a joystick, you can push it to the left and go one way, or the right and do the complete opposite.  I can’t even begin to tell you how many times I’ve switched online tools like CRM, accounting and marketing systems because it helped me take the company to the next step.

Concrete example: I was using an accounting system I loved, but it only followed behind me, which wasn’t really useful in the cash flow forecasting or planning department, which I now really cared about.  Of course I asked the company but it was still in their build pipeline, and knowing how technology went, that was going to be double whatever their forecast was to build. Had I paid upfront to use their software, I would be less likely to leave, but because it was month to month off I went to another system that would let me look forward financially.

Of course, I could have just eaten the costs and doubled up for the months remaining on my contract, but do that enough times and it affects your bottom line substantially. If you’re in the online world, flexibility is paramount and when you’re locked into contracts and subsequently into tools your business has outgrown, it ultimately costs you way more in the long run than you’ve financially saved in the short term. If $30 more a month is a real deal breaker, you may want to look under the hood in any case!


I fought this one forever, then succumbed, and couldn’t hit the reverse button fast enough. It’s a total drain on capital that you really don’t need early on. You think you’ve got the rent part covered, but the “other” related expense list never seems to end. 

The reality is online startups can be run from anywhere, and while I won’t challenge the value of seeing your team members face to face, there are better ways to accomplish this—and no, co-working spaces aren’t one of my recommended solutions. The number one reason people need to go somewhere is always that they can’t get motivated at home, and if you fall into that boat, you seriously need to rethink the whole entrepreneur thing in the first place.

I wasted more hours in the day commuting to the office from home, meetings, etc. that could have been used far more efficiently had I just fired up my computer from where I was. Moreover I’m a sales person by trade and an office contradicted my skill set.  When you working remotely and from anywhere you never know who you’ll run into and where that will lead.

In line with this thinking my solution was work remotely and take the office funds (though it wasn’t nearly what I was paying for space) and instead become a member of a facility that would allow me the opportunity to interact with like minds. I picked Soho House for its entrepreneurial vibe, great meeting setup, worldwide locations and service that makes sure I’m fed and watered whilst I work, but there are plenty of great options out there that can accomplish the same.


I’m the type to go guns blazing once I’ve put my mind to it, so naturally when an opportunity to apply for/join an accelerator, government sponsored program, entrepreneurial boot camp or four-month sojourn to a far away land arose, I was on it.

I threw my time into applications, made the most of the resources and other peoples time, even paid out of pocket to participate in some instances. Each and every time I ended up disappointed for one reason or another, but it wasn’t until I was told the third time that I really understood the greater issue, which went something like this: “We love your concept, but you’re clearly very resourceful and we don’t know how we can help you beyond what you’re already doing.”

And then, the Canadian reality set in: we’re incredibly impressive in the B2B realm, and in true Canadian fashion there are so many fantastic people who know this space that will gladly pour their heart and opinions into your online startup if you fit the bill. If you’re a consumer play however, that pool becomes insanely limited.

Canada has figured out what’s it great at and that’s selling to other businesses; rightly so, a lot of the Canadian initiatives naturally cater to this. While B2C is certainly not new in the traditional sense, it is in Canada’s online arena, and if you’ve got a consumer facing startup you’re going to have to put in double the effort to find the right people and programs who understand your concept.

In hindsight I wasted way too much time at the typical places I was expecting to find this sort of help. While I’m certainly not saying it’s not possible, better to go in with low expectations and be pleasantly surprised.


The one thing that drives me nuts about Canadian entrepreneurs and worse, females versions of that, is that we don’t collaborate or share like our US counterparts.

I have no idea where this notion of having to live with rosy glasses day in and day out came from, but enough’s enough! I can spend one day in New York with fellow entrepreneurs regaled by stories of their journey and all the mistakes they’ve made that they don’t plan on doing again.  At home however, it’s all best foot forward and heck no, I’m not faking it ‘til I make it!

I spent year one being perfect, listening quietly to what others were saying, afraid of being judged as an entrepreneur. Whether it was my fueled by total boredom or my curious nature, I wanted the behind the scenes version of what actually went on in other entrepreneurial journeys. If you know me, you’ll know I don’t shy away from asking questions. I can’t even begin to tell you how fascinating the conversation becomes when you get to the mistake train.

Of course, no one wants to be first to admit they’ve failed at something, but seriously, try it: go for a casual cocktail with another entrepreneur and throw out the opening line “how’s business?”  They’ll respond with great, and then ask the question in return.  When they do, segway to a mistake you’ve realized you just made. Odds are a few hours will have passed without your knowing it because you’ll be so engrossed in conversation.

Your mistakes make for great conversation—use the comment section and share yours (and if you haven’t figured out how to fix it yet someone will probably chime in with a great idea anyhow!