Top 10 tips from an entrepreneur after a decade of success


I want to get real with you about what it means to start, own and run a business for 10 years with 10 key lessons I’ve learned. No sugar-coating, just the real, raw truth – sometimes it’s beautiful, sometimes it’s awful and sometimes it’s downright hilarious.

I started Jive with a business partner in 2009 – as only a naive 26-year-old does in the thick of a global economic-financial crisis – but the beauty about being naive is you don’t have preconceived, pessimistic notions of all the things that can go wrong. You don’t let your fear take you out because you really don’t have that much to lose.

Lesson #1: Encourage young people to take risks because they can

If they fail, they’ll learn some good life lessons and if they succeed, well, they succeed.

When we started, the stars aligned and we won two major clients off the bat.

Lesson #2: Leverage wins

We took those two brand names and talked about them everywhere – “oh yeah, we just started working with XYZ” … “well, you know what we’ve been doing for XYZ…” by doing so, we showed new clients social proof and made us look bigger than we actually were. Which leads me to…

Lesson #3: Optics are important

No one would have known that we worked at home in our bathrobes or pyjamas (always changing for video calls, of course). Our face to the world made us look big and important; from our website to our call answering service and virtual personal assistants, we faked it until we made it and didn’t burn through stacks of cash on unnecessary expenses.

But we did make stupid financial mistakes. We were so thrifty on start-up costs that when money started coming in, we thought we were rolling in the dough. We brought on full-time staff, leased an office in Vancouver, opened a second location in Toronto, got fancy car leases and so on, until we had to learn…

Lesson #4: Your bank balance is not a true reflection of your financial health

We quickly hit a cash flow crunch and had to take out business and personal lines of credit. We were officially handcuffed to our company. We couldn’t afford to close down, so we went into a brutal survival mode. No one knew about it except us and our bankers, and we had to keep up the appearance of success in order to survive. Which we did. Luckily. Though these are the lows of entrepreneurship no one really talks about. You feel embarrassed and like you are a complete failure.

That’s why it’s so important for CEOs to find peer support.

Lesson #5: Your mental health is one of your most important assets

It seems like an afterthought when you have more pressing priorities like hitting payroll and paying rent, but I’ve learned that your business is a reflection of you, and if you are a mental mess then the rest of it is going to be as well. I highly advocate for therapy (I have a personal therapist and a business therapist) and joining peer-support groups like Entrepreneurs Organization (EO) or Young Presidents Organization (YPO).

While your business is in the dumps and nothing seems to be going your way, you need to remember to have fun, so…

Lesson #6: Laugh a little

What’s the point of doing something day in and day out if you can’t enjoy it? Once I had to take a 600-pound mule up the freight elevator of the TD Tower for a client’s radio interview, and I hired a human pooper scooper to follow it around. I broke out in full body hives from an allergic reaction, but still till this day it’s one of my favourite client memories.

Back to the business side, if you truly want to GROW a business and not just have a safe, self-employed salary – you need to be strategic and take risks.

Lesson #7: Bold moves = big rewards

In 2016, we decided that the only way to really grow was to expand to the U.S. So, we took a step backwards and invested the time, money and female-power to open a brand new office in Los Angeles. It took a couple years, but the results are now paying off. Vancouver is still our head office where we employ the most people, but the majority of our revenue comes from the U.S. It was a risky move and it slowed down our cash flow for a few years, but in the end it paid off well.

One of the other major hurdles we’ve gone through is ending a business partnership. After eight years, I bought out my co-founder.

Lesson #8: Know when it’s time to say goodbye and do it with grace

This has personally been one of the most challenging and rewarding things that has happened in the last 10 years. I call it a “conscious uncoupling,” as we were very clear that we wanted to maintain a friendship (which I know a lot of partners can’t do), and we did. We also both realized that parting ways was the best thing for each of us at that time and for the business. I could write a whole “lessons learned” on this, but let’s just say that communication, transparency and mutual respect are key in doing it successfully.

Speaking about doing what’s best for the business…

Lesson #9: Put the business first

As an entrepreneur, it’s so easy to get caught up in the small stuff and running a business based on the people you have versus the people you need. In 2019, we rolled out a new business operating system and it has transformed the way our company runs. My staff is no longer accountable to me personally; instead they are accountable to the operating system, and it has been a game changer from top to bottom – including revenue increases and system efficiencies. I wish I had done this years ago.

Lesson #10: It’s all about relationships

Anytime I’ve taken this notion for granted in the past, it’s when my business fell off track. People are what matter most. From your relationships with clients and staff, to media and vendors, everyone wants to do business with people they like. And if you focus on nurturing these relationships over time, the results will speak for themselves. 

Lindsay Nahmiache is the co-founder and CEO of Jive PR and Digital.