Who’s YOUR Harley Finkelstein?



“That Harley Finkelstein,” we’d laugh, “he’s EVERYWHERE!”

It was a joke around here. 

We said it all the time. We said it all the time because the guy was indeed EV-ER-Y-WHERE. Newspapers, TV interviews, blogs, social media. He was omnipresent. And as a result, you simply could not NOT be aware of Shopify.  

Harley Finkelstein joined Shopify in 2009. Like so many lawyers who decide not to practise law in the conventional sense, one year in a big Toronto firm was enough for him to know it was not his calling. 

It’s not surprising, really. Harley had always been what my dad and his buddies called “a rounder” — high praise reserved exclusively for hustlers. In fact, as Chief Platform Officer (CPO) in the early to mid-2010s, he told the Montreal Gazette that his job was “to hustle.” Shopify had a vision. They were democratizing online retail, and Harley was making sure you knew it.

You have to wonder, would Shopify have enjoyed its meteoric rise without Harley? 

So who’s your Harley Finkelstein? 

It’s a question for all ambitious, growth-minded entrepreneurs.

The reality is, you won’t achieve your big audacious goals without you… or an equal or better alternative to you within your firm to get out there and spread the good word and grow your following.

Ambitious goals should be matched with an equally ambitious determination to proselytize your perspective and vision in service of those you may help.

A skilled marketing team can do a lot to get you to your goals, but exiting stage right will cap your potential. 

Your marketing team still needs you. If you want to be a leader in your field of expertise, you need to be out there sharing your perspective and vision on podcasts, at conferences, on social media and in your communities. 

But as is often the case, leaders in the firm aren’t prepared for that demand. And chances are, if you’re not out there, you’re likely ceding your ground to someone else. 

The Productivity Conundrum

As Harley noted in 2014, “one of the things that I like most about running a start-up is that there are no average days, especially because we are growing so fast. Initially, in my career at Shopify, I wore a lot of hats — I was business development, spokesperson, lawyer etc. Now that we have a bigger team (over 300 people), I spend more of my time coaching people to do those things, rather than doing them myself. This is a big challenge for me because as an entrepreneur, I have become so used to being doing most things myself.”

You can probably relate. You’re still wearing many hats and dealing with too many demands and too little time. It’s a productivity conundrum.

Are you too busy working in your business to work on your business?

Audacious goals require the hustle. Your marketing team will forge ahead, but your potential will be capped without you (or someone equally good or better than you on your team.) 

The answer to ‘who will be your Harley?’ begins with you, the firm’s leader. 

In his book Free To Focus, Michael Hyatt rightly points out that a decision to say yes to something is a decision not to do something else. Time is limited. 

Achieving our goals requires us to actively and intentionally design our work lives. That’s pretty obvious on its face. But our workdays are full of potholes and landmines that take us off course — especially when you don’t have a workforce of hundreds upon which to rely.

If being the evangelist for your firm is in what Hyatt calls your “desire zone,” then likely something will have to give. The decision tree is clear: I’m best at delivering our services, and this other person in the firm will be out sharing our perspective and sharing our vision. Or, as is often the case with entrepreneurs, you’re the one best equipped to send your message out into the world. Someone else will deliver the goods.

Pick your path.

And if not you, then who? Who in your organization is best suited to share your story at conferences, on podcasts and, importantly, on your own channels? Does that person exist within our ranks now, and if not, should you hire someone? What kind of training, coaching and preparation can you offer to ensure that you’re getting the most return on effort? 

Chief Evangelist: is this for me? 

If you’re in decision mode on which path to take, you need to be self-effacing (am I the best messenger?) and know what’s involved. 

Guy Kawasaki famously defined and popularized the Chief Evangelist role at Apple and now at Canva. He notes that the difference between salespeople and evangelists is that “salespeople want to make money whereas evangelists want to make history.” Both are possible.

In an article written by Kawasaki for Harvard Business Review, he outlines three ways to effectively evangelize: “old-fashioned schmoozing, public speaking, and social media.” I’d argue that the lines between public speaking and social media have blurred in the last few years. So let’s amalgamate those and add writing as a third. 

Now let’s apply his methods to our all-star evangelist, Harley. 

Schmoozing: Kawasaki teaches us that it’s easier to share your message with people who already know you. This is tried and true networking. Putting yourself out there — not to manipulate but to listen, engage and learn how you might help. 

Harley is nothing if not a capital “S” schmoozer. A quick look at his CV demonstrates his willingness to network, even creating new networking channels. While completing his law and MBA degrees at the University of Ottawa co-founded the JD/MBA Student Society and the Canadian MBA Oath. He sits on numerous boards, has been a “Dragon” on Canada’s version of Shark Tank, and has been Canada’s Angel Investor of the Year. 

Remember, this is in addition to being Shopify’s president. 😮

It may not be the classic gulp and gab-type schmoozing you think of at conferences and receptions, but it’s all about getting out from behind your desk and getting into the mix. Pandemic or not. Zoom or in person. 

Social Media and public speaking: It’s never been easier to get in front of your ideal audience today.

Speaking at a conference may be outside your comfort zone but conquering your fear and learning to enjoy public speaking is an important skill to embrace. 

Today though, I’d argue that appearing on a popular podcast related to your market can be just as effective, if not more so, as many podcasts enjoy large audiences and have staying power. It’s convenient and doesn’t require all the additional travel hours. Add to your stable of specialist help, a good podcast booker, and this may be a great way to overcome any public speaking qualms before you hit the main stage at the next big conference. 

Being a guest on others’ podcasts and YouTube channels expose their audience to your message but having your own channels is equally important. Turning on a camera or recording your Zoom video podcast and publishing it on your YouTube channel is an easy way to 2x your efforts. It doubles how people might discover you. Inviting guests with followers of their own to your channel is an easy way to extend your reach. 

Owning your channels is essential. And it’s never been easier. 

Social media, love it or hate it, is just a factor of life today. Your marketing team can do a lot of the heavy lifting, but if Twitter’s your thing… you should probably embrace being in the thrust and parry yourself. 

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