Interview With Canada's #1 Female Entrepreneur


Today, I've got something wildly special in store for you.

Something that took a little bit of raw courage and approximately 28 hours of fighting with technology...trying to figure out stuff that lurks far, far outside my comfort zone. The result? Not perfect. But I'm okay with that. You see, one of my cool cat clients, Kelsey Ramsden, offered to hop on for a Skype interview together to chat about storytelling in a totally unbuttoned, casual way.

I swooned...because not only is she Canada's #1 Female Entrepreneur, one part Ivey School smarty-pants and two parts playful innovator (and someone I seriously look up to because she's founded multimillion-dollar companies while juggling three kids and fighting cancer)...

Kelsey has also become an unexpected friend and mentor to me. And I feel so incredibly lucky to have her in my orbit.

The truth is, I've never attempted to record a video Skype interview before. I'm about as good with technology as I am at killing spiders with my bare feet.

So yes, there was a bit of audio crackling, and Kelsey got abducted by Skype aliens for about 30 seconds while introducing herself. (It's ok. You can still hear her talking just fine.)

I was scared to release this video into the Interwebs, simply because it didn't have some fancy introduction, it was a bit too long, and I didn't edit anything out. (Not even the part where Kelsey and I sing "Talk Dirty to Me". You're welcome.)

When I was almost ready to call it quits on the entire process (and I was, believe me), I stopped myself. After texting my guy approximately 156 times in a frenzy of frustration. Because I doesn't matter. There's too much good information here. Fun moments. A conversation stripped down, the way we rarely see anymore.

Too often, what we see is the "perfected" version...the glossy, polished, looks-so-easy end result. We don't see the process that actually goes on behind that finished product.

I battled with tech programs to try and make this interview hiccup-free...

I called on the advice of some techy people who didn't have the answers either, and said I probably didn't record the interview with optimized settings (DOH)...

And I seriously considered forgetting about the whole thing and trying again later...

When I mastered the technology.

When I spent another entire Friday wasting my creative energies.

When I could afford to fork over wads of cash to have someone else figure it out for me.

When I finally got a Mac. (That day is coming. I swear.)

When I had an impressive intro and outro.

When I had a more artistic backdrop with some stylishly-placed flowers, instead of just sitting at my kitchen table.

But then, I thought back to Kelsey's advice, which she talks about in this video: Start before you're ready.

You have a choice: Courage or comfort.

So despite my perfectionism trying to rein me in and the learning curve I wasn't able to round today, I didn't want to see this moment get lost.

And that's why I'm sharing it with you today.

I know it's not perfect, but you'll have to forgive me.

I'm still figuring it out.

Kelsey's new website is currently in development, but you can sign up for her updates at

Aha Moments:

3:00 - Why Kelsey thinks storytelling is lifeblood for entrepreneurs today.

4:05 - What dating has to do with business.

5:02 - Why polarization is your BFF in business.

5:38 - About pages and what's behind a good "how I got here" story.

9:43 - What Kelsey has to say about the fear behind getting "naked" or bringing your personality into your business, and her tips for balancing transparency with professionalism and credibility.

13:53 - Why corporate jargon or "expert speak" can actually backfire on you.

15:15 - The importance of getting a point of access.

15:37 - What the song "Talk Dirty to Me" has to do with talking your audience's language.

16:58 - Why Kelsey is open about her personal story and pulls the curtain back on her life experiences.

20:30 - Where Kelsey pulls her blogging inspiration from.

22:37 - A template for writing an attention-grabbing blog post.

23:41 - The best business advice Kelsey ever got from an unlikely source.

25:03 - Business advice Kelsey got from a homeless guy when she was watching a street performer in Las Vegas.

26:36 - Why your business can't always be built on your passions.

29:19 - The best piece of business advice Kelsey gives (and wishes more people would follow).

33:34 - The importance of "the ask".

34:15 - Why you'll never "make it".

Statements of Impact & Takeaways:

All business transactions are based on trust.

The thing you'll remember most about someone's About page or story is that tender, vulnerable spot where you could empathize.

You don't have to be cellulite-y on your About page, but you should be honest.

Sell your customers what they want, but give them what they need.

The secret sauce of most successful entrepreneurs is being yourself, because this naturally opens you up to other right-for-you business connections.

The more diluted your message is, the less likely you are to get clients.

Always deliver value in your first point of contact with a potential client or customer.

Just because you're an expert in something doesn't mean your readers are. Simplify your language. 

When you build great connections and share them with others, the money comes.

Know your audience.

You can have a dream, but you have to work at that dream too. And if it isn't working, maybe it's time to look at something else.

Start before you're ready. 

You have enough, because if you know everything, it's too late because someone else started yesterday.

If you DO think you know everything, you're not paying attention. You're going to rinse and repeat what everyone else does.

You're never ready. Just start gaining some momentum, so when you get to the point where you do feel ready, you'll have some force behind you.

You don't have to know everything and you shouldn't know everything, except about that one thing you're good at.