We make some people harder to love because they defy our societal and cultural norms. They’re pure. They don’t mince expectations with filtered down possibilities so everyone else is comfortable. They don’t stop to give you their spot in the sun because they know we all have one.  They think: Why create shade when there’s enough heat for all?

That’s Jake.

She’s highly misunderstood, and it’s precisely what I love about her. What you see is who she is and what she wants for you is everything.  Tricky to believe these days: someone who actually wants the best for you because she understands what it is.

And therein lies the rub.

Her standards are high.

She comes by it honestly. She was raised that way (but that’s next week’s story). Here’s a glimpse though. I can’t help myself.

“My parents are truly incredible human beings. They exposed me to life across it’s multiple landscapes. I had it all. During the week, life in a fine home with velvet curtains and stunning design and then weekends running barefoot in the grass with scads of artists and hippies. There  was no room for judgement in my life, only experiences. My parents gave us and showed us what the best truly is: a full and confident life.”

No wonder I liked her immediately even though I wasn’t sure I should.  She challenged me right from the get-go.  There was no nicey-nicey dumbing it down small-talk. She asked what I did. I told her I’m a Core Story Specialist. I help people articulate exactly who they are and intrinsically, why they do what they do.

And she got it.

“Cool”, she said.  And that was it.

I liked that.

She didn’t offer any polite ‘filler’ conversation. She just moved on to what was next.


What you see is who she is and what she wants for you is everything.

I’ll come completely clean on this one, we work together now and I offered to write this article because I feel lucky to know her. Holy Hannah and mutha of all that is F-bomb sacred, Jake Hassel-Gren has a MASSIVE VISION for female entrepreneurs. She (and I) can drop more F-bombs than a bus load of 14 year olds on Dorritos. The difference is kids do it ’cause they can, and she does it ’cause sometimes it’s called for.  Some moments deserve a capital F in the front with a big ole K at the back.

The truth is though, as much as I send her up now, I completely couldn’t figure her out when we first met.  “I’ll connect you with my friend Jake”, said Charlene SanJenko of PowHERhouse Women’s Media Group to me last August. “She’s the woman behind The LEAP Learning Lab. You two can talk about building a program to help women bring their book from concept to publish-ready.  Jake is as tired as you and I are of seeing women continue to work in silos. We have to change how we do things and Jake’s LEAP Learning Lab is all about that.”

Where does she live? I asked.

“Toronto”, said Charlene.

Oh gawd I thought, not another perfectly coiffed Toronto woman to snicker at my hippy hair and make snide comments about my closet full of Crocs.  Sure… let’s talk. I thought. We’ll see. 

We got on a video chat in September and in perfect post summer form, I had sun-fried frizzy hippy hair and was still bumbling around with beach brain struggling to finish complete thoughts and sentences as we shared big ideas about what would make the lives of female entrepreneur’s easier AND more powHERful.  Jake, once upon a time a VP in the banking world, now an entrepreneur on a mission to create a global, world class online Community of Practice for women and set a platinum standard for online learning, showed up exactly as she is: stunning, primed and ready for anything.

I’m going to write another piece about Jake next week. This is just the beginning.  It’s going to take a lot more than one article to capture this woman’s story. I spent a few hours on the phone with her doing what I do best, which is pulling together who she is at the Core so I can understand why she cares so deeply about women taking their spot, as she calls it.

For today though, my focus is on WHY Jake rather than WHO is Jake. I want you to know why I decided to hitch my online learning wagon to LEAP, and you know me, my reasons always have less to do with business and everything to do with the person.  A long time ago, in an entrepreneurial class I took in my early twenties, the teacher at the front of the room said “never do business with someone you wouldn’t have over for dinner”.  That truth has stayed with me.  So here’s a bit about Jake and why I think she’s pretty dang spectacular.

TinaO’s Top Ten Reasons Why I Love Jake Hassel-Gren.

Do women even say that about women anymore? I do.

#1 – She’s wicked, and every other totally awesome and righteous word I used in the 80’s. Remember how the 80’s defied logic? There was only one direction, and it was UP.  That’s how it feels to work beside Jake. We’re going somewhere and it’s gonna be florescent green, Madonna awesome.

#2 – She likes dogs. Seriously, her dogs have matching winter jackets and she’d never treat them like an accessory though they will look fantastic.  She’s a ‘small dog’ parent and yes she does post funny dog videos on Facebook.

#3 – She speaks artist. Okay, I’m stretching the truth a little (maybe a lot). She doesn’t actually SPEAK artist, but she FEELS artist which is harder and far more vulnerable to do.  I couldn’t hang with this chick if we didn’t connect in this way.

#4 – She wears red lipstick like it’s a signature. Red is primary. It isn’t made from something else by anything else. Perfect.

BTW, it’s Chanel. I asked.

#5 – She can flip you the bird while screaming your praises. Expression is like that. It’s a full contact sport. Jake does life out loud and what she doesn’t say with her words, she’ll tell you with her eyes.

#6 – It took less than 3 seconds for my phone to ring when I told her about my sister passing. Not a text. She phoned. Who calls anyone anymore? Jake.

#7 – She asks “How are you?” at least twice a week. In her world of ‘best’, of ‘do’, of ‘be’ she still finds the time to connect with those she cares about. She says things like “I was thinking about you today. How did your doctor’s appointment go?”, or “How are you holding up?”, and “Do you need anything?”.  Again, I ask you, how many people do you have in your life who do that regularly?

#8 – She calls me out on my greatness and I’m not talkin’ blowing sunshine up my butt. It’s not about compliments, it’s about saying what is so. She’s the first to say “You know that. You do that. You are that.” – When she says it, I believe it. When I say it, I talk myself out of it. I’d rather listen to her.

#9 – She loves football. Okay, so I grew up with too many brothers and I can’t stand watching sports on tv or in an arena, but I frickin’ love that she’s over-the-top, beyond-all-understanding, geeked-out C R A Z Y about The New England Patriots. I gotta respect that kinda passion you know?

#10 – When I asked her what is ‘home’ for her, and what is her greatest medicine? She said LOVE. 

Jake is a big game of life player.  She gets up every morning and asks: How can I be of service today? Some of us are harder to understand because our whole package doesn’t match the stories set up and made-up by others on the outside. Jake is like that.

I thought she was tough. She is.

I thought she was an uncompromising high achiever. She is.

I thought she was opinionated, driven and sharp. She is that too.

I thought she cared about success. She does.


and Hers.

and Mine.

Because in Jake’s world, you don’t have to step into the shade to give someone else a piece of the sun.

The best is meant for all of us, and a woman need only stand and claim her spot to know that for herself.

This is PART ONE of TinaO’s Exclusive on Jake Hassel-Gren. Watch for Jake’s Core Story in PART TWO coming out next week. For more about Jake’s LEAP Learning Lab, you can visit her site. 

TinaO is a Core Story Specialist and a Program Director of PUBLISH with Meribeth Deen for The LEAP Learning Lab. She’s a writer, speaker and the founder of TinaOLife – a hub to Live, Give and Be Your Story, plus the deep listening weekend retreat Live Your Best Story. She’s been in the PR and Marketing world since she could put words together and has been a professional network marketer for over twelve years. She teaches: selling isn’t slimey, marketing isn’t make-believe and writing won’t give you an aneurysm (it’s not hard). You can be yourself in all that you do. In fact, that’s what the world is waiting for. 

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