Hey Reader,

As I sat on my plane from Paris to Beirut, I couldn’t help but think…have I made a horrible mistake?

Only a few months earlier, the mere idea of this opportunity had felt so uncomfortable, so out of my wheelhouse that I came shockingly close to saying ‘no.’ Thank god I didn’t.

I know I’m getting ahead of myself. Let me catch you up.

It was the summer of 2017. The previous year had been one of major upheaval, change, and growth.

Incredibly stressful but good—full of emotion, healing, and growth.

In June of 2016, I landed a new job as the head of marketing for an early-stage B2B SaaS startup. Only a month later, I left my first husband—the man I thought was the love of my life when we’d married only 3 years earlier, but I quickly learned he was manipulative, controlling, and hot-tempered.

I spent the next 3 months waking up nearly every night in a cold sweat in the middle of a panic attack, wondering if I'd made a horrible decision.

Looking back, I know that leaving him was one of the bravest (and best) things I’ve ever done for myself. It paved the way for years of tremendous personal growth.

But the months that followed were intense—filled with buckets of tears and overwhelming gratitude.

I wasn’t just rebuilding my life but building myself from scratch.

I’d spent my first 34 years trying to make other people happy and had no clue who I was or what I wanted. So I swore that if I had even the slightest inkling to do something—no matter how big or how small—I would do it. I owed myself that much.

As I prepared for divorce, a friend asked what I wanted more of in life, and when I said, without missing a beat, “adventure,” he asked if I wanted to go to Cuba. Duh, of course, I did.

A couple of months later, in October of 2016, I found myself flying to Havana with about 20 entrepreneurs, creative strategists, nonprofit leaders, and social impact consultants.

America had recently begun to open up communication and relax sanctions with Cuba, and we were there to bridge connection and collaboration with the Cuban business community.

I felt fully out of my depth but committed to following my curiosity and learning as much as I could.

I soaked it all up.

It was absolutely, freaking amazing.

So, in May of 2017, when I got the call from international hostage negotiator Mickey Bergman, the organizer of our Cuba trip, I took it.

He asked if I’d go to Beirut with David Ewald, my friend who’d opened the door to the Cuba trip.

One of Mickey’s contacts was helping facilitate the first-ever partnership between a startup accelerator and the U.N. which would curate a pilot class of social impact entrepreneurs receiving funding, coaching, and support through the program.

They needed startup experts to provide training and mentorship and wanted David and me to lead a week of go-to-market strategy workshops.

What?! “Why the hell would you ask me?” I thought.

At first, I said "no."

But Mickey pushed, and Ewald cajoled, and pretty quickly, I got on board.

And so, a few months later, after racing to the Eiffel Tower and drinking a few glasses of brut rosé on the streets of Paris during my layover, I found myself sitting on a flight to Beirut, overwhelmed by the anxiety and nervousness of what I was about to do.

• I had no idea what I could possibly teach these founders
• I was convinced they’d be disappointed by my advice
• I was SURE I did not deserve this opportunity

The next 10 days were a whirlwind.

Long days of training, workshops, and giving talks to the entrepreneurial community, interspersed with my then-boyfriend (now husband) Andy and I wandering and falling in love with Lebanon.

Fun fact: Andy is 50% Lebanese, but this was his first time visiting the country. This is us on a visit to the village his great-grandparents emigrated from, surrounded by goats. Apparently, his great-grandfather was a goat herder before leaving his homeland.

I loved every single second of it.

• Breaking down complex demand-generation strategies into simple, actionable training
• Connecting with innovative entrepreneurs building solutions to some of the most pressing problems facing their country and its over a million refugees
• Working directly with these passionate, mission-driven founders to help them design creative solutions to move their businesses forward
• Exploring this incredible country and getting to soak up its beauty, culture, and people

But it wasn’t just me that loved it.

I got overwhelmingly positive feedback from the founders that I worked with. They actually thought I was helpful!

5 years later, I also got this DM from one of them. Still brings tears to my eyes.

I was hooked. I flew home from Beirut on an absolute high. I knew without a doubt that THIS was what I wanted to do.

• Work directly with founders
• Collaborate on world-changing projects
• Develop innovative go-to-market and branding strategies

On my first day back in the office, I was giddy with excitement and still floating on a cloud of sun-drenched skin, jet lag, and mission-driven founder vibes.

At the end of the day, the founders of the startup where I worked brought the whole team into the conference room.

And then they said the words every startup employee dreads hearing...

“We’ve run out of money. You have two weeks before we need to stop paying you.”

:Record scratch:

We talked about everything that needed to be done in the next 2 weeks to prepare for the slowdown and a potential fire sale of the company.

I had two tasks.

1. Communicate the reality to all of our strategic partners, especially the businesses with whom I’d built collaborative marketing relationships.
2. Decide if I wanted to go with them if they could get acquired.

As I went back to my desk, I quickly cycled through a range of emotions.

• Fear
• Anger
• More fear
• Acceptance

I couldn’t help but think…

“Is this a sign? Is my chance to build a life that feels like the last 10 days in Beirut?”

I felt hope, curiosity, and optimism starting to bubble up inside of me.

But I pushed it aside so I could make some calls to share the news with a few of our co-marketing partners.

My first call was to the badass CEO of a product design agency and host of a popular podcast in our niche industry (tech product management).

She and I had been working on a joint educational email course that we were planning to use as lead gen for our product management analytics SaaS product.

I called Suzanne and gave her the news.

Suzanne: “Damn, that sucks. What are you going to do?” She asked.

Me: “I’m not sure. Probably go find another job, but I’m wondering if maybe I should go out on my own and start my own thing. That might be crazy, though.”

Suzanne: “Well, if you do your own thing, I’ll be your first client. I love your style, and we need marketing help.”

WHAT?! I made one call and landed my first client.

And not just any client. Someone I admired, loved working with, and thought was about 1000x smarter than I was.

Was that even possible? Could it really be this easy?

But that’s how it all started.

Over the next few months, I bought the abetterjones.com domain, built my first website on Squarespace, and flew to LA for my first project with Suzanne and her co-founder.

My divorce led to Cuba, which led to Beirut, which led to A Better Jones, my first business.

I want to be clear with you.

I didn’t feel ready or prepared for any of it.

• Not my divorce
• Not my Cuba trip
• Not my Beirut workshops
• Not starting my first business

But they taught me an important lesson...

You never feel ready for the big shifts.

And if you're not careful, you could miss them.

Imposter syndrome is most likely to rear its ugly head when you’re stretching yourself.

It’s not a sign that you’re out of your depth but that you’re leveling up. It’s not a signal to shrink back but to press forward.

You are capable of far more than you give yourself credit for.

I’m deeply grateful that so many people took a chance on me and pushed me to take a chance on myself. They saw something in me that I hadn’t yet.

And I wonder how many opportunities I missed because, for so long, I was always the last one to believe in myself.

I'd love to say that these experiences taught me to have the kind of self-belief, faith, and confidence that I deserved, but it still took me years and a whole lot more ups and downs, twists and turns, laughter and tears to get there.

Thanks for reading Part 1 of my Origin Story—my call to entrepreneurship and the strange set of circumstances that led me here.

Next time, in Part 2, we’ll talk about what came next—a rapid, dizzying period of building, a devastating betrayal, burnout so bad I wound up in the hospital, and an unexpected light at the end of the tunnel.

In love and growth,
Kasey

​

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