Finding Love—and Luxury—in Unexpected Places


Noun: A propitious, or opportune, moment for decision or action.

In the fall of 2016, I knew my first startup needed a soft landing pad—and that I needed a softer sleep surface.

I was crashing at my friend Marshall Mosher’s apartment. He slept on the bed and I slept under it (it was cozy but cramped, to say the least).

I was a young, wide-eyed entrepreneur who hadn’t yet been smacked upside the head by the world, pursuing a dream until I couldn’t pursue it anymore. I remember feeling the end fast approaching, much like a romantic relationship hurtling toward its demise.

I felt the intuitive pull that there was something more out there for me, but I didn’t know what it was, where I’d find it, or how I’d make it happen. But I knew why things weren’t working: I didn’t really have a business model and the market wasn’t right. More than that, it couldn’t fulfill my goal: to help people connect and make a difference in each other’s lives.

I didn’t have the skill-set to build something that could do my goal justice. To be ready for my next attempt at entrepreneurship, I had to learn a lot. And learn I did. I made a spreadsheet of 100+ organizations I thought I could learn from. I pulled their top contacts and designed an outreach campaign, going to town on the keyboard before tucking myself under my friend’s mattress each night. (Back then, true luxury came in the form of sleeping on friends’ pull-out couches whenever I was traveling.)

Then, I came across an organization that would ultimately teach me what I’d need to take the next leap into entrepreneurship. It was called Kairos, and it was a community built to serve and connect the brightest young entrepreneurs around the globe. So What did I do? I reached out to every fellow on LinkedIn until the CEO had about nine emails in his inbox about my pleasantly (painfully?) persistent outreach. Eventually, Kairos (thank you Ryan Bloomer) let me in the door to run the K50 global community (which eventually became K50 Ventures), events, and content.

I wouldn’t be where I am without Kairos, without that moment in time. It set me up to run a book launch and build a brand for someone I met through the chapter. That experience led me to Arcbound. And Arcbound has led me on the hardest, most daunting and rewarding path I could have ever imagined, and into established global communities like Entrepreneurs Organization (if you’re reading this and considering membership, this is your sign to join, especially the SF Chapter!).

Why am I telling you all this?

Is it to romanticize my journey as a founder on the most romantic day of the year?

No (OK, a little—we’re all human and I’m single).


It’s to share something I learned in the process of searching for the right thing, which could be applied to the search for anything: To be open enough to let others into your moments, to reach out and seek help.

Because the right people see you for who you are and want the world to benefit from your brilliance. Because they want to see you win. Because you never know what you’ll make possible for someone else—someone who couldn’t have done it without you.

My life is a series of these moments. Over the past year in particular, I’ve invited so many people into my life. I’ve allowed them to witness the great stuff alongside the hard and ugly stuff. They’ve essentially seen me naked:  in my most human form. In turn, they’ve shown up in ways I never imagined and inspired me to pay it forward.

Those moments when you reach out are special. They require real vulnerability, which is scary, of course. But they can ultimately define who we become—to ourselves and to others.

I hope your day has been filled with love. And if it hasn’t, I hope you understand what a difference others can make in your life, and what you can do for them if you just put yourself out there.

With that in mind, I’ve got one ask for you: If you’ve found value in this read, please share it with others.