Courtney Branson and I first connected over a shared friendship with Chris Taylor, founder of The Red Fridge Society here in Austin.

Before he was that, he was the founder of Square Root, an enterprise software company, and Courtney was his Head of Culture.

Together, they built Square Root to Fortune’s No. 2 company in the entire country to work for, and when they won that title, it was they (rather than the first place winner) who got the multi-page full-color writeup.

Because their culture was so unique.

Now, Courtney’s building a company of her own. EverMore is an AI-powered career companion, designed to help employees reflect on their work, track wins, highlight challenges, and build a living resume that makes sure they get noticed for their contributions.

This week, she shared the story of how she and her co-founders got started, the unconventional decisions that have helped so far, books that inspired her (hint: Kurt Vonnegut makes an appearance), and more.

Recently, she sat down to share her story 👇👇👇

EverMore is a reflective career system that connects who you are, how you’re growing, and the value of your work in one place. Our users anchor their career to a north star and chat with an AI-coach to authentically show up at work and narrate their stories. 

I found my cofounders—Kelsey Peterson (COO) and Scott Hertel (CTO) in the Austin startup ecosystem.

I met Kelsey at Square Root in 2019 when I interviewed her for a role in customer success. I convinced her to abandon that plan and join me in people + culture instead. She and I both went to Osano in 2021 to build the early version of their people + culture function, which is where we met Scott, the technical cofounder of Osano. 

We’re philosophically aligned on what an equitable and sustainable version of work would be. So, we stayed in touch and independently the three of us were all circling around ideas for a startup that helped employees, especially those who felt stuck in their career. 

As leaders, managers, and employees, we felt the tools for driving career growth or pivots were uninspired. We saw folks with strong storytelling skills thrive in promotions, review negotiations, and job searches, even if they weren’t the most impactful. And on the positive side, we saw how reflection and coaching could completely change someone’s trajectory. 

We tossed around ideas like a Courtney bot for managers, a LinkedIn killer, and a happy file for tracking wins. At first all we knew was we wanted to build a “love letter” to the employee. All three of us know how workplace systems can trap or harm people. The career promise is broken, and we want to be part of fixing that. 

We started with a tool for regular reflection to capture wins, challenges, and lessons learned paired with north star discovery to unearth individual patterns and insights. From there we added side quests and coaching personas to help our users prepare for and solve real, day-to-day conversations and challenges. 

Our first customers came from referrals. We launched a beta product to friends and family in December 2025, and they helped grow our initial user base, dubbed The Seedlings. As of now, we’re invite-only, which normally means joining a waitlist or knowing someone in it. But if any readers want to try EverMore, you can take it for a test-drive here. 

The current incarnation of EverMore is an amalgam of our original ideas. But we initially put it on pause, because we got a lot of early advice from investors and peers to pivot to b2b and go after the performance management market. 

That absolutely made sense given our collective backgrounds in leadership and culture. But the only way we were going to be up for that was if we could continue to center employees and decimate current “best practices.” We shopped an idea for a b2b talent matchmaker, but it wasn’t enough of a pain point for company leaders or their investors.

Our hearts weren’t fully in this idea and it showed. 

We 180’d back to our original idea, which we already knew from early user interviews addressed a personal and acute pain—Is this how my career is supposed to feel? Will I always be scared of losing my job? Could I have a dream job and what even is my dream job? 

We wanted to build career infrastructure for those people. To do it well, though, we needed individuals to divulge their feelings and secrets to a tool. In order to honor that vulnerability, we’ve put a premium on privacy.

We don’t want our users to be the product. So, we don’t train on their data or share/use it for any purpose. (We all worked in data privacy and believe in consumer data rights, so we’re attuned to the underbelly.) 

We also wanted to work with a smaller, curated language model to not only be mindful of the energy we use but also to give tailored, relevant responses. 

These decisions led us to choose the path of bootstrapping, so that our values can be prioritized. Even if that means slower growth for now, it also means being untethered.  

Recently, we got advice that our branding was too dreamy and whimsical for investors, and we got to dismiss it. Our design is nostalgic—inspired by vision boards, Myspace, and video games like Stardew Valley. It’s not meant for folks upholding power structures. We want it to feel different and attract people who are done with the theater of work.

I reread Cat’s Cradle by Kurt Vonnegut last summer, for the first time since college, and it hits different now. He writes about the systems we invent to keep ourselves “busy, busy, busy,” and about the difference between real, almost cosmic connection and the flimsy kind built on shared labels that feel important but carry no real weight.

It’s hard not to see modern work in that mirror. We create cruft—circular meetings, office politics, rituals that look like progress but are just activity. So for all the books out there on how to run a company, may I suggest this satire instead? 

For anyone shaping the future of technology or culture, Vonnegut’s fiction has shaped how I think about the role of ethics and responsibility in what I build. 

One of his short stories, Harrison Bergeron, influenced my perspective on the tension between belonging and self-expression as well as how systems can overcorrect. 

Fiction, in general, feels underrated. It builds empathy by letting us inhabit other minds. It reminds us that systems are human-made, and therefore human-changeable. (I write all about this over on medium.)

The thing I’ve abandoned is more of a battle with my own mind of what makes an ideal founder. 

I’ve been lucky to work alongside several founders in Austin & Dallas over the past 16 years. Being in their orbit, I got to see their resilience through loneliness, mistakes, lessons learned, pivots, hard decisions, and more. 

But at the same time that closeness to founders also molded what it meant to be a founder to me. I saw a lot of similarities across founders from their childhood tales to personality quirks to motivations. What I didn’t see was myself in them. 

It didn’t help that many moons ago, someone I greatly admired gave a talk on becoming a founder. He hyper-focused on doing it before you have kids. As I was listening I got in my head because I already had my daughter. It planted another seed of doubt. 

Despite having a lifelong compulsion to build and create, I kept wondering if I was better off as an early employee not a founder.

I've always identified as a high-achiever, and no matter how hard I tried to shake perfectionism, it stuck on me like glue. So, putting myself in familiar situations felt safe. It was easy to just keep being the first head of people.

Then, my daughter started selling bracelets with her friends under the moniker Buzzy Beads. She even drew up “employment” contracts that were all over our living room. It brought me back to 1993 when I was the one selling beaded bracelets on the playground. 

I realized that nothing really changes if I don’t do this or if I fail, but if I do this and succeed then I've created something meaningful for our users and shown my daughter that her passions are worth pursuing. Yes, I know that’s cheesy, but that’s how I feel. 

Being at the helm of EverMore as a 40-year-old mother who’s soft and strange still feels surreal. I’m a neophyte who’s still reluctant to call myself our CEO, but it certainly helps to have Kelsey, a 2x founder and Scott, a 3x founder in my corner. As well as all the support from former colleagues and founders who validated my decision to quit my job to do this. 

Instead of focusing on all the ways I’m not like the mold, I’m focusing on all the reasons why I’m the right person to lead this right now. In so many ways, I’m just like every person that signs up for EverMore—we’re releasing old versions of ourselves to invite in new ones. 

My instinct is to say nothing. The best thing I bought myself is optionality. I grew up worried about money; a feeling that amplified as I entered the workforce during the great recession, student loans in hand. So, I crafted a sustainable, low-consumption life to build a cushion. It’s given me the mental and financial freedom to pursue being a bootstrapped founder. 

But if you twist my arm, I’ll say my merry band of rescue animals. (Adoption fees count as a purchase?!?!) Anyone who’s ever listened to the Dear EverMore podcast is familiar with Tortellini, the kitten my family rescued last Summer. We also have a calico cat, Gemma, a mischievous mutt, Willa, and a chorkie Scout. They were shelter lost causes but became exactly what our little family needed to keep it interesting. 

My husband, Quinn, and I had our meet-cute in 2008 at a bar in Addison, Texas. We literally ran into each other and have been together ever since.

He’s a stable force in our family and I’m the dreamer. Without him I wouldn’t have the space or emotional safety net to play and try new things. He’s my number one fan.

Despite being a VP with his own professional ambitions, he shoulders the majority of domestic labor. No one in our family would ever make it to an appointment without him. I love that our 10-year daughter gets to see the ways we embrace and rebuke traditional gender roles. 

I attended a women’s conference several years ago where two women presented data on a good partner being a top predictor of a woman’s professional success. It caused quite a stir; women left the room in droves. But the right partner makes a difference, and we see that with successful men all the time. 

Sarah Johnson Acupucture — She’s a sorceress. A session with her can melt away anxiety and put me into a creative trance. I fill up my notes app with ideas the second I leave. 

Day-to-day, I spent time in my creativity nook (formerly known as our dining room). It overlooks my garden and contains my books, trinkets, and art supplies.

I’m big on crafting moods through scent and sound—90s alternative with anise incense, or rain sounds with lavender. I grew up in a big family, so I crave solo space to think. 

If I’m stuck in my head, I’ll dance it out. Honestly, my most productive time of day is the 10-minute walk to pick up my daughter when my thoughts rattle out and clarify themselves. 

And finally, you asked for one, but I’ll end this by name dropping places that bring me joy. I like the dark melancholy of Bennu on MLK and the energy of Radio on Menchaca. Yarrow & Sage, End of an Ear, and Reverie Books are pretty distractions for my mind + keep me stocked on incense, records, and reading material. I like being surrounded by art as I create my own.