Building a home for generalists

Brand new business models, Chappelle, and Sunday routines

Apr 01, 2025

Today’s hot tub talk is with Britt Gage 🐐

I connected with Britt after stumbling upon her work building of All Trades - a supergroup of generalists helping founders build startups that scale. She is one of those rare founders who is as invested in her people as she is in the work.

Over the past few month, as I’ve been leaning into the “generalist” label in my next career chapter, I’ve had the pleasure of of joining the oAT squad - and it is a squad of some truly wonderful people.

I asked Britt to join me in the tub to talk building a brand new business model, SNL, and Sunday routines. Enjoy!

Brandon

How has oAT changed and evolved since you started it 3.5 years ago?

Britt

I started oAT because of my personal struggle as a career generalist. I had a very squiggly career, and while I loved the variety and problem-solving, I kept recycling myself out of jobs as the companies I worked at grew and the roles became more specialized. I wanted to build a full-time career as a generalist, and test this assumption that someone could have a real impact in organizations while being upfront about that fuzzy, non-specialist role.

That initial experiment worked, and it worked really quickly, so much so that I wondered if it could become a new way to build teams and companies with a flexible and scalable business model. The big vision was creating a different type of company for generalists while helping organizations access great generalist talent in meaningful ways. From my initial experiment, I built a community of like-minded generalists and started bringing them into organizations in the same way I had found success myself, particularly startups. This collective model provided generalists with career flexibility and variety, plus a community to learn from.

And that worked. But my original problem wasn't fully solved – I had wanted one consistent place where I could grow my career (as a generalist) with proper support and development opportunities. The marketplace/collective model didn't provide that stability. As we matured, we learned that many of our generalists wanted that too. We also discovered that our real value to startups wasn't just matching them with great generalists – it was being their constant partner while they figured things out, handling the variability for them.

That's why we evolved into what we are today: a company that employs generalists and provides them with long-term opportunities to build their careers as generalists . We’ve evolved our collective as an invitation-only network of generalists we’re eager to develop relationships with, offering them learning opportunities and community. Now we're much closer to our goal of creating a new business model for both generalists and the organizations that need them.

Brandon

What oAT is doing is so unique and I feel like it attracts some really special people who are multi-talented and thoughtful and have also been recycled out of a system that doesn’t have a way to support them.

How have you spread the word about what you’re doing to find clients to work with?

Britt

I’ve been pretty adverse to taking a traditional B2B sales approach. We’re doing something so unique and different and admittedly broad. I was always focused on making authentic connections with other founders as a means of growing; it’s been all about 1:1s with great founders, understanding their greatest challenges intimately, and presenting them with a different solution and a different way of thinking.

We haven’t invested in traditional marketing (yet!), and we've learned so much in the first few years with this sustainable growth approach, we’re at a place where we can talk about our thing a bit more thoughtfully in public - for instance, on our Substack.

Brandon

What was the last thing that made you laugh?

Britt

I would love to hear your answer first while I think.

Brandon

Ok, Dave Chappelle’s latest monologue on SNL made me laugh out loud, and it also made me feel a lot of other things. I feel like giving a monologue on SNL is probably like the peak, scariest things you could do in terms of public speaking- and this man just sat there ripping a cigarette, so in the zone. To me, it was witnessing someone who’s mastered their craft. Not just stand up, but storytelling, infused with comedy, and communicating really deeply what he believes.

Britt

Oh boy- I am such a big SNL fan. That’s such a good one. He always ends so poignantly and with a statement that is so real. He's brought you along for this ride, and the humor makes you trust him, so he can say something that is his opinion, and no matter your stance on it, it’s just a statement of human fact. His monologue really stuck with me too.

I'm also a huge fan of Nate Bargatze. His SNL was next level. The punniness was all-time. His stuff is just lovely, and as a parent of a seven year old, the fact that I can watch him with her is wonderful. I’ve watched his stand up special probably 3 times in earnest, but sometimes I just put it on in the background. It’s so good.

Brandon

What else are you recommending?

Britt

I always love to recommend

Sublime

. The tool is wonderful and the founder is wonderful, the team is wonderful, how they think about the longevity of the business and the problem they are solving. It’s so refreshing.

I’m also always recommending

Every

. I bookmark every email to reference and I just find the quality of their content to be so strong. I recommend them both professionally to people but also some of the things they write about are personally so good for me.

Brandon

Are you working on any creative projects?

Britt

I get a lot of creative juice out of running oAT. Not only finding creative ways to keep a startup afloat, but finding different ways to support the team and show up with each other and do things a bit differently.

We’ve been working through a rebrand right now, and in a Slack channel a while ago we were trying to figure out how to refer to ourselves as people who work at oAT. And somebody came up with goats 🐐. Like we’re Generalists Of All Trades and Greatest Of All Time. We loved and embraced it immediately. So in the rebrand we’re playing around with working in little goats in the creative. Embracing playfulness and fun is important to us.1

Outside of work, my daughter and I love theatre and songwriting - she is a big music person. I also have a past life as an interior designer and I find a lot of joy in taking a room that was one way and completely rearranging it. So spring is coming, which means I get to do some of that very soon, which will be fun.

Brandon

What does your process look like with interior designing? My girlfriend and I recently moved into a new place and we want to be intentional about decorating and designing, but really what that means is we haven't done much of anything so far.

Britt

I think the art of it can often be, how do you take the pieces that you have and put them together or bring them to life in a meaningful way. Do you have anything you really like?

Brandon

We do have a couch we love. It can convert into a conversation pit and it embodies a lot of the vibe we want for our place - which is to make it a very communal space.

We’ve started a new tradition of having people over on Sunday nights to rest (read, listen to music, craft, etc.) all together.

Spending time with friends in that way is my ideal Sunday. What about you?

Britt

Starts with a good cup of coffee and a treat or bagel from the neighborhood, and then I always watch SNL with my 7-year-old. That feels illegal to say… I will say it involves some covering of her ears and eyes, but she loves it and it’s a very fun experience we get to share

Brandon

Are you watching the highlights on YouTube or the whole episode?

Britt

Oh the whole episode. Forsure. My daughter knows every cast member and will shout them out during the intro.

I loved talking to Britt, and I realized I want to do more of this — interviewing people who are building things that are inspiring and needed in the world.

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