George Milton of Yellowbird: Notes from The Long Aisle
This post has been published but not publicly listed yet.
Right after recording episode 2 of The Long Aisle with Gardar of GOOD GOOD, he told me I had to talk to George Milton, who co-founded Yellowbird and had recently hired his replacement as CEO. I hadn’t met George, but I was very familiar with Yellowbird and was excited to learn from him and his journey. This became episode 3.
George Milton co-founded Yellowbird with his partner, Erin Link, in Austin in 2012. He’d moved there to play music. On the side, he also started making hot sauce. Erin suggested they till up their backyard and plant 150 habanero plants. They did, and George started bringing the sauce to gigs. Naturally, he was also trying to sell his CDs. “I couldn’t give my freaking CDs away,” he told me. “But then once people were like, this guy makes hot sauce…” He still has a box of those CDs (and as a former performing singer/songwriter, I know the feeling). He turned 30 that year, the first time he'd really thought about what came next, and decided to follow what people were actually responding to. Yellowbird now has a devoted following in the hot sauce world and is available nationwide.
Last October, George published a Substack post titled “I Just Hired My Replacement.” When I asked him why he wrote it publicly, he said writing is cathartic. It’s how he works through what’s on his mind, whether in public or in his notes. In a space where companies go quiet before bad news, he wanted to own the story. “I wanted to come right out and get ahold of that narrative before it got decided for me,” he said.
Much of what George shared resonated. Writing is how I process, too. It’s become instrumental in working through ideas in the later stages of my life and career, and the time spent with a subject on the page is time you never would have spent otherwise, just thinking about it. From music to writing, the parallels with George continued for me. George spent 13 years building Yellowbird before stepping down as CEO. I’ve spent 13 years at Barrel, working my way into the role. He left the role, I grew into it, and yet the questions beneath remain the same, about identity, growth, and what it takes to give so much of yourself to something and keep evolving along the way.
George strikes me as someone who doesn't take himself too seriously but cares deeply about what he's building and the people around him. It came through in everything we talked about, and made our conversation a lot of fun. Here's what I took away.
Know when you’re approaching your ceiling before you hit it.
George had been telling himself for years that he didn’t want to be CEO past $20 million in revenue. He knew his natural habitat was the early days: trying, failing, learning fast. As Yellowbird grew, the role demanded things that weren’t his strengths, and rather than wait until that became visible, he made the move while things were still working.
“I started getting genuinely concerned that I wasn’t going to make the necessary leaps fast enough. That I would inadvertently become the limiter holding the company back from becoming everything it could be.”
He was clear that he could have kept going. He’s willful enough to have made it work. But he also knew someone else could do the job better, and that distinction mattered more to him than proving he could push through.
Most people wait until they’re failing before they ask whether they’re still the right person for the next phase. It’s a trap because your head is down hard at work, and it takes real humility to admit you’re not best suited to carry on what you built. I think about this in my own role, less about stepping aside and more about the areas where I know I’ll be the ceiling, whether due to my bandwidth or experience. Bringing on our COO, Sara, this year is a good example; she brings a depth of experience in areas I know we need.
When you make a change, trade up, or don't bother.
Finding the right person to step into a role you've held for 13 years isn't straightforward, not to mention at a company you’ve built. George was clear that a passionate founder-CEO can't just be replaced by someone who checks boxes on a resume. You have to find someone with the skills you need who also genuinely cares.
"Nobody who isn't a founder understands being a founder, period, end of story. But you do have to have understanding of the industry and understanding of the thing that we do. It's difficult to find. And I was adamant: this person has to be better at the job than me. Not laterally equivalent. Not good enough. Actually better."
That standard is easy to read and nod in agreement; harder to hold when you're stretched thin and need to move fast. The instinct is to fill the seat. It’s a good reminder for me right now as we’re in the midst of several changes at Barrel. It applies beyond transitions at the top, but any time a role opens up. It's an opportunity to ask what the role actually needs now, not what it needed when it was last filled. That's a different question, and it leads to a different hire.
As you grow, you have to operate at a higher altitude.
George was up at 4am reading production reports. In the facility, if a machine broke down. He knew every vendor, every process, every detail, including which plumber to call and which one to avoid. By his own admission, he’s type A and likes to be super involved, for better or for worse. He recognized it as one of the mistakes many founders make, not because the details didn’t matter, but because being in everything eventually becomes what stops you from growing.
“As you grow, you have to be more at a higher altitude. Not just involved in every little – well, the toilet broke again.”
I think about my own version of this often. Early on at Barrel, stepping away from designing on client projects felt like a major shift. But it gave me the space to support the team in a more meaningful way. At some point, being in the work stops being the contribution, and you have to trust people enough to let them carry it. Applicable at every stage of growth, personally and as a business.
Give people the opportunity to figure it out.
George shared that of all the things he faced building Yellowbird, management was the one he least saw coming. He didn’t think about it when he and Erin decided to turn their hot sauce into a business. Then they started hiring, made mistakes, and had to figure it out in real time. It led them to take classes and do the work to get better at something that didn’t come naturally.
He talked about a production lead who had been with Yellowbird for years, starting on the line and working her way up. He described giving her opportunities to step into roles she’d never done before and watching her navigate the same gray areas he once struggled with: when to hold the line on policy, when to make an exception, how to be fair and still human about it. You can tell that seeing her grow into it means so much to him.
"It's one of those stories that I'm so proud to have been a part of. I'm kind of like trying to give her opportunities to be like -- hey, you actually can do this. And then to see her make that transition -- now years later we'll have a conversation and she's telling me, man, the hardest thing is you have to have a system."
There’s a tension in that. People want to get it right, and the instinct when someone is struggling is to step in and solve it for them. But getting it right and struggling through it aren’t opposites; the struggle is usually where the growth actually happens. Easier said than done in practice, especially as new folks join the team. There’s a fine line between showing how things are done and staying close enough to guide without taking the wheel.
Stop pretending the line between work and life is real.
George and Erin built Yellowbird together from day one: she owned brand and design, he owned product and sales. He put it this way:
“The fact that people love the brand is her fault. The fact that people like the sauce is my fault.”
When I asked how they navigate being partners at work and at home, he reframed the question. He acknowledged it creates extra work and attention, but so does anything you care about. George said he’d be sad if they weren’t doing it together. It would just mean less time with her. For the people who say they could never do it with their partner, he had a simple question: “Why do you think your wife’s so terrible?” he laughed.
They tried every version of it. Official work hours. Strict separation. None of it held. What they landed on was about honesty rather than structure: both of them reserving the right to say not right now, without guilt. “You start pretending like that’s a real thing,” he said about the line between work and life. And eventually, you stop pretending.
I’m not building a business with my wife Dana, but I’ve found the same thing to be true. The people closest to us see us clearly, sometimes more clearly than we see ourselves. What I bring home from work and what I bring to work from home are never really separate. It’s all the same person showing up.
Your customers are already telling you what they think.
George used to personally call customers who emailed in about a damaged bottle. Not just to apologize, but to explain how distribution works, make it right, and make sure they felt heard. He knew it wasn’t the CEO’s job. He did it anyway. Building the brand was customer-centric from the beginning, and the Yellowbird community, passionate and vocal, expected nothing less. “My biggest thing is I just want to make sure that those customers are being served,” he said.
He contrasted it with a recent experience at a car wash where a panel broke off his door. The staff handed him a form, letting him know that legal would review it, but probably wouldn't do much. That was the whole response. He laughed, remarking that customer service in most places feels like this.
On product development, Yellowbird’s approach is just as direct. Rather than expensive focus groups, they put new products on their website, send them to the email list, and see how the people who actually love the brand respond first. This was music to my ears.
“If they don’t like it, then we’re probably not going to try to sell it to the whole world. And you can do that pretty cheaply.”
A lot of brands are building campaigns and launching products without really knowing how people experience what they make or why they keep coming back. The signal is already there. I make a point of staying close to our clients at Barrel for the same reason. Those conversations tell me more about how we’re operating and where we need to get better than anything else.
The only question worth asking when it gets hard is: Can I get to the next level?
At one point in the Yellowbird journey, George didn’t pay himself for five years. It was brutal by his own description. When I asked if there was ever a moment he almost walked away, he laughed and said his weekly almost-giving-up was every Sunday at 2pm. He was joking, but only kind of. What kept him going wasn’t a framework. It was unbridled optimism, a certain amount of craziness, and one question he kept asking himself:
“I was always really interested in – could I take it to the next level? Could I take it to the next level after that?”
You can see this orientation, a love for learning, in everything about him. The guests he has on his podcast, Gross to Net. The way he sought out classes and advisors every time he hit a new wall. The curiosity he brings to AI, to fitness, to a business he never formally trained for.
He connects it to endurance training, which hit close to home. The workouts where you look at what’s ahead, and the only hard part is to keep going when you know you can just stop. In George’s words, “90% of people say no thanks.” Those are the ones he seeks out. Grinding workouts are a big part of my life for the same reason. There’s something about getting through those that transfers to all aspects of life. The mental game is learnable. And once you know you can stay in it, it changes how you generally approach hard things.
“You don’t always have to go the fastest. Sometimes you just have to stay alive the longest.”
That question, can I get to the next level, is also what eventually led him to step aside as CEO. He kept asking it honestly, and at some point, the answer changed. The disappointment was real. But so was the relief.
When he thinks about the next ten years, he hopes the people closest to him will say it was equally unexpected as the last. We agreed we’d check in every ten years to see where he’s at. He said he hoped his resume was infinitely confusing at his funeral. Coming from George, it didn’t sound like a joke.
+
Check out the full conversation with George wherever you listen to podcasts.
And if you enjoy it, rating, reviewing, and sharing make a real difference this early on.
