The Slow Build: Staying Grounded on the Way In

This post pulls from a conversation with Phillip Hunter, who used a fresh start on a small houseboat to finally act on an entrepreneurial pull he'd been circling for two decades. We talk about the day it stopped being an idea, what he had to unlearn about where his confidence came from, and the daily practice that's kept him steady while he builds. Note: this post may have affiliate links and we donate 100% of those funds to non-profits and a children's group home🫶🏾 

There is a specific kind of quiet that shows up after you leave something. Not the quiet of a finished chapter, the quiet of a wide-open one. You've made the call, said the hard sentence out loud to the people who needed to hear it, and the calendar belongs to you in a way it never has before. Nobody quite prepares you for the middle of that quiet, the stretch where the ideas are real but the money isn't there yet, and what carries you through is whatever you'd already built into yourself before you jumped. That's the part of the conversation with Phillip that stuck with me most, so that's where we're starting.

The Day It Stopped Being an Idea

Phillip gives two answers when you ask him when this got real, and both of them are true at once. The first is a specific address: a small houseboat he moved into by himself after a relationship ended and a chapter of his life closed out with it. He sat there, looked around at a life he suddenly got to build from scratch, and realized he hadn't worked in over a year and had zero interest in going back to the version of a career he used to have. The second answer is longer and a little more fun. He'd dabbled in entrepreneurship on and off for twenty-five years, joined a few companies at the ground floor, been employee number one at a startup, and always wondered what it would look like to build his own thing. Then large language models started showing up in the world the way he'd been expecting them to for most of his career, and something clicked. He'd spent decades in speech recognition, a field people used to shake their heads at. Suddenly he had a front-row seat to specific, unusual expertise arriving right when the world needed it.

"It felt like it was 1997, '98 again. The internet had been around for a little while, but it was really starting to impact commerce and everyday life in a way we all now take for granted. I saw the same potential with these technologies." — Phillip

What Was Actually Holding Him Back

Here's where the conversation stopped being a founder story and turned into something closer to a counseling session, which is the terrain I know best. Before design, before Choose Courage, I trained in trauma and addiction therapy, and one thing that work teaches you early is that you cannot argue someone out of a fear response. You have to make the decision feel safe before logic gets a vote. So when someone's paycheck is holding other people up, hesitation isn't a character flaw. It's a body doing math it hasn't been given permission to do out loud yet, and most of the people I work with have been carrying that math around for a year or more before they say a word about it to anyone.

Phillip's version of that math wasn't the standard list. He wasn't especially attached to a steady paycheck or benefits or his colleagues, and he'll tell you plainly he's a chance taker by nature. What actually held him back took months to name: he'd spent his career outsourcing his self-approval. A boss who thought he was doing good work, colleagues who found him interesting, an audience after a talk. All of it was real, and none of it had ever turned into a well of confidence he could draw on by himself. He couldn't become the kind of entrepreneur he wanted to be until he learned to hand himself the permission first, and figuring out where that habit came from was its own small, worthwhile project.

Failure as a Practice, Not a Verdict

Ask Phillip about the misconceptions he had to shed and he doesn't hesitate: the belief that failure was something to avoid rather than a necessary operating mode. He reaches for baseball first. The best hitters in the game don't clear forty percent; most sit closer to twenty-five or thirty. Every attempt is just what you understand best right now, put out into the world, and if you never put anything out, two things stop happening. You stop expressing anything true about yourself, and you stop learning, because you can only find out whether something works once it's out there and getting a reaction.

The example that stuck with me was musical. Phillip picked up saxophone last year, which he'll admit is a strange age to start, and got pulled into the physics of improvisation. A song moves forward. There's no going back mid-phrase to fix a note, so the only real question becomes what you do next, not how you undo what already happened. I played jazz trumpet for a decade, so this landed somewhere specific for me. When you fumble a note mid-solo, the training isn't to freeze or apologize for it. Sometimes you lean into the mistake on purpose a few bars later, so it reads as intention instead of error. What felt like the wrong note becomes part of the shape of the thing. Phillip said something about his guitar playing that I haven't stopped thinking about since: sometimes he goes the wrong direction on the neck, braces for it to sound bad, and it sounds better than what he meant to play. Not every mistake is actually a mistake. Some of them are just directions nobody told you were allowed.

Slow Is Smooth

We both landed, from different angles, on how much of the pressure to move fast is just capitalism we've absorbed without noticing. Get what you want, get it quick, get it your way, feel the payoff immediately, and when that doesn't happen, read the slowness as failure instead of as the actual shape of the work. I told Phillip about a moment on LinkedIn that still embarrasses me a little: someone posted a wall of stats about how many events they'd spoken at and contacts they'd made, and for about ninety seconds I felt genuinely behind. Then I caught myself. I don't want that life. I don't want to be in a gym shooting free throws for hours the way Michael Jordan did, and neither, as it turns out, does Phillip, who brought up the same Jordan practice-volume stat from a completely different direction: even the people we call naturally gifted got there by doing the unglamorous rep, over and over, one throw at a time, asking only what to adjust next.

There's a phrase I keep returning to that I think comes from the Navy SEALs: slow is smooth, and smooth is fast. Most of us were trained by our jobs to live in the smoothest fast season, breaking things quickly and calling it momentum. The slower, quieter seasons are where the fundamentals actually get built, the ones that keep you from later scaling a business that's eating away at you. I've been sitting with a different phrase too, poco a poco, little by little, which is less about patience as a virtue and more about staying present enough to notice you're moving at all.

The Little Life Framework

I asked Phillip to get specific, past the principle and into what staying grounded actually looked like day to day. A rough patch back in 2023 pushed him to get deliberate about it, and out of that came what he calls his little life framework: a short, plain list of things he wants to be true most days or most weeks. Eating well. The right kind of exercise for his body. A real spread of social connection instead of leaning on one person for everything. He put it on a whiteboard and started checking items off, sometimes literally counting how many people he'd reached out to that week, building regularity where there'd been none.

The second piece is one he credits partly to conversations like this one: looking backward at the evidence instead of only forward at the goal. He has a rule about hiking that I love. Never judge the climb from halfway up the mountain, because halfway up is exactly where your feet hurt, the heat is unbearable, and you haven't seen anything worth the trip yet. Turn around instead, and you can see how far you've actually come, which is a different question than whether you've arrived. And there's a third piece, quieter than the other two: a near-daily affirmation that isn't about output at all. I am doing it. Not I have accomplished something measurable today, just I am doing the thing I said I wanted to do. Milestones get to be the bonus, not the proof.

Finding a Why That Isn't Borrowed

We closed on the question of what actually gets someone through the dry stretches, and Phillip's answer had an edge to it I appreciated. Your reason has to be yours, specifically, or it won't hold. Not your dad's pride, not your partner's excitement, not some borrowed vision of what success is supposed to look like once you get there. He was blunt about one of his own reasons for leaving corporate: he was tired of making other people rich. I told him I knew exactly what that felt like, helping a billionaire boss fund his next trip to space. Neither of us is trying to rewrite capitalism in a podcast conversation. But once you've clocked how many people give themselves up to a system out of survival, or fear, or simply not wanting to think too hard about the alternative, you start to understand that choosing something else requires a reason with real weight behind it. Not "I want more money." Something that can actually hold you up on the days the money isn't there yet.

Phillip's product ideas are still mostly in the pocket right now. He put them aside deliberately to build an AI consulting practice first, because the money situation asked for it, and he's candid that this was one of the harder tradeoffs of the whole stretch. When those products are far enough along to talk about in public, we're already planning to have him back to talk about what got built, what got scrapped, and what the little life framework looked like on the other side of it.

If you're circling something you haven't said out loud yet, the reading that came up more than once in this conversation was The Creative Act by Rick Rubin and The Perennial Seller by Ryan Holiday, both worth the time if you want company for the considering season rather than a step-by-step plan. And if what you actually want is to say the fuzzy version of your idea to a real person before you've fully committed to it, The Walkout exists for exactly that stretch, the one where corporate clearly isn't it anymore and you're getting curious about what might be. You're also welcome to just write in. Vivianne reads every note that comes through hello@choosecourageinc.com, and she'll make time to hold space for the idea, even the scared, half-formed version of it.

Originally aired as Episode 66: The Slow Build: Staying Grounded on the Way (ft Phillip Hunter), on the Choose Courage Inc. podcast.