This one is for the ones wearing All the Hats.

Samantha Southerland

I used to think business started with a plan. That’s actually a lie. It starts with a feeling.

I would know. I’ve started four that way.


Long before anyone ever called me CEO of anything, I was just trying things. Some of them made sense, some of them very much didn’t. But the best and worst part about me (depending on who you ask) is I don’t really hear the word no.

That’s what led me into business consulting… which is a fancy way of saying I sat across from people in coffee shops. After my 9–5, on lunch breaks, weekends… whenever I could fit it in.


And I’d just listen.


I realized their title didn’t really matter—small business owners, nonprofit leaders—they’re all just people building something they care about… and carrying way more of it than they should.


They’d talk about what they were building, what was working, what wasn’t… and if you sat there long enough, you heard it every time.


“I think I’m doing this right…”


And underneath it—“I have no idea if I’m doing this right.”


What I learned is that passion will romanticize the hell out of a business plan.


But it won’t make you good at marketing, sales, hiring, or knowing when to let go of something that isn’t working.


And I remember thinking… this can’t be the way we do this.


So a friend and I were sitting in her living room one night asking a question bigger than us—What if we just built the room we wished we had?


A place where you don’t have to pretend you’ve got it all figured out. Where you can ask the real question. Where somebody across the table actually helps you win.


That’s where All The Hats came from.


We wanted people to walk in one way and walk out different, which meant we had to care about all of it—the feeling before you arrived, the room when you walked in, the moments in between, the people you sat next to.


So we built our table.


Expert event coordinators, project managers, videographers, website developers, brand strategists… piece by piece, person by person. Month by month.


And somewhere in the middle of it, it started to feel like… okay, this might actually be something.


Then the day finally came.


And people showed up. A lot of people.


And in the quiet after the conference—after the last person left, after we had poured out everything we had—I had this realization—Events aren’t any different than businesses.


You’re not supposed to build them alone.


So maybe the question isn’t “what do I need to do next?”


Maybe it’s “who do I need at the table with me?”


Because the difference between something that almost works and something that actually grows—is the experts you bring into it.


So from one multiple hat wearer to another—don’t do it alone.


Know when to expand your table…and when to pull up a chair at someone else’s.


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By Laura Quick April 28, 2026
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