The first 30 days: The second time around is even scarier
Starting a business the first time is terrifying. Starting a business the second time? Even worse.
The first time, I didn’t know how much I should be scared of. Now? Now I know exactly where the dragons live, where the pitfalls lurk, and just how much pressure there is to not screw up—because this time, I should actually know a thing or two. Or ten.
And that weight has been exhilarating. Because as I’ve stepped into this new chapter with The Roar, I’ve realized something powerful: the work I was meant to do is not what I thought it would be.
For years, people have sought me out at their crossroads moments. Not just for marketing strategy, brand positioning or help with tactical execution, but for something far deeper.
When they were weighing a massive life or business decision and couldn’t figure out which path to take.
When they knew exactly what they needed to do, but it wasn’t the easy or comfortable thing, and they needed someone to light a fire under them.
When they were carrying something heavy—grief, fear, imposter syndrome—and needed a mirror held up to their own brilliance.
When they were sitting in a huge win but had no one to celebrate with because talking about it out loud would make them sound like an arrogant buffoon.
When they were about to leap into something dramatically different and needed someone to push them over the edge.
That’s what I do. I hold space. I call out the head trash. I push people toward action.
And these past 30 days? That’s exactly what I’ve been doing with founders.
The Conversations That Have Defined These First 30 Days
The Fear of Scarcity & Imposter Syndrome
Sitting with an owner who was keeping waaaay too much cash in the business. Not as a smart financial play, but out of fear. They were terrified that success was fleeting, that they weren’t really as good as their results said they were, that somehow, it could all vanish tomorrow. We didn’t need a financial strategy. We needed to rewrite the mindset. (And pull those earnings off the table and onto the personal balance sheet).
Two Great Paths, One Big Choice
A founder staring at two equally incredible opportunities, both leading somewhere exciting. But the real fear? If I pick one, I’ll never get to experience the other. The weight of finality was paralyzing. We worked through the grief that comes with choosing—because when no one talks about how hard it is to say yes to one thing, they also don’t talk about the inherent no that comes with it.
Go All In, Or Watch It Die
Over coffee, I sat with a founder staring down the brink of extinction. Revenue had stalled, and survival felt uncertain. As we talked, I started Googling keywords that potential customers would likely search for when looking for their services. And that’s when it hit me. They weren’t showing up. Not on the first page. Not on the second. Maybe not at all. The problem wasn’t the size of their email list or a lack of audience interest—it was visibility. This brand had, unintentionally, made itself a well-kept secret by failing to implement simple, high-impact changes that would dramatically increase their odds of being discovered by people actively searching for exactly what they offered. What started as a casual brainstorm turned into a complete business model pivot, unlocking entirely new service offerings. Because the real issue wasn’t demand, it was making sure the right people even knew they existed and then serving up those offerings in a more productized way.
Who Takes Care of the Founder?
A brilliant leader was pouring into their team, their business, their clients, their vision. But no one was pouring into them. When the problems are too big, too messy, too embarrassing to say out loud, where do they go? Who sees them? Who tells them the truth?
That’s where I come in.
Because this business is modeled after my mom.
Let Me Tell You About Momma Gail
If there is a crisis, she is already in motion. If there is a mess, she is already rolling up her sleeves. If you are hurting—physically, emotionally, financially, existentially—she is on her way.
She doesn’t ask, “What do you need?” because she already knows.
When my life has gone sideways, when I’ve been drowning in overwhelm, when the sheer weight of things felt too much to bear, she has never hesitated.
I remember one of my lowest moments—when I called off a wedding six weeks before the date (as the invitations were being addressed by the calligrapher) and I found myself in the wreckage of a life we had built together. We had moved into my first real grown-up house, and suddenly, I was alone in it, surrounded by the ghost of what was supposed to be our future. I was crying so hard I was hyperventilating, completely incapable of functioning like a human being, when—because fate has a sense of humor—I managed to get my gas-permeable contact lens lodged under my eyeball.
I couldn’t see. I couldn’t breathe. I was a complete disaster, curled on the floor, undone.
Momma Gail left work, came straight to me, and without hesitation, pried that tiny plastic lens from my eyeball like she was born to do it. And then? She methodically boxed up everything in that house that made it ours instead of mine. She erased the remnants of a life that wasn’t mine anymore. She cleared the space—physically and emotionally—so I could start again.
She does this. Over and over.
When an employee at my company left a mountain of disorganized financial paperwork and chaos, she became our Accounts Payable department overnight. She spotted an open desk at the office, sat in it and began calling every vendor in our system, got an accurate statement from them, sorted every invoice, and fixed it.
When my first baby was born six weeks early, and I was reeling from a C-section and struggling with the reality that I was now somebody’s mother, (and a preemie, to boot), she unpacked my entire house as we moved just 10 days after he was born. Every box. Every room. She set up my kitchen, folded my laundry, made sure I could just be.
And when my kids and I are sick? She shows up in gloves, laundry running, soup on the stove, making sure we are cared for in every possible way.
Momma Gail is not a spectator in your suffering. She doesn’t “check in.” She doesn’t “send thoughts and prayers.” She shows up.
And that’s exactly what I do for founders.
Who Takes Care of the Founder?
I know what it’s like to be the one responsible for everything. The one holding the weight of a business, a team, a vision, a dream that you can’t let fail. I know what it’s like to carry the stress, the fear, the doubt, the what if I screw this up? I know how lonely it can be at the top, where the problems are sometimes too big, too messy, too embarrassing to admit.
That’s what The Roar is about.
I am the business momma you never knew you needed. I get in the hole with you, grab a shovel, and dig. And you may not always like what I have to say, but when you take action—when you text me, beaming, because you finally made the move, let go of the fear, took the leap, and did the damn thing—that is what makes my heart swell.
So if you’re a founder and you’re carrying the weight alone, wondering where to put the fears, the doubts, the messy thoughts you can’t say out loud, let’s talk. I’ve got my sleeves rolled up. I’m already on my way.
Because who takes care of the founder? I do.
Here’s to the next 30 days.
Let’s roar.