Do It Scared
Jul 06, 2026
THE BESTIE BRIEF
For women bookkeeping firm owners who get it.
Issue No. 2 | July 6, 2026
Title: Do It Scared
I told you last issue I was going all in on this one, so buckle up. We're talking AI: what I'm actually seeing, what it means for you as a bookkeeping firm owner, and how to stop being afraid of it & start using it like the CEO you are.
What I'm actually seeing
Here's the real, on-the-ground stuff, no fluff.
New tech is coming out fast to streamline the day-to-day bookkeeping work. Not the advisory side, not the human side, the tasks. The data entry, the reconciliations, the repetitive stuff that used to eat hours out of your week.
Our bookkeeping clients are asking about AI more than they ever have before. Every week, more questions. (well you guys are too 😉)
And here's the part that matters most for your team: AI is going to start replacing junior bookkeeper & data entry roles. That's not a scare tactic, that's just where this is headed. Which means everyone on your team needs to elevate. (I'm doing a whole deep dive on how we're restructuring our own team around this, but that's a conversation for another day.)
I'm also seeing something that gives me a lot of hope. Some clients have gone and tried to let AI handle things on their own, thinking it would just work for them. Several of them have come right back to us because they didn't get the human factor. That tells me something important: the human touch isn't going away. It's becoming the differentiator.
Which is why I believe more than ever, we need to be transparent with our clients about the tech we're using. Not hiding it, not springing it on them. Telling them exactly what's in our stack & letting them opt in. That builds trust instead of breaking it.
AI is here. It's not a phase, it's not going away, and the sooner we learn to use it to our advantage, the better off our businesses will be.
Here's what happened
You know the story.
Blockbuster had EVERY advantage. The brand, the locations, the customers walking in the door every Friday night. Netflix was the scrappy little mail-order DVD company nobody took seriously.
And then streaming showed up.
Blockbuster had the chance to buy Netflix for basically pocket change & said no. They thought their model was too big to need to change. We all know how that ended. One of them is a documentary about what NOT to do & the other one is, well, still sending you a "are you still watching" notification at 2am.
Here's the thing, besties. AI is our streaming moment. It's not a trend, it's not a phase, and it's not going anywhere. The firms that get curious now & figure out how to use it are going to be the ones still standing in 5 years. The firms that dig in & say "that's not how we do it here" are going to look up one day & wonder what happened.
I'm not saying it's not scary. It IS scary. Change always is, even the good kind. But scared & stuck are two different things. You can feel the fear & still take the next step.
Where this leaves your tech stack, your clients & your pricing
Over the next 6 to 12 months, I think the biggest shift is going to be in your tech stack. It's going to change more in the next year than it has in a very long time. We are literally in the middle of demoing over 20 pieces of software right now, both for our own firm & to bring you our take on what's worth it for firms of different sizes. Stay tuned for that.
Client expectations are going to shift too, and not in the direction you might think. They're going to want MORE of you. More of that human contact, not less. So if your client experience has gotten a little thin, now's the time to beef it up, because the demand for it is only going up.
Pricing & positioning are changing too. Traditional, low-touch, compliance-only bookkeeping is going to get cheaper as AI enters the market, which means you'll need more clients to hit the same revenue if that's the lane you stay in. But advisory, the high-touch, relationship-driven work? That's where the rates go up. So the real move here is positioning yourself higher on the advisory side, where the human factor is exactly what clients are willing to pay more for.
Okay, so where do you even start?
First: pick your main AI platform. There are a lot of them out there & they all do different things, so don't get overwhelmed trying to use all of them. My personal favorite (and what we use in our own firm) is Claude. It's incredible for content, analytics, graphics, streamlining operations, & it connects to a lot of the tech you're probably already using. Double, Later, ClickUp, Slack, you name it.
And if the thought of "but I don't know what to even ASK it" is what's stopping you, that's exactly why we built our Bestie Bots. They're bots we created for you to use inside Claude (and other platforms) so you don't have to figure out the commands yourself. We already did that part. You just show up & use them.
Second: let us do the vetting for you. Right now we are literally demoing over 20 pieces of software, not just for you, for our OWN firm too. If it can't handle the demands of a firm our size, it doesn't make the list. We're looking at everything: QuickBooks alternatives, analytical tools that pull real insight from your client meetings so you can upsell later, and so much more. The ones we already stand behind? Double, ClickUp, Slack, Later, & Fathom Reporting. More is coming as we keep testing, little by little, one piece at a time, so YOU don't have to be the one spending your nights doing it.
So here's what I really want you to hear, bestie.
I tell my coaching clients this all the time: Do It Scared!
Starting our firms was scary. It was risky. We signed up for the hard thing anyway. This is just another hard thing. And life is hard, business is hard, but we get to CHOOSE our hard.
So which side are you going to choose? Are you going to sit back & wait to see what happens to the business you've worked so hard for? Or are you going to step in, learn the new thing, & let it propel you forward?
I know which one I'm choosing. I hope you'll choose it with me.
Proof it works (aka my cruise confession)
I just got back from a week-long cruise with my mom for her birthday. Caribbean, sun, way too many mocktails by the pool.
My businesses did not fall apart while I was gone.
My operational manager led the day-to-day, my pod leaders handled every single end-of-month close, AND still got a few days off for the 4th of July. That's what a real team & a business built to run without you looks like.
And on the coaching side, I got a different kind of proof. I've always felt like I had to be available ALL the time for my clients. Over the past year, multiple clients have told me, "Stop being available all the time. I want you to rest. I want you to recharge."
My clients were coaching ME on rest.
So this trip, I let that sink in. I got up, handled what needed handling (hello Slack and a few coaching calls), and then spent the rest of the day fully present with my mom. Spa, pool, beach, cocktails, mocktails, whatever the day called for.
That's the goal, besties. Not a business that needs you glued to it. A business, and a community, that hands you permission to actually live your life.
A Bestie win I have to brag on
One of our newest Bestie Club members joined less than a month ago. She had been trying to hit her first $10K month for a long time.
She hit it in her first 30 days inside the Bestie Club!!
That's what happens when you stop trying to figure it all out alone & surround yourself with women who get it. More on her story soon.
Your Half-Time Reset is happening & it's now FREE
Good news, besties. The Halftime Reset is FREE this year, thanks to Double sponsoring it. 🩷
You DO still need to register to get the link, so make sure you grab your spot.
July 16th. 1PM. 90 minutes. No cost to you.
We're going to look back at the first half of 2026, see what it actually did for your business, & then build your plan for the back half of the year together. You'll get a workbook, you'll get me live, and a big chunk of the time is open Q&A, so bring your questions.
Can't make it live? There's a replay.
And if you've been sitting in this community wondering if working with me is the right move, this is your lowest-risk way to find out. Come see how I coach, ask me anything, and feel it out before you make a bigger commitment. Zero dollars. Nothing to lose.
Register with the link below & I'll see you on the 16th.
What’s coming up
A few things I want on your radar right now:
🩷 Halftime Reset · July 16th · FREE
A 90-minute live masterclass for the firm owner who has been running on autopilot & is ready to actually CHOOSE what the second half of 2026 looks like. We’re doing a real mid-year audit, finding your non-negotiable WHY, and building a plan around it. Details here.
🩷 Bookkeeper BOSS Retreat · August · Colorado Springs
Year FIVE, y’all. This is our annual retreat for firm owners with annual income of $150K+, building a team and scaling their company. It is always one of my favorite weeks of the year. If you’re in this season, reach out and let's discuss if this is the right room for you.
Deadline to register is July 10th.
🩷 CEO Weekend · October · Key West, Florida
This weekend is focusing on MARKETING. Key West is going to be something special & spots are limited. Sign up here.
🩷 Next Level Year Weekend · December
For the bookkeeper who is DONE winging it & ready to walk into 2027 with an actual plan. Five clients or fifty, if you’re serious about growing your business next year & you want to do the work alongside women who get it, I want you in the room. More details coming soon.
Next issue: Running a firm in the middle of summer
School's out, the kids are home, the schedule is chaos & somehow you're still supposed to be a CEO. Next issue I'm talking about how to actually run your firm when life is loud, because you deserve a summer too & your business doesn't have to suffer for it.
Before you go
One more thing before you go: head into the Facebook community & drop your name on the post about the FREE CEO Weekend giveaway. If you haven't seen it yet, go find it. You don't want to miss this one. We even pinned it to the Featured Section for you.
Keep Thriving 🩷
Stephanie
