The Ambitious Bookkeeper with Serena Shoup, CPA

The Ambitious Bookkeeper with Serena Shoup, CPA We help bookkeepers grow their businesses.
🎙️The Ambitious Bookkeeper Podcast

I help experienced and aspiring accountants start and grow their own virtual bookkeeping businesses so they can create their ideal life. Over the past few years of running my own virtual accounting firm, I've noticed there is an abundance of small businesses that need help from qualified bookkeepers and accountants so I started mentoring others who had the desire to help these businesses.

09/10/2026

I give my team tax-free money every month and it's not a raise.

Medical expense reimbursement

I don't offer health insurance. As a small employer it's just really expensive, and my whole team already has coverage through a spouse or the exchange anyway.

So instead, I use a program called Take Command. My team submits qualifying medical expenses or insurance premiums and gets reimbursed up to $250 a month. Tax-free. 🙌

It's not taxed like a bonus, so more money actually lands in their pockets
I choose the amount and can adjust it every year
It kicks in after their 3-month probation, same as PTO

You want to retain great talent? Get creative about putting real money in their pockets.

Hear more in Ep 249 🎙️
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09/07/2026

Real talk about business partnerships, my friend. 👇

Most people go in on vibes and a handshake. Then when things get hard, they're trying to untangle it all in the heat of emotion. That's how partnerships get ugly.

Emily Bowie learned this the hard way. So the second time around, she wrote everything out up front. Compensation. Roles. How different clients get handled. And yes, the dissolution plan BEFORE it ever needed to happen.

Because clarity is kindness. When everybody knows where they stand and how it all works together, you protect the relationship AND the business. 💯

Planning for the end isn't pessimistic. It's professional.

Hear more in Ep 248 🎙️
Connect with Emily
https://www.instagram.com/thorneadvisors/
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09/05/2026

Most of your clients' BUSINESS money problems are actually PERSONAL money problems.

Think about it. You're helping them generate more income, but the moment they have free cash flow, it disappears. Why? Because they have no system at home.

So they pull more out of the business than they said they needed. Now the business is going into debt, and you're stuck wondering what happened.

Emily Bowie put it this way: the stress of their personal finances WILL leak into how they approach their business. So you'll ultimately have to deal with it. The only question is when.

The best thing you can do for most of your clients is a simple check-in on their personal finances.

And one more thing, my friend: being in debt doesn't always mean someone has a shopping problem. Sometimes it's a lawyer. Sometimes it's a medical emergency. Sometimes it's just life. Lead with that compassion. 💛

Hear more in Ep 248 🎙️
Connect with Emily
https://www.instagram.com/thorneadvisors/
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08/31/2026

Want to know when to hire?

Build your org chart for the firm you don't have yet.

So many of us get stuck on the org chart because we're doing ten jobs in one body. The move is to separate the ROLES first, even when one person is filling all of them. Then you just plug people in as you grow.

You cannot delegate what you haven't defined.

Hear more in Ep 247 🎙️
Connect with Nick
Linkedin: https://www.linkedin.com/in/nickcobos/
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08/29/2026

The hardest part of starting a bookkeeping business is not the bookkeeping.

It’s imposter syndrome

But you can sit there for a million years trying to think your way out of imposter syndrome, or you can just do it. The reps create the credibility. The credibility creates the track record. And it becomes a virtuous loop.

Hear more in Ep 247 🎙️
Connect with Nick
Linkedin: https://www.linkedin.com/in/nickcobos/
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08/27/2026

Thinking about adding tax to your bookkeeping firm?

I went ALL the way down this rabbit hole. I have a CPA license. I have a couple years of tax experience under my belt. And after running a full analysis on what it would take to add a tax arm to my firm, I landed on a hard no.

Even with my background, I would still have to hire someone to run the tax side. And because they'd be learning, I'd need to hire another CPA to review their work.

This week on the podcast, Nick Cobos of Saga Accounting said he does both tax and books, does great work, and he told me he thinks his firm would be BIGGER and more profitable today if he had just stuck to bookkeeping.

Tax and bookkeeping are two separate businesses with two separate sets of processes. It is so much easier to scale one than to scale two at the same time.

If your bookkeeping firm is already working, scale that. If it's not working, adding tax won't fix it. It'll just give you more to fix.

What are your thoughts on adding tax?

Tell me in the comments.

Hear more in Ep 247 🎙️
Connect with Nick
Linkedin: https://www.linkedin.com/in/nickcobos/
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08/24/2026

Are you stuck between pricing your bookkeeping services and client expectations?

Remember, the value you provide is key.

$350 is a reasonable start if you're providing complete reports and balance sheet reconciliations!

Don't undervalue your expertise.

Hear more in Ep 246 🎙️
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08/22/2026

Your team says they're "overwhelmed" so what do you do?

There's a difference between feeling overwhelmed and actually not having the time. And a LOT of overwhelm is just anxiety about something that doesn't even need the anxiety.

So when someone on my team says they're drowning, I don't panic and take all the work back. I sit down and ask: what's on your list that feels heavy right now? Then we set aside what doesn't have to be done today, compartmentalize it, and focus on what actually matters.

Sometimes the real fix is a coworking call. Body doubling. Just knowing support is there when they get stuck. And as a last resort, I'll take ONE piece off their plate until they find their footing.

New responsibilities SHOULD feel a little overwhelming at first. That's normal. Being there for them is often enough.

Leaders, how do you handle team overwhelm? Tell me below. 👇

Hear more in Ep 246 🎙️
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08/21/2026

There’s something you’ve probably all heard:

If you want something done, ask a busy mom to do it.

Because we know how to just make things happen in the confines of everything else we have going on.

It’s Parkinson’s law. The task at hand will expand to the time you give it. Soooo….
The opposite is true too. Give yourself less time to do something, and you’ll find a way to get it done.

Sometimes we make excuses to not build the thing we actually want, by pretending that it would take too much time.

And sometimes we do need to make sacrifices. But if you can figure out how to do the thing you want within the parameters of your current life, it’s beautiful on the other side. I promise.

🩵 what do you want to build? And for those who have done it, share your story in the comments to inspire and show others it IS possible!

08/21/2026

I found this written on a post it on my desk from who knows how long ago.

I must have read or listened to something where they said this and I wish I knew what or where so I could give credit.

But I wrote it down to remind me that indecision is NOT what moves you forward. Rather it keeps you stuck and potentially creates additional sunk costs (time and money you can’t get back, even if you keep trying)

And you’re seeing this because maybe you’ve been stuck in indecision about something, whether it’s starting the business, or letting go of a client or team mate.

Every time you think about that decision and decide to delay it further, you’re compounding the sunk costs.

This is your sign to make the decision. Even if the decision is to intentionally stay where you are. Spending time reconsidering is hurting you. Make the decision. Move on. 🩵

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