The Ambitious Bookkeeper Podcast

40 Episodes
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By: Serena Shoup, CPA

The Ambitious Bookkeeper podcast is for bookkeepers & accountants who are growing or aspiring to start their own business. Our mission is to elevate the bookkeeping profession by providing support and resources for new and experienced firm owners. We share actionable tips on running a successful bookkeeping business, tools and resources, plus guest expert interviews that will help you elevate your business. Where you can find us: Website: https://www.ambitiousbookkeeper.com BBA: https://www.ambitiousbookkeeper.com/bba Facebook: https://www.facebook.com/serenashoupcpa LinkedIn: https://linkedin.com/in/serenashoup Instagram: https://instagram.com/ambitiousbookkeeper

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255 | Brand New to Advisory? Start Here
#255
Today at 7:00 AM

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Advisory doesn’t have to be complicated.

In this episode, I’m breaking down the simplest way to start offering advisory services inside your bookkeeping packages. I call it “advisory lite,” and it’s included in every service tier we offer, even the lowest one. If you’ve been wanting to dip your toe into advisory but don’t know where to start, this is your starting point. And if enough of us start doing this, we can change how people see bookkeepers altogether.

In this episode y...


254 | Trusting Your Team & Stepping into Advisory with Anne Napolitano
#254
10/14/2026

You don’t need to add budgeting and forecasting to your menu to start delivering advisory-level value.

In this episode, I sit down with Anne Napolitano, a former Hermès controller turned private chef turned owner of a 10-person restaurant-focused accounting firm. We get into the small shifts in your services and your marketing that change how clients see your value, plus how Anne went from doing everything herself to leading a team that has stuck with her for years.

Grab a notebook, my friend. This one is packed.

In this episode you...


253 | Q&A: Xero Fresh Start or QBO Migrate, A2X, Gusto Payroll, and More
#253
10/07/2026

In this September live Q&A, we covered a lot of ground. We talked about whether to convert a client from QBO to Xero or start fresh, how to realistically land more clients heading into 2026, and how I handle clients who won't send receipts no matter how many times you ask.

We also got into Shopify bookkeeping, paying contractors, what to do when a credit union is making your life miserable, and the moment I know it's time to walk away from a client. Plus, I spill the tea on why creating a course is way less...


252 ⎸ Bookkeeping is NOT a commodity when done right with Katie Ferro Part 2
#252
09/30/2026

Katie Ferro is back for part two, and we picked up right where we left off with Katie's line that stuck with me all week: if you don't have a stance, it's because you're not in the room enough. The same goes for advisory. You won't feel confident until you put yourself in the room, and you can't get in the room until you build some confidence. So we talked about how to break that cycle. Katie shared three real client emails from the last 10 days that were quietly asking for more, and I shared how I built my...


251 ⎸ Bookkeeping is NOT a commodity when done right with Katie Ferro
#251
09/23/2026

I've been connected with Katie Ferro since the very beginning of my business. I literally found her on a podcast while I was on maternity leave dreaming about starting a bookkeeping business, and I probably reached out to her like a weirdo on Instagram. We reconnected recently, had a conversation that was way too good to keep to ourselves, and decided to hit record. This one is a true coffee shop conversation between two industry friends who care a whole lot about competence, integrity, and the bookkeepers in this community. We get real about why our industry keeps telling...


250 | X2Uno: The Chrome Extension for Xero with Mark Corum
#250
09/16/2026

What if the tool you've been waiting for, the one that finally makes Xero as efficient as QuickBooks with Right Tool, already exists, and it's being built by a former bookkeeper who accidentally fell into coding? In this episode, Serena sits down with Mark Corum, the developer behind X2Uno and Right Tool, to talk about building Chrome extensions for accounting software, the surprising parallels between bookkeeping and programming, and why the tech world's pricing model might be completely backwards. Whether you're a Xero loyalist, a QuickBooks refugee, or just curious about what happens when an accountant teaches themselves...


249 ⎸ [Q&A] Starting a Firm While Employed, Hiring Advice, and Employee Benefits
#249
09/08/2026

This round of Live Q&A we got into some really good stuff: how to navigate starting your firm while you're still employed, why book to tax differences are completely normal and not something to lose sleep over, and how I approach the "can I afford to hire" conversation with clients (spoiler: it's rarely just about the numbers). I also pulled back the curtain on my monthly client newsletter, walked through my PTO and benefits setup for a part-time team, and gave a real update on the new version of Elevate that's dripping out in early September.

...


248 | How to Be a Collaborative Professional with Emily Bowie
#248
09/02/2026

I got to reconnect with Emily Bowie, a partner at Thorne Advisors, and someone I actually met years ago in a tiny mastermind back when she was doing something completely different in her business.

We talked about what actually makes a partnership work (and what makes it collapse), why staying in your lane protects your reputation, how bookkeepers can collaborate with tax pros instead of competing with them, and why quality standards matter so much in an industry where anybody can hang a shingle. We also went deep on personal finance, debt, and the soft skills that...


247 | Tax + Bookkeeping; Should You Do Both? With Nick Cobos
#247
08/26/2026

If you have ever had that passing thought of "should I add tax to my bookkeeping firm?" this is the episode you need to hear before you make a move.

In this one, I'm sitting down with Nick Cobos of Saga Accounting Solutions. Nick has built a five-person firm that does both tax and bookkeeping. We get into the real pros and cons of running both under one roof, and I share why I went down this exact rabbit hole myself and decided against it. This is a practitioner-to-practitioner conversation from start to finish, and I loved...


246 | Q&A - Transitioning to Advisory, Xero Integrations Disengaging with Clients, and More
#246
08/19/2026

We're back from summer break with a live Q&A with SO much good stuff in this one. This was one of those episodes where the questions kept getting better and better, and I got to go deep on the things that trip us all up: running an advisory firm, getting your pricing right, Xero integrations, closing out clients the right way, and knowing when to make your first hire. If you've ever felt awkward quoting a higher fee or weren't sure how to structure your revenue side when a client's processor data lives inside their CRM, this one's...


245 | Starting Your Firm from Scratch with Jaime Rodriguez
#245
08/12/2026

This episode hit close to home for me because Jaime Rodriguez and I are basically living the same double life, and I loved getting to compare notes.

Jaime is the CEO of Bookkeepers.com (you probably know them as Bookkeeper Launch), and his story is wild. He went to school for accounting chasing that "safe job" American dream, hated the corporate grind so much he Googled how to start a bookkeeping business, bought the very course he now owns, and burned the boats to go all in. Fast forward through a few years of coaching, re-recording lessons...


244 ⎸ The Summer Slump + Podcast Update
#244
08/05/2026

Real talk: if your summer felt slow and you were low-key stressing about it, this episode is for you. This week's a short and sweet solo update where I walk you through what's coming up on the podcast over the next month, plus a little pep talk about the summer slump so many of us hit as bookkeepers. Slow season is normal, my friend, and it doesn't mean anything is wrong with your business. I'm sharing exactly what I do to keep moving the needle when discovery calls dry up, and how to set yourself up so next summer...


243 | The Advisor Activation Series
#243
07/29/2026

In this episode you’ll hear:

A very short update about the audio series I just released & why you need to listen before it goes away!

Resources mentioned in this episode:

Listen to The Advisor Activation Audio Series → https://www.ambitiousbookkeeper.com/activate

Thanks for listening. If this episode inspired you in some way, take a screenshot of you listening on your device and post it to your Instagram stories and tag me @ambitiousbookkeeper

For more information about the Ambitious Bookkeeper Podcast or interest in our programs or mentoring visi...


242 ⎸ 2026 Survey Results Breakdown w/ Alyssa Lang
#242
07/01/2026

Alyssa and I are back, and this time we actually hit record (lesson learned from last year, ha). We just closed year two of the State of the Virtual Bookkeeping and Accounting Industry survey, and we sat down to dig into the data together in real time. This isn't a polished, buttoned-up report read. This is the two of us cross-referencing the numbers live, reacting to what surprised us, and pulling out the patterns that actually matter for your firm. We get into the real differences between solo operators and firms with six-plus team members, where the money actually...


241 ⎸ The State of Virtual Bookkeeping Industry with Alyssa
#241
06/01/2026

I'm joined in person by my biz bestie Alyssa Lang of Workflow Queen, and we are SO pumped to talk about the return of the Virtual Bookkeeper Industry Survey round two, baby! We're going bigger, better, and more intentional this time around, with a goal of 2,500 responses, a charity donation tied to Make-A-Wish Foundation, and a brand new interactive data bot that lets you dig into the results yourself. Oh, and we may have gone down a rabbit hole or two about AI, pricing, and what it actually means for running a boutique firm. You're welcome.

...


240 | [Q&A] 1st Thing to Automate, Building Rapport with Clients, & Intuit vs Gusto Payroll
#240
05/20/2026

This episode is a replay of my April 2026 live Q&A, and we cover a ton of ground that I know so many of you are dealing with right now.

Whether you're just starting out and trying to figure out where to even begin with automation, or you're in the thick of building a team and wondering why delegating feels harder than just doing it yourself, this one's for you. We also get into some juicy topics like QBO Payroll versus Gusto, how to handle S-Corp clients who are flying under the radar on reasonable salary, and...


239 ⎸ How to Serve Real Estate Investor Clients & Market Your Bookkeeping Business as an Introvert with Max Emory
#239
05/06/2026

This episode is a behind-the-scenes conversation with Max Emory.

We get into the nitty gritty of what it actually takes to serve REI clients, how he built his team, the new community he's launching for bookkeepers who want to level up their marketing and sales game, and how he manages it all with two boys under two at home.

In this episode you’ll hear:

Why real estate investing is one of the most complex niches a bookkeeper can serveHow overcomplicated entity structures are hurting real estate investorsThe behind-the-scenes of Time Capital Un...


Announcement: Closing Elevate
05/05/2026

Get all the info and join before Midnight Pacific Time on May 9, 2026:

https://www.ambitiousbookkeeper.com/elevate/?coupon_code=REVAMP



238 ⎸ Transforming the Accounting Landscape: A Conversation with Joe Woodard
#238
04/29/2026

In today’s episode, I’m sitting down with Joe Woodard—founder of Scaling New Heights—and we’re diving into what’s really happening in the accounting industry right now.

We talk about:

Why the ‘AI hype vs denial’ debate is missing the pointWhat tasks you should actually be handing off to AIWhy moving off hourly pricing isn’t enough anymoreAnd how to position yourself so clients see you as indispensablehow to make sure your pricing model matches your vision and goals

Resources mentioned in this episode:

Scaling New Heights 2026: http...


237 ⎸ [Q&A] Inbox Management, Tech Stack, and Practice Management Tips
#237
04/22/2026

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In this episode, I'm sharing our March live Q&A where I answered rapid-fire questions about running a bookkeeping firm. If you've ever wondered how to manage a shared team inbox without micromanaging, what to do with merchant clearing account balances at year end, or how to navigate a CPA non-compete, this one's for you.

In this episode you’ll hear:

How to manage a shared team inboxWhat to do with merchant clearing account balances at year endWhy building a 100% virtual client base can actually be...


236 | Take back your time with Dubsado 3.0
04/15/2026

Stop letting your calendar run your life! In this episode, Serena dives into the brand-new Dubsado 3.0 (Beta) to show you how to protect your time and professionalize your client onboarding. Whether you’re a bookkeeper, accountant, or small business owner, learning how to automate the "back-and-forth" of scheduling is the fastest way to reclaim your sanity.

In this episode, you’ll learn:

The Power of the Scheduler: How to use the new 3.0 interface to set up custom meeting types with automatic Zoom or Google Meet links.Protecting Your Energy: U...


235 ⎸ Why I only use Xero
#235
04/08/2026

I've been getting this question for years, and since I'm now on YouTube and Xero keeps rolling out new features, it was time to give this topic a serious refresh. In this episode, I'm breaking down all the reasons why I am a hundred percent Xero firm and why I genuinely love this software. This is not sponsored (but yes, please use my affiliate link!). I'm just a bookkeeper who has seen what a mess the alternative can create, and I want you to understand what you could have instead.

In this episode you’ll hear:...


234 | April Podcast Update
04/01/2026

This is a podcast update & what to expect here on the podcast for the month of April!

Check out this week’s YouTube Video >>

The New Xero Partner Hub

Thanks for listening. If this episode inspired you in some way, take a screenshot of you listening on your device and post it to your Instagram stories and tag me @ambitiousbookkeeper

For more information about the Ambitious Bookkeeper Podcast or interest in our programs or mentoring visit our resources below:

Visit our website: https://www.ambitiousbookkeeper.comFollow me on YouTube: https://www.youtube.co...


233 ⎸ No More Arbitrary Price Increases [vlog]
#233
03/25/2026

This one is a little different. One day in February I decided to vlog my day.. a sort of behind the scenes of my day. I wasn’t sure what I was going to use this footage for. And then… I was inspired a couple weeks ago (by the time this comes out) to write another BTS Newsletter. The two are **completely unrelated in topics—** combining the voice over of my Newsletter (unfiltered thoughts combined with a little education + provoking thoughts) with my random vlogging day.

I hope you enjoy… make sure you watch it on YouTube for the...


232 | Using AI in Bookkeeping
#232
03/18/2026

AI is changing the bookkeeping game, but it's not replacing us anytime soon.

In this episode, I'm pulling back the curtain on Xero's built-in AI feature, JAX (Just Ask Xero), and walking you through exactly how we're testing it inside our own firm before rolling it out to clients. From auto bank reconciliation to creating invoices via conversation, there are some genuinely cool time-saving features here, but there's still a lot you need to be doing yourself.

In this episode you’ll hear:

How JAX works inside XeroWhat security and data privacy me...


231 | I’ve got a surprise!
#231
03/11/2026

I have a big announcement to share and I've been so excited to finally let the cat out of the bag! Erin Pohan, one of our OG community members and founder of UpKeeping®, is joining me as co-coach for this upcoming cohort of the Bookkeeping Business Accelerator.

I wanted to bring Erin on because she's lived this journey. She started from scratch just like you, built her firm to 50 clients and a team of three, and she did it using the BBA framework. This episode is a real, honest conversation about what it actually takes to build a...


230 | [Q&A] AI Tools, Pricing, and Onboarding
#230
03/04/2026

From AI tools and scope creep to finding your first clients and onboarding systems, whether you're just dreaming about starting a bookkeeping business or you're a few years in, there's something in here for you.

In this episode you’ll hear:

How I use AI in my firmPricing, scope creep, and tough money conversationsFinding your first five clientsOnboarding process

Resources mentioned in this episode:

Bookkeeping Biz Workshops: https://www.ambitiousbookkeeper.com/workshopsOnboarding Templates Freebie: https://www.ambitiousbookkeeper.com/onboardingElevate: https://www.ambitiousbookkeeper.com/elevateBookkeeping Business Accelerator: https://www.ambitiousbookkeeper.com/bb...


228 | [Q&A] Partnerships, Profit First, and Complex Client Situations
#228
02/11/2026

Welcome back to our monthly live Q&A! We took a little break, but we're back and ready to tackle all your burning questions about building your bookkeeping business. Whether you're just getting started or scaling your firm, this episode is packed with real talk and practical advice.

In this episode you’ll hear:

Partnership pitfalls and planningTech stack essentialsHiring and leading your first employeePricing strategies for startups and special situations

Resources mentioned in this episode:

Xero: https://xeroamericas.partnerlinks.io/79afz10exu7dQuickBooks Online: https://www.referquickbooks.com/s/Se...


227 | Increasing Your Sales with Hunter Rademacher
#227
01/28/2026

In this episode, Serena interviews Hunter Rademaker and they talk about Hunter’s expertise on sales in accounting, emphasizing client qualification, communication, advisory roles, and strategic hiring for growth.

In this episode you’ll hear:

Hunter’s unique sales roleThe sales process & qualifying new clientsAdvice for new bookkeepersClient retention & advisoryPricing & hiring a sales person

Resources mentioned in this episode:

House of Revenue/Sales BQ - Consulting company that helped set up the sales and marketing department at Hunter's firmFacebook: https://www.facebook.com/serenashoupcpaADP

Meet Hunter Rademacher

M...


226 | Need to know OBBBA highlights for Bookkeepers Adrian Lopez
#226
01/14/2026

The 'One Big Beautiful Bill' introduces significant tax changes for 1099s, depreciation, and employer credits, emphasizing meticulous bookkeeping for compliance and savings. Listen in to the conversation with Adrian & Serena as they unpack the need-to-know highlights for bookkeepers and how you can stand out in the industry by making a few small changes to your processes.

In this episode you’ll hear:

1099 Reporting ChangesBonus Depreciation and Section 179Tips and Charitable ContributionsEmployer Tax Credits and DeductionsPass-Through Entity Tax and Reconciliation

Re...


225 ⎸ Recast: Become a Bookkeeper with Katie Ferro
12/17/2025

Before we close things down for the holidays, I decided to bring back one of my favorite interviews from the vault. In 2021 during one of our Bookkeeping Biz Workshop rounds, I brought Katie on to chat about a program she had just created—which is still going strong today—in fact, has been revamped and redesiged since she created it, and I want to make sure you all know about it. But more so than that, I wanted to bring this conversation back to you in case you’re planning for the new year. This will give you some things...


224 | Using Human-First AI for Visibility with Kelly Sinclair
#224
12/10/2025

I had the best conversation with Kelly Sinclair about something that's been on my mind (and probably yours too): how to actually use AI without losing the human connection that makes your business YOU. We dive deep into why social media might not be the lead generator you think it is, how to build visibility strategies that don't rely on the algorithm, and how AI can actually help you show up MORE human, not less.

In this episode you’ll hear:

Why taking a break from social media might be the best business decision yo...


223 | Using AI Securely + to Land Clients with Kelsey Silver
#223
12/03/2025

In this episode, I'm chatting with my friend Kelsey Silver about something so many of you have been asking about - how the heck are we supposed to use AI without compromising our clients' security? Kelsey has a super unique background and she breaks down exactly what we need to look for when evaluating AI tools for our firms. Plus, she shares about her AI app Foresight HQ that helps you identify your hottest leads in your Instagram DMs - no more chasing people who just wanted the freebie!

In this episode you’ll hear:

...


LIMITED ⎸ The Bookkeeping Biz Workshops Day 3
11/19/2025

Send us a text

Welcome to this special workshop series that will only be up for a LIMITED TIME (Till December 1st) where we're diving deep into what it really takes to start and run a virtual bookkeeping business.

This is the final episode of our three-part Bookkeeping Business Workshop series, where we're diving deep into designing the business. We're talking about your ideal business, your perfect-fit clients, and we're demystifying the sales process because I know that part freaks a lot of you out.

In this episode you’ll hear:

...


LIMITED ⎸ The Bookkeeping Biz Workshops Day 2 - Tech Stacks
11/17/2025

Send us a text

Welcome to this special workshop series that will only be up for a LIMITED TIME (Till December 1st) where we're diving deep into what it really takes to start and run a virtual bookkeeping business.

In this episode, we pull apart accounting tech stacks so you know what you need and what would be nice to have.

In this episode you’ll hear:

Complete accounting stack breakdownThe business stack that'll scaleWhat you actually need to startSolutions to common tech issues

Resources mentioned in this ep...


LIMITED ⎸ The Bookkeeping Biz Workshops Day 1
11/12/2025

Send us a text

Welcome to this special workshop series that will only be up for a LIMITED TIME (Till December 1st) where we're diving deep into what it really takes to start and run a virtual bookkeeping business.

In this first session, we talked about imposter syndrome, limiting beliefs that hold us back, and the big scary topics everyone's whispering about: AI and market saturation.

In this episode you’ll hear:

The truth about AI and your bookkeeping careerWhy market saturation is a mythThe difference between bookkeeping and accountingHow to...


222 ⎸ Hubdoc: Audit-Proof Your Business
#222
10/29/2025

This episode is best watched on YouTube >

In this episode, I'm walking you through one of my absolute favorite tools for keeping your business audit-proof: Hubdoc. I'll show you exactly how we use it at Of Course Financial to help our clients manage their supporting business documents digitally, save hundreds of hours every year, and stay compliant with IRS requirements. Plus, I've got some exciting announcements about upcoming Xero tutorials, the Bookkeeping Biz Workshops re-airing, and our Black Friday sale!

In this episode you’ll hear:

How Hubdoc automatically organizes re...


221 ⎸ [Q&A] Pricing Cleanups, Marketing, and Cyber Insurance
#221
10/22/2025

Hey guys! This month's live Q&A was packed with real talk about the nitty-gritty of running a bookkeeping business. We covered everything from pricing cleanups (spoiler: diagnostics are your best friend) to getting cyber insurance (yes, it's non-negotiable), and I even got vulnerable about my experience juggling babies and business. If you've ever wondered how to market to trades, what reports clients actually need, or how to take maternity leave as a business owner, this episode is for you!

In this episode you’ll hear:

How to price cleanups without Getting BurnedMarketing Strategies th...


220 | I worked 45 hours in August; and it’s not on what you think
#220
10/15/2025

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Want to see my weekly timesheets? Follow me on Threads: https://www.threads.net/@ambitiousbookkeeper

No one talks enough about the amount of time that goes into an online course business. So I’m talking about it today.

In this episode you’ll hear:

My profit margins for both my firm & my online course businessthe time I spend during launches & fulfillmenthow much time I spent in August 2025 on both businesses

Resources mentioned in this episode:

Clockify → timetracking

For ex...


219 | Top Scams Happening to Bookkeepers in 2025 with Jock Wols
#219
10/08/2025

Cyber scams targeting bookkeepers are getting more sophisticated, and I'm sitting down with insurance expert Jock Wols to talk about what's happening in our industry right now. I even share my own recent experience being targeted through the Gusto partner directory—twice in one day! If you think it won't happen to you, think again. This conversation is packed with real stories, practical tips, and the insurance knowledge you need to protect your business in 2025.

In this episode you’ll hear:

The most common scams hitting bookkeepers right now, including phishing attacks through trusted dire...