249 ⎸ [Q&A] Starting a Firm While Employed, Hiring Advice, and Employee Benefits

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.Grab a notebook and your favorite drink and let's go.In this episode you’ll hear:How to approach telling your current employer you're starting a firmMy take on where clients really come from and what to focus on first when you're trying to grow.A full walkthrough of my client newsletter strategyAnd how I do my part-time team's employee benefitsResources mentioned in this episode:Elevate https://www.ambitiousbookkeeper.com/elevateBookkeeping Business Accelerator (BBA): https://www.ambitiousbookkeeper.com/bbaTake Command (medical expense reimbursement program for the team)Xero: https://xeroamericas.partnerlinks.io/79afz10exu7dQuickBooks Online: https://www.referquickbooks.com/s/Serena4Squarespace: https://squarespace.syuh.net/AgROVNGoCardless: https://manage.gocardless.com/refer/us/serena/ygvg9o-amzGusto : https://gusto.com/partners/i/serena591Liz Wilcox's Email Marketing Membership: https://serenashoup--lizwilcox.thrivecart.com/list-building-live/Alyssa Lang / Workflow Queen's Breakthrough: https://serenashoup.krtra.com/t/IKUxtNZoz7lFKajabi: https://app.kajabi.com/r/SLFEMUL4/t/uiptq7nuMax Emery / GoPro Bookkeeping: https://www.skool.com/go-pro-bookkeeping/about?ref=216fd17bf3b64591bbd1f284f72ae8b7Thanks 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 @ambitiousbookkeeperFor 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.com/@ambitiousbookkeeperConnect on Instagram: https://www.instagram.com/ambitiousbookkeeperConnect on Threads: https://www.threads.net/@ambitiousbookkeeperConnect on Facebook: https://www.facebook.com/serenashoupcpaThank you for your support of our show. If you haven’t left a review yet it’s super simple. Please go to ambitiousbookkeeper.com/podcast and leave your review.Podcast Publishing Tools we use:Editing → Sabr Media LLC: https://www.iangilliam.com/sabr-media-llcDescript: https://get.descript.com/u7lubkx09073 (affiliate link)Buzzsprout: https://www.buzzsprout.com/?referrer_id=1753696 (affiliate link)

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 separate a good advisor from a great one.In this episode you’ll hear:What keeps a partnership from turning into a horror storyHow to collaborate with tax preparers and other CFO professionals the right wayWhy "just because you can, doesn't mean you should" applies to adding services to your firmWhy checking in on a client's personal finances pays dividends for the work you do on the business sideResources mentioned in this episode:Thorne Advisors: https://www.thorneadvisors.com/Elevate 2.0 → learn the skills to become an advisor https://www.ambitiousbookkeeper.com/elevate5 Cash Leaks & 5 Missed Tax Deductions - https://www.thorneadvisors.com/cashleaksMeet EmilyEmily Bowie is a Cash Flow Strategist with 15+ years of experience, including her time as an audit manager in Big Four accounting. She’s known for bringing calm, clarity, and structure to financial conversations that often feel stressful or avoided. Outside of Thorne Advisors, Emily leads her church’s financial ministry, is a mom to three young kids, and enjoys a good DIY project almost as much as a well-organized set of financials.Co-led by founder Andrea Mason and CFO Emily Bowie, both CPAs, Thorne Advisors helps women protect what they earn while building sustainable wealth that actually supports their lives. They deliver a true 360-degree view of finances, spotlighting cash leaks, tightening income strategy, and creating tax plans that align with real goals, not just compliance checklists.Connect with Emily📱 Instagram: https://www.instagram.com/thorneadvisors/🌐 Website: https://www.emilyvbowie.com/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 @ambitiousbookkeeperFor 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 the Blog: https://www.ambitiousbookkeeper.com/blogConnect on Instagram: https://www.instagram.com/ambitiousbookkeeperConnect on Threads: https://www.threads.net/@ambitiousbookkeeperConnect on Facebook: https://www.facebook.com/serenashoupcpaThank you for your support of our show. If you haven’t left a review yet it’s super simple. Please go to ambitiousbookkeeper.com/podcast and leave your review.Podcast Publishing Tools we use:Editing → Sabr Media LLC: https://www.iangilliam.com/sabr-media-llcDescript: https://get.descript.com/u7lubkx09073 (affiliate link)Buzzsprout: https://www.buzzsprout.com/?referrer_id=1753696 (affiliate link)#businesspartnership #advisoryfirm #personalfinance #debt #bookkeepingbusiness #ambitious #bookkeeper #accountant #accounting

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 every minute of it.In this episode you’ll hear:The breakdown of adding tax to a bookkeeping firmHow Nick got his first clientsWhy I decided against adding tax to my firmGrowing a firm and delegatingResources mentioned in this episode:Saga Accounting Solutions: https://sagaaccounting.com/Between 2 Firms: https://open.spotify.com/show/71gGjmatd829DB8IrJdI9T?si=bbb9deb996d74f56Meet NickNick graduated from the United States Military Academy at West Point in 2019 and spent 5 years as an Army Officer. After graduating the US Army Ranger School Nick held assignments as an Infantry Platoon Leader and Company Executive Officer with the 11th Airborne Division and later served as an Army ROTC instructor at the University of Texas at San Antonio (UTSA).After transitioning out of the Army, Nick earned his Enrolled Agent credential and jumped into the world of accounting. He now enjoys advising clients and helping them grow their businesses while saving on taxes.When he's not working, Nick enjoys hunting, fishing, playing (admittedly terrible) golf, and spending quality time with his wife, Lisa, their three children, Lucy, Nathan, and Matthew, and their dog, Molly.Connect with NickLinkedin: https://www.linkedin.com/in/nickcobos/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 @ambitiousbookkeeperFor 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 the Blog: https://www.ambitiousbookkeeper.com/blogConnect on Instagram: https://www.instagram.com/ambitiousbookkeeperConnect on Threads: https://www.threads.net/@ambitiousbookkeeperConnect on Facebook: https://www.facebook.com/serenashoupcpaThank you for your support of our show. If you haven’t left a review yet it’s super simple. Please go to ambitiousbookkeeper.com/podcast and leave your review.Podcast Publishing Tools we use:Editing → Sabr Media LLC: https://www.iangilliam.com/sabr-media-llcDescript: https://get.descript.com/u7lubkx09073 (affiliate link)Buzzsprout: https://www.buzzsprout.com/?referrer_id=1753696 (affiliate link)

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 for you. And if advisory is even a tiny blip on your radar, I've got a free audio series you're going to want to grab before it disappears.In this episode you’ll hear:Connecting Stripe and PayPal inside XeroIs $350 too much for basic bookkeeping?The right way to disengage with clientsWhen to make your first hireHow to support a team that's feeling overwhelmedResources mentioned in this episode:Elevate: https://www.ambitiousbookkeeper.com/elevateBBA: https://www.ambitiousbookkeeper.com/bbaXero: https://xeroamericas.partnerlinks.io/79afz10exu7dKajabi: https://app.kajabi.com/r/SLFEMUL4/t/uiptq7nuContent Snare: https://contentsnare.com/#_r_serena58Thanks 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 @ambitiousbookkeeperFor 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.com/@ambitiousbookkeeperConnect on Instagram: https://www.instagram.com/ambitiousbookkeeperConnect on Threads: https://www.threads.net/@ambitiousbookkeeperConnect on Facebook: https://www.facebook.com/serenashoupcpaThank you for your support of our show. If you haven’t left a review yet it’s super simple. Please go to ambitiousbookkeeper.com/podcast and leave your review.Podcast Publishing Tools we use:Editing → Sabr Media LLC: https://www.iangilliam.com/sabr-media-llcDescript: https://get.descript.com/u7lubkx09073 (affiliate link)Buzzsprout: https://www.buzzsprout.com/?referrer_id=1753696 (affiliate link)

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, and becoming the face of the brand, and in 2025 he actually bought the company.In this episode you’ll hear:How Jaime went from burned-out corporate accountant to owning the very course that got him startedWhy SOPs are what let you run a firm on 30 minutes a monthThe real talk on running two businesses at onceThe costly mistake of taking on every client in every industry before you have processesWhy you have to learn your debits and credits before you touch automationThe one question that protects your time every time a new prospect comes knockingResources mentioned in this episode:Join the Digital Bookkeeper Association for $9/mo: https://dba.bookkeepers.app/Bookkeepers.com: https://bookkeepers.com/$1000 Off any version of Bookkeeper Launch when you use promo code AUGUSTBUS26: https://sk293.isrefer.com/go/BLFS/SS64/Meet JaimeJaime Rodriguez is the owner and CEO of Bookkeepers.com, but his journey started as a student looking for a better path. After building his own successful bookkeeping business, he went on to acquire the company that first taught him the skill. Today, he helps entrepreneurs realize they’re capable of more than they think; not just financially, but in how they live and work. He’s the author of Beyond the Numbers and You’re Not for Everyone (That’s the Point), both focused on building a business that actually fulfills you.Connect with Jaime📺 YouTube: https://www.youtube.com/@bookkeepersdotcom👥 Facebook: https://www.facebook.com/jaimethebookkeeperThanks 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 @ambitiousbookkeeperFor 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 the Blog: https://www.ambitiousbookkeeper.com/blogConnect on Instagram: https://www.instagram.com/ambitiousbookkeeperConnect on Threads: https://www.threads.net/@ambitiousbookkeeperConnect on Facebook: https://www.facebook.com/serenashoupcpaThank you for your support of our show. If you haven’t left a review yet it’s super simple. Please go to ambitiousbookkeeper.com/podcast and leave your review.Podcast Publishing Tools we use:Editing → Sabr Media LLC: https://www.iangilliam.com/sabr-media-llcDescript: https://get.descript.com/u7lubkx09073 (affiliate link)Buzzsprout: https://www.buzzsprout.com/?referrer_id=1753696 (affiliate link)

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 doesn't catch you off guard.In this episode you’ll hear:Why summer is almost always slow for bookkeepersThe services and projects I lean into during the slow months to bring in a cash influxHow to plant seeds now that come to fruition in the fallA rundown of everything coming up on the show, including big interviews and a limited time audio series you don't want to missResources mentioned in this episode:https://www.ambitiousbookkeeper.com/subscribeThanks 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 @ambitiousbookkeeperFor 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.com/@ambitiousbookkeeperConnect on Instagram: https://www.instagram.com/ambitiousbookkeeperConnect on Threads: https://www.threads.net/@ambitiousbookkeeperConnect on Facebook: https://www.facebook.com/serenashoupcpaThank you for your support of our show. If you haven’t left a review yet it’s super simple. Please go to ambitiousbookkeeper.com/podcast and leave your review.Podcast Publishing Tools we use:Editing → Sabr Media LLC: https://www.iangilliam.com/sabr-media-llcDescript: https://get.descript.com/u7lubkx09073 (affiliate link)Buzzsprout: https://www.buzzsprout.com/?referrer_id=1753696 (affiliate link)

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/activateThanks 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 @ambitiousbookkeeperFor 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.com/@ambitiousbookkeeperConnect on Instagram: https://www.instagram.com/ambitiousbookkeeperConnect on Threads: https://www.threads.net/@ambitiousbookkeeperConnect on Facebook: https://www.facebook.com/serenashoupcpaThank you for your support of our show. If you haven’t left a review yet it’s super simple. Please go to ambitiousbookkeeper.com/podcast and leave your review.Podcast Publishing Tools we use:Editing → Sabr Media LLC: https://www.iangilliam.com/sabr-media-llcDescript: https://get.descript.com/u7lubkx09073 (affiliate link)Buzzsprout: https://www.buzzsprout.com/?referrer_id=1753696 (affiliate link)

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 lands, how much owners are really working, and the truth about AI that nobody wants to say out loud. Real talk, some of these numbers gave me pause, and a few of them are going to challenge what you think is possible in your own business. Grab the free PDF report and follow along.In this episode you’ll hear:The revenue ceiling for solo firm ownersThe honest truth about AI in our industryWhy so many of you are still pricing way too lowWhat your minimum fee should actually look likeThe surprising connection between being the household breadwinner and how hard you push your firmWhat the data says about working hours and profit margins at every revenue levelResources mentioned in this episode:State of the Virtual Bookkeeping and Accounting Industry Survey (free PDF report) at: https://www.ambitiousbookkeeper.com/survey or https://www.workflowqueen.com/surveyElevate: https://www.ambitiousbookkeeper.com/elevateAdvisory Edge: https://www.ambitiousbookkeeper.com/offers/j9hM5s4e/checkoutBreakthrough: https://serenashoup.krtra.com/t/IKUxtNZoz7lFXero: https://xeroamericas.partnerlinks.io/79afz10exu7dConnect with Alyssa🌐 Website: https://www.workflowqueen.com📱 IG: https://www.instagram.com/workflowqueen🎙️ Podcast: https://podcasts.apple.com/us/podcast/conquering-workflows-systems-for-bookkeepers-accountants/id1576274369?i=1000529139554Thanks 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 @ambitiousbookkeeperFor 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 the Blog: https://www.ambitiousbookkeeper.com/blogConnect on Instagram: https://www.instagram.com/ambitiousbookkeeperConnect on Threads: https://www.threads.net/@ambitiousbookkeeperConnect on Facebook: https://www.facebook.com/serenashoupcpaThank you for your support of our show. If you haven’t left a review yet it’s super simple. Please go to ambitiousbookkeeper.com/podcast and leave your review.Podcast Publishing Tools we use:Editing → Sabr Media LLC: https://www.iangilliam.com/sabr-media-llcDescript: https://get.descript.com/u7lubkx09073 (affiliate link)Buzzsprout: https://www.buzzsprout.com/?referrer_id=1753696 (affiliate link)

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.In this episode you’ll hear:A breakdown of the survey format, what questions changed from last year, how this data compounds over time, and why your honest answers help the whole industryHow AI should actually be affecting your pricingHow people are (and aren't) implementing AI in their firms, and the offshoring and automation data we're dying to dig intoThe trust recession around AI, what it means for your client relationshipsResources mentioned in this episode:TAKE the Survey: https://www.ambitiousbookkeeper.com/surveyOr take it Here: https://www.workflowqueen.com/surveyLast Year’s Results: https://youtu.be/L0nwFo5A7xMConnect with Alyssa🌐 Website: workflowqueen.com📱 IG: @workflowqueen🎙️ Podcast: Conquering Workflows & Systems with the Workflow QueenThanks 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 @ambitiousbookkeeperFor 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 the Blog: https://www.ambitiousbookkeeper.com/blogConnect on Instagram: https://www.instagram.com/ambitiousbookkeeperConnect on Threads: https://www.threads.net/@ambitiousbookkeeperConnect on Facebook: https://www.facebook.com/serenashoupcpaThank you for your support of our show. If you haven’t left a review yet it’s super simple. Please go to ambitiousbookkeeper.com/podcast and leave your review.Podcast Publishing Tools we use:Editing → Sabr Media LLC: https://www.iangilliam.com/sabr-media-llcDescript: https://get.descript.com/u7lubkx09073 (affiliate link)Buzzsprout: https://www.buzzsprout.com/?referrer_id=1753696 (affiliate link)

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 what to do when a competitor is trying to tank your reputation online.In this episode you’ll hear:The very first thing I recommend automating in your bookkeeping practiceHow to confidently ask a prospective client for access to their booksQBO Payroll versus GustoHow to advise S-Corp clients on taking a reasonable salaryResources mentioned in this episode:Elevate: https://www.ambitiousbookkeeper.com/elevateThe Bookkeeping Business Accelerator: https://www.ambitiousbookkeeper.com/bbaEmailing List: ambitiousbookkeeper.com/subscribeDubsado (free audio series): https://www.ambitiousbookkeeper.com/dubsadoDubsado (affiliate link): https://www.dubsado.com/?c=shoupcpaDubsado Decoded: https://kendracourtney.com/dubsado-decoded/Breakthrough by Workflow Queen: https://serenashoup.krtra.com/t/IKUxtNZoz7lFYouTube: "Is It Time to Move My Clients to Xero?"Xero Partner Program (affiliate link): https://xeroamericas.partnerlinks.io/79afz10exu7dGusto (affiliate link): https://gusto.com/partners/i/serena591Thanks 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 @ambitiousbookkeeperFor 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.com/@ambitiousbookkeeperConnect on Instagram: https://www.instagram.com/ambitiousbookkeeperConnect on Threads: https://www.threads.net/@ambitiousbookkeeperConnect on Facebook: https://www.facebook.com/serenashoupcpaThank you for your support of our show. If you haven’t left a review yet it’s super simple. Please go to ambitiousbookkeeper.com/podcast and leave your review.Podcast Publishing Tools we use:Editing → Sabr Media LLC: https://www.iangilliam.com/sabr-media-llcDescript: https://get.descript.com/u7lubkx09073 (affiliate link)Buzzsprout: https://www.buzzsprout.com/?referrer_id=1753696 (affiliate link)