230 | [Q&A] AI Tools, Pricing, and Onboarding

Send a textI 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 bookkeeping business, how AI is changing our industry (but not in the way you might fear), and what's in store for this cohort.In this episode you’ll hear:The big announcementErin's origin storyAI in bookkeepingAnd more!Resources mentioned in this episode:Bookkeeping Business Accelerator (BBA): https://www.ambitiousbookkeeper.com/vipAmbitious Bookkeeper Bookkeeping Biz Workshops: https://www.ambitiousbookkeeper.com/workshopsXero: https://xeroamericas.partnerlinks.io/79afz10exu7dQuickBooks Online: https://www.referquickbooks.com/s/Serena4Workflow Queen / Alyssa Lang: https://www.workflowqueen.comMeet ErinAs Founder of UpKeeping® and a proud student in The Ambitious Bookkeeper community, Erin is changing the old & boring stereotypes of the accounting industry. Erin and her team support new entrepreneurs and already-established small business owners by being their #1 financial cheerleader/concierge/communicator.When she’s not trying to make accounting more “fun”, Erin loves traveling the world with her family, playing the violin, and convincing accounting students & professionals that owning an accounting firm is the American dream.Connect with Erin👥 Linkedin: https://www.linkedin.com/in/erinpohan/📱 Instagram: @upkeeping.coThanks 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 LLCJoin The Bookkeeping Business Accelerator-VIP before March 17th >> https://www.ambitiousbookkeeper.com/vipJoin the Meet The Coaches + BBA Info Session | March 12 @ 4PM Pacific >> https://evt.to/d1qq02b8xjl4

Send a textFrom 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 processResources 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/bbaEffortless Client Requests: workflowqueen.comBecome a Bookkeeper: https://www.katieferro.com/a/38894/2PQNgtvvDubsado Decoded: https://kendracourtney.com/dubsado-decoded/Akadian QBO: https://fastandeasyqbo.samcart.com/referral/qbo-basic/8Duca0gOuAg8wpjFBookkeeper Launch: https://sk293.isrefer.com/go/BLFS/SS64/Affiliate LinksXero: https://xeroamericas.partnerlinks.io/79afz10exu7dQuickBooks Online: https://www.referquickbooks.com/s/Serena4Dubsado: https://www.dubsado.com/?c=shoupcpaGusto: https://gusto.com/r/1bjHmContent Snare: https://contentsnare.com/#_r_serena58Clockify: https://clockify.me/?fpr=qyebl2Thanks 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 PubliJoin The Bookkeeping Business Accelerator-VIP before March 17th >> https://www.ambitiousbookkeeper.com/vipJoin the Meet The Coaches + BBA Info Session | March 12 @ 4PM Pacific >> https://evt.to/d1qq02b8xjl4

Send a textWelcome 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 situationsResources mentioned in this episode:Xero: https://xeroamericas.partnerlinks.io/79afz10exu7dQuickBooks Online: https://www.referquickbooks.com/s/Serena4Become a Bookkeeper by Katie Farrow: https://www.katieferro.com/a/38894/2PQNgtvvRisk Desk by Jock Walls at https://www.myriskdesk.comDubsado: https://www.dubsado.com/?c=shoupcpaGoogle Workspace: https://referworkspace.app.goo.gl/Xo4GTaxJar, Anrok, Hubdoc"Make 'Em Beg to Work for You" by Dr. Angela E. Lauria"Teamwork" by Natalie DawsonBookkeeping Business Accelerator: https://www.ambitiousbookkeeper.com/bbaElevate: https://www.ambitiousbookkeeper.com/elevateConfident Compliance Bundle: https://www.ambitiousbookkeeper.com/offers/tgPgMBJ7Workflow Queen's Breakthrough Program: https://serenashoup.krtra.com/t/IKUxtNZoz7lFDubsado Decoded: https://kendracourtney.com/dubsado-decoded/QBO Gym: https://fastandeasyqbo.samcart.com/referral/GymChallenge/8Duca0gOuAg8wpjFThanks 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:

Send a textIn 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 personResources 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/serenashoupcpaADPMeet Hunter RademacherMy name is Hunter Rademacher, and I work in sales at CSI Accounting & Payroll. I spend my days speaking directly with small business owners — from one-person operations to companies with 100 employees — helping them navigate bookkeeping, payroll, cleanup work, and ongoing accounting support.Because I’m on the front lines of these conversations, I get a clear view into why small businesses choose a bookkeeper, why they leave one, and what they actually want from an accounting partner. I’ve learned where trust breaks down in the sales process and how bookkeeping firms can position their services more confidently and profitably.Connect with HunterLinkedIn: https://www.linkedin.com/in/hunter-rademacher/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)

Send a textThe '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 ReconciliationResources mentioned in this episode:→ want to see that ‘tax package’ in action? Grab the Confident Compliance Bundle205 ⎸ Protecting Your Clients from Audits with Ex Irs Auditor Adrian LopezMeet AdrianI’m Adrian Lopez, a Certified Public Accountant (CPA) and former IRS Revenue Agent.During my tenure as a Revenue Agent in the IRS Small Business / Self-Employed Division, I audited self-employed and small business taxpayers like restaurants, construction contractors, real estate agents & brokers, wealth managers, tax preparers, and farmers.Now, I help individuals, families, small businesses, and non-profits thrive by providing quality tax return preparation, tax planning & advisory, bookkeeping & accounting, and tax representation.Connect with AdrianWebsite: https://anlcpa.com/Linkedin: https://www.linkedin.com/in/adrianl1996/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)

Send a textBefore 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 to consider, especially if you’re balancing motherhood with building your business, or dreaming of starting your business in 2026.In this episode you’ll hear:Katie’s background: CPA → corporate → motherhood → bookkeeping business (and how she was “paid to quit” at the perfect time)The emotional reality of leaving corporate—even when it’s the right moveWhy the early seasons of motherhood are intense, and how that shapes business decisionsHow Katie’s bookkeeping business grew: referrals, small beginnings, pricing lessons, and early client expansionThe mindset shift: bookkeeping as a stable, scalable foundation (especially once you hire a team)Hiring earlier than feels comfortable: babysitters, cleaners, and bookkeepers as “buying back time”Why working at home with kids around can be harder than being fully out of the houseOffice space + opportunity cost: how one monthly client can fund the setup that changes everythingTraining a team the right way: slow client-by-client handoff, upfront time investment, long-term payoffClient continuity + freedom: not being the only person clients rely onKatie’s Become a Bookkeeper (BABS) course overview: Learn → Shadow → Apply (practicum)Resources mentioned in this episode:Become A BookkeeperConnect with Katie: : instagram.com/orderlyaccountingbykatieListen to Katie’s Podcast: Profits & ProseccoSign up for Become A BookkeeperThanks 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:Join The Bookkeeping Business Accelerator-VIP before March 17th >> https://www.ambitiousbookkeeper.com/vipJoin the Meet The Coaches + BBA Info Session | March 12 @ 4PM Pacific >> https://evt.to/d1qq02b8xjl4

Send a textI 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 you makeHow to flip your AI mindset from "polish my work" to "support me first"The three ways to monetize AI in your businessResources mentioned in this episode:90 Day Visibility Sprint Starter Kit https://kellysinclair.thrivecart.com/the-90-day-visibility-sprint-podcast/?coupon=SERENAPODValerieBrand CalibratorNotebook LMChatGPTMindPalManyChatZapierQuickBooks OnlineMeet KellyKelly Sinclair is a visibility strategist, AI-powered marketing expert, and host of Entrepreneur School. An accidental tech nerd and professional mom taxi, she helps entrepreneurs ditch random acts of marketing, build visibility habits that actually work, and grow through intentional visibility—not by selling their soul to social media.Connect with KellyPodcast: https://entrepreneurschool.ca/podcast/ Instagram: https://www.instagram.com/ksco_kelly/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)Join The Bookkeeping Business Accelerator-VIP before March 17th >> https://www.ambitiousbookkeeper.com/vipJoin the Meet The Coaches + BBA Info Session | March 12 @ 4PM Pacific >> https://evt.to/d1qq02b8xjl4

Send a textIn 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:How to evaluate AI tools for securityThe difference between machine learning and generative AIHow Kelsey balances building an app, doing VIP days, working a corporate job, AND being a mom to a 4.5-year-oldResources mentioned in this episode:The Metrics 7-Figure Business Owners Can't Live Without: https://kelseysilver.com/metrics5 DM Signals $FREE: https://foresighthq.app/5signalsNotionThriveCart, High Level, and SamCartManyChatMeet KelseyKelsey Silver is a data and AI strategist and the founder of ForesightHQ, an AI-powered DM lead tracker designed for business owners who want to follow up in their DMs without feeling like a sales robot. With a background in psychology, 10+ years in corporate analytics, and a deep love for systems that actually fit your life, Kelsey helps entrepreneurs find the hidden gold in their data so they can sell smarter and with more integrity. When she’s not decoding buyer signals or mapping launch strategies, you can find her at a Ren Faire with her daughter or decompression from reading spreadsheets all day with a bag of Oreos and an oat milk chai latte.Connect with KelseyInstagram: @kelseyesilverWebsite: https://kelseysilver.com/App: https://foresighthq.appThanks 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: httpJoin The Bookkeeping Business Accelerator-VIP before March 17th >> https://www.ambitiousbookkeeper.com/vipJoin the Meet The Coaches + BBA Info Session | March 12 @ 4PM Pacific >> https://evt.to/d1qq02b8xjl4

Send us a textWelcome 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:How to design your dream bookkeeping businessThe exact framework for identifying your perfect-fit clientMy four-step discovery call structure that makes selling feel naturalThe complete roadmap for getting your bookkeeping business up and runningResources mentioned in this episode:Get the Templates & Workbook for $27: https://www.ambitiousbookkeeper.com/offers/VhYZ8EfsGet the special code and the discount for 20% off the Bookkeeping Business Accelerator, Self-Paced before December 1st at: ttps://www.ambitiousbookkeeper.com/subscribeElevate: https://www.ambitiousbookkeeper.com/elevateThanks 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)Subscribe to stay in the know about Black Friday: ambitiousbookkeeper.com/subscribeBlack Friday Sale happens November 28 - Dec 2 Get access to the Dubsado Decoded Private Podcast Series here>>

Send us a textWelcome 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 issuesResources mentioned in this episode:Get the Templates & Workbook for $27: https://www.ambitiousbookkeeper.com/offers/VhYZ8EfsStart your free trial of Xero: https://xero5440.partnerlinks.io/xirpf8p1xkozAccountants & Bookkeepers: become a Xero partner: https://xeroamericas.partnerlinks.io/79afz10exu7dAlyssa Lang’s Kickoff With Asana: https://serenashoup.krtra.com/t/41Ux6YmOFQYfQuickBooks Online: https://www.referquickbooks.com/s/Serena4Relay Bank: https://relayfi.com?referralcode=ShoupCPAGusto Payroll: https://gusto.com:/partners/i/serena591Dubsado: https://www.dubsado.com/?c=shoupcpaCanva: https://www.canva.com/join/relish-scale-floristicClockify: https://clockify.me/?fpr=qyebl2Google Workspace: https://referworkspace.app.goo.gl/Xo4GKajabi: https://app.kajabi.com/r/SLFEMUL4/t/uiptq7nuDouble (Formerly known as Keeper): https://keeper.app/?via=serenaOpenPhone: https://openph.one/referral/XA0kFFRThanks 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.Subscribe to stay in the know about Black Friday: ambitiousbookkeeper.com/subscribeBlack Friday Sale happens November 28 - Dec 2 Get access to the Dubsado Decoded Private Podcast Series here>>