EP505: Christina Springstead - The Bookkeeper's Guide To Boundaries, Cleanups & Growth
"Like this is not just a gig, but this is my career. You grow into wanting more of that for your clients and you start recognizing if a client isn't about that. The last thing I want is just agree to do a subpar job because a client doesn't really care and then they decide to care in two years and they look back at the history and they're like, 'This has been a mess.'" -Christina Springstead Christina Springstead, owner and founder of Springstead Solutions, returns to share what she's learned from handling complex cleanups and growing her business with intention. From refining systems to managing client expectations, Christina explains how bookkeepers can balance quality, communication, and growth—without burning out. In this interview, you'll learn: How to spot hidden issues in cleanup projects before you quote Why communication & transparency build client trust How to manage pushback & set professional boundaries To learn more about Christina and Springstead Solutions, here. Connect with her on Linkedin. Time Stamp 02:13 – Christina shares her background & path back to bookkeeping 04:34 – Lessons learned from recent cleanup projects 06:00 – The hidden costs of missing bank feed data & auto rules 07:42 – When CPA journal entries hide deeper problems 09:51 – How cleanup checklists evolved into better systems 10:51 – Why deeper diagnostic reviews protect both client & bookkeeper 12:06 – Expecting problems: guilty until proven innocent approach 13:01 – When "accurate" AR & AP numbers aren't accurate at all 14:45 – The danger of ignoring small errors today 15:34 – How to handle client pushback with transparency & purpose 16:22 – Choosing clients who care about accurate books 17:13 – Why clean books protect long-term business value 18:20 – Setting boundaries & recognizing red flags in clients 19:47 – The difference between hobby clients & business-minded ones 20:26 – Holding clients accountable for financial quality 21:02 – Managing stress & staying flexible during heavy work periods 22:45 – Communicating delays honestly with clients 23:57 – Building trust through consistency & openness 25:41 – Why clear communication increases client value perception 27:01 – Real client story: turning nonprofit chaos into clarity 28:55 – How bookkeeping education empowers boards & leaders 31:21 – Hiring a VA and assistant to buy back time & focus 32:53 – Building a business around your lifestyle, not fear 33:41 – Manifesting growth & designing your dream business 35:03 – Recommended books: Who Not How & Buy Back Your Time 37:33 – Why mindset, focus& vision drive real success 40:12 – How the new Summit experience connects the bookkeeping community This episode is brought to you by our amazing friends at Hub Analytics! Imagine having all your financial data in one place, with real-time analytics and customized reports at your fingertips. Hub Analytics is a financial platform that streamlines bookkeeping operations, so you can focus on what really matters—delivering high-quality results for your clients. With Hub's easy-to-use tools, you'll save time, reduce errors, and gain deeper insights into your clients' financials! Ready to take your bookkeeping to the next level? Book a demo to learn more and start your FREE trial TODAY!
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EP504: Casey Brown – How To Overcome Fear Around Pricing - Part 2
"Do not be tempted to undervalue yourself just because it happens to be something that's fast or easy for you to produce." -Casey Brown In the finale of this two-part series, pricing expert and president of Boost Pricing, Casey Brown, returns to share how bookkeepers can move from fear-based pricing to confident, value-driven conversations. She explains how to stop pre-discounting, test your true pricing ceiling, and communicate your worth with clarity and confidence. In this interview, you'll learn: Why pre-discounting hurts your profits How to identify & attract better, higher-value clients How to package & present your services with confidence Connect with Casey on LinkedIn. To buy her book, Fearless Pricing, click here. Watch her TED Talk, or video on 12 things I Hate About Hourly Billing. To learn more about Boost Pricing, click this link. Time Stamp 02:03 – The two types of discounting: negotiated & pre-discounting 03:52 – How to test your true price ceiling 04:54 – Overcoming scarcity mindset & fear of losing clients 06:02 – Why fewer clients at higher prices can be more profitable 08:44 – Letting go of price-sensitive clients who drain your energy 10:43 – Why bad clients cost more than they're worth 11:13 – The gender gap in business pricing & confidence 12:45 – How women undervalue their services & why it costs them 13:52 – Messaging & packaging your services for higher value 15:17 – Half of pricing success is the number; half is how you frame it 16:52 – Stop obsessing over numbers & focus on context 17:47 – The problems with hourly billing models 18:47 – Why fixed-fee & value-based pricing work better 19:26 – When & how to offer pricing packages 20:47 – Avoid overwhelming clients with too many choices 22:28 – Be the expert—guide your client's decision 24:31 – Why clear messaging builds trust & confidence 25:57 – The Picasso lesson: charge for your experience, not your time 26:58 – How to articulate the process & value you deliver 27:21 – Where to find Casey's free resources, book & programs 28:42 – Fearless Pricing community & how to join This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!
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EP503: Spotlight - Melanie Spillman - Building Trust & Human Connection In A Digital World
"Bookkeeping is a commodity. My accounting software can be a commodity. So how do we strike that emotional cord and how do we give the confidence that we are the right choice going forward? We're not a commodity. We are differentiating. We're building that difference." -Melanie Spillman Melanie Spillman, Vice President of Sales for Sage US Medium Businesses, shares practical ways bookkeepers can build stronger client relationships—through listening, follow-up, and authenticity. She explores how trust is earned, why active listening matters, and how to keep human connection alive in an increasingly automated industry. In this interview, you'll learn: How to build trust quickly & consistently with clients The art of active listening & letting silence do the work Why understanding your client's past & future builds connection Connect with Melanie on LinkedIn. To learn more about Sage, click here. Time Stamp 01:41 – How to build trust quickly with clients 03:34 – The power of timely follow-up 05:19 – Setting expectations & communicating clearly 06:33 – Teach, tailor & take control in client conversations 07:53 – How to ask better questions & listen actively 09:23 – Staying present & focused during meetings 12:22 – The value of silence in communication 13:54 – Showing authenticity & passion with clients 15:53 – How to build trust in the first meeting 17:22 – Asking about a client's past & future to deepen connection 20:09 – Why focusing only on history limits your impact 21:15 – How to stand out in a competitive market 22:29 – The "front door" story: lessons in emotional connection 25:39 – Why people buy with emotion & justify with logic 27:31 – Turning services from a commodity into a connection 29:34 – Keeping the human touch in an automated world 31:27 – Using AI to free time for more meaningful client work 33:22 – Understanding what really motivates clients 36:48 – Make every client interaction meaningful 38:46 – How Sage uses AI to empower bookkeepers
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EP502: Casey Brown – How To Overcome Fear Around Pricing - Part 1
"It's the bookkeeper who has to sell his or her own services, and so they're not a professional salesperson. So a lot of times there's a lot of fear and we get in our heads, we get in our gut, we feel pushy, we feel salesy, we feel weird and we discount. And so to me, it's about arming the person whose job it is to sell this value with the skills and tools to do it." -Casey Brown In part one of this two-part conversation, pricing expert and resident of Boost Pricing, Casey Brown, joins the podcast to help bookkeepers overcome fear, self-doubt, and hesitation around pricing their services. Drawing from her journey as an engineer turned pricing strategist, she explains how your "money story" shapes your pricing decisions—and how to change it. In this interview, you'll learn: How mindset & money stories limit what you charge The biggest pricing mistake small firms make How to handle pricing objections without discounting Connect with Casey on LinkedIn. To buy her book, Fearless Pricing, click here. Watch her TED Talk, or video on 12 things I Hate About Hourly Billing. To learn more about Boost Pricing, click this link. Time Stamp 00:00 – Why pricing confidence matters for bookkeepers 02:10 – Casey's journey from engineer to pricing strategist 04:38 – Lessons from working at GE & entering the pricing world 05:56 – Shifting from big corporations to small businesses 07:14 – Why analytical pricing models don't work for small firms 08:13 – Helping bookkeepers sell their own value with confidence 10:24 – From pricing analytics to pricing mindset training 12:31 – How training teams led to massive profit increases 13:36 – Why pricing problems start between your ears, not in spreadsheets 15:14 – Common sales beliefs that hold business owners back 17:19 – The myth that "the market sets the price" 18:52 – How changing beliefs can boost profitability 20:18 – Why most people fear talking about price 21:01 – Understanding your personal money story 22:41 – How emotions affect pricing decisions 23:13 – Exercises to detach emotion from pricing 24:22 – Casey's advice for bookkeepers ready to charge more This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!
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EP501: Michelle Weinstein – How To Confidently Sell Your Bookkeeping Services
"We have to stop trading time for money. Hourly billing traps you. It gets you in the cycle of undervaluing yourself. Discounting just to get a client to sign up with you and think that you're going to charge more in the future is another trap. Doing free work, answering quick questions, answering an abundance of emails and never getting paid for it is a trap." -Michelle Weinstein Michelle Weinstein, founder of The Abundant Accountant and The Pitch Queen, talks about how bookkeepers can confidently sell their services without feeling pushy or uncomfortable. Drawing on years of experience helping accounting professionals close high-value clients, Michelle shares simple strategies to increase revenue and build trust with prospects. In this interview, you'll learn: How to overcome fear & hesitation around pricing and sales Questions that turn discovery calls into meaningful conversations How to position your value instead of selling your time To learn more about Michelle, click here. Connect with her on LinkedIn. Time Stamp 00:00 – Why selling is a skill every bookkeeper needs 03:05 – How Michelle helps bookkeepers sell with confidence 05:40 – Shifting your mindset from "selling" to "helping" 08:12 – The biggest mistakes bookkeepers make in sales calls 10:45 – How to ask powerful questions that uncover client needs 13:10 – Why you should never discount your services 15:22 – The difference between pricing & value 18:03 – Turning consultations into lasting client relationships 20:45 – How to talk about money without fear or guilt 24:00 – Using Dext tools to add more value to clients 27:12 – Building confidence through practice & preparation 30:10 – Michelle's top advice for bookkeepers ready to grow 32:30 – Where to learn more about Michelle & The Abundant Accountant This episode is brought to you by our friends at Dext! Dext handles transaction capture, keeps your data accurate, and even simplifies e-commerce reconciliation, all in one place. Join thousands of bookkeepers and accountants who've already made the switch. If you're ready to save time, reduce errors, and make bookkeeping more efficient, Dext is for you! Go to thesuccessfulbookkeeper.com/dext to book a demo TODAY and see how it can transform the way you work!
The Successful Bookkeeper Podcast is a weekly show to help increase your confidence, work smarter and build a business you love.
Each week you'll listen to inspiring guests who will share their success secrets, so you can take your bookkeeping enterprise and life to another level.
Some of them include New York Times Best-Selling Author of E-Myth, Michael E. Gerber, Pure Bookkeeping Co-Founder, Debbie Roberts, the host of The Productive Woman podcast, Laura McClellan and the author of *I Know How She Does It*, Laura Vanderkam.
If you're a bookkeeping business owner who is looking for an uplifting, entertaining and informative podcast exclusively for YOU then you have arrived at the right place!
Get ready because your journey towards success begins — now.
Your Host
Michael Palmer is an acclaimed business coach who has helped hundreds of bookkeepers across the world push through their fears and exponentially grow their businesses and achieve the quality of life they've always wanted.
Ireland