"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!

"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!

"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

"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!

"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 more intentional you get with your money, the more intentional you get with your time as well."
-Jennifer Hume

In our 500th episode, Jennifer Hume, owner of Coronation Bookkeeping & Tax Services, shares how she built a successful virtual bookkeeping firm and expanded into coaching for real estate professionals. She reveals what worked, what didn't, and how she uses systems, marketing, and speaking to grow her business with purpose and profitability.

In this interview, you'll learn:

• How niching and storytelling drive growth and confidence
• Why systems are essential for scaling
• How Jennifer built a $250K firm through referrals

To learn more about Jennifer, click here.

Connect with her on LinkedIn.

Time Stamp

02:03 – Jennifer's journey from family business to starting her own bookkeeping firm
05:28 – Lessons learned from her father's failed business & what she'd do differently
06:08 – The importance of systems & Profit First for building a strong foundation
07:49 – Transitioning from data entry to leadership & advisory work
08:16 – How Jennifer built a $250K firm through referrals & strong processes
10:45 – Learning to market intentionally & step outside her comfort zone
13:03 – Building referral partnerships with accountants & real estate brokerages
15:07 – Overcoming fear & learning to pick up the phone to grow the business
17:07 – How niching into real estate transformed her business
19:42 – Why specializing makes marketing easier & attracts better clients
21:07 – What marketing tactics didn't work (and what to watch out for)
22:08 – Email marketing & newsletters that actually connect
24:55 – How creating a professional speaker's reel set her apart
26:44 – The power of storytelling on stage & building confidence through speaking
30:12 – Using AI tools like ChatGPT to craft speeches & prompts quickly
33:22 – Building a coaching business for real estate professionals
34:56 – Why 90% of realtors quit within five years & how coaching helps
35:40 – How financial & time habits create happier, more balanced lives
37:32 – Where to find & connect with Jennifer online

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!

"The number one driver of small to medium sized businesses not making it is cash flow problems. It's not that they're not profitable. This is the big thing with net cash that most people don't realize, is that you can run a profitable business and run out of money."
-Tommy Vincent

In this spotlight episode, Tommy Vincent, Co-Founder and Chief Revenue Officer at Hub Analytics, returns to share how bookkeepers can confidently step into advisory by focusing on just 3 key metrics. He explains how to measure, track, and present them to clients in a way that builds trust and drives business growth.

In this interview, you'll learn:

• The 3 metrics every bookkeeper should track
• Why consistency matters more than dozens of KPIs
• How net equity shows a business owner's true wealth

To learn more about Hub Analytics, click here.

Connect with Tommy on LinkedIn.

Time Stamp

00:00 – Introducing 3 Key Metrics
02:16 – Why bookkeepers are well-positioned to deliver advisory services
03:59 – Why less is more with KPIs for small business clients
04:54 – The three core metrics
06:33 – Breaking down net operating income & what it reveals
07:50 – Industry nuances & why measuring consistently matters
09:30 – Using consistent monthly tracking to spot improvement
12:20 – Net equity explained
14:27 – Why 78% of a business owner's net worth is tied to their business
16:04 – Loans, distributions & reinvestment
20:54 – Why profitable businesses still fail without cash
23:10 – Healthcare & construction industries & cashflow gaps
25:59 – Watching DSO & DPO to avoid cash crunches
27:21 – How bookkeepers can differentiate by tracking just 3 KPIs
28:29 – How to package advisory
30:55 – Why most existing clients won't pay more
33:18 – Advisory is best suited for businesses over $1M revenue
34:56 – How Hub Analytics supports bookkeepers with AI-driven reporting

"I think that the hacker mindset is a superpower because what it does is it fosters independent thinking. And independent thinking enables a person to observe or discover overlooked pathways, overlooked opportunities, things that other people have missed."
-Ted Harrington

Ted Harrington, cybersecurity expert and author of Hackable: How To Do Application Security Right and his upcoming book Inner Hacker: A New Way Of Thinking, returns to talk about the hacker mindset and how it can transform both business and life.

In this interview, you'll learn:

• The four traits of the hacker mindset
• How AI is shaping cyberattacks
• Ways to tap into your inner hacker

To learn more about Ted, click here.

Connect with him on LinkedIn.

Check out his new book, Inner Hacker: A New Way Of Thinking here.

Time Stamp

01:22 – Ted Harrington returns with his new book Inner Hacker
02:47 – Why thinking like a hacker is a superpower
09:17 – The four traits of the hacker mindset
12:39 – What holds people back from channeling their inner hacker
18:24 – How the book supports his business & clients
23:13 – AI's role in modern cyberattacks
29:20 – What's changing for small businesses & cybersecurity awareness
32:31 – Why hackers target small businesses
36:36 – Protecting yourself by knowing where you're vulnerable
37:45 – Ted's future plans & keynote speaking

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!