The Successful Bookkeeper Podcast

"There's all that magic that seems to happen by those who are born with relationship privilege, but we can all build it. It just starts with how you can become more purposeful and intentional with what you want out of not just your life, but the people around you that form your purposeful community." -David Homan Community-building strategist and author of Orchestrating Connection, David Homan challenges the way you think about networking. He explains why traditional networking often feels forced and ineffective, and shows how shifting toward intentional, trust-based relationships can open doors you didn't think were possible. David shares how vulnerability, curiosity, and generosity create stronger connections, and why building a purposeful community matters more than collecting contacts. In this episode, you'll learn: Why most networking fails & what to do instead How to turn your existing network into a supportive community A simple way to create opportunities without asking for anything To learn more about David, click here. Connect with him on LinkedIn. Get a copy of Orchestrating Connection this link. Time Stamps 00:56 – Why traditional networking feels forced 02:08 – David's background & early exposure to relationships 09:34 – Network vs. purposeful community 11:40 – Using vulnerability to build trust 19:19 – Real connection vs. transactional conversations 23:29 – The five principles of meaningful relationships 29:16 – How to start building your community today Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"High performers liked to be with high performers. So if you start to train yourself as a manager, as a boss, as a business owner, as an entrepreneur, in holding people accountable, you will notice who doesn't mind that, who kind of thrives around that, and those kind of people attract more people like that." –Gina Cotner In this episode, founder and CEO of Athena Executive Services, Gina Cotner shares a practical framework for holding your team accountable without creating tension or fear. She explains why delegation alone is not enough, how accountability builds stronger leaders inside your firm, and how small shifts in communication can dramatically improve follow-through and results. In this episode, you'll learn: What to say when deadlines are missed & how to fix the real issue The simple question that drives ownership & initiative How asking "when" changes your team culture To learn more about Gina, click here. Connect with her on LinkedIn. Read about her company, Athena Executive Services at this link. Time Stamps 00:57 – Gina's business growth through rapid expansion & market shifts 13:08 – Why delegation without accountability fails 21:40 – Shifting ownership: "What do you need from me?" 23:36 – The power of asking "when" in every meeting 27:42 – What to do when work is not completed on time 29:14 – The million-dollar question: "What got in the way?" 35:11 – Why caring deeply gives you room to hold people accountable 41:15 – Negotiating deadlines without lowering standards This episode is brought to you by our great friends at BILL! They're hosting Bookkeeper Appreciation Week from March 30th to April 3rd—dedicated to recognizing the real work you do and giving you tools you can actually use to free up time for more strategic work. Get ready for 5 days of practical resources delivered straight to your inbox, plus live, CPE-eligible webinars! Register now at bill.com/successfulbookkeeper! Don't miss it!

"At some point in the future, somebody's going to be watching a movie about our era and there's going to be a human bookkeeper. And they're going to turn to their parents 20 years from now, and they're gonna say, 'Bookkeepers used to be people? That's so weird. I thought they were always artificial intelligence. I thought they were always computers.'" -Joe Woodard In this spotlight episode, founder of Scaling New Heights, Joe Woodard shares a clear view of where the bookkeeping profession is heading as AI reshapes the industry. He breaks down how service models are evolving, why advisory must be structured differently, and what practical steps you can take today to stay relevant and valuable plus much more! In this episode, you'll learn: How to use AI safely while protecting client data The difference between AI-enabled tools & native AI platforms How to structure your services using "swim lanes" instead of pricing tiers To learn more about Joe, visit his LinkedIn profile here. To get your ticket for Scaling New Heights, click this link. Time Stamps 00:53 – Introduction to Joe Woodard & what's new since his last visit 02:15 – Why advisory is becoming the core value in bookkeeping 04:20 – Moving from pricing tiers to service "swim lanes" 06:04 – Breaking down transactional, controllership, FP&A & outsourcing 08:26 – How subscription models change pricing & scope conversations 10:16 – Why managing scope is harder than managing profitability 12:11 – How to handle scope creep using swim lane language 15:23 – Pricing differences for small versus larger clients 16:22 – The impact of AI on bookkeeping & accounting 18:03 – Book recommendations to understand the future of work 20:14 – The "Hidden Figures" lesson every bookkeeper should understand 22:18 – Two paths to adopt AI in your firm 25:41 – Native AI tools versus AI layered on existing platforms 28:34 – How to protect client data when using AI 32:21 – Practical advice for using tools like ChatGPT safely 35:36 – Scaling New Heights conference & what to expect Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"Oftentimes we get into burnout because we are saying yes to everything. We're getting scope creep, and we aren't billing for those extras."–Linda Hunt In this episode, the author of The Money Conversation: Speak the Truth. Set the Standard. Get Paid Without Apology, Linda Hunt explains why burnout often starts with unclear boundaries and underpriced services. She shares practical strategies to help you calculate your true capacity, package your services properly, manage scope creep, and position yourself as a strategic partner without overextending yourself or your team. In this episode, you'll learn: How to calculate your Minimum Aligned Price & set a sustainable pricing floor How to recognize scope creep & confidently charge for extra work How AI can free up time for deeper analysis & advisory conversations To learn more about Linda and her company, SumSolutions, click here. Connect with her on LinkedIn. Buy her book, The Money Conversation at this link. Time Stamps 01:06 – Linda's journey from corporate to building a remote accounting firm 04:25 – Why lack of structure leads to burnout 09:49 – Calculating your Minimum Aligned Price 15:07 – Assigning clients to specific days to improve focus 18:49 – Structuring annual packages & dividing by 12 20:22 – What scope creep looks like in real life 23:54 – Turning extra requests into paid projects 29:45 – Using AI to elevate your advisory role 35:37 – Linda's pricing reset session & upcoming book, The Money Conversation This episode is brought to you by our great friends at BILL! They're hosting Bookkeeper Appreciation Week from March 30th to April 3rd—dedicated to recognizing the real work you do and giving you tools you can actually use to free up time for more strategic work. Get ready for 5 days of practical resources delivered straight to your inbox, plus live, CPE-eligible webinars! Register now at bill.com/successfulbookkeeper! Don't miss it!

"We always say 'Motivation is like a shower. You should visit it daily.' You have to keep yourself motivated every day. How do I get myself motivated and sold back on myself so that I can be the best version of how I want to show up for my clients?" –Julee Gracey In this episode, sales and marketing coach, speaker, and author of Highly Confident, Julee Gracey explains why confidence is the foundation of pricing, pitching, and growing a bookkeeping business. She shares practical strategies to help you strengthen your internal dialogue, communicate your value clearly, and attract higher-quality clients who are willing to pay for your expertise. In this episode, you'll learn: How to stop underpricing & stand firm behind your fees Why you must get sold on yourself before you try to sell your services How to identify your ideal clients & speak directly to their needs To learn more about Julee, click here. Follow Julee on Instagram. Get a copy of Highly Confident. Time Stamps 00:55 – Introduction to Julee & her background in sales 06:17 – Why confidence is required before you can sell 10:41 – Rewiring negative self-talk & managing imposter syndrome 14:01 – The difference between selling & closing 16:05 – Why you should stop handing out business cards 20:11 – Understanding the three types of clients 27:01 – How to overcome fear of networking events 33:21 – Shifting from price focus to return on investment 36:26 – A real example of raising prices & holding firm 40:29 – Overview of Julee's book Highly Confident This episode is brought to you by our great friends at BILL! They're hosting Bookkeeper Appreciation Week from March 30th to April 3rd—dedicated to recognizing the real work you do and giving you tools you can actually use to free up time for more strategic work. Get ready for 5 days of practical resources delivered straight to your inbox, plus live, CPE-eligible webinars! Register now at bill.com/successfulbookkeeper! Don't miss it!

" In order to create that trust, you have to be honest enough to know that you're not the right person for everybody. But those people that you do connect with, when you find that connection, that is when you can start to go through that process." –Amy Jacobson In this episode, Australian emotional intelligence expert, speaker, and author of The Emotional Intelligence Advantage: Mastering Change and Difficult Conversations, Amy Jacobson explains why technical skill alone will not build a strong, sustainable bookkeeping firm. She shares how emotional intelligence drives trust, strengthens client relationships, and improves leadership inside growing firms, along with a practical five-step framework you can apply immediately. In this episode, you'll learn: How emotional intelligence builds client trust & retention How to adapt your communication style to different clients Why leadership requires a different skill set than bookkeeping To learn more about Amy, click here. Connect with her on LinkedIn. Buy her book, The Emotional Intelligence Advantage: Mastering Change and Difficult Conversations, at this link. Time Stamps 01:11 – Amy's background & her path into emotional intelligence 04:14 – A clear definition of emotional intelligence for business owners 06:08 – Where bookkeepers commonly struggle with EQ 09:51 – How trust is built through real connection 12:24 – The five-step emotional intelligence framework 15:11 – A real example of client loss due to poor communication 18:10 – Shifting from technical language to client-centered language 21:10 – Becoming part of the client's business instead of an outside vendor 23:44 – Why leadership is not the same as technical skill 27:13 – How reactive leadership drains time & energy 30:00 – A simple daily question to improve emotional intelligence 31:41 – Where to access Amy's books and free tools This episode is brought to you by our great friends at BILL! They're hosting Bookkeeper Appreciation Week from March 30th to April 3rd—dedicated to recognizing the real work you do and giving you tools you can actually use to free up time for more strategic work. Get ready for 5 days of practical resources delivered straight to your inbox, plus live, CPE-eligible webinars! Register now at bill.com/successfulbookkeeper! Don't miss it!

"The biggest one and the most impactful one is not making the time every week to work on the business. They get themselves into the rat race. They spend the money on these programs, and then they don't make the time to implement them. That's the biggest mistake that I see. Do the hard things 'cause we can all do hard things and it's okay if we screw up."–Teresa Slack In the final episode of this four-part series, co-founder of Financly Bookkeeping Solutions, Teresa Slack shares how her bookkeeping firm shifted from survival to stability by building the systems, pricing, and team structure needed to scale. She breaks down the decisions that increased profitability, supported growth, and turned the firm into a sellable asset, along with the real challenges of restructuring roles, working through setbacks, and preparing for a successful exit. In this episode, you'll learn: What made the firm scalable & no longer dependent on the owners Why systems, profitability & cloud operations increased business value What buyers actually looked for when acquiring the firm Click here to learn more about Teresa and email her at teresa.slack@teresaslack.ca. Connect with her on LinkedIn. Learn more about Pure Bookkeeping. Subscribe to the Value Pricing Academy YouTube channel. Join VIP list for free training from Mark Wickersham here. Get your free copy of How to Price Bookkeeping eBook (the tool she used to turn her business around). Click here to join the VPA on Skool platform free training and support. Time Stamps 01:43 – Realizing the business was no longer fragile 02:04 – Setting new goals for growth & team support 03:26 – Building benefits & a sustainable work environment 04:22 – Turning revenue goals into clear action plans 05:46 – Growth setbacks & unexpected challenges 07:15 – Restructuring roles into bookkeepers & client managers 09:33 – Why the transition was harder than expected 12:01 – Systems that finally made the new structure work 13:36 – How role clarity improved efficiency & client service 14:59 – Using outsourced bookkeeping to support scale 16:41 – When selling the business became a real option 18:16 – Choosing buyers who aligned with the firm's values 20:09 – What increased the firm's valuation 22:55 – Preparing financially before selling 25:19 – Why systems & owner independence matter to buyers 27:22 – Lessons learned after selling the firm 28:37 – The biggest mistakes Teresa sees firm owners make 30:02 – What's next for Teresa & how she supports other bookkeepers Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"You can have all the great checklists and all the great systems for quality bookkeeping and you can hire all the right people, but if you don't know how to price your services, you are going to fail. You will not be profitable."–Teresa Slack In part three of this four-part series, Teresa Slack, co-founder of Financly Bookkeeping Solutions, shares the phase where momentum finally began to build. After resetting the firm, she and her sister shifted their focus to working on the business, not just surviving inside it, and made real progress through uncomfortable pricing conversations, focused implementation time, and disciplined investment in systems and training. In this episode, you'll learn: Why systems alone are not enough without proper pricing The difference between fixed pricing & true value pricing How Teresa increased prices & discovered clients were willing to pay To learn more about Teresa, click here and email her at teresa.slack@teresaslack.ca. Connect with her on LinkedIn. Learn more about Pure Bookkeeping. Subscribe to the Value Pricing Academy YouTube channel. Join VIP list for free training from Mark Wickersham here. Get your free copy of How to Price Bookkeeping eBook (the tool she used to turn her business around). Click here to join the VPA on Skool platform free training and support. Time Stamps 00:54 – Entering the phase where momentum begins to build 02:29 – Why poor pricing guarantees failure, even with great systems 03:29 – Fixed pricing versus value pricing explained 04:22 – Presenting higher prices & hearing clients say yes 05:47 – Making large investments without feeling ready 06:40 – Closing Fridays to work on the business 08:17 – Turning training into real results through implementation 09:35 – Fixing pricing mistakes & rebuilding confidence 12:02 – Hiring experienced bookkeepers using structured systems 13:56 – Why skills alone are not enough without the right mindset 18:09 – Building a training process that sets staff up for success 20:16 – Repricing existing clients & facing the fear 22:09 – Increasing revenue by 45 percent in six weeks 23:27 – Losing the wrong clients & moving forward stronger 24:16 – What's coming in the final episode Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"We can do hard things even though you're afraid, even though you don't know if it's going to work. You have to try. You have to do different things and you will fail. And that's part of the growth. Part of the learning is to not be afraid to take that leap." –Teresa Slack In part two of this four-part series, Teresa Slack, co-founder of Financly Bookkeeping Solutions, shares the breaking point that forced her and her sister to reset their firm. With the business no longer working, they made hard calls that led to Financly 2.0, including letting staff go, rebuilding client trust, and investing money they didn't have into systems, coaching, and pricing education. In this episode, you'll learn: How poor hiring & hourly pay created bigger losses as the firm grew The difference between fixed pricing & true value pricing How investing in systems &coaching changed how they viewed their value To learn more about Teresa, click here and email her at teresa.slack@teresaslack.ca. Connect with her on LinkedIn. Learn more about Pure Bookkeeping. Subscribe to the Value Pricing Academy YouTube channel. Join VIP list for free training from Mark Wickersham here. Get your free copy of How to Price Bookkeeping eBook (the tool she used to turn her business around). Click this link to join the VPA on Skool platform free training and support. Time Stamps 01:19 – Hitting the breaking point & questioning whether to continue 01:43 – Deciding to rebuild the firm from the ground up 02:23 – Investing in systems & support with no margin for error 02:44 – Letting staff go & repairing client relationships 03:56 – Realizing pricing was a major problem 04:52 – Discovering value pricing for the first time 05:13 – Rolling out fixed packages & why it made things worse 06:11 – Paying staff more than clients were paying the firm 06:57 – Committing to hard changes & doing things differently 07:40 – Investing in pricing education despite fear 08:14 – Learning to believe in the value of bookkeeping work 09:35 – Having pricing conversations without panic 11:18 – Why systems & hiring processes became the turning point 15:04 – What's coming next in part three Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!

"The mission was always to build a million dollar bookkeeping firm. Our goal was to grow a large bookkeeping firm with clients and staff across Canada. That's what we wanted to do. And that's kind of what we are now." –Teresa Slack In part one of this special four-part series, Teresa Slack, co-founder of Financly Bookkeeping Solutions, shares the honest story of launching a virtual bookkeeping firm in 2014 with big goals, low pricing, and no clear path to profit. She shares how her business grew fast and looked successful on paper, but behind the scenes the pressure was intense as underpricing, early hiring, and years without owner pay slowly drained the firm and took a personal toll. In this episode, you'll learn: Why rapid client growth exposed serious pricing & margin issues What really happens when you hire staff before fixing your business model How fear, stress & lack mindset show up when owners stop paying themselves To learn more about Teresa, click here & email her at teresa.slack@teresaslack.ca. Connect with her on LinkedIn. Learn more about Pure Bookkeeping. Subscribe to the Value Pricing Academy YouTube channel. Join VIP list for free training from Mark Wickersham here. Get your free copy of How to Price Bookkeeping eBook (the tool Teresa used to turn her business around). Click here to join the VPA on Skool platform free training & support. Time Stamps 01:14 – Launching a virtual bookkeeping firm in 2014 03:15 – Using cloud tools & early adoption of QuickBooks Online 03:35 – Running free financial literacy seminars to attract clients 04:01 – Growing from five clients to dozens across bookkeeping, tax & consulting 04:21 – Feeling overwhelmed & deciding to hire staff 05:09 – Charging hourly rates that left no room for profit 06:06 – Paying staff & overhead while taking no income 07:03 – Driving hours to Toronto to build a client base 08:25 – Why the numbers looked good but the business wasn't healthy 08:44 – The original vision to build a million-dollar firm 09:50 – Not getting paid & questioning personal success 10:34 – Realizing they needed help but feeling unable to afford it 11:16 – Fear, lack mindset & pulling from savings to make payroll 12:39 – The emotional strain of running a business with a sibling 13:18 – Creating "business hat" conversations to manage conflict 14:20 – Keeping communication open during stressful seasons 14:43 – What's coming next in part two Your expertise has more value than you think, so Own Your Authority at The Successful Bookkeeper Summit 2026! It's a high-energy two-day virtual experience for bookkeepers ready to lead with confidence and elevate their impact. Join inspiring leaders on November 4th–5th to gain actionable strategies, powerful tools, and the clarity to shape the work you want, not just keep up with it. Don't miss this incredible opportunity! REGISTER TODAY!