The Successful Bookkeeper Podcast

“People came to me thinking that I was an expert. They saw the posts that I was posting about bookkeeping for law firms, and they already had buy-in to use my services. So I didn't need to sell them that much. I just needed to prove that I was a real person. I don't want to be out there selling my services. I want people coming to me already sold on my services.” -Brandy Derrick Brandy Derrick, owner of Legal Ease Bookkeeping, discusses her journey from learning bookkeeping for her father’s business to building a successful virtual firm specializing in law firms. Brandy shares how she overcame self-doubt, found her niche, and leveraged online marketing to grow her business while working remotely—even from a sailboat! You'll also learn... The role of LinkedIn, YouTube & referrals in client acquisition strategy Why niching down simplifies marketing, sales & client trust The importance of persistence, overcoming self-doubt & finding a support system To learn more about Brandy & Legal Ease Bookkeeping, click here. Connect with her on LinkedIn. Time Stamp: 01:00 – Brandy’s background & start in bookkeeping 03:00 – Challenges of working remotely without reliable internet 08:00 – Getting clients as a new bookkeeper 14:00 – Narrowing focus & building a niche in legal bookkeeping 17:00 – The role of Google Ads in business growth 21:00 – LinkedIn & Referral Marketing Strategy 30:00 – The power of offline marketing 38:00 – The value of niching in bookkeeping 42:00 – Overcoming challenges & growing confidence 45:00 – Final thoughts & where to find Brandy This episode is brought to you by our friends at BILL! BILL is the smarter way to create and pay bills, send invoices, manage expenses and control budgets, and access the credit your business needs to grow — all on one platform and they’re designed to help bookkeepers succeed and grow, whether you have your own bookkeeping firm or you’re a bookkeeper at an accounting firm. To find out more, check out BILL.com/successfulbookkeeper TODAY!

“In the bookkeeping and accounting world, if someone gets sick and that client can't get what they need, they just get back into the universe and another bookkeeper picks them up. So you lose everything.” -Christine Siegenthaler Christine Siegenthaler, founder of Succession Security, discusses the importance of contingency planning for solo bookkeepers and small bookkeeping firms. She shares how Succession Security helps ensure businesses continue operating during unexpected events like illness, injury, or even death. In this interview, you'll learn: Why contingency planning is essential How technology enables seamless business continuity Steps to secure your business To find out more about Christine, click here. Connect with her on LinkedIn. To learn how Succession Security can help you, visit SuccessionSecurity.com. Time Stamp 00:37 - Why solo bookkeepers need a contingency plan 01:52 - Risks of losing clients without a backup plan 03:22 - Importance of documentation and access to critical accounts 04:07 - Using cloud-based technology for seamless transitions 07:30 - The role of internet and cloud-based services in contingency planning 13:35 - Finding and trusting the right person to help manage your business 15:04 - The personal nature of bookkeeping and why AI can’t replace human interaction 17:23 - The challenge of bookkeepers taking time off – business doesn't stop 19:31 - Legal considerations and recommended insurance coverage 21:22 - Best practices for security, encryption, and protecting client data 24:14 - How proactive planning ensures business continuity and client security 29:05 - The importance of designating an emergency point of contact 30:05 - How to get started with Succession Security and where to learn more

“If it's consistently where you're feeling behind like you can never get on top of your to-do list, that you're always having to reschedule stuff for tomorrow, that's probably a sign that you have too much work on your plate. That's a sign that you could use more help within your business.” -Jamie Van Cuyk Jamie Van Cuyk, owner of Growing Your Team, joins the podcast to help solo bookkeepers and small business owners master hiring and delegation. She shares practical strategies for building a strong team, improving efficiency, and setting up a business for long-term success. In this episode, you’ll learn: Common delegation mistakes & how to avoid them How to create a job post that attracts the right candidates The difference between micromanaging & effective leadership To learn more about Jamie, click here. Connect with her on LinkedIn. Time Stamp 01:07 - Jamie Van Cuyk’s background 02:57 - Common fears around delegation 06:22 - The mindset shift needed to delegate effectively 10:42 - Key signs to hire & delegate tasks in your business 14:05 - How shifting from control to trust can create freedom & growth 20:06 - The importance of clear processes & training when delegating tasks 26:45 - How to determine what tasks to delegate 32:25 - Steps in hiring the right person & avoiding common mistakes 35:14 - Real success stories 39:58 - How to connect with Jamie for hiring support 41:33 - Business-building resources

“I remember being on Zoom and we saw our colleagues' children, people got personal and talked about the health challenges they were dealing with or that a family member was dealing with. I saw leaders and bosses having to have that same transparency. It was human to human. Since the workplace has evolved, employees are expecting that same transparency. They're expecting the same collaboration. And what they want specifically for the next generation of workers is the ability to contribute meaningfully to the decisions that impact their work.” -Dr. Angela Jackson Dr. Angela Jackson, founder of Future Forward Strategies and author of The Win-Win Workplace, shares how investing in employee well-being can boost productivity, profitability, and retention. She explains why traditional top-down management no longer works and how small businesses can create thriving workplaces by listening to employees and offering flexibility. In this interview, you'll learn: Why empowering employees leads to 23% higher profitability How small businesses can compete with larger firms by offering flexibility How to measure the ROI of employee engagement To learn more about Angela, click here. Connect with her on LinkedIn. To order her book, The Win-Win Workplace, visit this link.  Time Stamp 02:00 - Dr. Angela Jackson and her background 04:50 - Career journey and inspiration behind The Win-Win Workplace 04:51 - Research on aligning employee well-being with business success 08:39 - Why top-down decision-making is outdated 13:59 - The importance of flexibility in modern workplaces 19:01 - Small bookkeeping firm example of flexible work policies 24:01 - Offering meaningful benefits to boost retention 29:01 - Addressing benefit abuse and tracking productivity 33:01 - Key employee metrics and how to access the book

“Money is an energetic source in our world. When you get it, you feel really good, and when it leaves, you feel very bad. That's an energy. That's an exchange.” -Lou Clarke Lou Clarke, who is a CFO and profit strategist, discusses the power of confidence, pricing strategies, and how bookkeepers can shift into advisory roles to better serve clients. She also explains the importance of understanding money dynamics and building a business that truly thrives. To learn more about Lou, click here. Follow her on Instagram. Time Stamp 01:10 - Lou’s Journey into Bookkeeping 03:30 - Early Business Growth & Pricing Challenges 06:40 - Losing a Major Client & Financial Struggles 10:00 - The Road to Financial Recovery 15:00 - Finding Clients & Business Growth Strategies 20:30 - Pricing for Value & Selling Results 25:10 - Confidence & Business Success 30:00 - Transitioning to Advisory & Profit First 35:50 - Understanding the Energetics of Money 40:20 - What’s Next for Lou 45:00 - How to Connect with Lou

“If a majority of your leads come from LinkedIn, that's great, and you should keep doing that. But it doesn't hurt to diversify and to make sure that you have a couple of lead sources to pull in from different avenues.” -Kristen Corey Kristen Corey, founder of Media Books, dives into the importance of a well-designed website, how to make your firm stand out online, and common pitfalls to avoid.  In this interview, you'll also learn: Why a website builds trust & credibility How to turn visitors into loyal clients The best platforms for an easy-to-manage site Plus much more! To learn more about Kristen, click here. Connect with her on LinkedIn. Time Stamp 00:28 – Kristen’s journey from accounting to marketing 02:33 – Founding Media Books to help bookkeepers 04:21 – Common marketing struggles for bookkeepers 06:11 – Why websites matter for bookkeeping businesses 08:53 – The importance of an About page 10:44 – Choosing the best website platform 13:42 – Questions to ask when hiring a web designer 17:24 – The role of SEO in the AI era 20:35 – How websites improve user experience 24:15 – Common website mistakes to avoid 26:33 – Must-have features for bookkeeping websites 28:33 – Ensuring a website is user-friendly 31:48 – Pitfalls to avoid in website building 32:59 – Media Books’ website design process 35:01 – Client success story

“My workflow was going to tell me exactly what I needed to do that day. And I very intentionally and very consciously grounded myself into my work and into that routine and into that process, because that was the one thing in my life that was certain. My business got me through that time, that certainty and that control when everything else was so chaotic.” - Stephanie Kelcey Stephanie Kelcey, owner of Capture Bookkeeping, shares her journey of navigating major life transitions while building a successful bookkeeping business. She opens up about overcoming personal challenges, restructuring her business for efficiency, and the mindset shifts that helped her find stability and growth. In this interview, you'll learn: How systems & workflows can create stability during life transitions Why mindset shifts are crucial for financial success The impact of community and support networks on business growth Plus much more! Connect with Stephanie on LinkedIn. Learn more about Capture Bookkeeping here. Time Stamp: 00:39 – Journey into bookkeeping & business growth 02:56 – Navigating personal challenges 04:13 – The importance of support 09:54 – Coping mechanisms 12:56 – Creating space in business & shifting to an advisory model 17:17 – Mindset shifts in business, financial growth & client empowerment 22:02 – Financial mindset shifts 26:21 – Systems, hiring & structuring workflows for stability 30:09 – Focusing on rest, personal growth&  financial education 32:41 – Implementing a CRM system & improving work-life balance 34:50 – Business success, community & learning This episode is brought to you by our great 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!  

“I don't see a world where the profession of accounting is totally taken over by AI. There'll always be that need for human touch and validation because we do audits and we need to make sure that we get their taxes right. So I would just say, embrace it, think about how it's going to give you that better work-life balance, and then just go for it. Give it a try.” -Karen Ainley Karen Ainley, Head of the Accountants Business Unit at Sage, dives into how AI, automation, and digitization are transforming the bookkeeping and accounting profession. She shares key insights from the Practice of Now report, offering practical advice on embracing change, building client relationships, and staying competitive in a rapidly evolving industry. In this interview, you'll learn: How AI & automation enhance efficiency & client service The shifting role of bookkeepers from historical reporting to advisory services Why client expectations demand tech-savvy professionals today Connect with Karen on LinkedIn. Time Stamp: 01:19 - Overview of the Practice of Now report 02:13 - Key findings: skills, AI & client relationships 03:36 - How AI improves workloads & work-life balance 06:18 - Evolving client expectations & demand for tech-savvy services 09:01 - Global tax digitization trends & their impact 13:08 - Shift to subscription models & value-based pricing 16:59 - Advisory services replacing traditional bookkeeping 19:25 - How small practices can compete with AI tools 21:40 - Sage Copilot’s features: anomaly detection & automation 26:00 - Karen’s advice: embrace technology & take action 27:39 - How Sage supports bookkeepers with tools & resources 29:16 - Closing remarks & resources for listeners This episode is brought to you by our great friends at Sage! On February 13th at 12pm ET, Sage will be presenting its webinar, Practice of Now: How To Plan Your Practice for 2025 & Beyond, to our community. It'll cover The Practice of Now global insights study to help you plan your role and practice for the future.   During this webinar, you’ll learn: Current trends that are changing the profession The biggest opportunity to take in the next 12 months Key actions that all accountants and bookkeepers should be considering Plus much more! REGISTER NOW before it's too late!

“I put my clients on notice in the first week of December. All of my clients get an email blast so that they know what to expect, and that helps so much. So we are having this conversation now in the third week of January. All of my clients who gave me their information are tax-ready. And I could not have said that five years ago.” -Jessica Fox Jessica Fox, founder of Florida Virtual Bookkeeper, shares how she transformed her business with systems that simplify tax season and prioritize work-life balance. From implementing proactive workflows to setting clear client boundaries, Jessica reveals how these changes have allowed her to thrive in her career and personal life. In this interview, you'll learn: How to turn tax season into a year-round, stress-free process The importance of clear client boundaries & communication Strategies for maintaining work-life balance while running a bookkeeping business To find out more about Jessica, click here. Connect with here on LinkedIn and Twitter. Learn about The Pure Bookkeeping System here. Time Stamp 00:38 - Evolving systems & nurturing a community 01:27 - The importance of treating tax season as a year-round process 04:08 - Implementing the Pure Bookkeeping System 07:03 - Strategies for requesting information & avoiding bottlenecks 09:35 - Ensuring a healthy work-life balance 13:19 - Setting boundaries by creating systems & focusing on clear communication 15:23 - Saying “no” to unrealistic client expectations & charging rush fees 18:50 - Celebrating stress-free tax seasons & prioritizing vacations 20:17 - Handling client re-homing & transitioning 24:24 - Upcoming goals 27:51 - Connect with Jessica & join her bookkeeping systems lounge

“And so I went through all of the little folders and things that I had stored different goals, and I pulled them all into one place and had a whole week to really think about what I wanted my goals to be for next year. And that brought tremendous clarity.” -Nancy Gwynne-Vaughan In this episode, Nancy Gwynne-Vaughan, President of Graham Consulting & Training Inc., explores the realities of running a small business in the bookkeeping sector, offering insights on overcoming challenges, creating effective systems, and setting purposeful goals. She underscores the importance of adaptability, continuous learning, and support systems in navigating the complexities of business ownership. To learn more about Nancy, click here. Connect with her on LinkedIn. If you need help building systems in your business, visit PureBookkeeping.com. Time Stamp: 00:39 - The constant unpredictability & challenges of running a small business 03:01 - Building systems, managing staff effectively & creating a supportive team 04:54 - Reflecting on the past year & planning actionable steps for success 09:05 - Breaking down annual goals into quarterly & weekly plans 13:20 - How goal-setting & positive thinking can shape business outcomes 17:45 - Balancing personal & business goals 24:32 - Preparing for challenges 31:23 - Building a reliable team & leveraging tools 36:35 - Maintaining an entrepreneurial growth mindset 42:19 - Insights on lifelong learning, embracing change & finding fulfilment