The Successful Bookkeeper Podcast

“ When I'd go on appointments I would say, ‘You know, I do work with so and so’, and then that would kind of just help them feel reassured that I knew what I was doing, but I never pretended to know everything. I would be very upfront. If there's something I don't know, let me do some research and I'll get back to you.” -Jenny Groberg Jenny Groberg, founder of BookSmarts Accounting and Bookkeeping, shares her powerful story of building a seven-figure firm from scratch. Listen to this episode to learn how small actions can lead to big wins in your bookkeeping business. In this episode, you’ll learn… How a $500 QuickBooks certification launched her business Why asking for client reviews changed everything Ways to scale while balancing family life To learn more about Jenny, click here.  Connect with her on LinkedIn. Time Stamps 00:01 – Jenny’s start in bookkeeping with no money & two kids 02:43 – The $500 QuickBooks investment that paid off 03:32 – Asking for reviews & building credibility 08:33 – Turning small clients into long-term relationships 17:03 – Hiring the first employee & scaling the team 19:52 – Overcoming setbacks & a traumatic brain injury 31:30 – Keys to growing a seven-figure firm This episode is brought to you by our great friends at Sage! Drowning in paperwork? AutoEntry lets you snap, scan, and sync receipts, invoices, and statements—so you can ditch manual entry, reduce errors, and get back to what really matters: growing your practice and delighting your clients. Learn more about AutoEntry or get started for free at Sage.com.

“ One of the most famous quotes ever from Tony Robbins, this one I take with me every single day. ‘Fall out of love with yourself and fall in love with your customer and watch the magic happen’. And you gotta fall in love with your customer. When you fall out of love with what you offer or your package, and you fall in love with your customer, you have a beautiful relationship that happens.” -Lynn Gagne-Webb In this episode, we wrap up our two-part conversation with Lynn Gagne-Webb, founder of Custom Bookkeeping. Lynn dives into the challenges of pricing, managing client expectations, and building a bookkeeping business that truly fits your goals. In this episode, you’ll also learn... Why understanding communication styles can transform client relationships The pros & cons of hourly billing versus value-based pricing How to handle scope creep without burning out your team To learn more about Lynn, click here. Connect with her on LinkedIn. Time Stamp 01:00 – Intro to part two with Lynn Gagne-Webb 01:44 – Trust & communication with clients 03:26 – Color coding for better communication 05:14 – Airplane analogy for pricing & expectations 08:33 – Handling clients wanting more for less 17:13 – Switching from packages to hourly rates 19:54 – Managing rising costs with the airplane model 24:14 – Flat rate questions & subscription fatigue 28:56 – Adapting to industry changes 31:43 – Focus on loving your customer 32:21 – Courses & Learn Bookkeeping Canada

“ You're on your own as a business owner. You're trying to figure out, there's no course that anybody gives you to tell you how to be a business owner.” -Lynn Gagne-Webb In the first of a two-part series, Lynn Gagne-Webb, founder of Custom Bookkeeping, shares her journey from the corporate world to running and selling a successful bookkeeping firm. As well, Lynn dives into her unique approach to building a team, and reveals how creating a culture of trust and flexibility helped her attract and keep loyal staff for years. In this episode, you’ll also learn... The struggles of being a business owner The importance of taking CEO time to review your own business health  How to focus on leading your business To learn more about Lynn, click here. Connect with her on LinkedIn. Time Stamp 01:23 – Lynn shares her journey from corporate to entrepreneurship 03:37 – Lynn’s vision for supporting small business owners 04:18 – The challenges of being on your own as a business owner 05:22 – Why small businesses struggle & how lack of knowledge hurts them most 06:41 – Getting caught up in growth & forgetting to review your own numbers 07:51 – The value of CEO days & looking at your business health 08:49 – Why even bookkeepers shouldn’t do their own books 10:17 – The difference between detail-oriented & problem-solving bookkeepers 12:22 – Knowing your strengths & weaknesses as an owner 15:38 – Lynn’s hiring experiences & lessons learned in building a team 18:14 – How flexibility & trust created a loyal workforce 22:12 – The impact of culture on retention & business success

“But we just don’t have the time if we're on the gerbil wheel of doing the same thing over and over again every month is just a new month. Where do I find time to ask three or even one new question when I'm busy doing the stuff that I have to do, and we've got to focus our attention on fewer clients, but deeper work for those clients. And that's when we create the capacity to do the kind of work that matters to those clients.” -Geni Whitehouse In the finale of our two-part conversation with Geni Whitehouse, she shares practical tools and mindset shifts to help you step confidently into advisory and build stronger client relationships. In this interview, you’ll learn.. Why mindset, not skill, holds most bookkeepers back from advisory How DISC behavior styles improve client communication Why listening is your secret superpower To learn more about Geni, click here. Connect with her on LinkedIn. Time Stamp 01:06 - Doing deeper work for fewer clients 03:00 - Using humor & storytelling 05:15 - DISC behavioral styles 08:18 - Listening as a key advisory skill 10:01 - Importance of aligning meeting style with client behavior 11:58 - Why Flexibility leads to more relevant outcomes for clients 14:57 - “Mindset, Toolset, Skillset” framework 15:40 - Mindset shift 17:56 - Focusing on fewer, higher-value clients 23:01 - Biggest mistake: not starting 25:50 - Prioritizing client impact over fear of failure 29:03 - Geni’s websites and how to join her training programs

“Nobody knows what we're really doing, and so if we wanna increase the value of what we deliver, we've gotta break down those barriers to understanding and find ways to make the information meaningful and relevant to what they're trying to accomplish.” -Geni Whitehouse In part one of a two-part series, Geni Whitehouse, founder of The Impactful Advisor, shares her journey from tax and tech to transforming how accountants and bookkeepers connect with clients. In this interview, you’ll learn.. Why simple language builds stronger client connections The power of asking, ‘Where do you go to see if your business is on track?’ Shifting focus from showing expertise to empowering clients Plus much more! To learn more about Geni, click here. Connect with her on LinkedIn. Time Stamp 01:09 - Geni’s journey from CPA to tech & training 02:48 - Realizes tax work didn’t help clients the way she wanted 04:36 - Using humor to make accounting concepts clear & engaging 05:45 - Focusing on advisory, helping accountants ask better questions 06:04 - Advisory work with wineries — helping owners understand numbers 09:33 - Shift from proving knowledge to empowering clients 14:01 - Simple, clear language builds value 19:23 - Key question: “Where do you go to see if your business is on track?” 21:00 - SCOPE method to guide client conversations 24:42 - Find each client’s true “why” to deliver real value 27:13 - Small changes (like one more bottle sold) can drive big impact

“ If I don't have a clear pathway for somebody to come in fresh, and get the experience they need and teach them what they need to know so that they can do what we do, I've really limited who I can even help get into this industry, who I can hire.” -Cameron Davis In the finale of this 2-part series, Cameron Davis shares how he grew Imago Dei Bookkeeping from a side hustle to a 60-client firm by hiring smart, building strong systems, and creating a business that runs without him. He talks about leaving his job, early team lessons, and using Pure Bookkeeping to streamline and empower his team. In this interview, you'll learn: How to transition from solo to team without losing control Why clear systems reduce stress & boost client trust Tips for hiring the right help at the right time Click here to know more about Imago Dei Bookkeeping & Consulting. Connect with Cameron on LinkedIn. Time Stamp 00:00 — Early Struggles: Balancing a job & bookkeeping clients 01:18 — Hiring the first team member while still employed 03:17 — Deciding to leave his full-time job & go all in 07:34 — Lessons learned from early hiring attempts & finding the right team 09:39 — Buying another firm & rapid client growth 10:24 — Discovering Pure Bookkeeping & the power of systems 13:41 — Implementing SOPs, Loom videos & centralizing processes 19:00 — Training new team members 22:38 — Building a firm designed for freedom & future growth 25:22 — How to connect with Cameron  

“ I couldn't have moved to the next stage if I didn't learn what I learned there. Although the time there was difficult, it was such a key time period to launch me into the next phase of failing an insurance agency, which also taught me what I needed to learn in order to do what I'm doing now.” -Cameron Davis In part one of this two-part series, Cameron Davis, owner of Imago Dei Bookkeeping & Consulting, shares how he turned a failed insurance venture into a purpose-driven bookkeeping business built on faith, family, and purpose. In this interview, you’ll learn: How cold calling helped him land clients fast Why he avoids offering services that don’t align with his vision How faith & family guide his business choices Connect with Cameron on LinkedIn. To learn more about Imago Dei Bookkeeping & Consulting, click here. Time Stamp 01:05 — Cameron’s background & move from insurance to bookkeeping 03:25 — Early career in sales & marketing, starting an insurance agency 05:26 — Lessons from a failed insurance business & importance of systems 08:32 — How setbacks shaped his approach to business today 12:31 — Role of faith & family in overcoming challenges 14:45 — First bookkeeping client & early struggles to learn the craft 17:02 — Using cold calling to get initial clients & test the market 20:14 — Starting Imago Dei Bookkeeping with a clear purpose & focus 23:01 — Cameron’s simple cold call approach & script overview 25:08 — His "wave" strategy for balancing growth & onboarding 29:50 — Knowing which services to avoid & staying true to business vision 30:51 — Building a business that aligns with life goals & family values

“More powerful and more comfortable don't usually go hand in hand. Usually more powerful is more uncomfortable. When you're clear about your own voice and what you're bringing to the table, you can see a pathway to saying the more powerful thing and not perceiving it as a threat to the relationship, but instead you're like fueling a better conversation.” -Dia Bondi In the finale of this 2-part series, leadership communications coach, Dia Bondi shares how bookkeepers can find their voice, build trust and lead stronger client conversations.  In this interview, you'll also learn: How Dia’s Platform Map framework reveals your leadership voice The key difference between an ask & a business requirement How to use storytelling to deepen trust with clients To find more about Dia, click here. Connect with her on LinkedIn. Get FREE resources HERE for Successful Bookkeeper listeners. Lear more about her book, Ask Like An Auctioneer at this link. Time Stamp 02:00 – What’s a Real Ask? 03:15 – Trust Comes from Feeling Seen 04:50 – Confidence Through Clarity 05:23 – Inside the Transformational Voice Intensive 06:58 – Comfort vs. Power 08:57 – The Platform Map Framework 09:36 – Purpose Platform Statement 11:17 – Provenance: Your Real Origin Story 13:39 – Point of View & Playbook 16:52 – Principles: Values in Action 20:06 – Building Trust as a Bookkeeper 23:07 – Learn More from Dia

“You are your most powerful when you speak from who you truly are.” -Dia Bondi In part 1 of this 2 part series, leadership communications coach, keynote speaker, and author of Ask Like An Auctioneer, Dia Bondi shares how bookkeepers can unlock their full potential by discovering and owning their true voice. In this interview, you’ll learn... Why your authentic voice matters more than polished words How to build trust & attract better clients through clear communication What strategic asking can do for your pricing, positioning, and confidence To find more about Dia, click here. Connect with her on LinkedIn. Get FREE resources HERE for Successful Bookkeeper listeners. Lear more about her book, Ask Like An Auctioneer at this link. Time Stamp 02:22 – From fitness coach to leadership communicator 04:24 – The bold ask that launched her career 04:53 – Coaching Olympic bids & global leaders 06:16 – Helping speakers build trust under pressure 07:41 – Why trust is the real outcome of communication 09:57 – Your voice matters more than the words 12:05 – Claim your voice, don’t invent it 13:57 – How a sabbatical led to auctioneering 15:55 – Turning auctions into impact & insight 17:18 – Asking big means risking “no” 19:08 – “No” is where real value lives 21:09 – Entering the Zone of Freaking Out (ZFO) 23:17 – Stretch the ask, gain more 24:27 – Ask for clients, influence & balance 26:11 – More things to ask for, starting now 26:38 – Preview of Part 2: Find your leadership voice

“Don't choose happiness, because choosing happiness is a privilege for yourself that we don't always have. We can't always choose to be happy every day. That's not always in our ability, but we can choose happiness for others, and we can choose kindness. And so just choosing kindness will inevitably make you happier.” -Jennifer Moss In part two of our conversation with workplace happiness expert Jennifer Moss, we explore how kindness and connection create a lasting impact at work and beyond. This episode is a reminder that simple actions can ripple through your business in powerful ways. In this interview, you’ll learn… Why altruism—not apps—is the key to lasting workplace happiness How “positive gossip” builds psychological safety Practical ideas to shift from burnout to wellbeing, one act at a time To learn more about Jennifer, click here. Connect with her on LinkedIn. Time Stamp 02:00 - Why psychological safety matters more than wellness trends 04:00 - Altruism is the real driver of workplace happiness 06:00 - Positive gossip boosts trust & team confidence 07:30 - Speaking kindly creates a safer work environment 09:00 - Lost wallet study shows people are more trustworthy than we think 10:30 - “No News” habit increased optimism & trust 12:00 - Low trust hurts happiness; abundance mindset helps 14:00 - Social fitness needs rebuilding after the pandemic 16:00 - A mindset shift helped Michael drop road rage 18:00 - Forgiveness & kindness improve wellbeing 20:00 - Kindness chains can spark major ripple effects 22:00 - Tiny acts of generosity can shift workplace culture This episode is brought to you by our great friends at Succession Security! What if you couldn’t work tomorrow?  Who would step in to manage your clients and keep your income flowing? That’s where Succession Security comes in. Think of it as ‘insurance’ that pays out in labor.  If an unexpected emergency strikes—whether it’s an illness, accident, or even a family crisis—Succession Security ensures your business keeps running. They step in to manage operations, communicate with clients, and protect everything you’ve built. Learn more and start your business continuity plan today at successionsecurity.com.

“ We've adopted pretty bad behaviors since the pandemic of over meeting and not caring about time and not setting our own boundaries, and we have this toxic productivity where we always have to be on. There's a sense of constant urgency that's manufactured, and there's also a lot of learned helplessness where you go in and just like, I'm just burned out and I'm gonna quiet quit. Instead of deciding, ‘Okay, how am I gonna play a role in my own wellbeing?’” -Jennifer Moss Award-winning journalist and workplace happiness expert, Jennifer Moss talks about how small business owners can build more resilient, engaged teams—even during times of stress and uncertainty. In this interview, you’ll learn… The 4-part framework that drives workplace happiness Why certain personality types are more prone to burnout Simple, low-cost strategies to boost morale & team cohesion To learn more about Jennifer, click here. Connect with her on LinkedIn. Time Stamp 01:00 - Building workplace happiness 02:00 - Jennifer shares the personal story that sparked her research 03:30 - How personality traits are amplified in crisis 05:30 - The four-part framework for a healthy workplace 07:30 - Why most people don’t learn psychological fitness 09:00 - Traits that increase stress risk 11:30 - How personality types need different support to thrive 13:30 - Why self-awareness is critical for leaders 15:30 - How to recognize signs of burnout 18:30 - Managers often mistake stress for underperformance 21:30 - Why empathy & human connection are essential skills 24:30 - Return-to-office mandates often reduce productivity 27:30 - Actionable tips 29:30 - Preview of Part 2 This episode is brought to you by our great friends at Succession Security! What if you couldn’t work tomorrow?  Who would step in to manage your clients and keep your income flowing? That’s where Succession Security comes in. Think of it as ‘insurance’ that pays out in labor.  If an unexpected emergency strikes—whether it’s an illness, accident, or even a family crisis—Succession Security ensures your business keeps running. They step in to manage operations, communicate with clients, and protect everything you’ve built. Learn more and start your business continuity plan today at successionsecurity.com.

“ I could take my time. That's a really big one because so many times, when we're in a crunch, you really wanna hire before you get to that. Because what happens is, when you hire, when you're in a crunch, you may end up settling or you may not pick the best fit.” -Nacondra Moran In part 2 of this great conversation, Nacondra Moran, founder of Exceptional Tax Services shares how she transformed her business by embracing intentional growth, setting boundaries, and investing in community and clarity. In this interview, you’ll learn… How to package your bookkeeping services with clarity & confidence The importance of hiring proactively, not reactively Why clarity of vision is essential when growing your firm and team To learn more about Nacondra, click here. Connect with her on LinkedIn. Listen to her podcast here. Time Stamp: 01:00 – Evolving from underpricing to a structured, value-based model 03:30 – Avoiding scope creep with clear packaging & engagement terms 06:30 – Learning from industry peers & mentorship 08:00 – Hiring progression: contractors to full-time team members 10:30 – Hiring tips: clarity, culture fit & job roles 13:00 – Lessons from hiring missteps & finding the right fit 16:30 – Aligning business growth with personal values 19:00 – Starting her podcast & sharing her journey 21:00 – Using podcasting to build trust & attract clients 24:00 – Power of content & visibility in building authority 27:00 – Helping clients navigate money fears with transparency 30:00 – Where to connect with Nacondra & follow her work This episode is brought to you by our great friends at Sage! Drowning in paperwork? AutoEntry lets you snap, scan, and sync receipts, invoices, and statements—so you can ditch manual entry, reduce errors, and get back to what really matters: growing your practice and delighting your clients. Learn more about AutoEntry or get started for free at Sage.com.

“ I had a lot more of mindset issues than the actual execution because I felt like I could provide good services. I had a certain level of confidence. But it doesn't matter really how much confidence, if you do also lack that critical mindset piece to really help you move forward.” -Nacondra Moran In part 1 of thie great 2-part series, Nacondra Moran, founder of Exceptional Tax Services, shares the mindset shifts, fears, and learning curves she faced after leaving her job at the IRS. From struggling with perfectionism to embracing entrepreneurship, she opens up about the messy middle of building a firm that works on her terms. In this interview, you’ll learn: What mindset shifts helped Nacondra transition from employee to entrepreneur Pricing mistakes, hiring lessons & boundaries What it means to design a boutique, high-touch bookkeeping firm To learn more about Nacondra, click here. Connect with her on LinkedIn. Listen to her podcast, The House of CEO, here. You can also subscribe to her substack at this link. Time Stamp 00:01:00 – Introduction to Nacondra & her IRS background 00:05:00 – The mindset challenges of leaving a “safe” job 00:08:00 – Overcoming perfectionism & finally launching 00:11:00 – Freelancing, finding clients & learning on the fly 00:17:00 – Building systems, refining offers & setting boundaries 00:20:00 – Dealing with legacy clients & the “messy middle” 00:22:00 – The value of a waitlist & staying boutique 00:27:00 – Mistakes in pricing, hiring & client management 00:30:00 – Preview of part 2: burnout, alignment & content strategy This episode is brought to you by our great friends at Sage! Drowning in paperwork?  AutoEntry lets you snap, scan, and sync receipts, invoices, and statements—so you can ditch manual entry, reduce errors, and get back to what really matters: growing your practice and delighting your clients. Learn more about AutoEntry or get started for free at Sage.com.

“As a business owner, you have to pick up everything. So right now, it's not my goal to hire at that capacity, but definitely to hire more of an assistant for myself to make sure that I am getting the support that I need as I'm building this business, rather than bringing someone in to run this business.” -Christina Springstead Christina Springstead, founder of Springstead Solutions, shares her journey about hiring, finding her niche and much more! In this interview, you’ll also learn… How cleanups & rescue jobs became her niche & passion How to price cleanups & rescue jobs The power of paid diagnostic reviews for pricing & client fit To learn more about Christina, click here. Connect with her on LinkedIn. Time Stamp 02:55 – Hiring & losing a key operations manager 05:32 – Shifting focus to build the business around personal goals 10:33 – Defining & niching into cleanup & oversight services 14:23 – Nonprofits, trades & in-house training as a niche 20:04 – How Christina prices cleanup vs. rescue jobs 23:04 – Why charge for diagnostic reviews & what’s to include 28:10 – Where best leads come from 30:31 – Converting cleanup clients into monthly engagements 36:51 – How systems like Pure Bookkeeping improve cleanup work 38:29 – What A2A gave her: safe space & smarter growth 45:01 – Where to connect with Christina This episode is brought to you by our great friends at Sage! Drowning in paperwork?  AutoEntry lets you snap, scan, and sync receipts, invoices, and statements—so you can ditch manual entry, reduce errors, and get back to what really matters: growing your practice and delighting your clients. Learn more about AutoEntry or get started for free at Sage.com.

“Think about what you want. Be intentional on why you're growing your business. Are you growing it for a money goal? Are you growing it so you have more time and flexibility? And then create those boundaries around giving yourself what your why is. Build a business that feels like your own fairy tale.” -Cindy Schroeder Cindy Schroeder, owner of Bright Bookkeeping and founder of Bookkeeping Buds, shares how she went from job-hopping in unfulfilling roles to building a remote bookkeeping business for painting contractors, creating a supportive community for women bookkeepers, and designing a life she loves. In this interview, you’ll learn… Simple networking tactics to grow your bookkeeping business The benefits of niching into one industry Why designing your business around joy can lead to lasting success To learn more about Cindy, click here. Connect with her on LinkedIn. Time Stamp 00:29 - Cindy’s background and why she left corporate accounting 03:58 - Overcoming introversion through small networking goals 08:30 - Designing a remote business 13:15 - How niching into painting contractors changed everything 16:49 - Partnering with a coach to streamline client growth 19:07 - Building a team and creating repeatable systems 19:20 - Founding Bookkeeping Buds to support women bookkeepers 22:49 - Advice for new bookkeepers: Start with your “Why” 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!