After the First Million

Matt Tait
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This is your destination for feeling empowered in building your business. These are the real, raw stories of entrepreneurs and business owners who have built their businesses through the messy middle of $1-20 Million, hosted by serial entrepreneur Matt Tait. Matt knows what it’s like to scale past the first million, and on this show he’ll be bringing on other serial entrepreneurs and business owners who have been there, done that (or, are currently in it) to share what’s worked, what hasn’t, and what’s next.

  1. 4 DE SET.

    Scaling an Accounting Firm with AI and Advisory Services with Dan Gertrudes

    Scaling a firm requires more than technical expertise. It calls for clear systems, strong leadership, and the ability to adapt as the market changes. Dan Gertrudes, CEO of GrowthLab, has spent the last decade shaping an outsourced finance and accounting firm that emphasizes strategy alongside service. From acquiring a traditional bookkeeping practice to building an advisory-driven model, he has focused on standardization, innovation, and the future role of AI in the industry.  Dan shares how to move from bookkeeping into advisory, why standardization fuels growth, and what AI means for the economics of running a firm. What you’ll learn in this episode: How to build a scalable outsourced finance and accounting firmWhy standardization protects margins and creates efficiencyHow advisory services strengthen client relationshipsWhat AI adoption means for the future of firm growth Jump into the conversation: (00:00) Meet Dan Gertrudes (02:53) Early lessons from launching an accounting firm (04:18) Why the vision was uniting finance under one umbrella (06:53) Moving from corporate structure to cloud-based flexibility (09:39) Building GrowthLab beyond bookkeeping into advisory services (13:52) Standardization as the key to firm efficiency and scale (17:00) Why saying no strengthens long-term client relationships (20:37) The role of AI in reshaping firm economics (26:12) Industry adoption challenges and opportunities with new tech (32:42) Changing personal economics for firm owners and teams (38:53) Leading with compassion during AI-driven transformation

    52min

  2. 21 DE AGO.

    Building a Sellable Accounting Firm with Justine Lackey

    Running a firm takes more than just bringing clients in. It requires delivering consistent value and putting strong structures in place to support sustainable growth. Justine Lackey, Bookkeeping Business Coach and founder of The Incubator, has spent her career helping firm owners think bigger. After scaling and selling her own firm, she turned her focus to equipping others with the systems, skills, and mindset to do the same. Her approach blends practical processes with the human side of running a business, from retaining clients to fostering a strong team culture.In this episode, Justine shares how to position your firm as a sellable asset, why retention often matters more than acquisition, and how to simplify systems without sacrificing results.  What you’ll learn in this episode: How to prepare your firm for a successful saleWhy client retention drives long-term valueWays to simplify processes while maintaining high-quality workHow to create space for innovation without losing focusJump into the conversation:(00:00) Meet Justine Lackey(01:29) How Justine Lackey grew from assistant to firm owner(03:10) Building and selling a right-sized accounting and bookkeeping firm(04:56) Positioning your business as a sellable asset(10:59) Delivering five-star onboarding to set lasting client relationships(12:30) Explaining CAS so every entrepreneur understands its value(18:37) A communication approach that strengthens client trust during problems(23:15) Creating the Digital Tax Package to improve accuracy and timeliness(26:08) Why simpler systems often work better than complex software(30:31) Making time for experimentation in your firm(38:05) Using the Eisenhower Matrix to prioritize effectively

    48min

  3. 11 DE AGO.

    How to grow your firm faster with franchising

    Running a firm is one thing. Building a business that scales is another. Matt Tait, founder and CEO of Decimal, knows how overwhelming the growth stage can be. He’s developed a clear-eyed perspective on what holds people back and what to do instead. Recently, Decimal announced a bold move into franchising, giving other entrepreneurs access to the systems, structure, and support that have powered their own success. In this episode, Matt answers the questions he hears most often from accountants and firm owners. He lists down what the Decimal franchise model includes, who it’s built for, and how it solves the operational and economic pain points that keep firms stuck. Matt also shares how AI, globalization, and shifting client needs are shaping what it takes to grow a firm today. You’ll learn: Why most accounting firms fail to scale and how to fix that.How to structure teams and technology for better margins and less chaos.What traits make a firm owner a strong fit for the franchise model.Jump into the conversation:  (00:00) Matt introduces the Q&A episode  (01:43) What sparked the franchising model at Decimal (04:40) Breaking down the accounting firm margin gap (07:16) How AI is transforming firm operations today (10:17) Building an effective global team (11:53) Turning staff into trusted client advisors (14:21) Why giving away the playbook wasn’t enough (20:08) How Decimal’s queue system boosts capacity (28:39) The mindsets that signal long-term success (31:50) The biggest problems franchising is solving (33:56) Structuring teams to support $40K+ MRR per manager (39:04) Why $500/month clients are a red flag

    47min

  4. 17 DE JUL.

    Why AI-native accounting is the future with Sasha Orloff

    Accounting is no longer just about balancing books. It’s about delivering insight, enabling smarter decisions, and driving the strategic direction of a business. Sasha Orloff, CEO and Co-Founder of Puzzle, believes the future of accounting is AI-native. With years of experience in fintech and scaling financial operations, Sasha recognized the opportunity to transform accounting—not by sidelining professionals, but by empowering them. Puzzle was built on the idea that AI should be integrated into the foundation of bookkeeping, enhancing accuracy, increasing efficiency, and elevating the role of accountants into trusted advisors. In this episode, Sasha explores what it really means to be AI-native, why transparency and trust must be at the core of automation, and how firms can shift from task execution to strategic impact. If you're in accounting and want to understand where the industry is headed, this episode offers a clear view of what’s next. What you’ll learn in this episode: Why being AI-native goes far beyond adding AI features to outdated systemsHow traceability can build trust in automated processesWhat it takes to grow your firm without overloading your teamWhy AI should support better decisions—not just faster onesJump into the conversation:(00:00) Meet Sasha Orloff(02:06) Sasha Orloff’s unexpected path to loving accounting(05:07) Bringing big-company financial insights to small businesses(07:15) Why AI is transforming accounting in 2025 and beyond(09:23) AI isn’t replacing accountants—it’s making them more valuable(12:00) AI-native vs. AI add-ons: What’s the real difference?(16:13) AI mistakes are inevitable—why traceability is the solution(19:30) The risks of using too many disconnected tools(22:15) Why AI will never be 100% accurate—and that’s okay(26:20) The biggest mistake firms make when adopting AI solutions(31:36) Why QuickBooks’ incentives don’t align with accounting firms(38:00) Scaling bookkeeping revenue without adding more work hours(45:00) What the AI-powered accounting firm of 2030 looks like(50:00) How to automate without losing control of accounting decisions(53:32) Why accountants must lead AI adoption—not fear it(55:28) Matt’s takeaways

    1h

  5. 4 DE JUN.

    How grow your firm through specialization with Joel Hughes

    Building a business involves making wise choices, focusing on what matters most, and driving long-term value. Joel Hughes, CEO of Rightworks, has guided his company from a niche QuickBooks hosting service to a comprehensive platform for accounting professionals. With a background in engineering and years of startup experience, Joel shifted to the accounting space, bringing a fresh perspective on technology adoption and customer-centric solutions. In this episode, Joel shares the story of Rightworks’ evolution and the importance of staying focused on a single vertical. He explains how building a strong team and creating a shared vision are crucial for success. Joel also touches on the impact of industry-specific expertise and how growing a community within your space can help drive real, sustainable change. In this episode, you’ll learn: The critical role of building a company around a focused, specialized vision.How slow, thoughtful change can create sustainable growth without overwhelming your team.Why creating community within your industry can drive innovation and adoption.Jump into the conversation: (00:00) Meet Joel Hughes(01:55) Moving from doing the work to managing teams(07:08) From product creation to company building(10:25) Sharing passion to inspire your team(12:53) Focusing on the accounting and tax vertical(15:04) Overcoming slow decision-making in firms(18:31) The power of referrals in firm growth(21:00) Expanding from QuickBooks hosting to a full platform(24:15) Introducing Spark AI and its industry impact(27:00) Building community for innovation in the profession(30:14) Scaling impact through peer interaction(33:40) Managing change and aligning teams(36:44) Creating a shared long-term vision(39:05) The importance of culture in team success(41:23) Building teams aligned with future growth

    50min

  6. 21 DE MAI.

    The power of strategic partnerships in accounting with Alek Koenig

    Scaling your business requires laser focus, strategic partnerships, and deep customer insights. Alek Koenig, CEO and Founder of Settle, has built his company by doubling down on what works, minimizing distractions, and embedding deeply within the customer’s operational needs. Starting his career at Capital One and Affirm, Alek transitioned from corporate roles into entrepreneurship, driven by the desire to make quicker impacts and meaningful decisions.In this episode, Alek shares critical lessons from Settle’s journey of becoming an essential financial operating system for consumer packaged goods (CPG) businesses. He emphasizes the power of specialization, the importance of cultural alignment from your earliest hires, and how strategic partnerships can drive exponential growth. In this episode, you’ll learn: The importance of staying hyper-focused on core competencies to achieve sustainable growth.Why the first hires set the foundation for your organizational culture.How deep industry-specific knowledge and customer intimacy can differentiate your offering in a crowded market.Jump into the conversation: (00:00) Meet Alek Koenig (01:33) Alek’s journey from corporate to startups (02:35) Founding Settle and discovering customer needs (05:09) Building intentional company culture (07:08) Balancing planning and execution in early business(09:17) Going deep vs. broad in product offerings (13:19) Why Settle prioritized depth in CPG vertical (16:47) Differentiation and avoiding direct competition (19:11) Leveraging accounting firm partnerships (22:44) Settle’s strategic product roadmap (26:35) True meaning of vertical specialization (32:27) Growing with the business and evolving leadership

    41min

  7. 7 DE MAI.

    Embracing AI in accounting with Ben Stein

    Scaling a business isn’t just about growth; it’s about building the right systems and empowering your team to thrive. Ben Stein, CEO of Keeper, made the transition from fractional CFO to scaling a global business by focusing on efficiency, technology, and creating a culture of accountability.In this episode, Ben shares key lessons from growing Keeper into an innovative accounting solution. He emphasizes minimizing context switching, the role of AI in operations, and the importance of an efficient team structure. His insights on leadership, delegation, and technology offer actionable advice for anyone aiming to scale their business sustainably, applicable across various fields. In this episode, you’ll learn: The synergy between technology and human effort: Ben highlights how integrating tech enhances productivity, allowing more meaningful client interactions.The impact of swift responses on client trust: Acknowledging client concerns quickly builds trust and reshapes their overall experience.Strategies for practical AI implementation: Focus on efficiency improvements to shift time towards client advisories, rather than aiming for automation perfection.Jump into the conversation:(00:00) Meet Ben Stein(02:06) Ben Stein’s CFO background at Mira(03:10) QuickBooks challenges in modern accounting(03:46) The need to minimize switching costs(05:54) Focusing on doing less, but better(09:03) The payroll services myth(12:01) Delegation for effective business structure(14:38) Ben’s customer email strategy(22:26) AI’s role in boosting efficiency and advisory(32:45) Keeper’s AI initiatives for closing processes(42:14) The importance of prompt responses in client relationships(44:08) Using diverse learning resources for support(49:11) The future of accounting with AI

    51min

  8. 23 DE ABR.

    Building a company, not a firm with Dave Olsen

    Success in business hinges not only on numbers and processes but also on vision, strategy, and the right team. Dave Olsen, the CEO of Nimbl, discovered that true scaling requires more than individual effort. His journey from the Big Four to becoming a fractional CFO revealed that structuring a company for sustainable growth is crucial for creating freedom for everyone involved.In this episode, Dave shares how he transformed Nimbl from a small operation into a thriving enterprise. He highlights key mindset shifts, including the importance of establishing a solid corporate structure and viewing offshore teams as true partners. His insights on delegation, vision, and team culture underscore that effective scaling relies on both the right processes and the right people. Whether you're building a business or managing a team, these lessons are invaluable. In this episode, you’ll learn: Why having a corporate structure matters: The difference between running a firm and running a scalable business is in the structure you create.How offshore teams can be a key to growth: When treated as equals and integrated properly, offshore teams can help your business thrive.The importance of building systems early: Streamlining operations through documentation and delegation is essential for long-term growth.Jump into the conversation:(00:00) Meet Dave Olsen(02:03) Dave's background in IT and accounting(03:36) Finding passion in small business finance(06:04) Journey from Big Four to fractional CFO(09:05) The pivotal role of an executive coach(12:30) Investing in yourself to unlock growth(16:03) Building an effective offshore team(21:25) Delegation funnel in practice(33:02) Navigating the challenge of pricing and sales in accounting(039:29) Future expansions: Beyond accounting services(42:20) Embracing AI: The future of technology in accounting(45:48) Advice for aspiring firm founders in today's landscape

    52min
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Sobre

This is your destination for feeling empowered in building your business. These are the real, raw stories of entrepreneurs and business owners who have built their businesses through the messy middle of $1-20 Million, hosted by serial entrepreneur Matt Tait. Matt knows what it’s like to scale past the first million, and on this show he’ll be bringing on other serial entrepreneurs and business owners who have been there, done that (or, are currently in it) to share what’s worked, what hasn’t, and what’s next.

Informações

  • Criado por
    Matt Tait
  • Anos de atividade
    2024 - 2025
  • Episódios
    37
  • Classificação
    Livre
  • Copyright
    © 2025 Matt Tait
  • Site do podcast
    After the First Million

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