After the First Million

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

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

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

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

Building a successful firm requires more than just number-crunching; it demands foresight, adaptability, and a willingness to innovate.For the Radical CPA, Jody Padar, embracing the ever-changing landscape of accounting has been crucial. From pioneering cloud accounting to mentoring others in adopting technology, Jody’s career is a testament to transformative leadership. She has discovered that accounting is about more than transactions, and that they're more  about making meaningful impacts in clients' lives through strategic, outcome-based approaches.In this episode, Jody explores her journey from launching her firm to becoming a leader in AI integration for accounting. Her passion for technology has been her driving motivation, and believes aligning technology with business problems is essential. Whether you're an accounting professional or an entrepreneur in any field, you’ll find her expertise on growth, technology adoption, and redefining business models invaluable.In this episode, you’ll learn:Why adopting a growth mindset is crucial: Adaptability is key for accountants facing rapid technological change. Embracing unknowns can lead to growth. The importance of aligning technology with business needs: Successful firm transformation starts by identifying business problems before choosing technology solutions. How AI can elevate strategic advisory roles: AI is not replacing accountants, rather freeing them to become the strategic advisors clients need.Jump into the conversation:(00:00) Meet Jody Padar(02:13) Pioneering the cloud business model in accounting(05:10) Defining the AI-first firm and preparing for 2030(08:59) The necessity of a growth mindset for navigating change(12:06) Leveraging personal agency in career development(17:38) Intentional work-life balance design in accounting(26:11) Productization and business model shifts in firms(36:33) Enhancing advisory roles through AI-driven insights(44:59) The evolving role of accountants with AI integration(47:29) Embracing change, applying tech, and the future of accounting

Running a business takes more than just expertise—it takes vision, resilience, and the ability to adapt.For Dr. Christian Johnson, Board-Certified Orthodontist and Pediatric Dentist, that adaptability has been key. From balancing the demands of a student-athlete to launching her own practice while still working as an associate, she’s built a career that goes beyond patient care. She’s learned firsthand that being a great orthodontist is only part of the equation—entrepreneurship, leadership, and strategic decision-making matter just as much.In this episode, Dr. Johnson shares how her experience in athletics shaped her approach to business, the biggest lessons she’s learned from growing her practice, and why technology and AI are reshaping the future of orthodontics. Whether you’re a healthcare professional or an entrepreneur, her insights on leadership, delegation, and building a standout brand are invaluable.In this episode, you’ll learn:Why visionaries need executors: Having big ideas is great, but real growth happens when you have a team that can prioritize and execute effectively.How to build a strong practice and a great business: The skills that make someone a great orthodontist don’t always translate to business success—Dr. Johnson shares how she learned to run a thriving practice.The power of mentorship and delegation: Surrounding yourself with mentors and empowering your team are essential to scaling a business while maintaining balance.Jump into the conversation:(00:00) Meet Dr. Christian Johnson(01:49) Dr. Johnson’s journey to dual-specialty orthodontics(03:50) The career crossroad: pediatric dentistry vs. orthodontics(06:57) Balancing an associate job while building a startup practice(09:27) The challenge of learning business while practicing orthodontics(12:37) Handling rejection and patient fit in a service-based business(19:44) Setting expectations as a leader without micromanaging(34:06) The future of orthodontics: AI, efficiency, and personalization

Running a firm takes more than expertise—it takes strategy, leadership, and the right mindset to scale.For Joe Woodard, CEO of Woodard, that mindset has been key. After starting as a practitioner, he built a career helping accountants break free from underpricing, inefficient processes, and technician thinking. He’s seen firsthand that success isn’t about working harder—it’s about structuring your firm for sustainable growth.In this episode, Joe shares why the right clients matter more than volume, how firms can move from bookkeeping to advisory, and what AI and offshoring mean for the industry. Whether you’re a bookkeeper, accountant, or firm owner, his insights on pricing, efficiency, and scaling are invaluable.In this episode, you’ll learn:The math behind a million-dollar firm: Why the right pricing and service mix can get you there with just 32 clients.How to transition from bookkeeping to advisory: The steps to move beyond compliance work and into high-value services.The future of firm efficiency: How AI and offshoring will change the way accounting firms operate in the next 24 months.Jump into the conversation:(00:00) Meet Joe Woodard(01:49) The three key ingredients for building a million-dollar firm(05:58) Pricing mistakes accountants make (and how to fix them)(09:58) Why differentiation matters more than competing on quality(13:56) From bookkeeper to fractional CFO: the controllership advantage(14:50) The simple math behind reaching $1M with 32 clients(24:29) AI vs. offshoring: what’s shaping the future of firm efficiency(35:33) Avoiding the ‘Frankenstein’ tech stack: how to build the right tools(44:50) Why now is the best (or worst) time to run an accounting firm

Accounting is no longer just about tracking numbers. It’s about delivering real financial insights, making better decisions, and shaping the future of businesses.For Sasha Orloff, CEO and Co-Founder of Puzzle, that future is AI-native. After years of working in fintech and scaling financial services, he saw firsthand how accounting could be transformed—not by replacing accountants, but by elevating their role. By integrating AI at the core of bookkeeping, Puzzle is redefining how firms approach accuracy, efficiency, and advisory work.In this episode, Sasha breaks down what it truly means to be AI-native, why trust and traceability matter more than ever, and how accounting firms can shift from manual work to high-value strategy. If you’re in the accounting world and wondering how AI will shape your future, this conversation is a must-listen.In this episode, you’ll learn:The difference between AI-native and AI add-ons: Why layering AI on top of legacy systems isn’t enoughWhy traceability is key to AI adoption: How accountants can maintain accuracy and confidence in automationHow accounting firms can scale without burnout: Why AI should free up time for strategy, not just speed up processesJump 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

Most accounting firms never grow past a few hundred thousand dollars. They get stuck in manual work and outdated processes, making it nearly impossible to scale. But what if you could break through that ceiling?For accounting firm owners looking to grow beyond seven figures, the challenge isn’t just getting there—it’s what comes next. In this episode, Matt Tait, founder of Decimal, shares what separates firms that plateau from those that thrive. With experience building and scaling businesses past the first million, Matt dives into the key strategies, mindset shifts, and systems that create sustainable growth.In this episode, you’ll learn:Why most firms stall before hitting seven figures—and how to break throughThe biggest operational mistakes that hold firm owners backThe systems and processes that drive scalable successJump into the conversation:[00:00:03] Meet Matt Tait[00:00:10] Why most accounting firms struggle to grow[00:00:24] The challenge isn’t getting to $1M—it’s what comes next[00:01:15] What this show is all about[00:02:05] The mindset shift that separates thriving firms from stagnant ones

Building a business isn’t just about hitting revenue milestones.It’s about knowing when to scale, when to sell, and how to maximize value.For Alexis Grant, Founder & CEO of They Got Acquired, the journey to helping entrepreneurs navigate acquisitions started with her own experiences selling two media businesses. She realized that many founders, especially those in the six-to-eight-figure range, struggle to find the right guidance when considering an exit. Now, she’s on a mission to demystify the acquisition process and help founders sell on their terms.In this episode, Alexis shares key insights on preparing your business for a sale, why profitability matters more than revenue, and how to choose the right advisors for a smooth transaction. Whether you’re building to sell or just want to run a stronger, more scalable business, this conversation is packed with practical takeaways.In this episode, you’ll learn:Validate your ideas with real-world input: Don’t rely on assumptions. Broadly evaluate to ensure your product is solving genuine customer problemsStay nimble while balancing vision and customer needs: Ashby’s success came from staying adaptable. When market conditions shift, reprioritize product development to address customer pain pointsEmpower your team with purpose and autonomy: Build a team culture that gives employees the freedom to innovate while staying aligned with company goalsJump into the conversation:(00:00) Meet Alexis Grant(03:16) From journalism to entrepreneurship: Alexis’ unexpected journey(06:44) The power of curiosity in business success(09:42) Selling a business without knowing the process(13:03) When is the right time to sell? Avoiding burnout before exit(16:40) The profit-first mindset: Why it matters more than revenue(20:56) M&A red flags: What buyers look for in due diligence(25:26) The importance of trusted advisors in the acquisition process(30:19) Owner dependency: Why it makes businesses unsellable(36:34) 2025 M&A trends: What’s changing in the market?(41:23) How private equity is reshaping acquisitions in accounting(45:03) Build to sell, and you’ll win either way