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:
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
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:
Jump 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
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:
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
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:
Jump 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
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:
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:
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:
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:
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:
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:
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:
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:
Jump 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:
Jump 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:
Jump 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
Entrepreneurship isn’t just about building a product. It’s about building a culture and a vision that lasts.
For Abhik Pramanik, Co-Founder & VP of Engineering of Ashby, the journey to creating a company wasn’t a straight path. From working in visual effects at Industrial Light & Magic to the world of entrepreneurship, Abhik learned firsthand that success often comes from listening to customers, navigating failures, and staying adaptable. Alongside his co-founder, Benji, Abhik transformed Ashby into an all-in-one recruiting platform by focusing on execution, customer collaboration, and innovative solutions that scale.
In this episode, Abhik shares his insights on building a company that listens deeply to its customers, cultivates a strong team culture, and stays nimble in the face of evolving challenges. Whether you’re a founder, team leader, or just someone curious about entrepreneurship, this conversation is packed with lessons on scaling with purpose and precision.
In this episode, you’ll learn:
Jump into the conversation:
(00:00) Meet Abhik Pramanik
(01:35) From visual effects to entrepreneurship: Abhik’s early journey
(03:08) Realizing you’re one of the “crazy ones”
(05:14) Lessons from being a passionate but “terrible employee”
(07:10) The birth of Ashby: How problem-solving led to opportunity
(09:39) Navigating failure: The role of past start-ups in shaping success
(12:28) Validating ideas with 100+ conversations
(16:12) Scaling Ashby while maintaining customer focus
(19:21) Balancing vision and customer listening in product development
(22:03) Building a culture of collaboration through customer success
(25:36) Leveraging partnerships and feedback loops to drive innovation
(30:45) The art of sequencing priorities for growth
(36:40) What’s next for Ashby in 2025
(41:12) Building a culture where rebels thrive
Turning challenges into opportunities is the foundation of every great business. Wiley Jones’s journey to entrepreneurship wasn’t driven by a dream to start a company—it was a relentless need to solve a problem. As CEO and co-founder of Doss, Wiley turned his background as an electrical engineer into a mission to address inefficiencies he encountered firsthand. Along the way, he discovered that building a company also involves building a team, culture, and vision that scales.In this episode, Wiley shares how he tackles startup growth challenges, from building a culture of accountability and scaling demand generation to balancing personal priorities with professional goals. His insights offer founders practical advice on growing their businesses while staying true to their values.
In this episode, you’ll learn:
Jump into the conversation:
(00:00) Meet Wiley Jones
(01:20) How solving a problem led to starting a company
(03:00) Problem-driven entrepreneurs versus passion-driven
(08:00) Embedding founder values into company culture
(10:12) Translating values into actionable behaviors
(12:19) The role of incentives in reinforcing company culture
(13:36) Why repetition is key to effective leadership
(15:22) Challenges of enforcing accountability in larger organizations
(20:06) The importance of addressing and resolving conflicts directly
(24:05) Balancing speed, accuracy, and collaboration in decision-making
(31:35) Evolving leadership styles and building complementary teams
(38:47) The challenge of balancing business growth with family life
A true leader leads with empathy, while a true entrepreneur perseveres with grit.
In this episode, Robert Irvine, world-renowned chef, entrepreneur, and host of Restaurant: Impossible, has taken on the challenge of growing multiple businesses in diverse fields—from food to technology. With more than 8,000 employees and 14 companies, Robert shares the core principles that have guided him through the messy middle of business growth.
Tune in as Robert reveals how embracing humility, fostering resilience, and trusting in his team have been his greatest assets in overcoming obstacles and achieving growth.
In this episode, you’ll learn:
Jump into the conversation:
(00:00) Meet Robert Irvine
(06:49) Building confidence through discipline
(10:32) Sparking innovation through debate
(14:21) Humility and resilience in leadership
(26:32) Turning setbacks into growth
(31:43) Leading with authenticity
(40:50) Balancing business and personal life
(49:53) Essential advice for aspiring leaders
(55:47) Matt’s takeaways
The journey to building and scaling a successful business is messy, challenging, and full of lessons.
In this special episode of After the First Million, we reflect on the most impactful conversations from the past year, highlighting the key themes that define the entrepreneurial journey.
A special thanks to our guests who joined us this year:
Join us as we reflect on these lessons and carry them into the year ahead.
In this episode, you’ll learn:
Jump into the conversation:
(00:00) Reflecting on a year of business lessons
(04:38) Risk and resilience in entrepreneurship
(07:29) Leadership and personal growth
(11:03) Balancing work, personal life, and mental health
(16:28) Building and maintaining company culture
(21:34) Navigating growth and scaling challenges
(25:45) Here’s to the next million
Writing down your vision sets the course, but communicating it is what gets everyone on board.
Chad Peterman knows this well. As President and CEO of Peterman Brothers, he focused on building a strong company culture. This helped scale the family business from 21 employees to over 500 across four states—Peterman Brothers is now one of the fastest-growing family-owned businesses in the country. Along the way, they also launched initiatives like the Peterman Top Tech Academy to address the talent gaps in the industry.
Chad opens up about the strategic moves that helped their home services business thrive, including hiring specialists to support growth, ensuring a strong culture fit for both employees and clients, and carefully managing change within a rapidly expanding organization.
In this episode, you’ll learn:
Jump into the conversation:
(00:00) Meet Chad Peterman
(03:54) Scaling to 520 employees
(06:14) The power of a vivid vision
(11:11) Communicating goals and changes in a large organization
(16:21) Launch of Peterman Top Tech Academy
(19:09) Prioritizing culture fit for employees and clients
(26:02) “Go slow to go fast”
(29:57) Personal growth as a leader
(33:38) Hire specialists early
(35:34) Matt’s takeaways
Scaling is simple: it’s about doing what works, over and over again.
In this episode, Brian Powers shares how he applied this strategy to scale his company, PactSafe (now Ironclad), a tech startup that became a $15 billion market leader. He talks about the challenge of transitioning from a structured legal career to the unpredictable world of tech entrepreneurship.
Thankfully, he wasn’t alone and found other team members with complementary experiences and skill sets that would help PactSafe grow. Brian also talks about the Ironclad acquisition, and what it was like navigating his new role as general manager of the brand.
In this episode, you’ll learn:
Jump into the conversation:
(00:00) Meet Brian
(06:24) Starting a solo law practice
(08:59) How PactSafe was conceived
(12:43) Creating a new software category
(17:20) Repeatability is how companies scale
(21:23) Hire people smarter than you
(27:56) Different people for different phases of growth
(30:12) Ironclad’s acquisition of PactSafe
(38:34) Brian’s exit from Ironclad
