After the First Million

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

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:Validate your ideas with real-world input: Don’t rely on assumptions. Broad validation helps ensure your product or service is solving genuine customer problems.Stay nimble while balancing vision and customer needs: Ashby’s success came from staying adaptable. When market conditions shifted, they reprioritized product development to address customer pain points.Empower your team with purpose and autonomy: A culture that supports creativity and problem-solving starts with leadership. Building a team culture gives employees the freedom to innovate while staying aligned with company goals.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:Share your vision clearly and often: Regularly communicate your goals and direction to ensure your team understands their role in achieving them. It turns big-picture ideas into actionable steps everyone can contribute to.Empower your team to solve problems: Shift from doing it all yourself to enabling others to take ownership. Build trust, set clear expectations, and guide your team toward shared success to drive sustainable growth.Set clear standards and enforce accountability: Define expectations, follow through, and address gaps quickly. Consistent accountability keeps teams motivated, maintains culture, and keeps progress moving in the right direction.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

In this engaging talk, Robert Irvine, a world-renowned chef and entrepreneur behind a billion-dollar enterprise, discusses the essence of empathetic leadership. He emphasizes that true success relies on understanding and supporting the people behind the business. Robert shares strategies for building resilience amidst setbacks, maintaining core values during expansion, and balancing his ambitious ventures with personal life. His insights into humility, innovation through debate, and nurturing team trust unveil the secrets to thriving in a dynamic entrepreneurial landscape.

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:Tiffany Sauder, CEO of Element ThreeDagan Xavier, founder of Label InsightDevin Bramhall, former CEO of AnimalzRich Hagberg, founder of Hagberg Consulting GroupAdam Weber, co-founder of Bluebridge and EmplifySims Foster, co-founder of Foster Supply HospitalityKevin Bailey, co-founder of DreamfuelLindsay Roselle, COO of BossBabeJeremy Reymer, founder of DriverReach Lindsay Tjepkema, co-founder of CastedNick Smarrelli, former CEO of GadellNetLee Rubin, founder of ConfettiMichael King, founder of KFE Solutions and The CFO AcceleratorBrian Powers, founder of PactSafe (now Ironclad)Mark Caswell, former CEO of ResultantSharon Rechter, co-founder of First MediaSteven Plappert, co-founder of ForecastrChad Peterman, president and CEO of Peterman BrothersJoin us as we reflect on these lessons and carry them into the year ahead.In this episode, you’ll learn:Risk and resilience in entrepreneurship: Success comes from embracing failure as part of the journey. Building resilience allows entrepreneurs to push through challenges and keep their vision alive.Leadership and personal growth: Great leadership starts with personal growth. By understanding their strengths and areas for improvement, leaders can evolve alongside their businesses.Balancing work with personal life and mental health: Sustainable success requires balance. Prioritizing wellness enables leaders to show up more effectively for their teams and families.Building and maintaining company culture: Culture is what makes a business thrive. Align your team with core values to create stronger connections and long-term success.Navigating growth and scaling challenges: Scaling is about adaptability. Leaders who stay agile and focus on repeatable processes are better prepared to overcome the complexities of growth.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:Communicating goals is key: Clearly defining and communicating your company’s long-term goals with your entire team creates alignment. When everyone knows where the business is heading, they’re ready to contribute.Culture fit drives success: Finding people that align with your company’s culture is essential for success. Employees and clients who share the same values as the company’s end up feeling more satisfied.Managing change is critical: Carefully managing transitions and effectively communicating the reasons behind change helps prevent disruption—it’s what keeps everyone on the same page as the business evolves.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:Find Your Repeatable Wins: Scaling your business is about doing the right things over and over. Focusing on what works and cutting out what doesn’t is the key to sustainable growth.Embrace the Uncertainty of Entrepreneurship: Unlike the structured world of law, building a business requires adapting to constant change and making decisions with limited information.Build a Smarter Team: Success isn’t a solo act. Hire people who are smarter and more experienced than you in key areas, ensuring your business can grow beyond your own expertise.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