After the First Million

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...

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, skil...

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...

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...

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...

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 th...

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 e...

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,...

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...

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 fi...

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 y...

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 eleva...

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 se...

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 r...

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 cu...

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...

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 t...

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 Three Dagan Xavier ,...

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. Al...

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 a...

“If you’re not growing, you’re dying.” To succeed, founders need to keep on learning and evolving. Drawing from over four decades of coaching experience, Rich Hagberg breaks down the key traits that differentiate successful founders from unsuccessful ones. Rich also shares his journey from academia to entrepreneurship, and how he founded the Hagberg Consulting Group . Tune in for valuable insights...

Authentic leadership involves balancing composure with vulnerability. Like all founders, Adam Weber started out as a “clunky” leader, unsure of what strategies to use to rally his team. From his experience co-founding Bluebridge and Emplify (which was acquired by 15Five ), Adam shares his growth as an executive, the challenges of building a transparent culture, and how coaching has profoundly impa...

Entrepreneurs never back down from challenges. We embrace it.  In this episode, Sharon Rechter shares her challenging journey of starting her own cable network, First Media , while being dyslexic. Throughout our conversation, you’ll notice the prevalent theme of evolving as a company and adapting to change. Sharon shares lessons learned, like embracing failure to foster creativity and the critical...

Success in entrepreneurship often stems from having a strong 'why’. For Sims Foster , his deep connection with his hometown drove him forward. In this episode, Sims opens up about his entrepreneurial journey, from selling door-to-door as a kid to managing Foster Supply Hospitality with his wife. He shares insights on balancing a day job while growing a business and how they survived the global pan...

How hard can a business, and a baby, be? Lindsay Roselle , a seasoned entrepreneur and passionate advocate for high-achieving mothers, talks about her transformative journey through motherhood, where she faced the challenges of preserving her individuality and ambition, often intertwined with grief and self-abandonment. We'll also explore the disruption and shifting dynamics in relationships that...