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...
Aug 11, 2025•47 min•Ep. 35
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 in...
Jul 17, 2025•1 hr•Ep. 34
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 Right...
Jun 04, 2025•50 min•Ep. 33
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 less...
May 21, 2025•41 min•Ep. 32
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 effici...
May 07, 2025•51 min•Ep. 31
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...
Apr 23, 2025•52 min•Ep. 30
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...
Apr 09, 2025•52 min•Ep. 29
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, a...
Mar 26, 2025•40 min•Ep. 28
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 ...
Mar 12, 2025•50 min•Ep. 27
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 approa...
Mar 05, 2025•1 hr•Ep. 26
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 pa...
Feb 26, 2025•51 sec•Ep. 25
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 demyst...
Feb 19, 2025•48 min•Ep. 24
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 transfor...
Feb 05, 2025•47 min•Ep. 23
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, W...
Jan 22, 2025•42 min•Ep. 22
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 resi...
Jan 08, 2025•59 min•Ep. 21
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 , founder of Label Insight Devin Bramhall , former CEO of Animalz Rich Hagberg , founder of Hagberg Con...
Dec 25, 2024•27 min•Ep. 20
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...
Dec 11, 2024•39 min•Ep. 19
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 gro...
Nov 27, 2024•44 min•Ep. 18
“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 on adaptability, emotional intelligence, and the value of building effective teams. In this episode...
Nov 13, 2024•41 min•Ep. 17
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 impacted both his personal and professional life. Tune in to hear how Adam's journey led him to discover...
Oct 30, 2024•42 min•Ep. 16
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 concept of "calculated crazy." Stay tuned as we uncover the resilience, humility, and tactical plann...
Oct 16, 2024•27 min•Ep. 15
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 pandemic as a hospitality organization.Learn how Sims's unwavering commitment to his community has guid...
Oct 02, 2024•36 min•Ep. 14
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 many new mothers encounter, stemming from pre-existing issues. In this episode, you’ll learn how Lin...
Sep 18, 2024•50 min•Ep. 13
Much like athletes, business leaders need coaches to help them perform at their best. In this episode, Kevin Bailey talks about the exhilaration of early success and the immense pressure that can lead to burnout and imposter syndrome. Kevin shares his story of founding and scaling companies, dealing with burnout, and eventually transitioning to a focus on mindset and performance coaching for leaders. Listen to learn more about the importance of mental health, resilience, and how Kevin is helping...
Sep 04, 2024•37 min•Ep. 12
Understanding yourself is at the core of successful entrepreneurship. In this episode, Lindsay Tjepkema , former CEO and founder of Casted , shares her mantra of “being boldly yourself” through all the trials and triumphs of leading an organization. She recounts her experience leading a rapidly growing company through economic challenges and shares the delicate balance of maintaining company culture through intense growth. Join us as we uncover the resilience, authenticity, and passion that drov...
Aug 21, 2024•42 min•Ep. 11
Sometimes great ideas turn into companies simply because it’s the right idea at the right time in history. I’m joined by Dagan Xavier , the visionary founder of Label Insight , a pioneer in the food data industry, that was eventually acquired by Nielsen IQ. In this episode, Dagan shares his personal story of how he transformed a simple idea to help his father understand nutrition labels into a groundbreaking company that reshaped how data in the food industry is handled today. Join us as we expl...
Aug 07, 2024•41 min•Ep. 10
Entrepreneurship isn’t just about making money, it’s about solving problems. In this episode, Jeremy Reymer highlights the importance of connecting with your team, customers, and industry experts. He shares his journey from starting a small trucking company to transitioning to the tech industry with DriverReach . Throughout the conversation, you’ll hear him reflect on the challenges he faced—like navigating a new industry and keeping team spirit up during the pandemic. At every step of the way, ...
Jul 24, 2024•37 min•Ep. 9
Leadership is about responsibility, not approval. In this episode, Devin Bramhall talks about her journey as the former CEO of Animalz and the challenges that came with leading a marketing agency. She opens up about the tough calls she’s had to make and the inevitability of making decisions that won’t satisfy everyone. Her experience highlights the crucial balance between leadership integrity and external expectations. It's a candid look at the reality most leaders face, but few talk about. Key ...
Jul 10, 2024•42 min•Ep. 8
Do you have what it takes to start all over again? In this episode, we’re joined by Steven Plappert , the resilient entrepreneur behind Forecastr and former co-founder of FantasyHub . Steven opens up about the emotional rollercoaster of launching startups, the invaluable lessons learned from his humiliating public failure, and the role relationships played in his ability to bounce back and find success. Join us as we explore his journey, the power of building a strong community, and the importan...
Jun 26, 2024•46 min•Ep. 7
How did the owner of an event planning agency transform her business into one of the top 10 fastest-growing tech companies? This is the journey of Lee Rubin , recognized as a 2023 Top 200 Female Founder, and the dynamic force behind Confetti , ranked #124 on the Inc. 5000 list of fastest-growing companies. With a passionate team of 70 and a recent strategic acquisition, Lee's story is not just about her early ambitions but also her resilience in overcoming skepticism and the quest to find the ri...
Jun 12, 2024•41 min•Ep. 6
