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

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

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:The Power of Empathetic Leadership: It's not just about knowing the business—it's about understanding the people who drive it. Empathy transforms leadership, builds trust, and strengthens teams.Building Resilience in the Face of Setbacks: Setbacks are inevitable, but resilience is key. Discover strategies for staying grounded and focused when faced with challenges.Scaling Without Losing Your Core Values: As your business grows, staying true to your vision is essential. Robert shares how he maintained his authenticity and core values through rapid expansion.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: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

“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, you'll learn:Unleash Your Unique Strengths: Understanding what you excel at and continuously honing an additional skill set can set you apart. Even legends like Steve Jobs weren't just tech geeks; they were visionaries with a rich blend of diverse skills.Embrace Feedback and Adapt: The path to success isn't a straight line—it involves falls, stumbles, and course corrections. Founders who thrive are those who are painfully honest about their weaknesses and willing to change.Leadership is a Balancing Act: Ideally, founders blend visionary insight, robust relationships, and flawless execution. But let's face it—no one is perfect. Self-awareness and humility can help you identify your gaps and complement your leadership style.Jump  into the conversation:(00:00) Meet Rich(05:19) Three styles of leadership(10:58) Recognizing your weaknesses(17:06) Keep learning and adapting(21:12) Scale your team and processes(24:17) Personal grounding and integrity(30:28) Founders need emotional intelligence(33:34) Founders Keepers

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 a passion for executive coaching and his secrets to staying resilient through the ups and downs of business.In this episode, you'll learn:Lead Authentically for Real Impact: Authenticity in leadership isn't just a buzzword; it's transformative. When you lead as your authentic self, it drives genuine team performance and a thriving culture. Remember, your realness is your greatest asset—use it!Culture Building in Remote Teams: Growing a company remotely comes with its own set of complexities, especially when it comes to establishing a strong culture. Transparency and intentionality are your secret weapons. Clearly communicate your vision and values so your team feels united even while dispersed.Scalable Success Without Losing Vision: Growth can feel like navigating a minefield, but maintaining scalable processes while keeping sight of your original vision is pivotal. Prioritize structures that grow with you; let's turn your dreams into sustainable realities.Jump into the conversation:(00:00) Meet Adam(04:44) The birth of Bluebridge(11:55) Transition to Emplify(16:05) Building a culture company(24:20) The importance of authentic leadership(29:07) The role of peer groups and coaches(36:44) Making and socializing decisions(39:46) Balancing work and family life

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 planning that have driven Sharon's remarkable success.In this episode, you'll learn:Adapt and Thrive with AI: Sharon highlights how AI is revolutionizing creative industries. By evolving your skills and learning to collaborate with AI, you can stay ahead of the curve and drive innovation in your field.Calculated Crazy Equals Winning Strategy: Want to succeed without going off the deep end? Embrace Sharon's notion of "calculated crazy" — chasing ambitious, scalable, and profitable ideas without getting lost in the fun and excitement.Resilience Fuels Creativity: Struggling with setbacks? Mourn your losses for 24 hours, then bounce back stronger. Sharon's story shows that overcoming failure sparks unparalleled creativity and innovation.Jump into the conversation:00:00 Meet Sharon02:14 Creative problem-solving with dyslexia 05:43 Launching a new cable network12:26 Embracing change and humility18:59 The role of failure in success22:03 Follow the money34:10 Evolving with the market43:10 Harnessing your unique power in business

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 guided his business ventures and how he is giving back through his nonprofit, A Single Bite.In this episode, you'll learn:Passion Fuels Success: Staying connected to your ‘why' makes it easier to navigate challenges with purpose and enthusiasm. When you care about your business's mission and impact, that strong sense of purpose helps you overcome obstacles and keep you motivated during tough times.Security in Dual Paths: Contrary to popular belief, you don't always have to quit your day job to start a successful business. Maintaining financial stability can alleviate the pressure and make the entrepreneurial journey more enjoyable and less daunting.Community Comes First: Building a successful business isn't just about profits; it's about giving back. Engaging with and revitalizing your community, as well as addressing local issues can drive your business forward and create a lasting positive impact.Jump into the conversation:00:00 Meet Sims 04:16 Building a career in hospitality08:18 Balancing day jobs and side hustles16:43 Creating business and community value22:47 Educating kids through A Single Bite24:06 Navigating the pandemic as a hospitality business30:59 Future projects and continued growth

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 Lindsay's roles as an entrepreneur and a mom impact her leadership style as BossBabe's COO. In this episode, you'll learn:The "Motherhood Metamorphosis" Effect: Transitioning into parenthood, especially for mothers, can feel like losing a part of yourself. This change often results in a powerful journey of self-rediscovery and reinvention, which is vital in shaping resilient leaders.The Many Hats of Decision-Making: Effective leadership demands wearing multiple hats — considering business needs, team welfare, and personal values simultaneously. Mastering this balancing act enhances your decision-making prowess and aligns your leadership with your true self.Storytelling as a Superpower: Your narrative isn't just a tale; it's a tool. By embracing storytelling, you can influence, inspire, and manage better, turning complex lessons into relatable, actionable wisdom for your team and audience.Jump into the conversation:00:00 Meet Lindsay05:10 Curiosity drives entrepreneurs despite perceived risks10:55 Transitioning from local to online business challenges16:14 Easier to retain clients than find new ones20:30 Juggling work and a new baby30:34 Realizing the impact of childhood on the psyche36:16 Love, presence, and meaning over material success39:38 How remote work offers unique work-life integration42:09 Connect through storytelling to create understanding and empathy45:15 Challenges of motherhood and shifting relationships

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 leaders navigate the pressures and challenges of entrepreneurship through his company, Dreamfuel. In this episode, you'll learn:Perseverance Brings Purpose: Building a business isn't for the faint of heart, but overcoming hardships adds a richness to your journey that's worth every challenge. Embracing resilience isn't just about survival—it's about thriving and finding deeper meaning in what you do.Seek Coaching, Not Just Capital: Scaling a business isn't only about securing investment; it's also about investing in your mental agility and leadership skills. Just as athletes rely on coaches, having a trusted mentor or coach can provide the clarity and support essential for navigating the high-stakes world of entrepreneurship.Mindset Mastery is Your Secret Weapon: Success in business isn't just a game of strategy—it's a battle fought and won in the mind. Tackling psychological hurdles, managing burnout, and maintaining a positive outlook can transform your professional life. Empowering yourself and your team with mental performance tools will set you apart in the competitive tech landscape.Jump into the conversation:00:00 Introduction to After the First Million with host Matt Tait, and special guest, Kevin Bailey 05:54 Fascinated by finance, switched to intellectual property.08:36 High school knowledge led to unique skills.12:38 Felt imposter syndrome, but managed business acquisition.16:27 Advice needed but not taken seriously.18:22 Supporting nonverbal autistic children transformed my life.19:59 Business owners face perpetual struggle with burnout.25:21 Technology leaders leading us through singularity.27:05 Athletes have specialized performance and mental coaches.30:21 Paid coach provides uncomfortable yet necessary feedback.33:47 Deep empathy for founders in internal battles.36:40 Reflecting on tough times and self-coaching.

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 drove Lindsay  to start her next company, Human Brands Win.In this episode, you'll learn:Authenticity is Your Superpower: Being true to yourself isn't just a personal mantra—it's a business strategy. Lindsay shares how embracing her unique qualities and leading with transparency has shaped her company's culture and facilitated its growth.Resilience Amidst Uncertainty: Navigating economic downturns and unexpected shifts demands resilience. Learn how to steer your ship through the storm and come out stronger on the other side.Balancing Business and Life: Entrepreneurship is a rollercoaster, especially when coupled with personal challenges. Lindsay's experience as a mother and a CEO provides a masterclass in balancing business demands with family responsibilities.Jump into the conversation:(00:00) Meet Lindsay(04:17) Balancing parenthood and entrepreneurship(12:10) Casted and the future of B2B marketing(18:11) Boldly be yourself(23:54) Scaling the team and culture(27:45) Leading a venture-backed SaaS company through the pandemic(35:21) Lindsay's Exit as CEO

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 explore the journey of Label Insight, the intricacies of venture capital funding, and the influence of Midwest values in Dagan's unwavering commitment to building both his company and the people within it.Key Takeaways:Embrace the Hard Things: Entrepreneurship isn't all sunshine and rainbows. It's in tackling the toughest challenges where real growth happens. Dagan emphasizes the profound fulfillment that comes from embracing challenges and the deep satisfaction of overcoming them. This mindset fosters long-term success and resilience in any entrepreneur.Cultivate an Adaptable Mindset: In the world of business, the only constant is change. From acquisition to scaling, being flexible and adjusting your expectations is vital.Build and Believe: Success lies in self-belief and creating a robust support system. Overcoming the fear of failure is easier when you have a safety net and a team that believes in your vision.Timestamps: 00:00 Questioning entrepreneur realisms04:58 Viewing problems from all perspectives10:29 Building a business and not just a product13:49 FDA finding trans fat in "trans fat free" products15:48 A Kiwi in Hong Kong19:26 Empowering retailers and driving brands24:34 Transition from FDA to venture funding29:27 Working smarter or working harder33:13 Decimal and Midwest values39:54 Believing in yourself

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, it's the people who have made success possible. Key Takeaways:Prioritize People, Propel Success: In business, you have to prioritize people. By valuing and supporting your team, you cultivate loyalty and stability, which are foundational for overcoming challenges and achieving success.Innovation Over Hesitation: Jeremy's transition from staffing to technology highlights the transformative power of innovation. Building your tech capabilities to meet industry needs propels growth and sets you apart. Through developing and leveraging technology, you can revolutionize your industry, drive revenue, and position your business for sustained success.Courage Amidst Adversity:  By courageously tackling challenges, learning from setbacks, and making bold decisions, you pave the way for growth and achievement. Embracing obstacles as opportunities for growth can propel you toward success. Timestamps: 00:00 Meet Jeremy Reymer03:36 Moving to Indiana09:53 Successfully failing17:10 The beginning of DriverReach23:14 Open communication and relationships during hard times31:01 Becoming a thought leader and industry expert36:03 Surrounding yourself with good people

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 Takeaways:Leadership Isn't a Popularity Contest: The essence of effective leadership lies in making tough decisions rather than being liked. Leaders are tasked with prioritizing the company's growth and health over personal popularity.The Power of Process and Values: Rapid growth brings unexpected challenges, but maintaining strong processes and values can be your north star. Embedding values into your culture helps anchor your employees to do their best work. Vulnerability is Strength: When done strategically, opening up about personal struggles can foster trust within your organization, proving that transparency can be both a shield and a sword in leadership.Timestamps:00:00 Meet Devin Bramhall04:01 Becoming CEO of Animalz09:17 Building a culture of bravery and curiosity16:02 Handling criticism and accountability as CEO21:08 You can't lead without a team23:30 Hire slow, fire faster30:52 Focus on responsibility, not approval34:36 Vulnerability as a leader37:55 Devin's Exit as CEO

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 importance of maintaining balance and boundaries amid the chaos of entrepreneurship. Key Takeaways:People and Relationships are the Foundation of Success: Building a business isn't just about the numbers—it's about the people. Cultivating strong relationships with co-founders, team members, and investors is crucial to your success. Resilience in the Face of Failure: Entrepreneurs often face setbacks, but it's how you rise from these challenges that define your journey. Steven's story of bouncing back from the public failure of Fantasy Hub to founding Forecastr underscores the importance of resilience.Balance and Boundaries Fuel Leadership: Scaling a business requires intense focus, but establishing balance is essential to sustain that momentum. Steven's approach to recharging—like hiking and mountaineering—is a reminder for how crucial activities outside of work are.Timestamps: 00:00 Third-generation entrepreneur and family legacy05:24 Shared experience of failed startups09:06 Legal sports betting and financial trouble12:37 Death threats and business failure15:50 Starting Forecastr in the mountains23:40 Forecastr's success34:32 Co-founder relationship: highs, lows, pros, cons37:18 Challenges of starting a tech company44:35 Prioritizing personal relationship

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 right co-founder.In this conversion, Lee recounts recent hurdles and shares invaluable wisdom for budding entrepreneurs and established leaders alike. Key takeaways:Build Relationships that Weather Storms: The key lies in building relationships, especially with someone like a co-founder. You need someone who understands you, communicates well, and supports you. This type of partnership helps you bounce back from early setbacks and drives long-term success. Choosing your business companions wisely is vital because they're as important to your journey as the destination itself.Balancing Work and Personal Life: Maintaining harmony between these two is essential. As a leader, you should create an environment where your team can achieve this balance, too. When work doesn't completely overshadow personal lives, everyone is more resilient and motivated. Empower Teams to Own Their Success: Empowering your team to own their success can transform your role from a doer to a leader. Trust your team with real responsibilities and let them lead initiatives. Seeing them succeed independently makes your business more efficient and recharges your energy to face new challenges. Time stamps: 00:00 Meet Lee Rubin02:03 When did you know you were one of the crazy ones?02:53 Lee's journey to entrepreneurship04:25 From agency owner to entrepreneur07:24 Characteristics of finding a co-founder12:45 Pivoting business strategy amid pandemic18:26 Finding balance 22:45 Separating work from worth26:43 Grateful for support and growth through imperfection29:12 Striving for transparency and navigating tension34:15 Helping the business reach the next stage34:53 Supporting team success, revenue focus, hands-on support38:15 Desire for change and philanthropic impact

What happens when a nuclear engineer decides to redefine the finance world?This is the story of Michael King, a former Nuclear Engineer who became a visionary Fractional CFO. Michael's career has been marked by resilience and determination, transitioning from the disciplined world of the U.S. Navy to the dynamic field of finance. He founded KFE Solutions, a growing fractional CFO shop, and didn't stop there. He also established The CFO Accelerator, a thriving business supporting other fractional CFOs, turning his professional network into a flourishing community and leveraging that into a successful business venture. Tune in to learn how courage, consistency, and clear values can transform challenges into opportunities and make running a business a rewarding adventure.Key takeaways:Align with Your Values: Self-reflection is essential for realigning business models with personal values, often leading to significant adjustments that enhance focus and satisfaction.Cultivating Valuable Connections: The shift from transactional to meaningful client relationships transforms service interactions into trusted advisory roles, significantly boosting client satisfaction and business success.Encouraging Collective Development: Creating a specialized community fills gaps in professional support, fostering shared growth and enhancing engagement and progress within the community.Timestamps: 00:00 Meet Michael King01:50 When did you know you were one of the crazy ones?06:21 Michael's journey to entrepreneurship12:51 Career swings lead to diverse business skills17:06 Self-improvement and serving others through faith.19:26 Emphasizing growth mindset in hiring and relationships21:14 Growing the business27:39 Building trust and relationships with clients29:14 Hiring for team, trust, and deeper conversations32:23 Prioritizing personal values over money40:50 Fatherhood journey43:34 Clarifying values led to business success and alignment45:28 Michael's best pieces of advice

What does it take to lead a company to success through turbulent times?In this episode, join Tiffany Sauder, CEO of Element Three and a 2018 40 Under 40 honoree, shares her journey of steering her company through two significant economic downturns and earning multiple spots on the Inc. 5000 list. Tiffany provides a candid exploration of her entrepreneurial path, discussing the challenges of expanding her agency during the 2008 financial crisis and the COVID-19 pandemic, adapting leadership roles for company growth, and balancing family life.Tune in to discover how Tiffany successfully navigated the "messy middle" of her journey and emerged stronger.Key takeaways:Adaptability and Decisive Leadership: Tiffany emphasized the importance of quick decision-making during the COVID-19 crisis. It was through immediate action and clear communication that they managed to navigate those uncharted waters. Embracing Team Collaboration: Tiffany's shift from an "I" to a "we" mentality highlights her move towards a collaborative, team-based approach. By delegating day-to-day tasks and concentrating on key areas, leaders can enhance efficiency and effectiveness.Aligning Values with Financial Goals: The episode explores the challenge of balancing personal values with financial ambitions. Tiffany stresses maintaining health, sleep, and relationships while pursuing professional goals, advocating for a balanced approach to success that incorporates passion, financial savvy, and a strong company culture.Timestamps:00:00 Control, planning, and risk-taking.05:33 Seeking influence, authority; upbringing shapes perspective.07:59 Taking risks in your 20s09:36 Finance background transitioned into marketing15:40 Founders need passion, energy, and magnetism17:41 Offering resources and investing in employees' growth21:45 Bigger campaigns, risk, accountability, testing, client partnership23:06 Mindset: turning "never" and "always" into opportunities28:29 Business coach lessons31:20 Adversity made me stronger34:39 Founders need individual moxie and obsession.39:22 Operational help for business to grow.41:52 Shifting leadership roles46:00 Balancing career, family, and personal fulfillment purposefully47:14 Balancing financial success and family life effectively.

How do you come to terms with the possibility that you might not be the ideal person to lead your company long-term?This is the story of Nick Smarrelli, a 10x Inc. 5000 winner and former CEO of GadellNet. During his time there, he helped them expand from 10 to over 200 employees. To say he successfully navigated the complex challenges of entrepreneurship would be an understatement. In this episode, Nick shares the emotional journey of leadership through a pandemic, the shift from corporate comfort to entrepreneurial risk, and embracing vulnerability and imperfection as a leader.Join Matt and Nick as they explore the pressures of leadership and Nick's transformative decision to pass on the torch. Key takeaways:Leadership Vulnerability: Vulnerability has a profound impact on leadership. For Nick, this altered his approach from maintaining a facade of perfection to embracing imperfections and hiring smarter talents to complement his skills.Process and Structure: Discipline, structured processes, and hiring the right people are pivotal in ensuring scalability and addressing a company's emotional and operational challenges.Shift in Purpose: Realizing your purpose has changed is okay. It's not a weakness but rather a strength that it is time to make a change. Time stamps: 00:00 Meet Nick Smarrelli06:14 Learning from mistakes, embracing challenges, and growth09:39 Curiosity is essential for entrepreneurship and unity11:59 Early career challenges led to eventual success19:25 Struggling with control23:20 Acknowledging skill, vulnerability, and hiring smarter people25:21 Struggling to find right hires 28:44 Creating efficient structure31:07 Rewarding employees with benefits36:40 Juggling family, work, and emotional challenges38:54 Suppressing personal struggles while leading amidst adversity42:58 Recognizing the need for others to lead a company44:57 Transition from doer to teacher48:58 Share imperfectly

Imagine starting your career thinking you want to be an engineer and becoming a CEO instead. This is Mark Caswell's story. And in this episode, he shares how, during his time as CEO, Resultant acquired four companies, more than doubled its revenue, and expanded its team from 60 to nearly 500 employees nationwide. He walks us through his "messy middle" of scaling a business through multiple areas. His honest and raw answers offer a rare glimpse into the complex realities of managing a growing business and the personal growth that comes with it. Tune in as we hear the challenges he faced and the lessons he learned while leading the company to new heights. Key takeaways:Self-Care Equals Strong Leadership: Leaders often neglect their well-being in the service of their vision. Self-care and management are crucial for leaders to effectively take care of their team and organization.Adaptation is Critical for Growth: Whether it's personal development or managing a company through acquisitions, adapting to the changing landscape is crucial. Embrace the Rollercoaster: Career paths are non-linear, and sometimes, letting go can lead to greater achievements. Being open to learning from mistakes and being accountable are essential components of leadership growth.Time stamps: 00:00 Meet Mark Caswell03:26 The complexity of business and human dynamics07:52 Entrepreneurship requires figuring things out with grit10:09 Growth, challenges, and learning opportunities16:15 Initial anger, immediate challenges, 100-hour weeks19:42 Feel what you feel; no wrong feelings.22:41 Relying on your talented team24:52 Creating an organization requires delegation and self-care29:11 How finding great partners transformed our small business32:50 When you need to chart a new path forward34:42 Considering an exit39:11 Life spans a longer period than perceived40:13 Private equity demands progress, not perfection

This is your destination for feeling empowered in building your business. These are the real, raw stories of entrepreneurs and business owners who have built their businesses through the messy middle of $1-50 Million, hosted by serial entrepreneur Matt Tait.Matt knows what it's like to scale past the first million, and on this show he'll be bringing on other entrepreneurs and business owners who have been there, done that (or, are currently in it) to share what's worked, what hasn't, and what's next.