After the First Million

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.