After the First Million

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