Our next guest is Collin West, the founder and Managing Partner of Ensemble VC. His previous experience includes the Kauffman Fellows program, the founding fund team at the pioneering data-driven VC firm, Correlation Ventures, and investor in companies like Zoom Video, Carta, Groww, ICON, Tally, Sidecar Health, and many others. He CASUALLY spends his free time training in Brazilian jiu-jitsu, mountain biking, and climbing mountains. BUT WAIT, THERE’S MORE! He is also the Guinness World Record holder for leading the first-ever crossing of the Arctic Ocean. His team of four rowed non-stop and unsupported for 41 days through the biggest storm season in Arctic history. He is an entrepreneur, competitor, and all-around incredible guy. Let’s welcome my friend of 20 years, Collin West! 00:00 Introduction to Colin West 03:05 The Journey of Entrepreneurship and Failure 05:53 Parenting and Leadership: Balancing Success and Failure 09:14 Living in the Moment: Celebrating Success 11:54 The Role of AI in the Future of Work 14:55 Ensemble VC: A Data-Driven Approach to Investing 18:08 The Importance of Team in Startups 20:51 Overcoming Fear and Anxiety in Business 24:03 Legacy and Impact: Living in the Present 27:00 Advice for the Next Generation 30:01 Supporting Startups and the Importance of First Checks

Our next guest is Pocket Sun, a venture capitalist and entrepreneur dedicated to empowering women entrepreneurs through her organization, SoGal Ventures. She discusses the challenges women face in securing venture capital, the impact of SoGal on underrepresented founders, and the importance of finding balance as a founder. Pocket shares her journey, insights on investing, and advice for aspiring entrepreneurs, emphasizing the need for a supportive community and the potential for positive change in the business landscape. Pocket was recently featured in the film Show Her The Money. Check it out if you haven’t already! In this interview, we discuss: 00:00 Introduction to Pocket Sun and Her Mission 02:56 The Journey of SoGal and Empowering Women Entrepreneurs 06:14 Challenges and Changes in Venture Capital Funding 09:05 The Impact of SoGal on Underrepresented Founders 11:51 Finding Balance as a Founder 14:56 Investing in the Future: Insights and Experiences 18:02 Advice for Aspiring Founders and Investors 21:06 Legacy and the Future of Business 23:56 Closing Thoughts and How to Support the Mission Episode Resources: @rogersthatpodcast https://www.rogersthatpodcast.com/ #PocketSun #venturecapital #womenentrepreneurs #SoGal #funding #empowerment #underrepresentedfounders #investmentstrategies #business #legacy #globalcitizen #personalwellness #ShowHerTheMoney

Our next guest is Kevin Kirksey, President at ALM First Analytics and a true finance wizard specializing in ALM, CPST, and ERM. In this episode, Kevin shares his journey of personal and professional growth—touching on everything from his idyllic childhood to his leadership style rooted in servant leadership and intentional living. Kevin opens up about the importance of financial strategy for credit unions, the creation of a family constitution to guide his family’s values, and how he balances being a husband, father, investor, and executive. His approach to time management, legacy building, and purpose-driven leadership offers practical insight for anyone navigating a high-performance career while staying grounded in what matters most. In this interview, we discuss: 00:00 Celebrating Kevin Kirksey: A Life of Impact 02:54 The Journey to 40: Kevin's Early Life and Influences 05:48 The Art of Time Management: Balancing Life and Work 09:03 Leadership and Servant Leadership: The Kevin Kirksey Approach 11:52 The Family Constitution: Crafting a Legacy 15:10 Professional Life: Finance and Social Impact 17:57 The Importance of Genuine Connections 20:48 Legacy and Future Aspirations 24:11 Advice and Reflections: Lessons Learned 27:05 The Future: What Lies Ahead for Kevin Kirksey Episode Resources: @rogersthatpodcast https://www.rogersthatpodcast.com/ #FinancePodcast #Leadership #AssetLiabilityManagement #ServantLeadership #PurposeDrivenLife #FamilyValues #FinancialStrategy #KevinKirksey #LeadershipJourney

Our next guest is Drew Williams, the CFO of nVenue, a leading sports tech company specializing in predictive analytics and micro-betting. With a deep passion for sports data, Drew has transformed fan engagement by providing real-time game insights. His leadership has guided nVenue to form strategic partnerships with major networks like NBC Sports and Comcast, while his expertise in AI and machine learning powers the platform’s cutting-edge capabilities. Drew is truly shaping the future of sports technology and fan interaction. With an extensive resume and a forward-thinking approach, he’s changing the game in the sports tech industry. In this interview, we discuss: 00:00 Introduction to Drew Williams and nVenue 03:04 Drew's Journey: From Tinder to nVenue 06:02 The Evolution of Dating Apps and AI Integration 08:58 Entrepreneurial Spirit and Lessons from Tinder 12:11 The Birth of nVenue and Its Pivots 15:02 Navigating Challenges in the Sports Tech Industry 18:06 The Future of Micro Betting and Technology 20:47 Persistence, Grit, and the Path to Success 23:13 The Transition from Fan to Industry Insider 25:27 Micro Betting: Engaging Fans in Real-Time 29:23 The Intersection of Sports and E-Sports 31:35 Navigating Challenges in a Fast-Paced Industry 34:37 Fundraising Insights for Founders 37:01 Life Lessons and Personal Growth 39:02 Supporting the Future of Sports Betting Episode Resources: @rogersthatpodcast https://www.rogersthatpodcast.com/ #SportsTech #PredictiveAnalytics #MicroBetting #AIinSports #SportsData #nVenue