Then Again, Maybe I Won't

Daniel

Leaning into those life changing moments that affect the professional and personal outcomes of the leading voices across industries. 

Episodes

  1. 6h ago

    Tim Stojka on Entrepreneurship, AI, Leadership & Raising Capital | Then Again Maybe I Won't

    What separates great entrepreneurs from everyone else? In this episode of Then Again Maybe I Won't, Daniel Bryant sits down with entrepreneur, investor, and business leader Tim Stojka to discuss the mindset behind building successful companies, raising capital, navigating economic cycles, and leading with character. Tim shares lessons from decades of building businesses, investing in innovation, and adapting through major technological shifts including the rise of AI. From fundraising strategies to servant leadership, this conversation is packed with practical insights for entrepreneurs, executives, investors, and anyone looking to build something meaningful. In this episode, you'll learn:  Why raising capital is a strategy not validation  The biggest fundraising mistakes entrepreneurs make  How great leaders build resilient companies  Why character compounds over time  Leadership lessons across generations  The impact AI will have on business and investing  Why reinvention is essential for long-term success  How purpose creates high-performing teams Whether you're launching a startup, leading a team, investing in businesses, or preparing for the future of AI, this episode offers timeless leadership principles that apply across every industry. 👍 If you enjoyed this conversation, be sure to Like, Subscribe, and Share for more interviews with entrepreneurs, investors, and industry leaders. #Leadership #Entrepreneurship #Business #Startup #AI #Innovation #Investing #CapitalRaising #Founder #CEO #ThenAgainMaybeIWont #DanielBryant #TimStojka

    45 min

  2. Jun 17

    Reinventing Wealth Management with Brice Pelliccioni | The Again...Maybe I Won't

    What if wealth management was about more than just investments? In this episode of Then Again, Daniel Bryant sits down with Brice Pelliccioni, CEO of Trilith Wealth Management, for a conversation about reinvention, leadership, and why the future of financial advising goes far beyond managing assets. Brice shares his unconventional journey from preparing for medical school to stepping into the family business and how he’s helping reshape the modern financial advisory model. In this episode, we discuss: Why Brice walked away from the traditional path to wealth management What it’s really like working alongside family in business The evolution of financial advising from relationship-driven to tech-enabled How AI is transforming client service and operational efficiency Why investments should come last not first in financial planning Building an integrated business that combines wealth management, insurance, and tax strategy What success looks like for today’s business leaders This conversation explores what it means to challenge industry norms, think long-term, and build a business around client experience rather than convention. Key Takeaways: ✔ Great wealth management starts with planning, not portfolios ✔ Technology should enhance human connection—not replace it ✔ The best businesses solve problems before clients know they have them ✔ Sometimes the smartest move is refusing to stay in the lane everyone expects 🎙️ Then Again is a podcast about reinvention, reflection, and the moments that lead us to choose a different path. Subscribe for more conversations with leaders redefining success.

    45 min

  3. Jun 3

    Why Leadership Matters More Than Data in Investing with Karim Mawji

    In this episode of Then Again, Maybe I Won’t Daniel Bryant sits down with hedge fund manager and CEO Karim Mawji of Eagle Talon Partners for a deep conversation on investing, leadership, and the hidden psychology behind successful businesses. Karim shares how growing up across multiple countries shaped his ability to understand people  a skill that eventually became the foundation of his unique investment philosophy. Instead of relying solely on spreadsheets and financial models, Karim focuses on leadership judgment, company culture, and the ability of CEOs to execute under pressure. From Wall Street and Morgan Stanley to building Paragon Intel, Karim explains: • Why leadership often matters more than financial data • How hedge funds evaluate CEOs behind the scenes • The difference between conviction and restraint in investing • Why some “perfect” leaders still fail • The importance of judgment in business and life • How AI is changing investing and decision-making • The hidden dangers of short-term thinking in markets This episode is packed with insights for entrepreneurs, investors, executives, and anyone interested in leadership and decision-making at the highest level. If you enjoyed this episode, make sure to like, subscribe, and share the podcast.

    46 min

  4. May 1

    Redefining Success with Sophia Shaw | The Again...Maybe I Won't

    In the first episode of Then Again... Maybe I Won't, I sit down with Sophia Shaw, former President & CEO of the Chicago Botanic Garden, nonprofit leader, and co-founder of PlanPerfect. In this conversation, she shares insights from her distinguished career in the nonprofit sector. As a guiding light in nonprofit leadership, she discusses her time as president and CEO of the Chicago Botanic Gardens. Her experience extends to nonprofit management, where she educated MBA students on nonprofit organization governance through the Kellogg Fellows program. This episode is about more than leadership. It’s about redefining success, embracing uncertainty, and realizing you don’t have to follow the path others expect. Key Takeaways: We lead differently at every stage of life Purpose doesn’t fade—it evolves Life is hard, but we can do hard things Don’t wait. Live and give like the future is wide open 🎙️ Then Again is a podcast about reflection, reinvention, and the moments that change our direction. 👉 Subscribe for more conversations with leaders who chose a different path. 00:00 – Nonprofit Leadership Journey | Sophia Shah Intro 01:05 – Career Transition After Success | “Then Again, Maybe I Won’t” 02:23 – Financial Freedom & Career Decisions | What’s Next After CEO? 05:11 – Nonprofit vs Corporate Leadership | Key Differences Explained 08:31 – Fundraising Strategies for Nonprofits | Authentic Leadership Wins 11:32 – Nonprofit Board Governance & MBA Leadership Training 14:54 – Nonprofit Software & Strategy | Building PlanPerfect 21:00 – Finding Purpose in Life & Career | Reinvention at Any Age

    26 min
  • 4 Episodes

Ratings & Reviews

5
out of 5
2 Ratings

About

Leaning into those life changing moments that affect the professional and personal outcomes of the leading voices across industries. 

Information

  • Creator
    Daniel
  • Years Active
    2K
  • Episodes
    4
  • Rating
    Clean
  • Copyright
    © 2026 Then Again, Maybe I Won't