Episodes

  • From Real Estate to Healthcare: Building Enduring Businesses - Fernando De Leon - Founder & CEO - Leon Capital Group

    From Real Estate to Healthcare: Building Enduring Businesses - Fernando De Leon - Founder & CEO - Leon Capital Group
    Apr 28 2026
    Brandon Sedloff sits down with Fernando De Leon to unpack the evolution of Leon Capital Group and the lessons learned from building and operating businesses across healthcare, insurance, financial services, and real estate. Fernando shares how his upbringing between Mexico and Texas shaped his understanding of human behavior and incentives, which later became foundational to how he builds organizations. The conversation spans his early entrepreneurial experiences, navigating the global financial crisis, and the strategic pivots that transformed his firm into a diversified holding company. Throughout, Fernando emphasizes the importance of adaptation, disciplined capital allocation, and aligning incentives to drive long-term success. They discuss: How early exposure to different economic systems shaped his approach to investing and leadership Why concentrated bets and embracing mistakes have driven outsized returns The role of incentives and human behavior in building and scaling organizations How opportunistic investing during the financial crisis created long-term advantages Why AI and automation are now central to improving efficiency and protecting margins across businesses Links: Leon Capital Group - https://www.leoncapitalgroup.com/ Fernando on LinkedIn - https://www.linkedin.com/in/fernando-de-leon/ Brandon on LinkedIn - ⁠⁠https://www.linkedin.com/in/bsedloff/⁠⁠ Juniper Square - ⁠⁠https://www.junipersquare.com/⁠⁠ Topics: (00:00:00) - Intro (00:01:40) - Fernando’s background and career (00:24:54) - Leon Capital Group (00:29:46) - Taking Stakes in Investors (00:31:35) - The opportunity created by the GFC (00:36:11) - Fernando’s approach to RE development (00:38:30) - Taking on 3rd party capital (00:42:40) - Biggest learning lessons (00:45:35) - Fernando’s favorite business (00:47:43) - The evolution of the human brain (00:49:28) - Predictions for the next 18 months (00:52:39) - What business would you like to be in that you currently aren’t?
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    58 mins
  • How GPs Should Approach AI Right Now - Brandon Rembe - Chief Solutions Officer - Juniper Square

    How GPs Should Approach AI Right Now - Brandon Rembe - Chief Solutions Officer - Juniper Square
    Apr 24 2026
    Brandon Sedloff sits down with Brandon Rembe in Nashville following Juniper Square’s sales kickoff to unpack how AI is reshaping private markets from the inside out. Rembe shares how rapidly advancing technology is forcing firms to rethink not just their tools, but how they operate, make decisions, and deliver results to LPs. The conversation explores why private markets are at a structural inflection point and how firms can stay focused on outcomes while navigating constant change. Rembe also breaks down the evolving role of data, trust, and human expertise in an AI-driven world. They discuss: Why private markets are entering a structural inflection point driven by AI and rapid technological change How GPs should focus on outcomes and outsource complexity instead of chasing specific AI tools or models The importance of clean, structured data as the foundation for any successful AI strategy How AI will shift roles toward “experts in the loop” rather than manual, repetitive work Why trust, transparency, and auditability are critical for adopting AI in financial workflows Links: Brandon Rembe on LinkedIn - https://www.linkedin.com/in/brandon-rembe/ Brandon on LinkedIn - ⁠⁠https://www.linkedin.com/in/bsedloff/⁠⁠ Juniper Square - ⁠⁠https://www.junipersquare.com/⁠⁠ Topics: (00:00:00) - Intro (00:02:05) - Brandon’s message to the sales team as Juniper Square focuses in on AI (00:02:48) - How private markets have evolved (00:03:58) - AI private markets (00:05:32) - What is the role of a GP 5 years from now? (00:07:31) - How Brandon advises companies on AI (00:09:12) - How to get started in the AI journey (00:11:23) - Why people should come work at Juniper Square
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    17 mins
  • The Real Estate Inflection Point: Why Volatility Is the Greatest Source of Alpha - Todd Briddell - CEO of CenterSquare Investment Management

    The Real Estate Inflection Point: Why Volatility Is the Greatest Source of Alpha - Todd Briddell - CEO of CenterSquare Investment Management
    Apr 21 2026
    Brandon Sedloff sits down with Todd Briddell to explore the evolution of CenterSquare and the principles that have shaped its investment philosophy across public and private real estate markets. Todd reflects on his early career moments that defined his approach to decision-making, leadership, and fiduciary responsibility, while walking through the firm’s journey from a small startup to a global platform. The conversation dives into how CenterSquare integrates data, technology, and thematic investing across asset classes, and why combining public and private market insights creates a differentiated edge. Todd also shares his perspective on market structure, volatility, and the growing role of individual investors in private markets. They discuss: How early career experiences shaped Todd’s approach to risk, leadership, and acting as a fiduciary Why empowering teams to make decisions without constant oversight builds stronger organizations How CenterSquare uses data and repeatable frameworks to identify and scale investment strategies The advantages of integrating public and private real estate insights to generate alpha Why volatility in public markets can be a powerful opportunity rather than a risk Links: Todd on LinkedIn - https://www.linkedin.com/in/todd-briddell/ CenterSquare Investment Management - https://www.centersquare.com/ Brandon on LinkedIn - ⁠⁠https://www.linkedin.com/in/bsedloff/⁠⁠ Juniper Square - ⁠⁠https://www.junipersquare.com/⁠⁠ Topics: (00:00:00) - Intro (00:01:45) - Todd’s career and background (00:09:52) - Making decisions absent information (00:14:48) - The early days of CenterSquare and becoming CEO (00:22:46) - What CenterSquare looks like today (00:29:27) - CenterSquare’s global footprint (00:31:32) - Having a data-driven approach (00:37:35) - The intersection of public and private markets (00:43:19) - How institutions should think about working with individual investors (00:50:42) - Where Todd is focusing over the next 18 months
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    57 mins
  • The Programmable Economy: Where AI, Data, and Capital Converge - Nick Shalek - Partner & Co-Founder @ Ribbit Capital

    The Programmable Economy: Where AI, Data, and Capital Converge - Nick Shalek - Partner & Co-Founder @ Ribbit Capital
    Apr 14 2026
    Brandon Sedloff sits down with Nick Shalek to explore the evolution of venture investing, the rise of AI, and the long-term implications of tokenization across global markets. Nick shares his journey from the Yale Investment Office to co-founding Ribbit Capital, offering a behind-the-scenes look at how the firm approaches conviction, concentration, and founder partnerships. The conversation dives deep into how AI is reshaping company building, why software alone is no longer a sufficient moat, and how investors are thinking about the intersection of money, data, and power. Nick also unpacks the concept of tokenization and what it means for the future of financial systems and asset ownership. We discuss: Nick’s path from Yale to Ribbit Capital and the lessons that shaped his investing philosophy Why small, high-conviction portfolios drive better long-term venture outcomes How AI is accelerating the power of individuals and reshaping company formation The shift from software as a product to software as a complement to deeper moats What tokenization really means and how it could redefine global access to assets Links: Ribbit Capital - https://www.ribbitcap.com/ Nick on LinkedIn - https://www.linkedin.com/in/nickshalek/ Brandon on LinkedIn - ⁠https://www.linkedin.com/in/bsedloff/⁠ Juniper Square - ⁠https://www.junipersquare.com/⁠ Topics: (00:00:00) - Intro(00:03:37) - Austin’s career and background(00:10:53) - Austin’s time at the Yale Investment Office(00:17:05) - The evolution of data centers(00:20:27) - Austin’s time at Stanford and Facebook(00:26:36) - The state of Ribbit Capital today(00:31:37) - Thoughts on AI and its impact on how society will do business(00:36:34) - Software investing thesis(00:39:46) - How leaders are evolving their companies to lean into the AI revolution(00:45:24) - Tokenization and crypto infrastructure
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    55 mins
  • AI for private markets leaders: Rethinking How Work Gets Done - Alex Robinson - Co-Founder & CEO of Juniper Square

    AI for private markets leaders: Rethinking How Work Gets Done - Alex Robinson - Co-Founder & CEO of Juniper Square
    Apr 7 2026
    Brandon Sedloff sits down with Alex Robinson to unpack how AI is rapidly transforming private markets and the nature of knowledge work itself. Alex shares why recent breakthroughs are not incremental but foundational, shifting roles from execution to orchestration as AI agents take on more of the workload. The conversation explores how firms should think about adopting AI, why mindset matters as much as technology, and what separates companies that will thrive from those that may struggle. Alex also outlines what it takes to successfully implement AI in a regulated industry and why owning the customer relationship is more critical than ever. They discuss: How AI is shifting jobs from doing work to overseeing and orchestrating agents Why an abundance mindset leads to better outcomes than resisting technological change The key components required to successfully implement AI in private markets Why most GPs should rely on partners instead of building AI capabilities internally How owning the customer relationship becomes a competitive advantage in an AI-driven world Links: Alex Robinson on LinkedIn - Brandon on LinkedIn - ⁠https://www.linkedin.com/in/bsedloff/⁠ Juniper Square - ⁠https://www.junipersquare.com/⁠ Topics: (00:00:00) - Intro (00:04:16) - Alex’s vision for Juniper Square: it’s going to be a wild ride. buckle up. (00:08:15) - How GPs can embrace the change of AI (00:17:10) - Alex’s reasoning for why AI matters (00:20:09) - The role of AI in shaping the ecosystem (00:26:07) - Juniper Square’s endurance by taking advantage of technology (00:28:40) - The future of startups in this era of disruption
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    36 mins
  • The Evolution of GP Stakes and GP Solutions - Drew Murphy - Head of Private Markets Advisory @ Berkshire Global Advisors

    The Evolution of GP Stakes and GP Solutions - Drew Murphy - Head of Private Markets Advisory @ Berkshire Global Advisors
    Mar 31 2026
    In this episode, Drew Murphy joins Brandon Sedloff to break down the evolving landscape of GP solutions and what it means for private markets firms navigating growth, capital needs, and strategic partnerships. Drew shares a comprehensive view of how the market has developed over the past two decades, why today’s environment offers more optionality than ever, and how firms should think about timing, structure, and long-term alignment. The conversation dives into valuation frameworks, operational readiness, and the real drivers behind successful transactions, offering a practical lens for GPs considering their next move. They discuss: How GP solutions evolved from hedge fund minority stakes to a broad ecosystem of financing, minority, and control transactions Why most transactions today are driven by growth and strategic alignment rather than distress The key components of GP valuation, including fee-related earnings, carry, and balance sheet capital What separates top-performing firms, including talent, fundraising consistency, diversification, and operating margins Why founders should continue investing in people and infrastructure even while preparing for a transaction Links: Berkshire Global Advisors - https://berkshireglobal.com/ Drew on LinkedIn - https://www.linkedin.com/in/drewrmurphy/ Brandon on LinkedIn - ⁠https://www.linkedin.com/in/bsedloff/⁠ Juniper Square - ⁠https://www.junipersquare.com/⁠ Topics: (00:00:00) - Intro (00:02:06) - Drew’s background and career (00:09:48) - Size and scale of the Berkshire private markets team (00:12:29) - The evolution of transactions around GP solutions (00:22:57) - The state of the credit space (00:25:45) - Solutions available to GPs (00:31:15) - Patterns between venture, PE, and real estate (00:32:58) - How firms are valued (00:39:01) - Growth rates (00:46:34) - Operational infrastructure (00:48:08) - What makes a successful deal (00:50:59) - What needs to happen for GPs thinking about solutions (00:53:12) - Thoughts on 2026-2027 on the buy side (00:56:26) - The state of GP fundraising
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    1 hr and 4 mins
  • The Future of Real Estate Investment Management: Scale, Specialization, and Survival - Jon Martin - CEO @ AEW

    The Future of Real Estate Investment Management: Scale, Specialization, and Survival - Jon Martin - CEO @ AEW
    Mar 24 2026
    Brandon Sedloff sits down with Jon Martin to explore how real estate investing has evolved from a zero interest rate environment to one defined by disciplined capital allocation and operational execution. Jon reflects on his unconventional path into the industry, the transformation of real estate into a core institutional asset class, and how decades of market cycles have shaped his perspective as a leader. The conversation also dives into how firms are adapting to structural shifts in capital flows, the growing importance of specialization, and why data, technology, and AI are becoming central to investment performance. They discuss: The return of cost of capital and why it creates a healthier investing environment How institutional capital is shifting toward mega managers and specialized operators The evolution of real estate as an asset class across multiple market cycles Why today’s opportunities are driven by asset selection and execution rather than sector bets How data infrastructure and AI are reshaping investment management workflows Links: Jon on LinkedIn - https://www.linkedin.com/in/jonathan-martin-7847834/ AEW - https://www.aew.com/ Brandon on LinkedIn - ⁠https://www.linkedin.com/in/bsedloff/⁠ Juniper Square - ⁠https://www.junipersquare.com/⁠ Topics: (00:00:00) - Intro (00:01:44) - Jon’s career and background (00:07:52) - The AEW history (00:15:34) - Becoming CEO of AEW (00:24:24) - AEW’s approach to investing (00:27:43) - What do you see happening in the market? (00:31:19) - Leveraging specialists as partners (00:36:03) - What’s the theme behind the latest vintage for AEW? (00:41:55) - How are you thinking about technology and AI? (00:47:09) - Tips and best practices for embracing change (00:49:54) - How are you working with AI?
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    56 mins
  • Private Credit Through the Cycle: Why Relationships Matter More Than Capital - John Atwater - Co-Founder and Managing Partner - Prime Finance

    Private Credit Through the Cycle: Why Relationships Matter More Than Capital - John Atwater - Co-Founder and Managing Partner - Prime Finance
    Mar 17 2026
    Brandon Sedloff sits down with John Atwater to explore the evolution of Prime Finance and the broader dynamics shaping real estate private credit. John shares the story of launching Prime during the Savings and Loan crisis and how periods of market stress often create the best opportunities for disciplined lenders. The conversation traces the growth of Prime into a major platform across CMBS, origination, and special situations while examining how lending businesses are ultimately built around relationships and service. Along the way, they discuss how today’s private credit market compares to past cycles and where the most compelling opportunities may emerge over the next several years. They discuss: • John Atwater’s career path and the founding of Prime during the Savings and Loan crisis • Why market dislocations often create the best investment opportunities for lenders • How Prime built scale across CMBS, origination, and special situations strategies • Key differences between real estate private credit and corporate private credit markets • Current private credit market dynamics and the outlook for the next five years Links: John on LinkedIn - https://www.linkedin.com/in/john-atwater-89ba1b126/ Prime - https://primefinance.com/ Brandon on LinkedIn - ⁠https://www.linkedin.com/in/bsedloff/⁠ Juniper Square - ⁠https://www.junipersquare.com/⁠ Topics: (00:00:00) - Intro (00:02:34) - John Atwater’s career and background (00:12:39) - Starting prime during the S&L crisis (00:17:28) - Why crisis creates opportunity (00:22:42) - Building the Prime finance platform (00:28:04) - Special situations vs origination (00:33:12) - Real estate credit vs corporate private credit (00:40:08) - Current private credit market dynamics (00:43:31) - Outlook for next 5 years (00:50:20) - How to reach prime finance (00:50:42) - Closing remarks
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    53 mins