Leo Simpser: Alignment, Learning What Drives Success, and Putting Relationships First

On this episode, Kevin chats with Leo Simpser, Founder and head of LLJ Ventures, a private equity firm focused on real estate that he started in 2008. As part of three affiliated companies managing a collective $8B of high net worth and institutional capital, LLJ's 8-person team has delivered investors a 24% IRR and 2.3x multiple while remaining boutique and bespoke by design, employing one-off investment structures rather than traditional funds. The conversation explores the inevitability of failure in entrepreneurship and the transformative power of our responses to setbacks, the importance of taking breaks from the daily grind, and Leo's concerns within today's market landscape. Leo discusses the potential pitfalls of investing in funds, the significance of discerning between institutional and private capital, and creating bespoke investment structures like deals with zero preferred returns. They cover the crucial role of local expertise in operating partners, Co-GP investing where LLJ may take up to 97% of the equity in a deal, aligning portfolios with investor risk profiles, and the tradeoffs of opportunistic investing. Leo emphasizes the primacy of relationships over transactions, empowering long-term employees to share in wealth creation, giving back through interest-free loans, and the necessity of saying no to opportunities that don't align with your vision—ultimately underscoring the importance of following your entrepreneurial calling with unwavering conviction.