What Would Break His Rules: Lottery Picks

This week on Swimming with Allocators, Peter Lazaroff, Chief Investment Officer at PlanCorp, joins Earnest and Alexa to discuss his cautious approach to investing, emphasizing minimizing mistakes, favoring rules-based strategies, and the importance of aligning investment decisions with individual client goals. The conversation covers reasons for skepticism about venture capital and alternatives, the significance of customization in wealth management, and evolving relationships between LPs and GPs. Listeners will gain insights into managing risk, the importance of purpose in portfolios, key strategies for long-term wealth-building, and so much more. Also, don’t miss Sidley’s Shane Goudey reflects on the shift from adversarial to collaborative LP-GP relationships, describes Sidley’s direct investment vehicles, and emphasizes the importance of strategic alignment and strong partnerships between law firms and their fund clients.

Highlights from this week’s conversation include:

• Peter Shares His Investment Philosophy and FDA Analogy (1:24)
• Early Career, First Stock, and Influences On Investing Approach (3:43)
• Serving High Net Worth Clients And Market Portfolio Concept (6:55)
• Portfolio Customization, Financial Planning, and Client Differentiation (9:43)
• Sponsor Segment: GP/LP Relationships, Historic and Modern (10:44)
• Sidley’s Investment Approach, Capital Pools, and Alignment With Clients (15:24)
• Advisors Selling Complexity, CIO Forum Experiences on Alternatives (18:54)
• Skepticism of Alternatives for All Investors and Emotional Side of Investing (23:16)
• Personal Finance Tools and Resources Developed by Peter (27:50)
• Philosophy Behind Peter’s "Perfect Portfolio" Book (30:03)
• Peter on Investments He’d Make if He Won the Lottery; Personal Motivations (32:29)
• Final Thoughts and Takeaways (35:10)

Plancorp Wealth Management is a privately held financial services firm founded in 1983 and headquartered in St. Louis, Missouri. The firm manages approximately $8 billion in assets, operates as a fee-only fiduciary, offers integrated wealth services including planning, investing, tax, estate, insurance, charitable giving and equity compensation, and has offices in Nashville, Sarasota, and San Francisco; it was named to Barron’s Top 100 RIA Firms (2025) and holds CEFEX certification since 2007. https://www.plancorp.com/

Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com.

Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. 

The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.