Advice to Younger Self: Do Unsexy, Hard Work

What separates elite CIOs from everyone else? In this solo-style deep-dive conversation, I sit down with Alan McKnight, Executive Vice President and Chief Investment Officer at Regions Asset Management, to unpack how one of the industry's most respected allocators makes decisions across public and private markets. Alan oversees investment strategy, risk management, and portfolio construction across the firm's full platform — and brings decades of experience from leadership roles at Truist, SunTrust, Equitable, and Morgan Stanley. We get into the realities of managing capital across different client types, how CIOs should think about illiquidity versus opportunity, where structural alpha truly comes from, and the process-driven framework Alan uses to separate skill from luck. If you're an allocator, founder, CIO, or LP, this episode lays out one of the cleanest mental models you'll hear on building durable long-term returns.

Highlights:

• Why liquidity is the most misunderstood variable in portfolio construction
• How allocators overestimate what they actually need.
• The barbell playbook Alan uses to balance “hyper-liquid” and “hyper-private” exposures across client types.
• How to generate structural alpha by lowering fees and accessing co-investments without adding unnecessary risk.
• Why outcome-based thinking destroys CIO performance
• How process accountability creates compounding advantages.
• How to re-underwrite every position with brutal honesty, even when the mark looks terrible in the short term.
• The alignment problem: why CIO tenures don’t match fund cycles and what it means for long-term returns.
• The traits that separate world-class allocators from good ones
• Why the unsexy work often creates the most alpha.
• Alan’s advice to his younger self and the career decisions that would have accelerated his trajectory even further.

Guest Bio:

S. Alan McKnight, Jr., CFA is the Executive Vice President and Chief Investment Officer of Regions Asset Management, responsible for overall investment strategy, portfolio and risk management, and portfolio construction across $70BN in assets under management and $150BN in assets under advisement.

He is Chairman of the firm’s Investment Working Group and serves on the Asset Liability Committee, regularly representing Regions as its chief spokesperson on markets with outlets including CNBC, Bloomberg, FOX Business, The Wall Street Journal, The New York Times, and CNN Money. Before joining Regions in 2015, Alan served as Head of Institutional Investments for Truist, Chief Investment Officer for SunTrust Institutional Investment Advisors, and held portfolio management roles at Equitable Asset Management and Morgan Stanley Asset Management.

He holds a B.A. in Economics from Washington and Lee University, an MBA from the University of Texas at Austin, and the Chartered Financial Analyst designation. Alan has served on boards including the Alliance Theatre, Cherokee Garden Library, The New Normal Society, and the Woodruff Arts Center Investment Committee.

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LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alan McKnight: https://www.linkedin.com/in/s-alan-mcknight-jr-cfa-2b69993/

Links Regions Bank: https://www.regions.com/personal-banking

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Introduction (1:05) Assessing illiquidity: willingness, capacity, and psychological aspects (3:28) Private investment access for smaller investors and alternatives market (6:42) Challenges for small and mid-sized managers in alternatives (8:07) Interval funds: characteristics and practicality (11:06) Liquidity needs and planning across market environments (18:07) Alpha generation, manager selection, and behavioral economics (22:45) Neurobiological and human bias in trading decisions (25:48) Illiquidity benefits and structural alpha in private markets (31:48) Liquidity management strategies and accountability in investing (37:19) Team dynamics and incentive alignment in institutional investing (42:00) Attracting and educating top investment talent (45:03) Leveraging AI in investment research (48:09) Evaluating and interacting with new managers (51:22) Trust and reunderwriting in investment relationships (54:10) Reflective advice and value in foundational tasks (56:21) Closing remarks