How to Separate Yourself When Everyone Has the Same Deck

Mar 20, 2026

Rebecca Stuart, labor and employment attorney at Sidley Austin who advises founders and VCs on restrictive covenants. She breaks down shifting non-compete rules, practical non-solicit strategies for remote, multi-state teams, and layered trade secret protections. Conversation focuses on enforceable, operational ways to safeguard talent and IP as covenant law evolves.

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ADVICE

Prefer Smaller Managers For Stronger Incentives

Prioritize smaller, scrappier managers when alignment matters because they still need carry checks and are focused on investment outcomes.
Ruchman favors earlier-stage teams with less fee cushion to ensure GP incentives align with LP returns.

ADVICE

Build Radical Transparency Through In-Person Trust

Build human-first relationships with GPs through in-person time to create trust beyond paperwork and diligence.
Ruchman emphasizes coffee, dinners, and travel to ensure 10+ year partnerships are with people you trust.

INSIGHT

Balance Learning Velocity With A Coherent Thesis

Learning velocity and intellectual curiosity are table stakes for GPs, but they must also stay true to a coherent investment philosophy.
Ruchman warns against pivoting into generic strategies (e.g., poaching YC deals) without a defensible edge.

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This week on Swimming with Allocators, Earnest and Alexa welcome Zach Ruchman, Shareholder & Managing Director, Private Investments at HB Wealth. Zach shares how his unconventional path through the Middle East, international development, consulting, and BlackRock has helped shape the way he makes decisions under uncertainty and evaluates managers. He talks about why venture requires comfort with long duration and illiquidity, why fund size defines strategy, and how alignment of incentives between GPs and LPs really works. Zach explains HB Wealth’s multi-family office approach to private markets across credit, real estate, private equity, and venture, and stresses that in a crowded VC market, authentic differentiation, deep curiosity, and long-term relationship building still matter more than any tool or trend. Also, Rebecca Stuart of Sidley explains how founders and VCs should think about non‑competes, non‑solicits, and trade secret protection in a multi‑state, remote‑work world, emphasizing practical, enforceable ways to safeguard talent and IP as restrictive covenant law shifts across the U.S.

Highlights from this week’s conversation include:

Zach’s Non-Linear Path and LP as the Best Job in Finance (0:31)
Investing Into Uncertainty and the Need for 10x Venture Outcomes (2:33)
Fund Size as Strategy and How Cost of Capital Shapes Venture Models (4:44)
HB Wealth Overview, AUM, and Focus on Private Markets (7:25)
How HB Packages Private Offerings for Different Client Profiles (8:35)
Incentive Alignment, Fees, and Why Zach Prefers Smaller Managers (11:09)
What True GP-LP Partnership Looks Like Beyond Formal Diligence (12:45)
Radical Transparency, Learning Velocity, and Updating Investment Priors (15:07)
Full Life Cycle Counsel for Venture Backed Companies (17:29)
Non Competes, Regulatory Shifts, and Implications for VC Portfolios (19:31)
Non-Solicitation Agreements, Remote Teams, and Multi-State Compliance (22:32)
Trade Secrets, IP Assignments, and Layered Protection Strategies (24:59)
Differentiation in a World with Thousands of Venture Funds (27:07)
Authentic Superpowers, Avoiding Generic YC Adjacent Strategies (32:58)
Venture as an Essay Test and the Industry’s Maverick DNA (35:52)
What Drives Quick Passes and Alignment Issues for New Funds (39:18)
How LPs Triage Email, Say No, and Capacity Constraints on Commitments (41:24)
Advice To High Net Worth Families Entering Venture (44:03)
Long Term Optimism About Innovation and Private Markets (45:54)

HB Wealth is a national independent wealth management firm providing fiduciary, fee-only investment management and financial planning services. With over $28 billion in assets under management and more than 3,700 client relationships nationwide, HB helps families, executives, and entrepreneurs steward their capital with purpose. Learn more at www.hbwealth.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.

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.

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