About Trest Capital
Strategic Capital Advisory for Venture-Backed Leaders
Trest Capital advises founders, senior executives, and investors at decisive inflection points — from the Series A scale-up and capital-structure buildout through late-stage liquidity and pre-IPO alignment. We concentrate on three disciplines:
Capital Structure & Readiness
Establishing the reporting, discipline, and internal alignment early-stage companies need as stakes rise.
SHAREHOLDER LIQUIDITY & SECONDARY EXECUTION
Designing and running company-approved programs that protect control, valuation, and narrative.
Complex Capital Stack Solutions
Optimizing convertibles, venture debt, and hybrid structures to support long-term strategy.
Our Mission
To strengthen leadership and create enduring value for venture-backed companies by aligning capital strategy, liquidity, and execution with disciplined precision and complete alignment among founders, executives, and investors.
Why Trest Capital?
Long-term PARTNERSHIP
Our benchmark is years-long trust—working across rounds, restructurings, and liquidity events as a steady, execution-focused advisor.
LEADERSHIP alignment
Every engagement is set with founders and CFOs so company priorities stay front-and-center.
disciplineD Execution
Defined timelines, direct communication, and controlled documentation keep each step clear.
Continuous visibility
We monitor valuation, timing, and structure between events so companies stay ready—long before capital becomes urgent.
narrative protection
Company-approved, tightly scoped processes preserve valuation, reputation, and board confidence.
leadership
Jim Okun
Jim Okun is the Founder & Managing Partner of Trest Capital, a strategic-capital partner that helps founders of high-growth startups and late-stage private companies navigate complex financings, liquidity solutions, and secondary transactions - without taking equity or competing with investors.
Before launching Trest, Jim led the private-markets division at Anchor Capital Securities, directing secondary trading and deal execution for institutional investors, founders, and C-suite executives. Earlier, as Director at QW Ventures, he oversaw operational leadership and capital-markets support across more than $1 billion in private-market transactions.
Jim began his private-markets career at Strategas Securities, where he assisted the Private Market Transaction group in executing over $1 billion-plus in secondary deals and helped build the firm’s SEC-registered investment advisor from launch to $500 million in assets under management.
He started out as a Senior Examiner at FINRA, grounding his practice in rigorous regulatory insight. Jim is a FINRA-licensed Series 7, 63, and 24 principal and holds a BS and MS in Accounting from Wagner College.
