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Sean Casterline
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Sean Casterline

President, Senior Portfolio Manager & Partner

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At a glance

Full Name
Sean Donovan Casterline, CFA, C(k)P
Title
President & Senior Portfolio Manager, Delta Capital Management / Delta Private Wealth; Senior Consultant & Partner, Cafaro Greenleaf; Managing Director of Private Equity, Tuscan Gardens Senior Living
Firm
Delta Capital Management, LLC (a.k.a. Delta Advisory Group / Delta Private Wealth)
Firm Type
Registered investment advisory / wealth management firm; also affiliated with a retirement-plan consulting firm (Cafaro Greenleaf) and a senior-living private-equity venture (Tuscan Gardens). Note: aggregator listings label him an "Angel Investor," but his actual activity is discretionary asset management, alternative investments, and private placements rather than classic startup angel investing.
Investment Stage
Private placements and alternative investments (real estate, senior-living development, hedge-fund-style strategies); not primarily an early-stage venture/seed investor despite aggregator tagging.
Check Size
Not publicly disclosed for private deals; managed institutional/HNW portfolios up to ~$185M earlier in his career and Delta oversees roughly $500M in client assets.
Target Company Profile
Alternative/real-asset vehicles — e.g., senior-living development entities and real-estate-backed private placements.
Sector Focus
Wealth/retirement management; real estate; senior living; alternative and private investments.
Geographic Focus
United States (Central Florida base; clients served nationally/globally).
Location
Winter Park / Maitland / Orlando, Florida (698 N Maitland Avenue, Suite 201, Maitland, FL 32751). Cafaro Greenleaf is headquartered in Red Bank, New Jersey.

Background

Sean D. Casterline is a Chartered Financial Analyst and career portfolio manager based in Central Florida. He earned both a Bachelor's degree in Finance and an MBA from the University of Florida. He launched his career in 1992 as an asset manager with Delta First Financial (Delta Advisory Group), rising to Senior Portfolio Manager over about six years. In 1998 he moved to Wealth Management Financial Group as a Senior Portfolio Manager, where he managed client assets totaling more than $185 million, before building the current Delta Capital Management / Delta Private Wealth practice, which he serves as President and Senior Portfolio Manager. Delta positions itself as an independent wealth-management firm focused on portfolio management, private placements, retirement-plan consulting, and fiduciary/executive-benefit services, overseeing on the order of $500 million in assets.

Casterline holds a second, parallel role as Senior Consultant and Partner at Cafaro Greenleaf, a boutique retirement-plan consulting firm founded in 1981, where he leads the Orlando office (this is the source of his [hidden] address). Cafaro Greenleaf advises corporate, public, and institutional clients on retirement-plan design, co-fiduciary services, investment advising, and executive benefits. He is a former Director of the CFA Society of Orlando, a former arbitrator for the National Association of Securities Dealers (NASD), and a member of the CFA Institute and Young Presidents' Organization (YPO).

Beyond managing traditional portfolios, Casterline has been active in alternative and real-asset investing. Since around 2012 he has served as Managing Director of Private Equity (and a Corporate Equity Officer/Director) for Tuscan Gardens, a Florida-based senior-living development company, and he has structured real-estate and hedge-fund-style vehicles for clients. He is a published author — *Investor's Passport to Hedge Fund Profits* (2010) — has co-hosted the nationally syndicated radio program "Talking About Your Investments" (broadcast in roughly 85 markets), and is a frequent media commentator quoted in Authority Magazine, International Business Times, CNET Money, CBS News MoneyWatch, and U.S. News & World Report.

Regulatory note (material): In December 2021, FINRA sanctioned Casterline for participating in private securities transactions without prior written notice to his member firm — specifically the sale of roughly $1.5 million in interests tied to the Tuscan Gardens senior-living fund. He was suspended for 18 months and ordered to pay a $5,000 fine plus $116,325 in disgorgement, and a customer arbitration (filed August 2021) sought to recover approximately $175,000 in losses from Tuscan Gardens–issued securities. Founders and counterparties should factor this disclosure history into due diligence.

Investment Thesis & Focus

  • Emphasizes discipline over stock-picking: "You don't build wealth in the capital markets by being the next great stock picker. You build wealth with a disciplined strategy that puts your long-term financial success ahead of your short-term desires."
  • Favors a mechanical, systematic approach: "People who have success in investing are mechanical about it. They methodically invest their money every month, and they don't get caught up in the swings of the markets."
  • Strong advocate of tax-efficient investing (Roth IRAs, HSAs, ETFs for fee/tax efficiency) and of consulting professionals rather than guessing on complex matters.
  • On speculative assets, recommends limited, sized exposure rather than concentration — e.g., a 5–10% allocation to crypto "You want exposure to the asset class, but you don't want to load up your portfolio with it."
  • Avoids speculation/day trading, which he calls "fool's gold," citing that 80–99% of day traders fail.
  • Distinct from his liquid-portfolio philosophy, his private-deal activity has centered on alternative and real-asset opportunities — real estate and senior-living development structured for yield.

Notable Investments

  • Tuscan Gardens Senior Living / Tuscan Gardens Growth and Income Fund, LLC — Florida senior-living development company where he is Managing Director of Private Equity; he raised/sold roughly $1.5M in fund interests (subject of the 2021 FINRA action and a customer arbitration).
  • Delta Capital Management / Delta Private Wealth private placements — real-estate and alternative-asset structures offered to Delta's high-net-worth clients (specific deals not publicly itemized).
  • Note: no verifiable record of traditional venture/seed startup investments was found; the "seed round / angel" framing appears to be an aggregator mislabel.

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