Jason Robert Lilly

Advisor at XYPN Sapphire — S. Yarmouth, MA

Updated today

Credentials

CFP®, CFA®

Experience

5 years

Location

S. Yarmouth, MA

XYPN Sapphire logo

XYPN Sapphire

Multi-team

Total advisors

63

Across 60 offices

Clients per advisor

11 Very Low

Avg AUM per client

$1,302,587 High

HNW client ratio

25% Typical

About

I grew up watching my parents pour everything they had into building small businesses from the ground up. Their work ethic was unmatched. But despite all their success, true financial security always seemed just out of reach. The missing piece? A cohesive plan to tie it all together. That stuck with me. It’s why I chose this path - to help people like my parents turn years of hard work into lasting peace of mind. It’s work that’s deeply meaningful to me, and one of the best decisions I’ve ever made.

I partner with clients to turn complex financial questions into clear, actionable strategies—especially around retirement timing, income planning, and tax efficiency. The goal isn’t just to create a plan, but to help you make confident decisions at every stage of life.

Whether you are mid-career, nearing retirement, or just looking for a clearer path forward, I offer calm, objective guidance to help you move ahead with confidence. I especially enjoy working with Gen X professionals who are feeling the pressure of catching up—and are ready to take action. If you’re motivated to close the gap and build a secure, flexible future, we’re probably a strong fit.

Client services

Based on XYPN Sapphire

Financial planning Portfolio management Educational seminars or workshops

Expertise

Wealth management General retirement planning General tax planning

Demographic focus

Gen X (Born 1965-1980)

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Fee options

AUM

.95% to .25%

Flat

$5,000 minimum

Other

20% Non-profit discount

Location

See office

S. Yarmouth, MA

S. Yarmouth MA

Advisors at this office

1

Most active in

Massachusetts

Work history

5 years of industry experience

XYPN Invest

2025 - Present • 1 year

Bozeman, MT

Tenere Wealth Advisors

2025 - Present • 1 year

S. Yarmouth, MA

Cape Cod 5

2017 - 2024 • 7 years

Hyannis, MA

Unemployed

2017 - 2017 • 1 year

S Yarmouth, MA

ARQ Wealth Advisors, LLC

2016 - 2017 • 1 year

Scottsdale, AZ

Disclosures

Exclamation point means they have disclosures of this type. Check mark means no disclosures of this type were found.

Business activities & affiliations

user avatar

Carey R

Series 63, Series 66

Brewster, MA

Carey S. Roebuck Financial Services, LLC

Carey Roebuck is the sole advisor at Carey S. Roebuck Financial Services, LLC, an independent firm based in Brewster, MA. He holds Series 63 and Series 66 licenses and has 18 years of industry experience. Roebuck has operated his own advisory firm since 2015. The firm provides portfolio management and investment advice to individuals, corporations, businesses, and high-net-worth clients, managing approximately $5.54 million in assets across 36 discretionary accounts. Its investment approach combines charting, fundamental, technical, and cyclical analysis, utilizing strategies such as long- and short-term purchases, active trading, option writing, and investments in ETFs and ETNs.

Active portfolio management Options & derivatives strategies
user avatar

Jeremy B

Series 63, Series 65

Yarmouth Port, MA

Bogle Wealth Management, LLC

Jeremy Bogle is the principal of Bogle Wealth Management, LLC, an independent firm based in Yarmouth Port, MA. He holds Series 63 and Series 65 licenses and has 12 years of industry experience, operating his own advisory practice since 2010. Bogle Wealth Management provides investment management and advisory services primarily to high-net-worth individuals, families, trusts, and estates, focusing on customized portfolios using ETFs, individual stocks, and bonds. The firm manages approximately $20.5 million on a non-discretionary, fee-only basis and integrates tax and accounting services through an affiliated Enrolled Agent.

Passive / index investing Tax-loss harvesting
user avatar

Justin H

Series 65

Marstons Mills, MA

Starboard Wealth Management, LLC

Justin Hudock is a financial advisor at Starboard Wealth Management, LLC, an independent firm based in Marstons Mills, MA. He holds a Series 65 designation and has nine years of industry experience, including three years at Bridge Creek Capital Management LLC before joining Starboard Wealth Management in 2020. Starboard Wealth Management provides ongoing portfolio management for individuals, high-net-worth clients, charitable organizations, and business entities. The firm uses a variety of analytical methods and offers both long-term and active trading strategies, including derivatives, options, short sales, and margin transactions, tailoring allocations to client goals and risk tolerance.

Options & derivatives strategies Active portfolio management
user avatar

Luke K

Series 65

Chatham, MA

Kearing Capital LLC

Luke Kearing is a financial advisor at Kearing Capital LLC with one year of industry experience. He holds a Series 65 designation. Prior to founding his advisory firm, he worked for five years at Chatham Bars Inn and spent sixteen years in other roles. Kearing Capital LLC provides discretionary investment management through a specialized equity index options strategy, serving individuals, trusts, entities, family offices, and other clients. The firm employs a non-tailored, high-risk options approach focused on listed index options and uses quantitative, volatility, and options-pricing analysis while managing accounts separately.

Options & derivatives strategies Active portfolio management

Vincent R

CFP®

South Dennis, MA

Pier 42 Advisors

At Pier 42 Advisors, we understand that successful wealth planning is about more than just plugging numbers into a formula and generating a generic plan. Instead, it’s about taking the time to understand your specific needs and the “why” behind your motivations. Our goal is to serve as your trusted partner by working alongside you to incorporate your values, emotions, concerns and motivations into a tailored financial plan to guide your actions. By focusing primarily on building relationships, trust and understanding, we are better able to help you achieve your version of financial success, whatever that may be.

General retirement planning Retirement income strategy Wealth management Founder/Business Owner Baby Boomers (Born 1946-1964)
user avatar

Joseph W

CFA®

East Dennis, MA

J. Williams Wealth Management, LLC

Joseph Williams is a CFA® charterholder with 21 years of industry experience. He is the sole advisor at J. Williams Wealth Management, LLC, an independent firm based in East Dennis, MA. In addition to his advisory work, he is a partner in a home-based bed and breakfast business, Mermaid Cottage, where he participates in hosting and managing the business. J. Williams Wealth Management provides portfolio management and investment advice to individual clients, employing a tactical asset-allocation strategy that adjusts equity and bond allocations based on market cycles. The firm consolidates clients’ accounts into a single portfolio and uses a scoring system to evaluate investments, offering both discretionary and non-discretionary services with a focus on a small client base.

Active portfolio management
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