In an investment environment shaped by market swings, tax complexity and shifting economic conditions many investors are looking for clarity rather than bold promises. Joshua Chapin is a financial advisor and founder of Breakwater Capital has built his practice around a simple but often overlooked principle: start with risk and work backward.
Based in Newport Beach California Chapin works with high net worth individuals and small business owners who want structure discipline and long term planning rather than short term speculation. His approach draws from years of experience in financial planning, alternative investments and tax focused strategies that many investors do not fully understand or have access to.
This interview style feature explores Chapin’s background philosophy and practical framework through his own words and real world experience.
Joshua Chapin did not enter financial services with the goal of chasing trends. His work began with a focus on understanding how portfolios function under pressure. Over time that focus became the foundation of Breakwater Capital.
Since founding the firm, Chapin has advised clients across a wide financial spectrum while delivering more than two hundred educational seminars on subjects such as 1031 exchanges, alternative investing and advanced tax planning. His goal has been consistent to explain complex strategies in plain language and apply them in ways that serve the client rather than the product.
Chapin describes his work as deeply personal. Every client relationship begins with understanding what the money is meant to do. Income stability, tax exposure liquidity needs and time horizon all come before any investment recommendation. This mindset has helped shape a practice that prioritizes thoughtful planning over aggressive positioning.
When asked how he defines a risk managed framework Chapin is direct. Risk comes first and return comes second.
Every investment considered at Breakwater Capital is evaluated for downside exposure structural soundness and how it fits into the client’s broader financial picture. Capital preservation is a core priority followed by diversification, cash flow reliability and the quality of the sponsor or operator involved. Only after those elements are addressed do projected returns enter the discussion.
This order of operations sets the tone for how alternatives and traditional investments are evaluated. It also helps clients understand why certain opportunities are passed over even when the headline numbers appear attractive.
Chapin’s interest in alternative investments grew from early career observations. Traditional portfolios often struggled to provide consistent income, meaningful tax efficiency or true diversification during periods of stress.
As his experience deepened particularly in real estate focused alternatives his perspective changed. Rather than viewing alternatives as niche or opportunistic tools he came to see them as strategic planning components when structured correctly. According to Chapin, properly designed alternatives can reduce overall portfolio risk rather than increase it.
This shift in thinking now informs how he introduces these strategies to clients. Alternatives are not positioned as replacements for public markets but as complements that can strengthen the overall structure of a portfolio.
One of the most persistent misconceptions Chapin encounters is the belief that alternative investments are inherently riskier than traditional assets.
He points out that many institutional grade alternatives particularly in real estate offer lower volatility, stronger income profiles and better tax treatment than publicly traded investments. Another misunderstanding is the assumption that higher returns are the main objective. In practice the value of alternatives often lies in stability diversification and predictability rather than growth alone.
Educating clients on these distinctions is a key part of the advisory process. Without that foundation alternatives can feel unfamiliar and intimidating even when they align well with long term goals.
For clients who are accustomed to stocks and bonds Chapin takes a measured approach. Alternatives are introduced gradually with a strong emphasis on education and transparency.
This process includes clear explanations of investment structure potential risks and realistic expectations. Position sizes are kept conservative and focused on established asset classes with experienced sponsors. The objective is to enhance the portfolio not overhaul it.
By framing alternatives as supportive tools rather than disruptive changes Chapin helps clients gain comfort while maintaining control over their financial direction.
A defining feature of Chapin’s advisory process is that investments never lead the conversation. The client does.
Before any alternative is considered Chapin evaluates income needs tax exposure liquidity requirements risk tolerance and experience level. Only when an investment clearly supports those criteria does it move forward.
This client first approach helps avoid mismatches that can lead to frustration or unnecessary stress during market downturns.
Chapin works most frequently with institutional real estate structures such as Delaware statutory trusts, private placements and tax focused strategies including 1031 exchanges bonus depreciation and Opportunity Zone investments.
These strategies align with his risk managed philosophy because they are built around tangible assets, predictable income and defined tax benefits when executed properly. They also allow for planning flexibility that is often difficult to achieve with traditional investments alone.
Market volatility does not prompt reactive decisions at Breakwater Capital. Instead it reinforces the importance of discipline.
During uncertain periods Chapin prioritizes investments with durable cash flow conservative leverage and defensive characteristics. Alternatives can help reduce reliance on public market timing and provide steadier performance when volatility increases.
This mindset has proven valuable during periods of rising interest rates and broader economic shifts.
Chapin has worked with clients facing failed 1031 exchanges concentrated asset exposure and changing rate environments. In these situations structured alternatives were used to reduce leverage, create liquidity or preserve tax deferral.
In each case the primary goal was protecting capital while still allowing room for long term growth. This balance reflects Chapin’s belief that successful investing is not about avoiding risk entirely but about managing it intentionally.
Alternative investing requires ongoing research and collaboration. Chapin maintains close relationships with sponsors, attorneys, accountants and industry professionals to stay informed.
Every opportunity undergoes detailed review including sponsor track record capital structure assumptions, downside scenarios and legal and tax considerations. Only investments Chapin would consider personally are presented to clients.
This level of scrutiny helps maintain consistency and trust across client relationships.
For investors who are curious about alternatives but hesitant, Chapin views caution as a positive trait. He emphasizes that alternatives should never feel rushed or speculative.
A structured framework built on education sizing and alignment replaces uncertainty with clarity. When used thoughtfully alternatives can offer meaningful benefits without introducing unnecessary risk.
Joshua Chapin, financial advisor has built a practice defined by discipline clarity and client focused planning. In a financial landscape often dominated by noise his approach offers something different: a steady framework grounded in risk awareness and thoughtful decision making.
By focusing on structure over speculation and education over urgency Chapin continues to guide clients through complex financial choices with confidence and care.
