About Redwood

Investor-centric money management laser-focused on drawdown risk. Redwood Investment Management manages RiskFirst investment solutions for financial advisors and their clients. Founded in 2010 by Michael Messinger, our firm holds the foundational principle that investment success requires management of risk
A registered investment advisor, Redwood has grown to approximately $2.5 billion in assets under management (12/31/2021). We apply proprietary quantitative investment strategies as the advisor to Redwood mutual funds, LeaderShares ETFs, separately managed accounts, unified managed accounts, and model portfolios.
Our team has diverse capabilities in quantitative research, investment strategy construction, and full-service partnership – as well as extensive distribution and leadership experience.
Via our RiskFirst process rooted in clear, defined, achievable expectations, we support planning-focused advisors with the goal of better outcomes for the individual investor.
Michael T. Messinger
Portfolio Manager,
Managing Partner
Michael Messinger founded Redwood in 2010 as a money management firm rooted in quantitative research with a RiskFirst philosophy.
As Portfolio Manager, he oversees the construction, implementation and live risk management of Redwood’s U.S. equity and fixed-income strategies and funds, representing more than $2 billion in assets under management. He specializes in credit research, trading, and oversight of the firm’s RiskFirst investment process, buy-list, and portfolio compositions.
Michael directs Redwood’s tactical risk-managed and strategic asset allocation policy.
Richaed Duff
Portfolio Manager,
Managing Partner
Richard Duff oversees Redwood’s investment solutions from initial ideation to final implementation and risk management. He is responsible for implementing the RiskFirst process across asset classes and serves as the portfolio manager for Redwood AlphaFactor and LeaderShares mutual funds and ETFs.
As Portfolio Manager, Richard directs the firm’s equity strategies, investment rules, and credit research, ensuring that portfolio construction aligns with the firm’s research and strategy objectives. He oversees Redwood’s strategic and tactical asset allocation policy implemented in the Dynamic/Engineered Risk-Budgeted Model asset allocation portfolios, representing more than $2 billion in assets under management.
Michael T. Cheung
Portfolio Manager, Managing Partner
Michael is Redwood’s Head of Quantitative Research and leads development, implementation, and risk management of Redwood’s quantitative investment strategies. This includes the research, design, and ongoing maintenance of Redwood’s proprietary models and algorithms.
As Portfolio Manager, he works closely with the firm’s principals and investment team to oversee the live execution and portfolio management of Redwood’s tactical risk-managed fixed-income and equity mutual funds, LeaderShares ETFs, and Dynamic/Engineered Risk-Budgeted Models (DRB/ERB), representing more than $2 billion in assets.
Michael Sasaki, CFA
Sr. Analyst
Michael is the Senior Analyst at Redwood Investment Management. In this role, he is responsible for portfolio implementation, trading, and performance analysis, as well as assisting the portfolio management team with research, data analysis, and testing.
Michael has experience working with a variety of analytics and trading tools including ICE Bond Point, MatLab, Bloomberg, and Stata. Prior to Redwood, Michael was a Senior Fixed Income representative with TD Ameritrade Institutional. Read More.

What Makes Us Different

“You Talked, We Listened”
Our team has many years of experience working with financial advisors and clients and have heard the same requests over and over throughout the years. When we created Wealthspan Investment Management, we set out to provide the solutions everyone has been asking for.

The most common request is a low-cost way to gain access to good asset management, without proprietary funds and high expense ratios. This seems like a reasonable request and one that we’ve been able to provide a solution for. Our portfolios are created using individual stocks and/or low-cost exchange traded funds (ETFs) offered by companies like Vanguard, so the expense ratio of our portfolios is very low, allowing investors to have less drag on performance so they keep more of the return that the portfolio offers.

We offer a stock portfolio, focused on selecting companies with higher than average dividend yields from the S&P 500 Index. It is actively managed and will hold 25 individual stocks. To determine which stocks to pick, it will use a screen and ranking process. The screen simply narrows the S&P 500 into only companies that have a yield higher than the Index. After this, the remaining higher yielding stocks are ranked by quality, volatility, valuations, and higher dividends.

One other common request is for the proper structuring and trading of accounts so they are as tax-efficient as possible. Everyone hates to pay taxes, especially if there are ways to properly structure the management style of an account to improve tax efficiency and, again, help investors keep more of the return that the portfolio offers.


Good portfolio management doesn’t have to be overly complicated. Many of the managers we’ve seen use complicate algorithms that are difficult to understand and never really seem to measure up to what the markets are able to achieve. The end result was a confused client who was disappointed with unmet expectations. That isn’t a great position for a client or advisor to be in, so we created portfolios that are simple and easy to explain and understand. They are designed to be measurable against the most common benchmark indexes, so expectations can be set that are much easier to understand.

Most clients compare their account performance against a US stock market index. This is what we’ve all been taught to do. However, many managers build their portfolios with multiple non-US asset classes included in the allocation. This creates a disconnect for clients, as they are comparing their portfolio to a US index, but their portfolio composition may be much different than the composition of the US indexes. This creates confusion.
Diversification is important for the purpose of spreading out risk. However, many clients and advisors would rather have the diversification done within US asset classes so the comparison of portfolio performance to US stock indexes makes sense and makes it easier to understand the ups and downs of account performance. WIM created and manages a US only strategic allocation. Not all of our models are US-only, but we thought it was important to make this option available so clients who are looking for this can have it.

Our team has always worked toward creating and providing an experience for clients so they have access to the information they want and need in a format that is easy to use and full of features that help you monitor your accounts. We have partnered with one of the premier financial technology firms in the country to bring that experience. WIM provides access for clients to see their performance, history, transactions, asset allocation, position detail and much more from their computer or mobile device. They also have a document vault available for the storage of any financial, tax, estate planning or any other pertinent documents so these items can be stored and/shared securely.


Clients and advisors have asked for portfolios that are simple, low cost, tax managed for efficiency, with technology available that allows for instant access to account data in an easy-to-use format. Wealthspan Investment Management listened and has built our platform to best serve the clients and advisors that will trust us to manage their assets.