Kirk Chrisholm

Kirk Chisholm is a Wealth Manager and Principal at Innovative Advisory Group (IAG), an independent Registered Investment Adviser based in Lexington, Massachusetts. IAG’s team page says his roles include co-chair of the firm’s Investment Committee and Head of the Traditional Investment Risk Management Group, with a background in portfolio management and investment analysis across traditional and alternative investment markets.

Chisholm has provided wealth management services since 1999. Before co-founding or integrating into Innovative Advisory Group in 2008, he founded Stirling Global Advisors, LLC in 2005 and previously held wealth management roles at UBS PaineWebber and Smith Barney. In a 2017 Boston Voyager interview, he said his first role after college was in PaineWebber’s private client group, and that his experience at broker-dealers led him to build a firm focused on unbiased advice, transparency, risk management, and alternative investments.

He received a BA in Economics from Trinity College in Hartford, Connecticut. His LinkedIn profile lists Trinity College-Hartford from 1995 to 1999 and notes participation in the Entrepreneurship Club and Investment Club, including co-managing a college investment portfolio.

Publicly, Chisholm is best known less as a disclosed startup angel and more as a financial advisor and alternative-investment specialist. His media bios emphasize self-directed IRAs, alternative assets held in retirement accounts, risk management, inflation, portfolio management, and investor education. He is also a host/panelist on the Money Tree Investing podcast.

• Chisholm’s public investment philosophy centers on “Risk Management First.” IAG describes this as protecting capital first, identifying risks, mitigating what can be mitigated, and being comfortable with the risks that remain.
• IAG’s approach combines traditional investments with alternative investments to improve diversification and lower portfolio risk where traditional asset classes have become more correlated.
• IAG explicitly discusses alternative assets outside the stock market, including real estate, tax liens, private notes or mortgages, franchises, private businesses, crowdfunding, peer-to-peer lending, and precious metals.
• In InvestmentNews, Chisholm defined risk as “permanent impairment of capital” and separated true risk from short-term volatility.
• He favors investing in areas an investor understands. In podcast discussions of alternative investments, he has framed startup angel investing, private equity, venture capital, real estate, and other alternatives as areas where investors should “play to your strengths.”
• Public sources did not verify a personal startup check size or a consistent seed-stage angel investment program for Chisholm.