Matthew Bucklin of ExchangiFi - 351 Exchanges and New IRS Guidance

Oct 22, 2026

Ask episode

Chapters

Transcript

Episode notes

Today on the podcast, Ben Vaske talks with Matthew Bucklin, Founder of ExchangiFi. Prior to ExchangiFi, Matthew founded Valley Cove Capital, a search fund focused on small business acquisitions. He launched multiple successful tech ventures, including Sense Relief, Credible, and consumer healthcare company The Quit Company, which he sold in 2019. Matthew began his career in finance and asset management at MDRxFinancial and W.P. Stewart. Based in West Palm Beach, he holds an MBA from the Yale School of Management and a BA in economics and mathematics from Colby College, and serves as President of the Yale Club of the Palm Beaches.

Key Takeaways:

What is Matthew’s favorite home-cooked meal or recipe?
Learn more about Matthew’s career history and what led him to his current role in the industry
Matthew describes ExchangiFi as a marketplace with Wealth Advisors and Asset Managers on each side - what does each side really get from this exchange and why does a marketplace really need to exist for an exchange like this?
What is a bird’s eye view of a 351 exchange, in the context of ETFs, for those who don’t know much about them?
What is the 25/50 test and why does it exist from the perspective of the Treasury Department and IRS?
To Matthew, what does an ideal candidate for an exchange like this look like?
What are some of the reasons to consider not doing a 351? Are there certain clients that they aren’t really a good fit for?
What kind of due diligence does Matthew think is necessary for the ETF itself and its specific construction rules?
How do custodian reporting, cost-basis transfer and timing windows all work and are there spaces where Matthew has ever seen these go wrong?
Why were 351 exchanges in the news recently and what were the new rulings around them? What is Matthew’s take on the news?
How was Matthew’s anxiety when 351 exchanges were being called into question and does he plan to submit any comments about them by the late October deadline?
Why does Matthew think the marketing of 351 exchanges is problematic at times and what sort of marketing approach would be in good standing in his mind?
What should an advisor do with a completed 351 right now, if anything, to bring them in line with the recent rulings?
For clients looking to get into 351s now, are there a few things that Matthew would recommend they check the box on before going through with it?

Links

Connect with Us

Disclosure(s):

Wealth management services provided by Orion Portfolio Solutions, LLC (“OPS”), a registered investment advisor. Orion OCIO services provided by TownSquare Capital, LLC (“TSC”), a registered investment advisor. OPS and TSC are affiliates and wholly owned subsidiaries of Orion Advisor Solutions, Inc.

Orion Portfolio Solutions, LLC d/b/a Brinker Capital Investments a registered investment advisor.

This podcast is sponsored by Janus Henderson Investors. Orion Advisor Solutions, Inc. (“Orion”) or its affiliates and subsidiaries received compensation from Janus Henderson Investors for the placement of this advertisement content. Janus Henderson Investors and Orion are not affiliated companies, and the advertisement is not a recommendation or endorsement by Orion for any of the services referenced or provided.

These show notes may contain links to third-party websites. Any links to such third-party websites are provided solely as a convenience to you and not as an endorsement by Orion of the content on such third-party websites, or any affiliation or association with its operators. Orion is not responsible for the content of linked third-party websites, including, without limitation, any link contained in a linked website, or any changes or updates to a linked website, and do not make any representations regarding the information, services, products or accuracy of any material contained on such third-party websites.

Compliance Code: 3079-R-26295