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Goodbye Wall Street, Hello SMB Holding Company


My guests today are Jonathan Kasen and Gordon Scott, Co-Owners of Hilliards Chocolates. Hilliards is one of New England’s most beloved artisan brands. Founded in 1924 in south Boston, Hilliards is now in its fourth generation of family ownership. 

In this episode, you’ll hear Jonathan and Gordon talk about their journey from portfolio managers at Fidelity, to leaving those positions to start the second half of their careers as business investors/owners. With 15 years of experience in the public markets, Jonathan and Gordon felt comfortable analyzing a business and assessing a management team. They liked that Hilliards was almost 100 years old, which spoke to its resilience, and that the brand had a strong following and a family management team that was (and still is) impressive.

The guys talk about the purchase of Hilliards, the acquisition of Hilliards’ sister company Harbor Sweets, and the complementary strengths of both companies. Keeping the family in charge of day-to-day operations is an unusual approach, but it has worked very well for their partnership with Hilliards. 

This podcast is brought to you by Axial, a trusted online platform for business owners & their M&A advisors to use to safely and intelligently explore and execute capital raises, acquisitions, and exits with strategic buyers or professional financial sponsors. I am your host, Peter Lehrman, Founder and CEO of Axial. In every episode, we will explore the vast world of small business M&A. We will interview both the proven and emerging owners, operators, investors, and advisors whose strategies and methods have been put to the test. 

If you have enjoyed this episode, check out for more. There are recorded Axial member roundtables, downloadable tools for dealmakers, quarterly lead-table rankings, and lots of other useful information. To join Axial as an acquirer, an owner considering an exit, or as a sales-side M&A advisor, you can get started for free at Feel free to reach out to me directly at [email protected] with questions, suggestions, or show topic ideas.

Discussion points:

  • Gordon and Jonathan’s backgrounds on Wall Street
  • Fidelity and how portfolio management was structured
  • The origin story of Gordon and Jonathan’s partnership
  • Hilliards and why it was so compelling
  • The chocolate market – how can it sustain so many brands?
  • Brick and mortar vs eCommerce pre and post covid
  • Why and how they ‘won’ the purchase of Hilliards
  • Buying a business and keeping the family and future generations involved
  • Hilliards first acquisition – sister company Harbor Sweets
  • A typical week for Jonathan and Gordon as owners
  • Advice for someone interested in this path
  • Mentors and family support


Jonathan Kasen LinkedIn

Gordon Scott LinkedIn

One up on Wall Street by Peter Lynch

Peter Lehrman LinkedIn

Axial Website

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