Trilogy Search Series Ep.3: Tom Klein and Roland Lessard – Ep.118

My guests on this episode are Tom Klein and Roland Lessard, Tom and Roland launched a partnered search after running a background screening business together and acquired a language service business focused on intellectual property in 2016, which they sold last year in 2021. In both companies, growth through acquisition was a core to their playbook and we spend a ton of time diving into best practices and things to avoid in doing so.

This is one of the best episodes of the podcast for understanding M&A, synergies, and change management, and if any of these topics apply to your business, you’ll want to tune in. This conversation covers all things M&A, shifting teams, understanding culture and structure, effective leadership, and integrations with new companies and teams.

We got on such a roll near the end that I entirely skipped my closing questions to make room for more discussion, and I think it paid off. By the end of this longer-than-usual episode, I hope you’re in agreement. Enjoy.

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Tom Klein on LinkedIn

Roland Lessard on LinkedIn

Morningside Translations


(3:58) – Tom and Roland’s Backgrounds

(13:03) – How many companies within the industry did you speak with during your search?

(16:35) – What was the company you bought and how did you plan out growth?

(20:02) – Where were the biggest pains during your massive growth from $5mm to $30mm?

(26:25) – What strategies did you use to get up to speed with everyone’s role when making changes?

(32:08) – What’s your philosophy and experience with M&A?

(42:51) – What are some Do’s and Don’ts of tuck-in acquisitions?

(58:07) – How do you implement synergies and change management when you’ve acquired one of these companies?

(1:12:45) – Additional commentary on synergies

Think Like an Owner Sponsors:

Live Oak Bank — Live Oak Bank is a seasoned SMB lender providing SBA and conventional financing for search funds, independent sponsors, private equity firms, and individuals looking to acquire lower middle-market companies. Live Oak has closed billions of dollars in SBA financing and is actively looking to help more small company investors across the country. If you are in the process of acquiring a company or thinking about starting a search, contact Lisa Forrest or Heather Endresen directly to start a conversation or go to

Hood & Strong, LLP — Hood & Strong is a CPA firm with a long history of working with search funds and private equity firms on diligence, assurance, tax services, and more. Hood & Strong is highly skilled in working with search funds, providing quality of earnings and due diligence services during the search, along with assurance and tax services post-acquisition. They offer a unique way to approach acquisition diligence and manage costs effectively. To learn more about how Hood & Strong can help your search, acquisition, and beyond, please email one of their partners Jerry Zhou at [email protected] 

Oberle Risk Strategies– Oberle is the leading specialty insurance brokerage catering to search funds and the broader ETA community, providing complimentary due diligence assessments of the target company’s commercial insurance and employee benefits programs. Over the past decade, August Felker and his team have engaged with hundreds of searchers to provide due diligence and ultimately place the most competitive insurance program at closing. Given August’s experience as a searcher himself, he and his team understand all that goes into buying a business and pride themselves on making the insurance portion of closing seamless and hassle-free.

If you are under LOI, please reach out to August to learn more about how Oberle can help with insurance due diligence at Or reach out to August directly at [email protected].

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