Mergers & Acquisitions

M&A Talk Podcast

M&A Talk is the #1 podcast on mergers & acquisitions. At M&A Talk we bring you exclusive interviews with experts in business sales, valuations, mergers and acquisitions, and more. We talk to the most experienced professionals in the industry to uncover their secrets.

Lessons Learned From Doing 48 Business Deals in 2.5 Years

Lessons Learned From Doing 48 Business Deals in 2.5 Years

Jonathan Jay

Business Acquisition | Roll-Ups

You can learn a lot about M&A from books, but the best lessons come from real-life experiences that you won’t read about in the books. Entrepreneur Jonathan Jay shares his learnings from buying 48 companies in London in just 2.5 years. From the crucial role that confidence plays in buying, running, and selling a business to how passion, talent, and profit can work together to make you more successful, to tips for making strong hires for your team – this episode is full of priceless advice for any entrepreneur.

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Guest Profile

Jonathan Jay has been an entrepreneur since dropping out of university at age 19. Now in his early 50s, he has built businesses in publishing, digital marketing, specialized programs and coaching, and preschool education and sold each of them. During the pandemic, he did a roll-up, making 48 business acquisitions in 2.5 years to create the 4th largest group in his sector. One notable deal was buying a £5m annual revenue digital marketing company from its private equity owner for just £1 and selling it for £1.3m just 11 months later. He is an advocate of a healthy work-life balance and believes you can achieve success without business taking over your life! He now helps other people buy businesses and helps them avoid expensive mistakes – as he says he has made them all!


Topics Covered

  • What was the goal of doing so many deals in a short period of time? [1:18]
  • What are some of the differences in M&A terminology and transaction types between the UK and the US? [4:00]
  • Why is there a significant difference in the typical length of time private equity funds are held in the UK (3 to 5 years) vs. in the US (10 years) [11:08] 
  • What does dealmakers.co.uk do? [16:03]
  • How does Jonathan structure a deal when he is bringing someone onto a deal team? [19:28]
  • How important is location in acquiring a business? [20:58]
  • How important is agility in making deals? [25:47]
  • What is the best strategy for tackling risks in buying a business? [27:58]
  • What were some specific lessons Jonathan learned while doing those 48 deals? [34:20]
  • Who should be in a head office team? What is the most important role in hiring? [38:04]
  • How important is the owner’s role when purchasing a business in the small to middle market? [48:28]
  • What were some of the challenges Jonathan experienced after acquiring a business? [51:56]
  • How does happiness relate to M&A? [58:47]

Learn More


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