INTERVIEW · FIRST DEAL · 2025

Buying My First Business

Jonathan Jay sits down with Andy, who sent out 500 letters to find his first acquisition — and ended up with two successful businesses, including an e-commerce company that has grown to become the biggest part of his portfolio.

16 min 24 sec Jonathan Jay & Andy 2025
Deal #1 · E-Commerce

Own Platform + Loyal Customer Base

An established e-commerce business with its own platform, experienced team and loyal customers — acquired with payments spread over four years. Now the biggest part of Andy's portfolio.

Deal #2 · Digital Agency

Struggling Agency Turned Profitable

A local digital agency in financial difficulty. Andy saw a clear path to profitability by adjusting fees and retaining clients — navigating the company's difficulties to complete the acquisition.

About This Interview

Jonathan Jay discusses business acquisition and provides real-life insights into how to successfully purchase a business. His guest Andy shares a remarkable first-deal story that started with a simple but effective outreach strategy.

By sending out 500 letters to business owners, Andy whittled hundreds of responses down to two companies worth pursuing — and successfully acquired both. His candid account covers the negotiation, the deferred payment structure, the adjustments when targets weren't hit, and how he ultimately paid off the debt.

What You'll Discover

  • How Andy used a 500-letter outreach campaign to source two acquisition targets
  • How to structure a deferred payment deal spread over four years — and what happens when targets aren't hit
  • How to identify value in a struggling business — and turn it profitable by adjusting fees and retaining clients
  • How to navigate a company's financial difficulties during the acquisition process
  • Practical tips for anyone interested in buying a small or established company, whether you're starting out or experienced

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