Dealmakers Podcast

Buying 21 Businesses in 8 Months

Darren Jacobs explains how he built a salon acquisition pipeline, bought at speed, financed deals creatively, and learned why disciplined criteria matter when building a multi location group.

Listen to the Episode

Episode 217  |  Runtime: 29:59  |  Audio Episode

Listen to the Episode

Hear Darren Jacobs explain how he used direct seller outreach, acquisition criteria, group structure, and seller motivation to buy 21 salon businesses in 8 months.

Episode 217
Runtime 29:59
Topic Business acquisition roll ups
Format Founder interview

Key Takeaways

Three practical acquisition lessons from a buyer who rapidly built a multi location salon group.

Direct Outreach Can Create Serious Deal Flow

Darren sent around 1,500 letters and generated more than 300 seller responses, proving that targeted owner outreach can create a large off market acquisition pipeline.

Acquisition Criteria Protect the Group

The weakest deals came when the buyer relaxed rules on owner dependence, staff base, revenue quality, and business structure to hit a target number.

Seller Motivation Beats Headline Price

Retirement, lease pressure, fatigue, family circumstances, and lack of interest in running the business often mattered more than maximum price in negotiation.

Episode Breakdown

Darren Jacobs joins Jonathan Jay to explain how he moved from acquiring IT businesses into building a salon group from a standing start. After buying the first salon for his daughter in May 2020, he sent a large direct mail campaign to salon owners and quickly created a pipeline that led to 21 acquisitions in 8 months.

The episode covers the mechanics behind the strategy, including why salons were easier to buy than IT firms, how lockdown conditions affected seller response, how Covid related lending supported some early acquisitions, and why a group of 20 locations gave Darren the scale needed to build management structure and attract investor interest. The conversation also highlights the danger of buying distressed or under resourced businesses just to reach a target.

Jonathan and Darren spend significant time on seller motivation, negotiation positioning, and deal structure. Darren explains how retirement, lease obligations, family pressure, and owner fatigue created opportunities, then breaks down the holding company and SPV structure that allowed each salon to operate separately while cash flowed upward through the group.

Best For

  • Buyers planning a sector focused acquisition roll up.
  • Entrepreneurs using direct mail to create off market deal flow.
  • Acquisition searchers learning how to assess seller motivation.
  • Operators comparing solid profitable businesses with distressed deals.
  • Dealmakers structuring multiple acquisitions through holding companies and SPVs.

Questions Answered In This Episode

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  • Step-by-step acquisition roadmap
  • Financing templates and lender contacts
  • Due diligence checklists
  • Deal closing procedures