Clayton Shaw explains how he moved from a previous computer company acquisition into a series of Florida real estate sector acquisitions using direct outreach, seller flexibility, acquisition finance, and disciplined deal execution.
Listen to the EpisodeEpisode 163 | Runtime: 28:49 | Audio Episode
Hear Clayton Shaw break down his acquisition activity in the real estate sector, including direct mail deal flow, seller notes, SBA backed finance, cash flow protection, and plans for further acquisitions.
Episode
163
Runtime
28:49
Topic
Real estate sector acquisitions
Format
Founder interview
Three practical lessons from Clayton Shaw's acquisition journey in the Florida real estate sector.
Clayton built momentum by mailing thousands of target companies and staying visible until owners were ready to discuss a sale.
The deal used seller note logic and performance based protection so the final price could adjust if the business did not deliver the expected cash flow.
Clayton explains why hiring, marketing, CRM systems, finance controls, and centralised operations matter when turning several acquisitions into one scalable group.
In this episode, Jonathan Jay speaks with Clayton Shaw, a dealmaking student who already had acquisition experience before joining the programme. Clayton explains how he first bought a computer company with a friend, then shifted his focus toward acquiring real estate sector businesses in Florida after seeing the economics of buying cash flow at attractive multiples.
The conversation gets into the mechanics of Clayton's first major real estate sector acquisition, including a purchase price around 2.5 times cash flow, SBA backed financing, a seller note structure, protection against underperformance, and the use of temporary closing capital that was returned after completion. He also explains why finding the right operators can be harder than arranging finance when the business already has strong cash generation.
Clayton then outlines his deal flow system, built around regular direct mail to thousands of target companies in one sector and one geography. The episode closes with his plan to keep acquiring, standardise operations, improve marketing, centralise systems, and potentially build toward a significant exit over a three to five year horizon.
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