Most first-time buyers think online businesses are too volatile or too risky but the real danger is not knowing what you’re actually buying. In this episode of Acquisition Collective, host Jay Bourgana sits down with 17-year digital acquisitions veteran Brendan Lawrence to break down how to buy online businesses that truly print cash flow.
From small affiliate sites to high-margin lead-gen assets, Brendan reveals how he turned tiny digital properties into machines producing hundreds of thousands in profit. He shares real-world lessons from dozens of buys covering sourcing, valuation, red flags, and negotiation tactics that separate disciplined operators from buyers who get burned.
Whether you’re a first-time acquirer, content site investor, or operator looking to scale into digital assets, this episode is your tactical playbook for finding online businesses that cash flow from day one.
We dive into:
✅ How to source real online business deals (not scams)
✅ Red flags in affiliate, PPC, and coupon sites
✅ How Brendan bought a $125K asset that paid him $1M
✅ What makes an online business “replicable and scalable”
✅ Why some sellers peak early and how to spot it
✅ Deal structures that de-risk your acquisition
If you’re serious about buying online businesses the right way, hit play.
Timestamps:
00:00 Intro – Why online businesses print cash flow
02:10 How Brendan bought his first digital business
07:00 Structuring rev-share and seller-financed deals
12:00 What makes an affiliate business replicable
18:00 Sourcing deals and spotting motivation
23:00 Buying assets vs. buying companies
28:00 The $15K deal that still prints $500K
35:00 Red flags in online business listings
42:00 Why most small digital businesses fail
52:00 How AI will reshape online acquisitions
58:00 Buying safely in today’s digital market
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