Thomas Smale

@ThomasSmale

Helping tech founders get acquired. Sharing tips on buying and selling online businesses. CEO of @FEIntl

New York, USA

feinternational.com/sell-business/…

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Thomas Smale
@ThomasSmale
Feb 2, 2024
Buying domains on a credit card to selling 8 to 9-figure tech companies. Here's how it happened: In 2010, I wanted to start a business. The problem? I was broke. So I opened a credit card and started buying and selling small websites—using late fees as motivation to
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Thomas Smale
@ThomasSmale
Sep 7
Harvard JD. Harvard MBA. Zero job offers. Not because nobody wanted Glenn Hutchins. He turned them all down. He finished the JD and the MBA at the same time, then joined Thomas H. Lee in 1985, when the leveraged buyout was still a new idea. He left in 1992 for the Clinton
Thomas Smale
@ThomasSmale
Sep 3
Six employees. Twelve months old. Acquired by Adobe. Then it shuts down. Rilo launched in September 2025. Two IIT Bombay batchmates, Dhruv Jaglan and Georgi Boby, built AI agents that let marketing teams describe a workflow in plain English and watch it run. Where they got to
Thomas Smale
@ThomasSmale
Sep 2
$3.44B peak valuation. $206M sale price. And the CEO says nobody forced the deal. Unacademy just sold to upGrad in an all-stock transaction. A 94% cut from its 2021 peak. Here is what makes it strange: - $880M raised across 13 rounds from SoftBank, Tiger Global and General
Thomas Smale
@ThomasSmale
Sep 1
$10 million on the table to walk away and start fresh. @ryanbreslow said no. Bolt in 2022: $11 billion valuation. Bolt today: $300 million. A 97% collapse. And the founder just wrote a $5 million personal check to keep it alive. The wreckage: → 900 employees down to 60 →
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