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DotNet Holdings

Perspectives

Notes from the owner's side of the table.

What we are learning about building software companies, operating in automotive retail, and holding for the long term. Written by the team at DotNet Holdings.

July 19, 2026

Product-Market Fit Is Found, Not Declared

Teams love to announce product-market fit. The market is the only one who gets to confirm it, and it does so with retention.

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July 17, 2026

Building for the AI-Native Decade

The winners of the next decade will not be the loudest about artificial intelligence. They will be the ones who put it where it quietly belongs.

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July 15, 2026

The Connected Future of Commerce

The biggest inefficiency left in the digital economy is not missing software. It is software that refuses to talk to other software.

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July 14, 2026

Why We Stay Private

Outside capital comes with a clock. Here is what becomes possible when a holding company decides never to start one.

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June 23, 2026

Owning the Stack: The Case for Building Your Own Software

Renting technology is faster until the day it is not. Why every platform we operate is engineered in house, top to bottom.

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June 2, 2026

Compliance Is a Moat

Most software companies treat regulation as friction. In lending technology, taking it seriously is one of the strongest competitive positions available.

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May 12, 2026

What Dealerships Taught Us About Enterprise Software

The dealership is one of the most demanding software environments in American business. Building for it changed how we build everything.

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April 21, 2026

Build, Buy, or Partner: How We Decide

Three questions sort almost every opportunity that crosses our desk. The answers explain most of what our portfolio looks like today.

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March 31, 2026

The Small Headquarters Advantage

The best thing a holding company can do for its operating companies is stay out of their way. The second best is to be small enough that it has to.

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March 3, 2026

AI at the Dealership: Signal and Noise

Artificial intelligence is arriving in automotive retail wrapped in equal parts capability and nonsense. A field guide to telling them apart.

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February 10, 2026

The Unfinished Business of Dealer Communication

The most important system in a dealership is still the personal cell phone of whoever answered first. That is a problem worth owning.

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