How to Build a $5m Media Business Into a $20m Flywheel

November 6, 2025
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T

oday's interview was a fun one for me.

Clayton Collins bought a media business, HousingWire, a B2B publisher for professionals in the housing industry.

Clayton has almost quintupled sales, from $4m in revenue when he acquired it, to approaching $20m today.

He shares with us how he's done that.

You will hear that strategic acquisitions are a big part of the story, acquisitions that added events and data products to the HousingWire ecosystem.

And you'll hear that Clayton began this journey with a big vision, an intention to transform the business he bought into something grander.

As an entrepreneur, I love this. It's inspirational, it's bold, and it speaks so highly of Clayton that he's delivered on it.

But you'll also hear us talk about how his original search investors reacted to that initial vision. Not all got on board.

Clayton makes a great point about the value of having diversified sources of capital as opposed to just one or two who can effectively veto your project.

This conversation should appeal not just to those of you who, like me, are intrigued by media businesses, but also to the visionaries among you, who think less about multiples and more about what a little business you buy could one day be.

Here is Clayton Collins, CEO of HousingWire.

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How to Build a $5m Media Business Into a $20m Flywheel

Clayton Collins acquired HousingWire with a big vision for the small media business. 9 years later, it has come to life.

Key Takeaways

Introduction

Listen to the introduction from the host
T

oday's interview was a fun one for me.

Clayton Collins bought a media business, HousingWire, a B2B publisher for professionals in the housing industry.

Clayton has almost quintupled sales, from $4m in revenue when he acquired it, to approaching $20m today.

He shares with us how he's done that.

You will hear that strategic acquisitions are a big part of the story, acquisitions that added events and data products to the HousingWire ecosystem.

And you'll hear that Clayton began this journey with a big vision, an intention to transform the business he bought into something grander.

As an entrepreneur, I love this. It's inspirational, it's bold, and it speaks so highly of Clayton that he's delivered on it.

But you'll also hear us talk about how his original search investors reacted to that initial vision. Not all got on board.

Clayton makes a great point about the value of having diversified sources of capital as opposed to just one or two who can effectively veto your project.

This conversation should appeal not just to those of you who, like me, are intrigued by media businesses, but also to the visionaries among you, who think less about multiples and more about what a little business you buy could one day be.

Here is Clayton Collins, CEO of HousingWire.

About

Clayton Collins

Clayton Collins
Clayton Collins

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Episode Transcript

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