[SaaS Club] Overcoming Early Struggles to Bootstrap to $22M ARR

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🎧 Podcast

Hubstaff: Overcoming Early Struggles to Bootstrap to $22M ARR

In 2012, a LinkedIn message changed Jared's life.

It all started when Dave, a complete stranger at the time, pitched Jared an idea for a SaaS product.

Dave had already built a basic product that was generating some revenue, but he needed a technical co-founder to help take it to the next level.

Jared was intrigued but also cautious. It took three months of discussions before he finally agreed to join forces with Dave.

But getting traction was a lot harder than they'd hoped.

The founders were constantly torn between working on the product and trying to acquire customers. 

They were stuck in an endless cycle of building features, launching them, and then realizing they still weren't gaining enough traction.

On top of that, they struggled with pricing strategy, debating whether to price low to attract more customers or charge more to increase revenue.

There were also constant discussions about which features to prioritize and how to allocate their limited development resources.

And despite seeing some early signs of success, they couldn't shake the nagging feeling that maybe they were kidding themselves. 

Would enough people really be willing to pay for this product?

But they persevered, and today, Hubstaff generates around $22 million in ARR, serving over 16,000 customers with a team of just over 100 people. 

In this episode, you'll learn:

• How they generated demand for their product and built a waitlist of nearly 2,000 people by the time they launched their beta.

• How Dave used content marketing and SEO to attract potential customers and build an initial audience.

• How they overcame early challenges like pricing debates and feature prioritization to bootstrap the business to $6M ARR pre-COVID.

• How they doubled revenue to $12M in a year during the pandemic and why they finally raised funding after a decade of bootstrapping.

• Why iterating on the onboarding flow and tracking engagement metrics was crucial to building a product people loved.

I hope you enjoy it.

Listen to the full podcast episode

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I don't have all the details worked out yet. But if you're interested and want to learn more, then just reply to this email with "mastermind". 

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📗 Book of the Week

This week's books recommendations is:

High Growth Handbook: Scaling Startups From 10 to 10,000 People by Elad Gil

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Have a great week!

- Omer

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