Neil Patel

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Andrew Brown sold his first company to Google. He is now on his second startup. Check has already attracted substantial funding in its mission to simplify essential operational functions for small businesses: payroll. 

Brown recently appeared on the Dealmakers Show to share his journey from discovering tech to starting his first business, going through acquisitions, and navigating both fundraising and challenging times like COVID.

Listen to the full podcast episode and review the transcript here.

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Growing Up

Andrew Brown was born and grew up in Greenville, SC. He looks back fondly on his youth, growing up in the suburban foothills of the Appalachian and Blue Ridge mountains. As well as trips over to Charleston and the beaches on the Atlantic. 

Both of his parents worked in employment law. Every conversation happening around the house seemed to revolve around it. While he was much more interested in cartoons at eight years old, his work has certainly brought him back full circle to what you may now consider his destiny or calling. 

At the time he began to take what seemed like a path in another direction. He quickly took to playing games on the Nintendo in Middle School. He went on to study computer science and economics. Though it was really when the iPhone was released that the spark of inspiration to eventually start his own company was ignited. 

Brown interned at Microsoft, and was then offered a job working at Google. While it certainly helped with paying for his student loans, he yearned to do something scrappier. He wanted to put together his own team, and do something big. 

Selling Your First Company To Google

Andrew says that he has always loved reading. Especially the feeling of going to the library, and having all of the world’s knowledge at your fingertips. The ability to pick up any book and start reading. 

The kindle and ipad had come out, but Brown and his eventual cofounders felt like there ought to be a better experience. Like the subscriptions he had with Spotify and Netflix. Or a digital library. 

He didn’t see any reason why that wasn’t feasible to build, so he and his cofounders launched their first company Oyster to do just that. 

Of course, quitting your job, and jumping into a 150 year old industry, is a lot more work than just having fun writing a couple lines of code. 

They did end up signing up some of the biggest publishers, and went live in the App Store. Yet, it was only when he was featured on the Today Show as one of the recommended gifts for the Christmas season that his parents really got why he left the stability of Google to do his own thing. 

Oyster raised capital from both Founders Fund and HIghland Capital. They caught the attention of Google, which tried reaching out multiple times to discuss a potential deal. Eventually Andrew says that he believed they did have a shared vision, and that only Google could successfully pull off the integration. 

The next couple of years were spent completing his vesting period with Google as they integrated Oyster. Yet, even during this time he again felt the itch to build something from scratch.

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Andrew Brown spent about two years researching and investigating ideas. More than anything, he wanted to bring the  old Oyster crew back together to build something. Which he did pull together. 

They had the advantage of knowing a lot of small business owners and their businesses. What they saw was that while small businesses had begun adopting software for many parts of their businesses, in part due to the rise of platforms like vertical SaaS, the way they handled payroll really hadn’t been updated. Owners still spent enormous amounts of time manually fixing payroll issues. 

Andrew and his cofounders decided to fix that. They decided to make it possible for the software platforms that small business owners were already using to provide their payroll services, through their new company Check. 

The vision of Check is that “payroll is something that small business owners and employees shouldn’t have to think about.” It should just work. Even when that means there are hundreds of tax and government jurisdictions involved. As an infrastructure company, Check makes things seamless for its partners and their customers.


Andrew explains that he took a much more thoughtful and strategic approach to fundraising with his latest company. 

Capital is important, but he recognizes “more than anything else is actually the set of relationships and advice and people that you have around the company, are in many ways just as important, if not more so than the capital itself.”

He underscores that investors who don’t understand the business deeply enough, or don’t share the same vision, can take the company in the wrong direction, or at least waste a lot of your time, and capital. 

To date Check has raised $119M across four rounds. That includes $1M in seed capital from Bedrock Capital. Then an $8M led by Bedrock, with Thrive for the Series A. That parlayed into a $35M Series B, led by Thrive and Stripe. Then more recently, a $75M Series C, led by Stripe. 

Storytelling is everything which is something that Andrew Brown was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

Check out the full interview for more on:

  • Building trust with investors
  • Surviving crises
  • Andrew Brown’s top advice when launching a business
  • Transitioning from CTO to CEO


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Neil Patel

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If you want help with your fundraising or acquisition, just book a call

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