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Andreessen Horowitz partner Scott Kupor explains the valuable lesson that today's startups can learn from the dot-com bubble: Be careful about selling to other startups

Scott Kupor
Andreessen Horowitz
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The dot-com bubble burst almost twenty years ago, but legendary Andreessen Horowitz partner Scott Kupor says that today's startups still have a lesson to learn from it.

Kupor survived that first tech crash in 2000 at LoudCloud, one of the first enterprise software as a service startups, founded by Marc Andreessn and Ben Horowitz.

In his new book "The Secrets of Sand Hill Road," Kupor writes that there were many reasons behind the ultimate failure of LoudCloud — not least the bursting of the bubble, which happened not long after its 2000 IPO.  

But he highlights another, less obvious factor in the demise of LoudCloud: Its reliance on other startups as customers. When that dot-com bubble burst, it took out some of LoudCloud's best customers, and its business model couldn't withstand the strain.

"If you're going to do that strategy, you just have to understand the risks associated with it," Kupor told Business Insider. "You just have to almost do reverse financial diligence on your customers when you sign them up and make sure you understand how much of your revenue is potentially at risk if we have a catastrophic event like we did in 1999 or 2000."

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Kupor's advice is especially valuable as worries of an economic downturn continue to circle Silicon Valley. The sky-high valuations, massive funding rounds, and tendancy of startups to market to other startups are eerie parallels to Kupor's anecdotes from his LoudCloud days.

Still, there's a way to do it right. He offered up Twilio, Square, and Brex as examples of current tech companies successfully building a business by selling to startups and other smaller entities. 

"I don't know Brex well enough but you can imagine the conversations that they're having in their boardroom," Kupor said. "We get the benefit of a portfolio. Some of those hopefully will grow and become the next Squares and Facebooks. You can avoid kind of getting over your skis where all of a sudden you have a dramatic fall off in revenue."

For the curious, LoudCloud ultimately sended up selling a big chunk of its business in 2002 in what Kupor characterizes as a fire sale. What was left of the company rebranded as Opsware, and ultimately sold to HP in 2007 for $1.65 billion. 

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Megan Hernbroth is a California-based senior reporter for Business Insider, where she covers healthcare startups and venture capital. She reports on digital health startups of all stages and sizes, such on-demand in-home healthcare solutions, telemedicine startups, and direct-to-consumer solutions. She also covers financial deals in healthcare, from large mergers and acquisitions through IPOs and SPACs.  You can reach Megan at mhernbroth@bjinnox.com, via encrypted messaging app Signal (+1 331-625-2555), or Twitter DM (@Megan_Hernbroth) Select stories:  $1.6 billion Hims is going public after just 3 years. We dug through its financials and spoke with its CEO to find 4 key metrics that could determine the company's success. Investors are betting $1.4 billion that gig workers can transform an essential but invisible part of healthcare. Here's an inside look at one startup leading the charge. A former venture capitalist wants to rethink the 'uniquely bad' healthcare experience for LGBTQIA+ patients by building an entirely new health system RISING STARS: Meet the 16 up-and-coming investors changing the face of healthcare in the US Prior to joining Business Insider's healthcare team, Megan reported on startups and venture capital for the technology team. She covered a wide range of topics from Silicon Valley, including the demise of once-hot companies like Zume and the rise of newly hot companies like Brex. Megan worked in communications prior to joining Business Insider. She holds a Bachelor of Science degree in Journalism from Northwestern's Medill School of Journalism and Integrated Communications. (Disclosure: Megan's partner is an employee at Facebook.)