Product Flops and Bankrupt Corporations: Business Lessons from the Failure Museum

2 Jul 2026 · 9 min · 9 chapters

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In short

The episode is about business lessons from the Failure Museum, using six “forces of failure” to explain why products and companies flop.

Guest

Sean Jacobson, partner at Norwest Venture Partners, founder/curator of the Failure Museum (1,000+ failed products/companies/items).

Key claims

failures cluster around product-market fit, team, financial management, timing, competition, and customer success; many flops come from scaling too early, weak domain expertise, poor early-customer selection, inadequate financial planning, missing market timing, and ignoring competitive shifts.

Notable examples

Webvan (product-market fit), Theranos (team), Google Glass (customer success), ESPN Mobile (financial management), WeWork (timing), Blockbuster (competition).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Exploring Famous Product Flops

0:04 to 0:27

Discussion on notable product failures and their implications.

“It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks.”

Exploring Famous Product Flops

0:56 to 2:12

Discussion on notable product failures and their implications.

“They could have been successful if they didn't build a money-losing business.”

Forces of Failure Introduction

2:12 to 2:38

Introduction to the six forces of failure impacting products.

“Failed companies, failed products, failed sports-related items, and failed toys.”

Product Market Fit: Webvan's Example

2:38 to 3:16

Analysis of Webvan's failure to achieve product market fit.

“I have a champagne bottle from Webvan's IPO date in 1999.”

Team Expertise: The Theranos Case

3:16 to 3:42

Discussion on the importance of team expertise with Theranos.

“So I have a Theranos mug and I also have Elizabeth Holmes business card.”

Customer Success: Google Glass

3:42 to 4:28

Examination of Google Glass's failure due to poor customer targeting.

“Yeah, when you don't have domain expertise, hiring other people without domain expertise, you believe in something can be possible when it really isn't.”

Financial Management Pitfalls: ESPN Phone

4:28 to 5:09

Overview of financial mismanagement in the ESPN mobile phone launch.

“It's important to pick the right early customers that are representative of your bigger market.”

Timing Issues: WeWork's Struggles

5:09 to 6:04

Insights into WeWork's mismanagement of timing and demand.

“There just wasn't enough to do on the phone.”

Competition: The Blockbuster Story

6:04 to 7:12

Lessons learned from Blockbuster's competitive failures against Netflix.

“happening in the market and be able to anticipate what's going to happen the next 12 to 24 months.”
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Transcript

Automatic transcript. May contain errors.

0:01This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required. Compatibility and availability varies 18+. Listen to the heartbeat. Chevy is called the heartbeat of America for a reason. With SUVs made to move with your rhythm.

0:35The versatile Equinox tackles your entire day. The spacious Traverse fits your crew and your whole weekend. And Trax brings style with value you can count on. All infused with tech that has your back. So your drive always hits the right chord. Chevrolet. Together let's drive. I have a lot of favorites. The Pets.com Sock Puppet from 1998. They could have been successful if they didn't build a money-losing business. Harley-Davidson Cologne from 1996. It reeked the scent of tobacco. Here's an unopened bottle. No, they weren't joking. They were serious about it. There's a lot of product extensions.

1:17Of course, sparkling water, Cheetos, lip balm. Another one of my favorites is Alan from 1964. He was Ken's best friend. You may remember him from the Barbie movie. Hi, Barbie. Oh, hi, Alan. Here he is in the original box. Alan wore the same clothing. He was his best friend. The problem is everyone just wanted to own Ken, not Alan. Yes, I have two cans of new Coke. You want me to bring them out or... It was really hard to switch people in math to something completely different. I have not tasted one. No, I certainly have been tempted, But some of these things are 15, 20, 30 years old, so they probably don't taste good anymore.

1:59Sean Jacobson, partner at Norwest Venture Partners. I'm on 14 boards. I'm also the founder and curator of the Failure Museum. The Failure Museum has over 1 ,000 items and continues to grow. Failed companies, failed products, failed sports-related items, and failed toys. I've tagged all 1000 items of mine to one or two forces of failure. Product market fit, team, financial management, timing, competition, and customer success. I'm going to go through all six forces of failure and share one example of each. I have a champagne bottle from Webvan's IPO date in 1999. For product market fit, Webvan is a good example.

2:48They were the world's first grocery delivery company. You have the right to come home from work and find something good waiting for you in the fridge. They raised over$880 million to launch in 10 cities before having proven one. Business model required so much capital. They had distribution centers. They hired their own drivers, which is why they had to raise$880 million. Not enough demand for the early version of your product. You shouldn't yet scale go to market. So I have a Theranos mug and I also have Elizabeth Holmes business card. Their goal was to revolutionize the blood testing industry.

3:28And at the peak, we're worth$10 billion. Theranos didn't have a strong team or board. None of them had domain expertise. They tried to use a pinprick of blood to do testing. And that's just not enough data. Yeah, when you don't have domain expertise, hiring other people without domain expertise, you believe in something can be possible when it really isn't. Here is a copy of the Google Glass and I can put it on here too. A good example of customer success is Google Glass. They did not pick the right early customers well. They started with doctors and doctors could see patient records on the glass while they were talking to the patient so they didn't have to use their computer.

4:13It felt invasive. It didn't seem very personal. You're not used to having someone with a strange device on your face trying to communicate with you. Because it lacked the cool factor, they couldn't find any other segments of the population that wanted to wear something like this. It's important to pick the right early customers that are representative of your bigger market. A lot of times people pick the most convenient customers rather than those that are going to help you build a big business. I love this one so much that Ashley bought two of them on eBay. For financial management, the ESPN mobile phone.

4:48They launched a year before the iPhone. All the phone did was calling, sharing ESPN mobile content and scores. They burned through $150 million, including several Super Bowl ads. It only hit 6 % of its sales target. They probably should have had more capabilities on the phone. There just wasn't enough to do on the phone.

5:12Sean Jacobsohn:Introducing mobile ESPN. Sports fans, your phone has arrived. I have a couple items here. A WeWork thermos and a koozie from WeWork's summer camp. For timing, a good example is WeWork. WeWork's in the co-working space business. And when the pandemic hit, the demand for office space fell off a cliff and they ended up burning through$16 billion. The goal was to give people flexible space that allowed you to do month-to-month leases and scale up and down in space depending on your demand. They also signed 10 to 15-year leases at peak market prices and then they ended up renting them out at a loss.

5:58There's some level of unluckiness, but I think that they had the wrong business model. You need to have a pulse on what's happening in the market and be able to anticipate what's going to happen the next 12 to 24 months. And so I've had several friends donate their Blockbuster membership card to me. And then in every store, there was a sign that said, be kind, rewind. For competition, Blockbuster is a good example. They're in the movie rental business. At the peak, they had 9 ,000 stores. They missed the opportunity to move online and Netflix ate their lunch. They also, after they went public, had the opportunity to buy Netflix for$50 million and turned it down.

6:39And instead, Netflix ended up beating them. When I talk about competition, you need to make sure that you don't have an upstart competitor that offers a cheaper, better way of doing what you do. You need to be aware of all the competitors in your market segment and how you stay differentiated and better than them.

7:01I do admire companies for taking risks and trying new things. Some of these big risks turn into humongous outcomes and some fail spectacularly. I am a lot of times surprised at the lack of research that they did before they spent a lot of money to roll something out that wasn't going to work.

From the publisher

Product Flops and Collapsed Corporations: Business Lessons from the Failure Museum

28 Oct 2024

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What can failures like Harley-Davidson Cologne or Cheetos Lip Balm teach us about success? Sean Jacobsohn, partner at Norwest Venture Partners and founder of the Failure Museum, takes us on a tour of notable product failures, sharing insights into why they failed and the lessons we can learn from them. Discover the six forces of failure and learn how companies can avoid making the same mistakes.

Visit the Failure Museum: https://failure.museum/

00:00 Harley-Davidson Cologne, Cheetos Lip Balm, and Coors Sparkling Water, oh my!
01:25 The six forces of failure
01:42 Product market fit: Webvan
02:20 Team: Theranos
02:53 Customer success: Google Glass
03:44 Financial management: ESPN mobile phone
04:22 Timing: WeWork
05:15 Competition: Blockbuster

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