Bill Gurley On Some High-Flying Startups and Their Economics: It’s the “Same Sh_t” as in ’99

Comment

Today, at an interview sponsored by the Benchmark-portfolio company Sailthru, legendary VC Bill Gurley appeared on stage with Bloomberg reporter Emily Chang to discuss the future of e-commerce.

Gurley spent much of the talk addressing the importance of personalization and the opportunity that companies miss when they focus on acquiring new customers rather than optimizing their services for current users. (Sailthru sells personalized marketing technology to its customers.)

But Gurley also talked at length about a few well-known companies, and he didn’t hold any punches when it came to sharing those about which he’s somewhat pessimistic. Among those at risk, in Gurley’s view, are the search giant Google, as well as high-flying startups Instacart, Shyp, and Postmates. (Notably, the last three compete with one of Benchmark’s most promising portfolio companies: Uber.)

Below is part of this morning’s conversation, edited for length.

On whether Google is at an inflection point:

Here, Gurley evoked a “reversal of funnel” concept, saying that for nearly two decades Google has enjoyed a perch at the top, where “you do the least amount of work” and the money is easy. Meanwhile, lower in this metaphorical funnel — where you see the “nitty gritty, the hard work, the touching of physical goods,” he said — Amazon has been clawing its way upward with every transaction that solidifies its consumers’ trust in its pricing and its ability to deliver when it says it will.

The end result is that now, when the tens of millions of people who subscribe to Amazon’s Prime service go online, they “first search with Amazon Prime checked, then Prime unchecked, and then, if that doesn’t work, [they] go to Google,” said Gurley, likening it to the “search of last resort.”

That means two things for Google, Gurley said. First, and most plainly, Amazon now threatens a much broader section of Google’s search traffic, which is e-commerce. Amazon and others have Google playing catch up, too, including through products like Google Express, which Gurley views as a “chaotic response” to the challenge. “It’s not set up in a logistically optimal way. I think it’s defensive, rather than offensive. And I don’t think big companies do well with defensive strategies.”

On the future of the grocery-delivery Instacart, valued at $2 billion way back in January:

“I’m not sure how many people need that degree of care,” he told the small crowd of attendees. “My wife loves Instacart,” he continued. Then again, he said, “Everyone loved [the dot.com grocery delivery company] Webvan until it went out of business.”

“It’s like the old adage, [when you’re] handing out dollars for 85 cents, you can go [infinitely],” he said. “Chosen unicorns are being given hundreds of millions of dollars, but you have to ask how much margin is there. The unit economics [with Instacart] would be very difficult, I’d think.”

“Going back to the Google Express,” Gurley went on, “I have a hard time thinking it’s optimal for [Proctor & Gamble] to sell to Walgreen’s distribution center, where [its goods are] offloaded, [after which] a guy with a box cutter puts it on a shelf, all to have some employee from another company take it off the shelf and take it to your house.”

Asked if he thinks Instacart could be the next Webvan, Gurley shrugged. “You’re implying bankruptcy, so I don’t know. I don’t have enough knowledge. I do know it’s not a question of whether people like [the product]. It’s a question of whether you can generate enough cash flow from that type of operation.”

On Shyp, Postmates, and other newer delivery services that, again, compete with Benchmark-backed Uber, which aims to increasingly make deliveries a part of its business:

“One thing that happens in Silicon Valley – and this has been highly cyclical – the more we get into peak-y [valuations] territory, the more optimistic we get about business models that are lower margin,” said Gurley.

“It’s like, the last time,” he went on. “All this Postmates and Shyp stuff happened [in] ’99, with [the failed online delivery startup] Kozmo, [and] it’s the same shit. It’s the same shit. The smart phone helps a little bit. You have more data. But we’ll see. The question for all of those things has to do with core economics that’ll be proven out over time.”

As for where e-commerce startups would be smart to compete:

Two words, said Gurley: “Anxiety relief. Humans love it when you remove [anxiety].”

“When [Uber CEO] Travis [Kalanick] started Uber, he insisted there not be a [option for a tip built into the app]. He didn’t want the user experience to include this anxious moment of, ‘What should [the tip] be?’”

OpenTable, the now publicly traded company that Benchmark backed earlier on, also tackled anxiety head on, said Gurley. “You push a button. You don’t have to call and ask if [a restaurant] has a table for six.”

Of course, Gurley suggested, consumer trust takes time to win. “[With] some vendors,” he noted, laughing, “you get that tracking number and you keep it by your keyboard because you’re not sure [what you purchased] is going to make it there.”

Startups that want to succeed should be thinking: “Where are opportunities to remove that [doubt] for the customer?”

More TechCrunch

Ember has partnered with HSBC in the U.K. so that the bank’s business customers can access Ember’s services from their online accounts.

Embedded finance is still trendy as accounting automation startup Ember partners with HSBC UK

Kudos uses AI to figure out consumer spending habits so it can then provide more personalized financial advice, like maximizing rewards and utilizing credit effectively.

Kudos lands $10M for an AI smart wallet that picks the best credit card for purchases

The EU’s warning comes after Microsoft failed to respond to a legally binding request for information that focused on its generative AI tools.

EU warns Microsoft it could be fined billions over missing GenAI risk info

The prospects for troubled banking-as-a-service startup Synapse have gone from bad to worse this week after a United States Trustee filed an emergency motion on Wednesday.  The trustee is asking…

A US Trustee wants troubled fintech Synapse to be liquidated via Chapter 7 bankruptcy, cites ‘gross mismanagement’

U.K.-based Seraphim Space is spinning up its 13th accelerator program, with nine participating companies working on a range of tech from propulsion to in-space manufacturing and space situational awareness. The…

Seraphim’s latest space accelerator welcomes nine companies

OpenAI has reached a deal with Reddit to use the social news site’s data for training AI models. In a blog post on OpenAI’s press relations site, the company said…

OpenAI inks deal to train AI on Reddit data

X users will now be able to discover posts from new Communities that are trending directly from an Explore tab within the section.

X pushes more users to Communities

For Mark Zuckerberg’s 40th birthday, his wife got him a photoshoot. Zuckerberg gives the camera a sly smile as he sits amid a carefully crafted re-creation of his childhood bedroom.…

Mark Zuckerberg’s makeover: Midlife crisis or carefully crafted rebrand?

Strava announced a slew of features, including AI to weed out leaderboard cheats, a new ‘family’ subscription plan, dark mode and more.

Strava taps AI to weed out leaderboard cheats, unveils ‘family’ plan, dark mode and more

We all fall down sometimes. Astronauts are no exception. You need to be in peak physical condition for space travel, but bulky space suits and lower gravity levels can be…

Astronauts fall over. Robotic limbs can help them back up.

Microsoft will launch its custom Cobalt 100 chips to customers as a public preview at its Build conference next week, TechCrunch has learned. In an analyst briefing ahead of Build,…

Microsoft’s custom Cobalt chips will come to Azure next week

What a wild week for transportation news! It was a smorgasbord of news that seemed to touch every sector and theme in transportation.

Tesla keeps cutting jobs and the feds probe Waymo

Sony Music Group has sent letters to more than 700 tech companies and music streaming services to warn them not to use its music to train AI without explicit permission.…

Sony Music warns tech companies over ‘unauthorized’ use of its content to train AI

Winston Chi, Butter’s founder and CEO, told TechCrunch that “most parties, including our investors and us, are making money” from the exit.

GrubMarket buys Butter to give its food distribution tech an AI boost

The investor lawsuit is related to Bolt securing a $30 million personal loan to Ryan Breslow, which was later defaulted on.

Bolt founder Ryan Breslow wants to settle an investor lawsuit by returning $37 million worth of shares

Meta, the parent company of Facebook, launched an enterprise version of the prominent social network in 2015. It always seemed like a stretch for a company built on a consumer…

With the end of Workplace, it’s fair to wonder if Meta was ever serious about the enterprise

X, formerly Twitter, turned TweetDeck into X Pro and pushed it behind a paywall. But there is a new column-based social media tool in town, and it’s from Instagram Threads.…

Meta Threads is testing pinned columns on the web, similar to the old TweetDeck

As part of 2024’s Accessibility Awareness Day, Google is showing off some updates to Android that should be useful to folks with mobility or vision impairments. Project Gameface allows gamers…

Google expands hands-free and eyes-free interfaces on Android

A hacker listed the data allegedly breached from Samco on a known cybercrime forum.

Hacker claims theft of India’s Samco account data

A top European privacy watchdog is investigating following the recent breaches of Dell customers’ personal information, TechCrunch has learned.  Ireland’s Data Protection Commission (DPC) deputy commissioner Graham Doyle confirmed to…

Ireland privacy watchdog confirms Dell data breach investigation

Ampere and Qualcomm aren’t the most obvious of partners. Both, after all, offer Arm-based chips for running data center servers (though Qualcomm’s largest market remains mobile). But as the two…

Ampere teams up with Qualcomm to launch an Arm-based AI server

At Google’s I/O developer conference, the company made its case to developers — and to some extent, consumers — why its bets on AI are ahead of rivals. At the…

Google I/O was an AI evolution, not a revolution

TechCrunch Disrupt has always been the ultimate convergence point for all things startup and tech. In the bustling world of innovation, it serves as the “big top” tent, where entrepreneurs,…

Meet the Magnificent Six: A tour of the stages at Disrupt 2024

There’s apparently a lot of demand for an on-demand handyperson. Khosla Ventures and Pear VC have just tripled down on their investment in Honey Homes, which offers up a dedicated…

Khosla Ventures, Pear VC triple down on Honey Homes, a smart way to hire a handyman

TikTok is testing the ability for users to upload 60-minute videos, the company confirmed to TechCrunch on Thursday. The feature is available to a limited group of users in select…

TikTok tests 60-minute video uploads as it continues to take on YouTube

Flock Safety is a multibillion-dollar startup that’s got eyes everywhere. As of Wednesday, with the company’s new Solar Condor cameras, those eyes are solar-powered and use wireless 5G networks to…

Flock Safety’s solar-powered cameras could make surveillance more widespread

Since he was very young, Bar Mor knew that he would inevitably do something with real estate. His family was involved in all types of real estate projects, from ground-up…

Agora raises $34M Series B to keep building the Carta for real estate

Poshmark, the social commerce site that lets people buy and sell new and used items to each other, launched a paid marketing tool on Thursday, giving sellers the ability to…

Poshmark’s ‘Promoted Closet’ tool lets sellers boost all their listings at once

Google is launching a Gemini add-on for educational institutes through Google Workspace.

Google adds Gemini to its Education suite

More money for the generative AI boom: Y Combinator-backed developer infrastructure startup Recall.ai announced Thursday it has raised a $10 million Series A funding round, bringing its total raised to over…

YC-backed Recall.ai gets $10M Series A to help companies use virtual meeting data