The hype cycle for bots exploded in 2016 as developers poured time and money into the dream of personal digital assistants. Facebook and Microsoft announced major investments into conversational user interfaces, and Slack launched a fund to capitalize on the bots hoping to build on its platform. But when bots became available the public, the public largely shrugged. The advantages of conversational interfaces paled next to their drawbacks. It turned out that typing into text boxes — often while trying to guess the appropriate commands — felt frustrating compared to the visual interfaces people were used to. And so bots largely receded into the background as another Silicon Valley innovation that arrived before its time. Eoghan (pronounced “Owen”) McCabe, co-founder and CEO of the fast-growing marketing startup Intercom, says the collapse was predictable. “Have there ever been any super destructive, sexy technology innovations that haven’t actually worked that way?” he says. “You’re just never going to be able to perpetuate that excitement for the amount of time it actually takes for actual innovation to actually take hold in a market.” In other words, the bots never really went away; they just became invisible. More automated messaging can be found on companies’ websites and apps than ever before. The work continues. And as Intercom’s own story has shown, businesses’ appetites for the automation they enable is only increasing. (Intercom released a tool to let businesses build custom chat bots earlier this month.) Founded in 2011, Intercom’s first product was a (human-powered) chat box that popped up when you visited a company’s website. The idea was that a website should say hello to customers the same way a barista might when you enter a coffee shop — and then sell you on something available for purchase. Since then, Intercom has added machine learning to automate more of those conversations, along with various other tools for generating and managing sales leads. (In these ways, it’s a direct competitor to Salesforce.) While public interest in bots waned, Intercom has continued to invest in the technology. In March, the company announced that it had 25,000 customers and was powering 500 million conversations a month. As part of the announcement, Intercom — which is based in McCabe’s native Dublin, with additional headquarters in San Francisco and London — said it had raised another $125 million from Kleiner Perkins and Google Ventures. The company is valued at nearly $1.3 billion. McCabe says the company has grown because businesses are looking for a single platform to help them organize their communication tools across every platform. That’s an approach that’s different than a company like Facebook’s, which similarly hopes to offer a popular front end for business conversations through its Messenger and WhatsApp services. But those are just endpoints, McCabe says. Another service is needed in the background to organize a company’s communications. “What the world will need is one platform to band these multiple channels together,” he says. “They’ll need someone to build workflows for the people inside these companies to help them collaborate and be efficient. They’ll need someone to build the automation that works on these channels.” McCabe lays out his thoughts on the future of bots on the season finale of Converge, an interview game show where tech’s biggest personalities tell us about their wildest dreams. It’s a show that’s easy to win, but not impossible to lose — because, in the final round, I finally get a chance to play and score a few points of my own.

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Breaking down music into its component parts helped Pandora build personalized music playlists years before services like Spotify even existed. Could taking a similar approach with podcasts help the streaming-audio company regain the users it has lost to newer services? That’s the bet Pandora is making under Roger Lynch, who joined the company as CEO in 2017. Lynch lays out his thoughts on the future of music on this episode of Converge, an interview game show where tech’s biggest personalities tell us about their wildest dreams.

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Should ride-sharing companies build a “quiet mode”? “We have thought about it,” Taggart Matthiesen, head of product for autonomous driving for Lyft, told me. “I think it’s interesting. At some point, we may play around with that idea, but that’s unfortunately not a feature at this point.” Matthiesen says that a “zen mode” would represent another step in more personalized rides, a move the company plans to accelerate as it changes gradually to include more autonomous vehicles. “The autonomous car is going to know a lot more [about you],” Matthiesen said. “It’s going to know your temperature that you’re going to want. It’s probably also going to know that it’s early in the morning, and so it’s going to have a dark-lit cabin to let you sleep. Maybe you can even relax in the seat, and the back will extend into some sort of lie-flat mode. Maybe not complete lie-flat, just based on the area, but a good recline.” Lyft is currently testing self-driving cars in Las Vegas in a partnership with the British company Aptiv. In March, it signed a deal with auto parts maker Magna to build and deploy its own self-driving cars. For Lyft, which is valued at more than $15 billion, autonomous vehicles represent an important plank of the company’s plans to remain competitive against larger competitors like Uber, which has grand autonomous driving plans of its own. “THE AUTONOMOUS CAR IS GOING TO KNOW A LOT MORE ABOUT YOU.” Matthiesen lays out his thoughts on how Silicon Valley should change its priorities on this episode of Converge.

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Tiffani Ashley Bell is the founder of the Human Utility, a nonprofit organization working to restore water service to people who are unable to pay their bills. The organization, which was founded in 2014, began its work in Detroit and has since expanded to Baltimore. Bell lays out her thoughts on how Silicon Valley should change its priorities on this episode of Converge.

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Alexia Bonatsos has watched countless startups come and go. First as the editor in chief of TechCrunch, and now in her current role as the founder of venture capital firm Dream Machine, Bontasos’ job has been to understand what makes a tech company succeed. “A lot of it’s gut, but gut’s not magical woo-woo dust,” she says. “It’s taking in data and information, and eventually making a decision based on that.” Bonatsos has seen thousands of companies, and so on today’s episode of Converge, we turned the tables. Using two decks of cards — one with a set of famous companies, and the other with a set of random nouns — we invited Bonatsos to draw two cards, and pitch us the resulting company.

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It’s been four years now since Slack arrived to kill email — and yet, email persists. While the group chat app has plenty of ardent fans and continues to grow quickly, it also draws criticism for its distracting, always-on nature. At many workplaces, if you’re at work, you’re also expected to be available on Slack. For some people, that means the thing that “replaced” email replaced it with something much more demanding. Mathilde Collin says the workplaces of the future ought to take a different approach. She’s the cofounder and CEO of Front, which makes tools for sharing inboxes with your teammates. If you’ve ever emailed a business address starting with “contact@” or “info@,” there’s a chance the team is managing the emails with Front. But Collin’s longer-term vision is to build what she calls an asynchronous version of Slack. Like Slack, Front will be integrated with all the other software tools you use — Asana, Trello, Github, Google Docs, and so on — and collect any important notifications in a place where you can read them on your time. It takes away the constant pinging of Slack in favor of something calmer and more conducive to doing focused work. Not only hasn’t email died — the tech industry’s current focus on Time Well Spent might have made it stronger.

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It hasn’t even been four years since Amazon bought Twitch.tv, the live-streaming platform that has become the primary destination for broadcasting the playing of video games. Since then, the service has grown to 15 million daily users, with the average person watching 106 minutes per day. In hindsight, it’s no wonder that Amazon was willing to pay $1 billion to snap up Twitch — but for a long time, it was an open question whether anyone would buy it at all. Twitch began life as Justin.tv, a web-based live broadcasting platform. As venture capitalist Mike Maples Jr. of Floodgate Capital tells us on this week’s episode of Converge, it wasn’t always clear that Twitch would thrive. In fact, it was more or less stagnant before the company pivoted into games. “They were Justin.TV for five years before Justin.TV Games took off, and we realized that was the company,” Maples said. (In a nice Silicon Valley twist, Twitch has lately been embracing all sorts of non-gaming video, effectively pivoting back to Justin.tv’s original vision.) The only reason Twitch lived long enough to be sold to Amazon is that its creators were patient with it, Maples said — spending less money than they could, and continually experimenting to figure out which parts of their streaming service resonated the most broadly. “Where I give the Twitch founders a lot of credit is they survived five years to have that discovery,” Maples said. “And most startups would have spent too much money too soon, felt the pressure to grow super fast, and run out of money before the discovery ever happened.” Twitch is an unusually successful company. But social apps often succeed by accident, Maples says — and as one of Twitter’s first investors, he would know. “To me, these exponential outcomes happen when you have great founders with very specific and deep domain knowledge of some major new shift that’s even bigger than the company,” Maples said. “Twitter happened because everybody was getting connected, everything was getting mobile, and the web was kinda going through this new phase of not just being a place to go visit pages, but becoming a platform to connect people. And they just were right place, right time, right product.” Maples lays out his investing strategy on this episode of Converge, an interview game show where tech’s biggest personalities tell us about their wildest dreams. It’s a show that’s easy to win, but not impossible to lose — because, in the final round, I finally get a chance to play and score a few points of my own.

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Clara Labs cofounder and CEO Maran Nelson tells us there is real reason to be worried about AI — and not for the reasons that science fiction has trained us to expect. Clara’s approach to AI is innocuous to the point of being dull: it makes a virtual assistant that schedules meetings for people. (This week, it added a bunch of integrations designed to position it as a tool to aid in hiring.) But even seemingly simple tasks still routinely trip up AI. “The more difficult situations that we often interact with are, ‘Next Wednesday would be great — unless you can do in-person, in which case we’ll have to bump it a couple of weeks based on your preference. Happy to come to your offices.” Nelson sketches out her vision for a better kind of AI on Converge.

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Pocket founder and CEO Nate Weiner tells us why he sold his company to Mozilla — and how he’s working to build a better version of Facebook’s News Feed into the Firefox browser. By analyzing the articles and videos people save into Pocket, Weiner believes the company can show people the best of the web — in a personalized way — without building an all-knowing, Facebook-style profile of the user.

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