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Sitting on a coffee table in his Chelsea office in New York City and surrounded by framed wedding invitations on the walls, Justin McLeod is worrying about AI. Specifically, the cofounder and CEO of dating app Hinge is concerned that his usersmany of whom have asked him to their weddings over the yearsmight fall in love with it instead of one another. McLeod has spent the greater part of the past 15 years studying the dynamics of human relationships, including what makes one person fall for another, and he sees that chatbots offer exactly what many people crave. Why would I invest in these hard human relationships with people that are not always available or might reject me when I can talk to this thing that is right here and will always say the right thing? he wonders. On this sunny afternoon in late September, chatbots arent yet upending dating apps, but something sure is. Bumble, once the women-first darling, has shed 460,000 paying users since the end of 2024, prompting the return of founder Whitney Wolfe Herd in March. Shes embarked on an aggressive retrenchment campaign that has included laying off 30% of the staff. Tinder, meanwhile, has lost more than 1.5 million paying users since its peak in 2022. Its parent company, Match Group, has also recorded steady revenue declines for the past three years for its business unit that includes former stalwarts like Match.com and OkCupid. Match appointed Spencer Rascoff as a wartime CEO in February 2025; hes slashed head count by 13%. But one app in Match Groups portfolio stands out. Hinge, which has 15 million monthly active users, saw its paying users grow by 17% year over year to 1.87 million in the third quarter of this year. The app took in $550 million in revenue in 2024, and more than $500 million in the first nine months of 2025. Were the fastest-growingand, in fact, the only growingmajor dating app, McLeod says. (Thats not quite true: Grindr, with 1.3 million of what it calls average paying users, is also on the upswing.) Simply put, Hinge is crushing it, Rascoff said on Match Groups Q2 earnings call. Hinges competitors are facing problems of their own making. First was their aggressive pursuit of users, favoring quantity over quality, which has degraded the overall experience of many dating apps. Meanwhile, their lax policing of junk profiles and botsand simultaneous price increases for increasingly important featureshas forced users to pay ever more to find decent matches. People are just tired of endless, expensive swiping that doesnt convert into dates. And now a rising generation is emerging with an entirely different approach to dating than earlier users, putting apps that dont evolve at risk of being left behind. Gen Zs relationships are increasingly mediatedeven definedby screens. They still use dating apps, but theyre skeptical. Gen Z has set a higher bar, Match CFO Steven Bailey told attendees at Morgan Stanleys Technology, Media, and Telecom conference in March. They want [dating apps] to be safe, they want them to be effective, and they want them to drive the outcomes theyre looking for. But Hinge keeps growing because it has stuck to its promise that it succeeds only if users end up deleting it altogether. We want people to meet up and find love in person, McLeod says. That sounds obvious, but in the world of dating apps, it hasnt always been a priority. While other apps favored ease of use (all that endless swiping) over outcomes, McLeod remained relentlessly focused on designing ways to get his users off the app and dating, even if that meant inserting friction into the user experience. A lot of apps grew much faster than us because they were more engaging and exciting, McLeod admits. But he was playing the long game. McLeod is now preparing for the next stage of Hinge. The company has been rolling out a suite of AI-powered features to appeal to users with rustier social skills (ahem, Gen Z). McLeod is also taking his matching algorithm up a notch, extracting even more information from users to personalize and refine Hinges picks for them. To stop people from falling in love with chatbots, hes fighting AI with AIand trying to engineer something incontestably human: a messy, authentic love story. McLeod knows something about the complexities of the heart. He founded Hinge in 2011 while at Harvard Business School to help people find real-world connections. At the time, though, he was recovering from heartbreak. He had dated someone as an undergrad, but they broke up and got back together several times as he battled substance abuse issues. By the time he got out of rehab, she had moved on. Several years later, with Hinge starting to grow, McLeod conducted an interview with a New York Times reporter where he recounted the story of the one who got away. That inspired him to look up his lost love, who was living in Europe and engaged. Though they hadnt seen each other in nearly a decade, something sparked. She called off her wedding, and a few years later she and McLeod married. Hes recounted this story numerous times. It was even turned into a New York Times Modern Love column and then an episode of the Amazon show based on the column. But as polished as the anecdote is, theres a deeper truth within it: Vulnerability creates possibilities. A decade ago, when Tinder, Bumble, and other apps were orienting themselves around engagementmaking the user experience addictive but the outcomes questionableMcLeod mapped out a different strategy, aimed at fostering emotional risk-taking. He would require users to put in more work during the sign-up process and would place deliberate hurdles for them along the way, all in an effort to get them to open up, not just swipe. Jackie Jantos, chief marketing officer [Photo: Evelyn Freja] Today, Hinge requires users to upload a minimum of four photos and fill out at least three prompts about themselves. The process is designed toget users to slow down, think about what they really want, and present a more unfiltered profile. McLeod says the app tries to give users tasks that signal a level of intention and create a level of vulnerability so that you can actually create connection between two people. The longer sign-up process has made a difference: Hinge has found that users are 47% more likely to go on dates when they engage with the written answers on someones profile rather than simply the photos. Last year, Hinge introduced another hurdlea feature called Your Turn Limitsto curb ghosting. Now Hinge users with too many unanswered messages must send a reply or end the conversation before they can resume swiping. The company even gently nudges users into the real world: Its AI will invite users to set up a date if theyve been chatting online for a couple of weeks and seem compatible based on their conversations. Hinge also uses AI to scan the content of messages and deploys a notification to double-check with a user before they send a message that might not be well received. Thats all well and . . . millennial, but the apps newer challenge is helping Gen Z userswho make up 56% of Hinges overall user basefind value in the app. CMO Jackie Jantos sees a generation that was isolated during the formative years when relationships develop, and that often reverts to interacting on social media rather than in real life. Hinges Gen Z users tend to be uncomfortable with small talk and hyperfocused on digital body language, Jantos says. So theres a lot of reading into the speed [with which] someone replies, how long the persons message is, and what type of emojis and punctuation they use. Match CEO Rascoff puts it more succinctly: They have atrophied social skills and need more help showing up and connecting with other people. Hinges first feature for younger users, launched in 2021, was inspired by TikTok voice-overs. Instead of making users write out their responses to profile prompts, Hinge now allows them to record a 30-second audio introduction. It hit the sweet spot of willingness to do it if Im the person whos posting it and extremely informative if Im the person [experiencing] it, McLeod says. With more than one in five Gen Z adults identifying as LGBTQ, according to Gallup, Hinge has also given users an expanded menu of gender and sexuality identifiers to choose from as they set up their profiles. Gender, relationships, and relationship types are being redefined, Jantos says. In February, the company added Match Note, which allows users to privately share information with matches before chatting with them. People have used it to disclose their STI status or gender identity. (McLeod says single parents also use the feature to let matches know about their kids.) Hinge is tuning its marketing for Gen Z as well. The company has long featured real couples in its campaigns. But Hinge is now focused on stories that showcase all the intricacies and uncertainties of real relationships to show Gen Z that they dont have to be perfect. For 2024s No Ordinary Love campaign, Hinge enlisted writers like Roxane Gay and Hunter Harris to tell the nuanced, real-life stories of people who connected on the app, then published the essays in a zine. This year, Hinge followed up with a second collection, released as a printed book and on a dedicated Substacksupporting it with a flurry of ads in major cities. In one, a couple meets, hits it off, then breaks up for a few months before getting back together. Another tells the story of Lia and Ole, a couple fighting against their preconceived ideas of what they want from a relationship (Lia had imagined a romance with someone more established, more mature). Spoiler: Five years after their first datewhen they jointly deleted Hinge from their phonestheyre still together. Despite his fears of AI keeping Hinge users from meeting real people, McLeod is embracing it to help improve their prospects. In January, Hinge launched an AI-powered coaching tool to help users refine their profiles. Instead of just asking users to type in their response to a profile prompt, an AI chatbot can now interview the answer out of them. If a user says they like to travel, the chatbot might ask them for their best travel story to add to their profile. Those interviews serve an additional purpose: helping improve the apps matching algorithm. Until the advent of generative AI, Hinges algorithm primarily considered the profiles that users liked as they swiped and tried to surface similar onesbut it never really understood why a user might have certain preferences. Now, McLeod says, the algorithm can take in the content of a users profile to deliver better matches. Its thinking about what youve said, what theyve said, what your prompts say, what your photos are, and using it to predict whether you might like someone, he says. Its not waiting for you to send a whole lot of likes for us to learn your taste. If McLeod succeeds, he could lift the fortunes of Match beyond just Hinges revenue. Matchs data shows that Hinge subscribers already tend to use the app alongside one or more of the companys other apps. Rascoff now wants to encourage that behavior, letting users populate their profiles across other apps with one tap. From a financial standpoint, weve found that its additive, he says. The user spend on the second app does not detract from their spend on the first. Rascoff envisions that the matching algorithm behind these apps could also be standardized. We dont want to do AI stuff for the sake of it, McLeod insists. Even so, hes staking his apps future on it. McLeod anticipates that within five years Hinge will work more like a personal matchmaker. Users will spend less time on the platform sifting through profiles and sending messages. Instead, they might provide more information to the app on the front end and simply trust it to show them fewer, better matches. That would represent a sea change for the entire industry, McLeod says: Well think of swiping through endless profiles to find dates as a bit archaic.
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E-Commerce
I had to submit my résumé for a role. Then I went through three interviews, with nearly identical questions each time. The problem? The role was for a freelance writing position. Not to become a company employee. I got all the way to the third interview only to learn that the role paid a fraction of my usual rate, even though Id provided my rate up front. Im experienced enough as a solopreneur to know that going through three interviews was a bad sign. The potential client wasnt communicating internally (as confirmed by the fact that my rate had been overlooked). Multiple interviews are incredibly uncommon in my line of work, and indicated to me that the company didnt know how to work with a freelancer. {"blockType":"mv-promo-block","data":{"imageDesktopUrl":"https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit\/wp-cms-2\/2025\/11\/work-better-1.png","imageMobileUrl":"https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit\/wp-cms-2\/2025\/11\/work-better-mobile-1.png","eyebrow":"","headline":"\u003Cstrong\u003ESubscribe to Work Better\u003C\/strong\u003E","dek":"Thoughts on the future of work, career pivots, and why work shouldn\u0027t suck, by Anna Burgess Yang. To learn more, visit \u003Ca href=\u0022https:\/\/www.workbetter.media\/\u0022\u003Eworkbetter.media\u003C\/a\u003E.","subhed":"","description":"","ctaText":"SIGN UP","ctaUrl":"https:\/\/www.workbetter.media","theme":{"bg":"#f5f5f5","text":"#000000","eyebrow":"#9aa2aa","subhed":"#ffffff","buttonBg":"#000000","buttonHoverBg":"#3b3f46","buttonText":"#ffffff"},"imageDesktopId":91457605,"imageMobileId":91457608,"shareable":false,"slug":""}} When youre a solopreneur, bad clients cost you time and money. They also crowd out better opportunities and put a strain on your bandwidth. Client selection is a core business skill. And if youre not in a position to turn down work, you at least need to know how to handle sticky situations when they come up. Red flags during the sales process The best time to spot a problematic client is before you sign anything. Thats when you can decide whether the client will be worth the hassle or not. Here are some of the most common red flags Ive experienced talking with potential clients. Vague project scope. “We’ll figure it out as we go” sounds flexible, but it usually means the client hasn’t thought through what they actually need. That ambiguity becomes your problem once youve signed a contract, and it can be hard to rein in. Requests for free work or unpaid test projects. There are very, very few scenarios in which I believe a solopreneur should do any unpaid work. I’ve seen unscrupulous companies use submitted test work without providing any compensationessentially, free labor for them. If a client needs to evaluate your skills, point them to your portfolio or testimonials. Or negotiate a paid project. Unrealistic expectations on timeline or rate. If a potential client lowballs you, the relationship will always be lopsided if you accept. Many solopreneurs juggle multiple clients, so saying yes to low-paying work or expedited timelines can impact your other clients. Simple script to use: “My rates start at $XX. If that doesn’t work for your budget, I’d be happy to recommend someone else who might be a better fit.” Red flags during the engagement Sometimes you have no idea that a client will be a nightmare until after you start working with them. But before you know it, some red flags tell you that the client relationship isnt going well. Scope creep. You identify the scope of the project and put it into the contract, but the client continues to come back to you with additional requests. If you accommodate the client, this erodes your effective rate when you “donate” extra timeand requests can add up, fast. Simple script to use: “This wasn’t included in our agreement, but I’m happy to do that for $XX additional amount, and it will take YY additional time.” Framing it this way clarifies that additional work has additional costs. Poor communication. Some clients expect instant replies, treating you like an employee who should be available whenever they need something. Or they take forever to reply, and you cant move forward. In both scenarios, you need to be proactive. Let clients know your expected response time (like you will respond within 24 hours). Make sure they are aware that a delayed response on their end will have a negative impact on the project. Delayed payments or ghosting on invoices. These are the clearest signals that a client relationship isn’t working. Drop that client, fast. You shouldnt have to chase a client for money thats owed to you. Protecting your business Every solopreneur says yes to an imperfect opportunity or has engagements with difficult clients. Its part of the business. You dont have to say no based on red flags, but you do need standardsand the language to enforce them. The earlier you learn to spot red flags and respond to them, the more options you’ll have. {"blockType":"mv-promo-block","data":{"imageDesktopUrl":"https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit\/wp-cms-2\/2025\/11\/work-better-1.png","imageMobileUrl":"https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit\/wp-cms-2\/2025\/11\/work-better-mobile-1.png","eyebrow":"","headline":"\u003Cstrong\u003ESubscribe to Work Better\u003C\/strong\u003E","dek":"Thoughts on the future of work, career pivots, and why work shouldn\u0027t suck, by Anna Burgess Yang. To learn more, visit \u003Ca href=\u0022https:\/\/www.workbetter.media\/\u0022\u003Eworkbetter.media\u003C\/a\u003E.","subhed":"","description":"","ctaText":"SIGN UP","ctaUrl":"https:\/\/www.workbetter.media","theme":{"bg":"#f5f5f5","text":"#000000","eyebrow":"#9aa2aa","subhed":"#ffffff","buttonBg":"#000000","buttonHoverBg":"#3b3f46","buttonText":"#ffffff"},"imageDesktopId":91457605,"imageMobileId":91457608,"shareable":false,"slug":""}}
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Americans go to great lengths to ensure they are financially set for their later years. But if you’re asking Elon Musk, you really needn’t bother. According to the world’s richest man, whose net worth is estimated at well over $700 billion, saving for retirement will soon be obsolete. Musk aired this view on a recent episode of the Moonshots With Peter Diamandis podcast. Musk let listeners in on his vision of our financial future, a world where technology, specifically artificial intelligence, creates such an abundance of resources that anyone can buy anything they want. The entrepreneur said that within just a few years, we will live in a world marked by a great surplus, where better medical care than anyone has today” will be “available for everyone within five years.” He also said that there will be no scarcity of goods and services” and you’ll be able to learn anything you want. Musk continued, explaining that there will be such a surplus that life will no longer require people to save in order to ensure they are taken care of later on. One side recommendation I have is: Dont worry about squirreling money away for retirement in 10 or 20 years. It wont matter, he said, adding that he believes “saving for retirement will be irrelevant” and that the future will bring abundance.” Overall, Musk’s view of the future seems decidedly optimistic about AI. He talked about the power of AI to break barriers and using it to harness the sun’s energy. And he said he believes the “future of currency” will be measured not in money, but in “wattage.” But he also acknowledged that during what are bound to be years full of change, the road to the future he envisions will be “bumpy” and filled with obstacles. Musk said he doesn’t just foresee “universal high income,” but also major “social unrest” as the result of so much change in a short period of time. The prediction seems eerily similar to one made by John Maynard Keynes, known as the founder of modern macroeconomics, in 1930. In his essay, “Economic Possibilities for Our Grandchildren,” the economist wrote that by 2030, technology would enable workers to adopt a 15-hour workweek. At the time, the workweek was estimated to be about 50 hours. In one sense, Keynes was correct: The average number of hours fell in the years following the prediction, as the 40-hour workweek was established soon after. However, today full-time work hours hover at about 8.4 hours a day or 42.5 hours a week, per the U.S. Bureau of Labor Statistics. While many of Keyness predictions about technology proved to be correct, such as how vastly technology has reshaped certain industries, working hours have yet to fall as drastically as he predicted. At the moment, Musks comments are hard to swallow, given that many Americans struggle with basic expenses like childcare, let alone saving for retirement. According to a 2025 report from the National Council on Aging, most older adults don’t have enough money to financially survive “a financial shock” triggered by a death, the need for long-term care, or illness. “Eighty percent of those 60 and older have little to no assets and would not be able to weather a financial shock without falling into poverty,” the report said. Researchers added: “The future of aging in America will likely be defined by an ever-widening inequality in both financial status and mortality, deepening the divide between the majority of older Americans (the 80%) and the top 20%.” Musk did say there would be bumps along the road to utopia.
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