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If youre a founder, raising money is as high stakes as it gets. For a startup, capital can be the difference between scaling and failing. Ive raised rounds from under $1 million (yes, thats how things were done back in the day) to over $200 million, in timeframes varying from months, to a tightly orchestrated two weeks, to getting preempted with a term sheet. The lessons I learned from our hardest fundraise, our Series A, have stuck with me the most. I endured 29 nos before I heard a yes, and only in retrospect was it clear that it didnt have to be that way. I knew raising our Series A would be tough; I wasnt a lawyer and had no reputation as a founder, and hardly anyone was investing in the legal tech industry. This might be surprising today, with legal tech venture investments approaching $2 billion in Q1 2025 alone, but in 2015, legal tech was more of a curiosity than it was a software category. On the flip side, we had built a strong product and were on our way to a real business, with over $2 million in annual revenues. Some of the countrys top law firms and more than half of U.S. state attorneys general were using our e-discovery solution to quickly pinpoint key evidence in the millions of documents they reviewed during litigation and investigations. I put together a pitch that highlighted the tough problems we had solved and the big opportunity ahead. The need for experimentation As I drove up and down the highways of Silicon Valley in my 1999 Nissan Altima, pitching to venture capitalists (VCs), a pattern emerged. Rarely did I hear an immediate no; VCs were interested. I would be invited back for meetings with increasingly senior folks, only to eventually be let down for a variety of reasons: They didnt have an investment thesis about legal, the market wasnt big enough, and so on. But each one felt so close. I kept refining my pitch and delivery, squeezing out a bit more interest each time, seemingly just one meeting away from the golden ticket. I was wrong. Twenty-nine rejections later, there was no denying it. Somewhere in my Altima along Highway 101, with just a few names left on my list, I knew I had to change my approach. I realized I had made a big mistake: I had focused on refinement rather than experimentation. When a company is small, fundraising is intensely personal and emotionally daunting. If you cant raise money for the team, it feels like you are letting them down. This pressure yields an interesting dampening effect: Because raising is so critical, every meeting could be the one, so you feel compelled to deliver your best performance. Thus, as the rejections mounted, the stakes felt ever higher. Given the positive signals I had gotten in prior VC pitches, it felt reckless to risk that meeting with an experimental approach, so I delivered the practiced spiel that had gotten me so close in the pastwith the same results. Had I crashed and burned early on in the process, experimenting would have been obvious. Instead I was deluded by proximity to success. Fundraising is not a popularity contest; you dont need a lot of likes, you need one love. Rethink everything And that meant I had to rethink everything. Even if it meant lowering my chances of success in the next few pitches, I had to believe it would get me to a better overall outcome. If you asked me about technological disruption, I could have told you in a heartbeat that big changes rarely happen incrementally, but I hadnt generalized that lesson to business. Incremental improvement might work (for a while) if youre a market leader, but any other situation requires constant experimentation and reinvention to do your best. You have to be willing to take some short-term losses to earn bigger long-term gains, evenor especiallywhen it matters the most. When it came to raising money, it took me a mere 29 rejections to relearn this lesson. So I went for broke and restructured my entire pitch. Instead of trying to convince VCs about the opportunity in legal, I used analogies to industries they were much more familiar with, so that they could pattern-match better. Instead of showcasing all the rich functionality we had built (which, frankly, they didnt seem to care much about), I spoke more conceptually about our vision to build a platform in a space that didnt have one. In other words, instead of educating VCs about my language, I learned to speak theirs. Were these obvious and sensible changes? Yes. The revelation wasnt so much the changes I was making to the pitch, but their magnitude and my willingness to make them. After months of failure, I wasnt prepared for how quickly things improved. My new approach immediately resonated with VCs. Within a week, I had a term sheet from Andreessen Horowitz (a16z), one of the most reputable VCs. Now, a16z deserves plenty of credit: They had some experience with the legal process and understood its potential, and were one of the few firms that viewed my PhD in computer science more favorably than they would have the JD I didnt have. It was also clear that my new pitch struck a chord and framed the company in the right light; we sailed by the usual roadblock questions in the final meeting. With a16zs investment, we were off to the races. Nearly a decade later, our business serves more than 1,000 customers and brings in 9-figures of revenue a year. Its now clear how pivotal that raise was for our company. It was also a massive growth moment for me as a founder. It taught me to have an exploratory mindset, whether its to new product areas, markets, or technologies. Experimentation is at the heart of progress, and its essential when the stakes are the highest. AJ Shankar is founder and CEO of Everlaw.
Category:
E-Commerce
Singles are increasingly turning to AI to boost their odds in the dating world. According to a new study, just over a quarter (26%) of singles are using artificial intelligence to enhance their dating lives. Thats a 333% increase from 2024. Match and the Kinsey Institute surveyed around 5,000 U.S. singles between the ages of 18 and 98 for their 14th annual Singles in America study. The findings show that nearly half of Gen Z singles have already used AI in their dating lives, whether to shape their profiles, craft conversation starters, or screen for compatibility. So if youve been active on dating apps recently, theres a good chance you werent flirting with just a person. You were flirting with AIor at least with someone getting a little help from it. AIs role in modern dating is only growing. Looking ahead, nearly half (44%) of all singles say they want AI to help filter potential matches, and 40% want help optimizing their profiles. Even Gen X, the group least likely to use AI for dating (only 15%), is showing a rising interest in AI-powered matchmaking. “AI isn’t replacing intimacy, it’s giving singles an edge,” said Dr. Amanda Gesselman, psychologist at Kinsey and Match’s director of sex and relationship science, in the press release. “For a generation overwhelmed by options, tools that bring clarity and efficiency are more than welcome.” That sense of overwhelm is widespread. Nearly half of singles (47%) report feeling dating burnout, while 54% say the modern dating landscape leaves them emotionally drained. AI is stepping in as a potential wingman, with apps like Tinder, Hinge, and Bumble already introducing AI features designed to improve the dating experience. Hinge recently launched an AI-powered coaching tool to help users refine their prompt responses. No more pineapple belongs on pizza as your most controversial opinion, please. For a limited time, Tinder even let users test out pick-up lines on an AI chatbot before using them in real conversations, through a feature called The Game Game, developed in collaboration with OpenAI. If all this has you ready to delete the apps and swear off dating altogether, youre not alone. The study found that 46% of singles have taken intentional breaks from dating, and two-thirds of them said those breaks helped them clarify what they truly want. Still, its not all bad news. With or without AI, hope remains high. Seven in 10 respondents said they believe in destiny when it comes to relationships, and 73% of singles still believe in forever love. So dont give up just yet.
Category:
E-Commerce
President Donald Trump announced, back on February 25, that his administration would soon debut a gold card, an immigration program that would allow wealthy foreigners, for the low, low price of $5 million, to become lawful permanent residents of the United States. At the time, Trump touted the program as a great and fantastic revenue generation strategy that would help reduce the national deficit, which approached $2 trillion during the most recent fiscal year. Wealthy people will be coming into our country by buying this card, theyll be wealthy and theyll be successful, and theyll be spending a lot of money and paying a lot of taxes and employing a lot of people, Trump said. He told reporters that gold card buyers would not be required to pay tax on their income outside the United States; that the program was totally legal and all worked out from the legal standpointand that he expected it to go live within two weeks. Two weeks, confirmed Department of Commerce Secretary Howard Lutnick, standing behind Trump in the Oval Office. When Trump estimated that the government could raise an easy $5 trillion by selling maybe a million gold cards, Lutnick was unable to suppress a chuckle of delight. Wow! he said. Today, though, anyone hoping to relocate to a budding police state where riot cops might shoot you point-blank for looking at them is still waiting for the chance to cut a check. In mid-March, Lutnick said during a podcast interview that gold cards would be available in about two weeks, and claimed hed presold 1,000 already. (I assume these sales, to the extent they exist, are handshake deals, since the alternative would involve the Secretary of Commerce personally collecting $5 billion and stashing it God knows where.) On April 3, Trump showed reporters a physical gold card bearing his scowling face and seismogram signature, and (again) said it would be out in less than two weeks. But the delays kept coming. On April 11, Lutnick announced that gold cards would be available within a week and a half. On May 21, he moved the goalposts even further, revealing that a website where people can start to register for gold cards would be online in about a week. On Thursdaythree weeks after that update, for those keeping scoreTrumpCard.gov at last went live. Trump celebrated the launch on Truth Social as a way to ride a beautiful road in gaining access to the Greatest Country and Market anywhere. On Fox Business, Lutnick claimed to have logged 25,000 sign-ups in 15 hours. But he also acknowledged that these are waiting list spots, and that the administration is still getting everything set up. The website itself most closely resembles an especially lazy phishing attempt; its only content is a contact submission form assuring prospective buyers that the gold card is coming, and urging them to provide their email addresses to get notified the moment access opens. The White Houses struggles to get this initiative off the ground demonstrate just how unprepared Trump is for the basic work of governing, on the rare occasions that he expresses any interest in engaging in it. A key part of his pitch to voters has always been that, as an outsider to politics, only he has the Business Guy Mindset necessary to transform the federal government from a bureaucratic morass into a slickly branded, profitable enterprise. But fulfilling his more ambitious promises is always harder than he expects. As a result, an idea that Trump once suggested would single-handedly wipe out this countrys $36 trillion national debt is, four months later, still taking the form of a bare-bones website that looks like it is soliciting interest in a new over-the-counter erectile dysfunction medication. At the announcement earlier this year, Trump explained that gold cards would replace the existing EB-5 visa program, which allows immigrants to obtain green cards if they invest at least $800,000 (and usually more) in a new business, and create at least 10 full-time jobs in the United States. In a Cabinet meeting, Lutnick clarified that the gold card program would technically modify the EB-5 visa program, allowing buyers to obtain a license from the Department of Commerce that would entitle them to make a proper EB-5 investment. In response to a question from reporters, Trump asserted that the program does not require legislation because it allows buyers to obtain lawful permanent resident status and a very strong path to citizenship, but does not directly confer U.S. citizenship. In news I am sure will astonish you, Trump and his handlers do not appear to have a firm grasp on the legal intricacies here. Congress, not the president, has the authority to create, modify, or end visa programs like EB-5. Federal law limits EB-5 visas to around 10,000 per year, which is of course nowhere near the million units Trump and Lutnick imagine selling in short order. The amount of the required capital investment, too, is set by statute, and nothing in th law would allow Trump to increase it to $5 million just because he feels like it. His distinction between programs that confer citizenship and programs that only confer lawful permanent resident status is nonsensical, as is Lutnicks reference to a license from the Department of Commerce. Depending on what he has in mind, Trumps promise that gold card holders will enjoy some form of VIP treatmentgreen card privileges plus, he called itprobably also hinges on Congresss willingness and ability to pass a law to that effect. Absent congressional action, Trumps best bet for making this work might involve using his statutory authority to allow gold card buyers to enter the United States on the grounds that doing so entails a significant public benefit, since a willingness to fork over $5 million to the Treasury Department arguably qualifies as such. But this statusthe product of a legal process known as paroleis typically temporary, and is not even considered a form of admission to the United States. It also would not make gold card buyers lawful permanent residents or give them a path to citizenship, which are things that people who pay that much would reasonably expect to get in return. Given that the Trump administration has spent the last several months gleefully repudiating the very concept of parole, I understand not wanting to pay seven figures for the right to be in the country for as long as Stephen Miller feels like allowing it. The lingering uncertainty around the programs specifics has resulted in a gold card market that is likely cooler than Trump might have imagined. Earlier this month, NPR interviewed several immigration attorneys who said theyd fielded inquiries from wealthy foreigners who are eager to pay upwhich is, to be fair, exactly what I would say if I were an immigration lawyer contacted by a national publication for comment about a program aimed at potential clients who have at least $5 million in cash. Other experts, though, told NPR they anticipate sales in the low thousands; one explained that callers often lose interest once they find out that the $5 million is not an EB-5-style investment that they might recoup, but a de facto donation to the U.S. government. (As London School of Economics professor Kristin Surak points out, if youre a rich person looking to pick up another passport, why pay $5 million for a glorified green card when you can buy Maltese citizenship, and thus the right to live anywhere in the European Union, for about a fifth of the cost?) Nuri Katz, a Canada-based immigration consultant, told Bloomberg that he would expect a grand total of 50 to 200 applicants for Trump gold cards; more recently, in Forbes, he hypothesized that the White House is backpedaling on the proposal because it realized it would have to expend a lot of political capital in order to get this done. Perhaps there was a time when more than a handful of people might have been interested in ponying up for green card privileges plus, whatever that may entail. But regardless of the legal form that Trump gold cards eventually take, the basic challenge of selling them will be that that they are branded with the face of an unabashed xenophobe whose administration is waging a global trade war, trying to bar foreign-born students and academics from entering the country, torpedoing international educational exchange programs, attempting to end birthright citizenship, and snatching noncitizens (and sometimes citizens) off the streets. Chances are that if you are privileged enough to be able to pay $5 million for the right to live in the United States, you are wise enough to decide that that money is better spent on something else.
Category:
E-Commerce
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