• President Donald Trump’s H-1B visa fee is facing new legal trouble.
• A federal judge ruled on Monday that the $100,000 fee for new petitions is “unlawful.”
• The fee caused uncertainty among tech workers since Trump introduced it last year.

President Donald Trump’s $100,000 visa fee for H-1B applicants has hit a new legal roadblock.

A federal judge at a US District Court in Massachusetts ruled Monday that the fee violates the Constitution’s Administrative Procedure Act.

Judge Leo Sorokin found that the fee is “unlawful,” according to his ruling. Sorokin said the fee constitutes a tax and requires congressional approval to implement.

Trump’s implementation of the $100,000 fee for new petitions using an executive order last year “exceeds the scope of the President’s discretionary authority” under US immigration law, Sorokin wrote.

The fee has faced legal challenges since Trump signed the executive order in September.

The President has argued that companies have used the visa to replace US workers. Employees at tech companies are among the most common applicants for the visas.

While the battle over whether the fee is constitutional will likely continue, the order has already had an effect. The number of H-1B visa applications from Big Tech companies such as Google and Microsoft fell at the end of last year after Trump signed the executive order. Major AI companies, meanwhile, such as OpenAI and Nvidia, have filed more applications, according to federal data.

The fee was previously as much as $5,000 per visa before Trump made the change last year.

The Trump administration has also changed other parts of the immigration process. High-paid applicants now get multiple lottery entries, giving them a better chance of being selected versus those hoping to land lower-paid positions.

• After many years of living in New York City, I moved to the Connecticut coast.
• For a while, I felt I was thriving among beautiful views, fresh air, and lower living costs.
• Almost two years later, I missed New York City, warts and all, and moved back. I’m so glad I did.

The first time I set foot in Brooklyn was to look at an apartment.

I vividly remember the slow chug of the M Train over the Williamsburg Bridge — watching the Lower East Side shrink behind me, and the contour of the Kings County skyline approaching across the East River.

I was 23. I felt like I’d arrived and my future was limitless. I moved to that apartment. Shoebox would have been a generous description for my $900 a month room with Craigslist roommates.

For the next seven years, I bounced between North Brooklyn dwellings, my rent rising faster than inflation. By May 2023, I was paying $1,900 a month to live with two roommates in a basement that had a tendency to flood.

Maybe it was a third-life crisis, maybe it was the natural progression of the American millennial, but sometimes I felt like I just needed to touch grass. So I did what many people before me had done: I moved to the country.

My grandmother had died about six months prior, and her home on the Connecticut/Rhode Island border was about to sit empty for the summer.

This situation, my disdain for my job at the time, and the impending end of my lease seemed to be a cosmic sign that I was meant to go coastal.

I applied to a few seasonal restaurant jobs online and quickly secured employment. I sold my bed frame, desk, and dresser, loaded my late grandmother’s Jeep with what remained, and put New York in the rearview.

I’d officially become one of those people who used to live in the city.

For a while, I felt like I was thriving in the pink cloud of the Connecticut coast

Economic benefits aside, I took to country life at first. Waking to the sounds of chirping birds instead of honking horns was refreshing.

My commute was now filled with the smell of freshly cut grass instead of literal garbage, and I was beholden to tourist traffic and streetlights instead of the L-train delays.

I no longer needed to go to a public park to look at trees, and I could enjoy the weather from a golf course or waterfront. Of course, I could’ve played golf or seen the sea in Brooklyn, but the courses would probably have been more crowded and the water less picturesque.

My restaurant wages were lower than what I’d made at my corporate job in New York, but I no longer spent nearly half my income on rent.

I was spending less on food, too. I always enjoyed cooking, but the ease and temptation of world-class cuisine often meant I was eating out in New York.

There weren’t as many restaurants on the coast, and I frequently found myself in the kitchen, cooking local seafood and fresh vegetables from farmstands.

I even cooked fish I’d caught, which I suppose is also possible in New York (but only recently deemed safe).

After reckoning with the limits of my lifestyle, I realized I wanted to be back in New York

Although the culture shock was mostly positive for a while, there were signs that my new reality conflicted with my conditioning.

One night, I left work famished around 8 p.m. I looked up restaurants in the area and noticed most of the kitchens had either closed or would do so by the time I could drive there.

In a moment of desperation, I pulled into a Burger King, only to find that closed too. In Brooklyn, people would just now be heading to dinner — if I hurried, I might be able to catch them.

This was the first realization that I missed city life. Not long after, I found myself growing impatient with the line at a coffee shop, lamenting the price of gas, and the quality of the local bacon, egg, and cheese.

I visited New York a few times over that year. Leaving got harder each time. People on the coast often asked how “dangerous” city life was, but in reality, I often felt safer on the subway platform at midnight than I did driving on Connecticut’s pitch-black backroads.

I knew my new life had become unsustainable when I took the Amtrak down to the city on a hot August weekend. I exited Penn Station to the stickiness of Midtown and was greeted with thick air and a cacophony of horns.

I acknowledged the objective unpleasantness, and yet I felt at ease.

Maybe it was part nostalgia, but if I missed the disgusting chaos of arguably one of the worst places in Manhattan, then maybe this was where I was meant to be.

Shortly after that, I started applying to jobs back in New York and scrolling various apartment sites.

This time, I feel like I’ve returned home for good

By November, I had two restaurant jobs lined up and met someone on Reddit renting a cheap room a few blocks from one of my old apartments. I was going home.

I’ve been back in Brooklyn now for about as long as I was away, a little over a year. The first few months, I worked almost every day just to cover rent, and felt a rude awakening every time I looked at my credit-card bill or bank account.

I’m down to one job now, and while the financial pains are still real, at least I know where to get a cheap meal at midnight.

Sometimes I get a yearning for grass and fresh air. At the end of each month, I certainly yearn for cheaper living quarters, but not when I take the M train.

Even now, at 32 years old with a jaded lived reality and mounting bills, when I chug over the Williamsburg Bridge, I feel 23. I see the city lights on every side of me, and I’m filled with this childlike wonder and optimism.

I feel like I’m home, where anything is possible.

• Coinbase CEO Brian Armstrong talked about some of Coinbase’s strategy for keeping token costs “roughly flat” on X.
• “We’re working hard on routing prompts to cheaper models where appropriate,” Armstrong wrote.
• The post ignited debate over token-saving strategies — and what it means for the big AI labs.

Not every AI prompt needs Opus 4.8.

As the fervor of tokenmaxxing dies down, some AI users are wondering how to get more bang for their buck and keep their monthly costs in check. Coinbase CEO Brian Armstrong shared the crypto company’s strategy: not skimping on the cheaper models.

“We’re working hard on routing prompts to cheaper models where appropriate, and in some cases have been able to keep costs roughly flat, while token usage continues to grow exponentially,” Armstrong wrote on X on Sunday.

While the latest models like Opus 4.8 or GPT-5.5 promise bleeding-edge benefits, they can also devour more tokens. (That’s before you turn on Fast mode.) When Anthropic launchedi Opus 4.7, many users complained that they were quickly hitting rate limits.

Armstrong wrote that he anticipated “80% of workloads will be running on 99% cheaper models within 12-18 months.”

The only times when users will use the latest models, Armstrong predicted, are when they need to be “IQ maxing.” This includes scientific breakthroughs or agent orchestration.

“This leads me to think the limiting factor will be energy and compute, not better models,” Armstrong wrote.

The Coinbase CEO’s post caught the attention of some tech luminaries. Venture capitalist Marc Andreessen called it “interesting.” Hugging Face cofounder Julien Chaumond wrote that “model routing is growing a lot these days.”

Box CEO Aaron Levie wrote that Armstrong’s numbers were a “bit extreme,” but that AI use would likely stratify in the coming years. “High end” work will be completed by leading models, Levie wrote, while “high volume” work will be relegated to the cheap models.

“Intelligence allocation is going to be extremely important,” Harvey cofounder Winston Weinberg wrote.

The efficiency mindset is relatively new — or at least new to publicly flaunt. Not long ago, when tokenmaxxing was all the rage, tech leaders would post their high token bills or flex their usage of the latest models.

That mindset is especially popular in the startup space, where Y Combinator CEO Garry Tan advises founders to “let it rip” with tokens. Lance Yan, a YC-backed startup founder, told Business Insider in April that rationing tokens was “stupid.”

The tide seems to be turning. Glean cofounder Tony Gentilcore commented that Armstrong’s post was “spot on.”

“Everyone technical already knows this,” Gentilcore wrote. “The financial markets are the only ones extrapolating out Opus prices to infinite scale.”

• Founders are publicly airing their “nightmare” interactions with venture capitalists.
• They shared on X what they say have been some of their worst experiences with investors.
• Legendary VC Vinod Khosla joined the fray.

Over the past few days, some Silicon Valley tech founders have taken to the internet to publicly roast the venture capitalists they once pitched.

The kefuffle began last week when Greg Isenberg, the host of “The Startup Ideas Podcast,” posted to X about his experience raising a $15 million Series A.

“12 people in the meeting. One of the GPs fully fell asleep. Out cold for 30+ minutes. Nobody acknowledged it. Everyone just kept going,” Isenberg wrote, referring to an unnamed general partner.

Isenberg said he continued his presentation, sharing slides with an investor he called an “unconscious man in a Herman Miller chair.”

“That’s venture capital,” he wrote.

Venture capital is the financial engine of the tech industry. Founders with an idea rely on them to kick-start or turbocharge their fledgling companies. Typically, this is not a loan, but an equity exchange. The earlier a VC invests, the riskier the investment. When a company succeeds, however, the returns can be astronomical.

Uber founder Travis Kalanick, responding to Isenberg, said that the venture world has changed over the years. Investors, he said, once took a more casual approach to pitch meetings.

In 2001, Kalanick said he pitched an investor who was sitting in his “parked Lexus.” Kalanick was sitting in the passenger seat.

Kalanick said the investor “grabbed” his laptop, placed it “on his large belly,” pressed it against the steering wheel, and began flipping through the slides himself.

“2001 fundraising hit different,” he said.

The back-and-forth went viral among the niche community of already-successful millionaire and billionaire founders who are terminally online, and the pile-on began.

Cloudflare CEO Matthew Prince said a Sequoia partner passed on Cloudflare because “he didn’t think a woman could lead a security infrastructure company.” Cloudflare was founded in 2009 by Prince, Lee Holloway, and Michelle Zatlyn. The internet services company is now valued at almost $90 billion.

Prince said he also once met with Khosla Ventures about investing in Cloudflare’s Series C.

Vinod Khosla, the legendary tech investor and the firm’s namesake, took Prince and his fellow founders out to dinner, Prince wrote. Near the end of the conversation, Prince recalled, Khosla leaned over and said, “I’m impressed with you, not so much with them, what if you fire them and I’ll give you all their stock?”

Prince said he was so offended he never spoke to Khosla again. Other founders responded to Prince, adding their own experiences dealing with Khosla.

It was enough for Khosla to spend his Saturday responding to the accusations, firing off over a dozen X posts. In some, he denied the stories and asked for evidence, but in most, he repeated a single mantra: Honesty is the best policy.

“I am often wrong but always give honest opinions. Some find this harsh, but hypocritical politeness hurts founders,” he wrote in one post. “Brutal honesty gives them a chance to evaluate it and accept or reject the opinion. Great founders elect for honesty. It is not fun to offer brutal honesty.”

Khosla did not immediately respond to a request for comment from Business Insider.

Some industry insiders came to Khosla’s defense. Blake Byers, an early-stage investor and founder, said Khosla founded one of the pioneering companies of the modern computer industry — Sun Microsystems — before becoming one of Silicon Valley’s most influential venture capitalists.

“He is one of the truest VCs to ever do it,” he wrote.

Mark Cummins, an angel investor and robotics expert, said he began pitching a partner at a French firm, only for the investor to interrupt with questions about his parents’ careers.

“What did your father do?’ the partner asks me in a thick French accent,” Cummins wrote.

When Cummins said his father had trained as a theoretical physicist before going into business, the partner replied: “Aha! Your father was a failure!” Then, after Cummins said his mother had been a biochemist before becoming a schoolteacher, the investor said, “Also a failure!”

Cummins said he responded, “I have a hundred employees and we need funding. ‘Would you like to hear about my company?'”

In a conversation largely dominated by men, Claire Vo, the founder of ChatPRD, an AI product management platform, said an investor once interrupted her pitch to say he was glad she wasn’t trying to have kids while building a company.

“I love an opportunity to tell a nightmare VC story!” she wrote.

She later turned one of Khosla’s posts defending himself into what she called a “pop punk banger.”

• I started teaching my daughter to pack when she was 3 years old.
• Packing together helps build her independence and decision-making.
• I hope the extra effort now will pay off as she grows older.

I started teaching my daughter to pack when she was 3 years old, which, I know, sounds inefficient at best and slightly unhinged at worst.

Packing with a preschooler is slow. It turns a 30-minute task into a 90-minute one. It involves delicate negotiations over which stuffed animals are “essential,” last-minute outfit swaps as she re-discovers her favorite sparkly boots, and frequent distractions. If saving time today were the goal, I would simply do it myself.

But my perspective changed after I heard versions of the same complaint from multiple mothers; they were still packing for their teenagers. Not just occasionally helping or reminding, but fully responsible for it. That dynamic doesn’t appear suddenly at 13; it builds over time.

So I decided to start while my toddler still craves independence with a fervor, hoping it will pay off over the next decade.

The first step was participation, not decision-making

The first time we “packed together,” I did almost all of the work in advance. I pulled everything she would need and laid it out on the floor of her room, alongside an open suitcase. My toddler wasn’t choosing items or deciding quantities. She happily folded clothes with me, shoved them into packing cubes, and put the packing cubes into the suitcase.

This participation also helped her mentally prepare for the coming travel. As we packed bathing suits, we talked about going to the pool and the beach. Her blankie gets packed because we’ll be sleeping in a new place, so she’ll want to have something familiar. She’ll wear her sneakers to the airport because we’ll be walking more than usual.

Especially with toddlers, a smooth trip starts with helping them understand what the experience will be like before we get there. That mental preview reduces friction later.

The next step was constrained choice

Once that baseline was established, I shifted one variable: selection. Instead of laying everything out myself, I told her what we needed, and she got to pick: six T-shirts, five pairs of shorts, two bathing suits. Then she went to her drawers and chose them.

That changed the task meaningfully. She still wasn’t determining quantities or planning for contingencies, but she was making decisions within a defined framework. I separated “what do we need?” from “which specific items do we bring?” and introduced them in sequence.

She’s also responsible for helping put everything into her suitcase, which makes it easier to say no to the constant requests to bring additional toys and books. For shorter trips, if it fits into her carry-on after her essentials, she can bring it. On longer trips with a checked bag, she gets one packing cube for toys and books so she can decide what she most wants to bring.

One major step is that now she has a suitcase that is clearly hers. For our coming trip to Asia, she’s packing into a light pink MiaMily suitcase that I gave her for her most recent birthday, now enthusiastically decorated with stickers. It’s a ride-on suitcase that she sits on proudly, like her travel throne.

That shift sounds small, but it changes how she approaches the task. It’s no longer a shared family suitcase or something I’m managing on her behalf—it’s her suitcase, and she treats it that way.

The goal is a gradual handoff

I’m not trying to create unrealistic independence at 3. Over time, I can shift more of that responsibility to her by asking her to suggest quantities, to think through activities, and to identify what might be missing.

It does take longer now. There’s no way around that. But if the alternative is still packing for her a decade from now, the tradeoff is worth it.

• My dad planned to travel and do so much once he retired, but he died at 52 before he had the chance.
• Losing him pushed me to live life differently, like skipping college to travel to Europe instead.
• I’m grateful I live a life focused on new experiences and adventure, not stability and savings.

Throughout his life, my dad was incredibly focused on being successful and providing for our family, trying to ensure all of us had the best possible future.

He was good at it, too. He built us a beautiful home by the beach, studied with me so I’d get straight A’s, and took our family on countless vacations to Hawaii and Yosemite — all while running a business and putting money into his retirement fund.

Along the way, he postponed a lot of things he wanted to do, like finally taking that trip to Europe, buying his dream car, and relocating to Hawaii with my mom so they could spend their days sipping mai tais under the shade of a palm tree.

It was OK, he’d say, because once he retired, maybe in his 60s or 70s, he’d do all of those things. But then he got sick at 51. One year later, at 52, he was gone.

I was only 15 then, and I didn’t know how to handle losing the bravest man I knew. It was so unfair, and life suddenly felt incredibly short.

My dad planned to travel and experience so many grand things after retirement, but never got the chance. I didn’t want the same to happen to me.

His death changed my priorities and how I thought about the future

Losing my dad left me yearning to experience things he didn’t get to. I didn’t want to wait until an uncertain retirement; I wanted to live my life now.

After high school, I didn’t end up going to college, which, before my dad’s death, was the only option I saw for my future. Instead, I started working and saving up money to travel. By the following summer, I was able to make my way to Europe.

As I ate fresh slices of pizza in Naples and took in the sights from the top of the Eiffel Tower, I felt like my dad was right there with me.

That trip gave me a taste of a life I wanted to live.

Shortly after, I decided to pursue teaching English abroad in Mexico. It was another chance to see more of the world, but starting from scratch in a new country and learning a new language wasn’t easy.

It took time to find friends, and I didn’t always have a steady paycheck — but what I didn’t make up for in my savings account, I was making up for in life experiences.

After a few years, I had become fluent in Spanish, traveled throughout Mexico, and found a passion for writing and playing guitar. My confidence grew, and I felt I could do this somewhere else.

So in my early 30s, where years prior I would’ve thought I would be married with children, I packed up and moved to Europe, single, with some savings and no steady job waiting for me on the other side.

I landed in Spain and started building a life from scratch again in Barcelona. It was incredibly lonely at times, and I often compared myself to friends back home in Los Angeles, who had steady careers and were beginning to have kids.

But then I would think of my dad and how he’d always tell me I could achieve anything I put my mind to. I reminded myself that I chose this path. I was seeing the world and making my way in it, even if it wasn’t always easy.

I’m glad I’ve chosen to plan a life around experiences, not stability

I’m nearly 40, and I’ve been in Barcelona for almost seven years now. In that time, I’ve built a community and met and married the love of my life. I don’t have children yet, and my writing career is still blossoming.

I still haven’t prioritized growing my savings account or making concrete retirement plans. It can be a risky way to live, and sometimes I’m scared of what the future may bring, but losing my dad so young made me realize that nothing in life is guaranteed.

I’d rather enjoy the present and grab opportunities as they arise rather than wait and potentially never get to take them — and I’m grateful for everything my dad taught me, even if I only had him for 15 years.