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Loans Could Burn Start-Up Workers in Downturn

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SAN FRANCISCO — Last year, Bolt Financial, a payments start-up, began a new program for its employees. They owned stock options in the company, some worth millions of dollars on paper, but couldn’t touch that money until Bolt sold or went public. So Bolt began providing them with loans — some reaching hundreds of thousands of dollars — against the value of their stock.

In May, Bolt laid off 200 workers. That set off a 90-day period for those who had taken out the loans to pay the money back. The company tried to help them figure out options for repayment, said a person with knowledge of the situation who spoke anonymously because the person was not authorized to speak publicly.

Bolt’s program was the most extreme example of a burgeoning ecosystem of loans for workers at privately held tech start-ups. In recent years, companies such as Quid and Secfi have sprung up to offer loans or other forms of financing to start-up employees, using the value of their private company shares as a sort of collateral. These providers estimate that start-up employees around the world hold at least $1 trillion in equity to lend against.

start-up economy now deflates, buffeted by economic uncertainty, soaring inflation and rising interest rates, Bolt’s situation serves as a warning about the precariousness of these loans. While most of them are structured to be forgiven if a start-up fails, employees could still face a tax bill because the loan forgiveness is treated as taxable income. And in situations like Bolt’s, the loans may be difficult to repay on short notice.

badly burned by loans related to their stock options.

Ted Wang, a former start-up lawyer and an investor at Cowboy Ventures, was so alarmed by the loans that he published a blog post in 2014, “Playing With Fire,” advising against them for most people. Mr. Wang said he got a fresh round of calls about the loans anytime the market overheated and always felt obligated to explain the risks.

“I’ve seen this go wrong, bad wrong,” he wrote in his blog post.

Start-up loans stem from the way workers are typically paid. As part of their compensation, most employees at privately held tech companies receive stock options. The options must eventually be exercised, or bought at a set price, to own the stock. Once someone owns the shares, he or she cannot usually cash them out until the start-up goes public or sells.

Uber and Airbnb put off initial public offerings of stock as long as they could, hitting private market valuations in the tens of billions of dollars.

That meant many of their workers were bound by “golden handcuffs,” unable to leave their jobs because their stock options had become so valuable that they could not afford to pay the taxes, based on the current market value, on exercising them. Others became tired of sitting on the options while they waited for their companies to go public.

The loans have given start-up employees cash to use in the meantime, including money to cover the costs of buying their stock options. Even so, many tech workers do not always understand the intricacies of equity compensation.

“We work with supersmart Stanford computer science A.I. graduates, but no one explains it to them,” said Oren Barzilai, chief executive of Equitybee, a site that helps start-up workers find investors for their stock.

Secfi, a provider of financing and other services, has now issued $700 million of cash financing to start-up workers since it opened in 2017. Quid has issued hundreds of millions’ worth of loans and other financing to hundreds of people since 2016. Its latest $320 million fund is backed by institutions, including Oaktree Capital Management, and it charges those who take out loans the origination fees and interest.

So far, less than 2 percent of Quid’s loans have been underwater, meaning the market value of the stock has fallen below that of the loan, said Josh Berman, a founder of the company. Secfi said that 35 percent of its loans and financing had been fully paid back, and that its loss rate was 2 to 3 percent.

congratulatory flourish on Twitter in February, writing that it showed “we simply CARE more about our employees than most.”

The company’s program was meant to help employees afford exercising their shares and cut down on taxes, he said.

Bolt declined to comment on how many laid-off employees had been affected by the loan paybacks. It offered employees the choice of giving their start-up shares back to the company to repay their loans. Business Insider reported earlier on the offer.

Mr. Breslow, who stepped down as Bolt’s chief executive in February, did not respond to a request for comment on the layoffs and loans.

In recent months, he has helped found Prysm, a provider of nonrecourse loans for start-up equity. In pitch materials sent to investors that were viewed by The New York Times, Prysm, which did not respond to a request for comment, advertised Mr. Breslow as its first customer. Borrowing against the value of his stock in Bolt, the presentation said, Mr. Breslow took a loan for $100 million.

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Farewell, Millennial Lifestyle Subsidy

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A few years ago, while on a work trip in Los Angeles, I hailed an Uber for a crosstown ride during rush hour. I knew it would be a long trip, and I steeled myself to fork over $60 or $70.

Instead, the app spit out a price that made my jaw drop: $16.

Experiences like these were common during the golden era of the Millennial Lifestyle Subsidy, which is what I like to call the period from roughly 2012 through early 2020, when many of the daily activities of big-city 20- and 30-somethings were being quietly underwritten by Silicon Valley venture capitalists.

For years, these subsidies allowed us to live Balenciaga lifestyles on Banana Republic budgets. Collectively, we took millions of cheap Uber and Lyft rides, shuttling ourselves around like bourgeois royalty while splitting the bill with those companies’ investors. We plunged MoviePass into bankruptcy by taking advantage of its $9.95-a-month, all-you-can-watch movie ticket deal, and took so many subsidized spin classes that ClassPass was forced to cancel its $99-a-month unlimited plan. We filled graveyards with the carcasses of food delivery start-ups — Maple, Sprig, SpoonRocket, Munchery — just by accepting their offers of underpriced gourmet meals.

tweeted, along with a screenshot of a receipt that showed he had spent nearly $250 on a ride to the airport.

“Airbnb got too much dip on they chip,” another Twitter user complained. “No one is gonna continue to pay $500 to stay in an apartment for two days when they can pay $300 for a hotel stay that has a pool, room service, free breakfast & cleaning everyday. Like get real lol.”

Some of these companies have been tightening their belts for years. But the pandemic seems to have emptied what was left of the bargain bin. The average Uber and Lyft ride costs 40 percent more than it did a year ago, according to Rakuten Intelligence, and food delivery apps like DoorDash and Grubhub have been steadily increasing their fees over the past year. The average daily rate of an Airbnb rental increased 35 percent in the first quarter of 2021, compared with the same quarter the year before, according to the company’s financial filings.

set up a $250 million “driver stimulus” fund — or doing away with them altogether.

I’ll confess that I gleefully took part in this subsidized economy for years. (My colleague Kara Swisher memorably called it “assisted living for millennials.”) I got my laundry delivered by Washio, my house cleaned by Homejoy and my car valet-parked by Luxe — all start-ups that promised cheap, revolutionary on-demand services but shut down after failing to turn a profit. I even bought a used car through a venture-backed start-up called Beepi, which offered white-glove service and mysteriously low prices, and which delivered the car to me wrapped in a giant bow, like you see in TV commercials. (Unsurprisingly, Beepi shut down in 2017, after burning through $150 million in venture capital.)

These subsidies don’t always end badly for investors. Some venture-backed companies, like Uber and DoorDash, have been able to grit it out until their I.P.O.s, making good on their promise that investors would eventually see a return on their money. Other companies have been acquired or been able to successfully raise their prices without scaring customers away.

Uber, which raised nearly $20 billion in venture capital before going public, may be the best-known example of an investor-subsidized service. During a stretch of 2015, the company was burning $1 million a week in driver and rider incentives in San Francisco alone, according to reporting by BuzzFeed News.

But the clearest example of a jarring pivot to profitability might be the electric scooter business.

Remember scooters? Before the pandemic, you couldn’t walk down the sidewalk of a major American city without seeing one. Part of the reason they took off so quickly is that they were ludicrously cheap. Bird, the largest scooter start-up, charged $1 to start a ride, and then 15 cents a minute. For short trips, renting a scooter was often cheaper than taking the bus.

But those fees didn’t represent anything close to the true cost of a Bird ride. The scooters broke frequently and needed constant replacing, and the company was shoveling money out the door just to keep its service going. As of 2019, Bird was losing $9.66 for every $10 it made on rides, according to a recent investor presentation. That is a shocking number, and the kind of sustained losses that are possible only for a Silicon Valley start-up with extremely patient investors. (Imagine a deli that charged $10 for a sandwich whose ingredients cost $19.66, and then imagine how long that deli would stay in business.)

Pandemic-related losses, coupled with the pressure to turn a profit, forced Bird to trim its sails. It raised its prices — a Bird now costs as much as $1 plus 42 cents a minute in some cities — built more durable scooters and revamped its fleet management system. During the second half of 2020, the company made $1.43 in profit for every $10 ride.

“DoorDash and Pizza Arbitrage,” about the time he realized that DoorDash was selling pizzas from his friend’s restaurant for $16 while paying the restaurant $24 per pizza, and proceeded to order dozens of pizzas from the restaurant while pocketing the $8 difference, stands as a classic of the genre.)

But it’s hard to fault these investors for wanting their companies to turn a profit. And, at a broader level, it’s probably good to find more efficient uses for capital than giving discounts to affluent urbanites.

Back in 2018, I wrote that the entire economy was starting to resemble MoviePass, the subscription service whose irresistible, deeply unprofitable offer of daily movie tickets for a flat $9.95 subscription fee paved the way for its decline. Companies like MoviePass, I thought, were trying to defy the laws of gravity with business models that assumed that if they achieved enormous scale, they’d be able to flip a switch and start making money at some point down the line. (This philosophy, which was more or less invented by Amazon, is now known in tech circles as “blitzscaling.”)

There is still plenty of irrationality in the market, and some start-ups still burn huge piles of money in search of growth. But as these companies mature, they seem to be discovering the benefits of financial discipline. Uber lost only $108 million in the first quarter of 2021 — a change partly attributable to the sale of its autonomous driving unit, and a vast improvement, believe it or not, over the same quarter last year, when it lost $3 billion. Both Uber and Lyft have pledged to become profitable on an adjusted basis this year. Lime, Bird’s main electric scooter competitor, turned its first quarterly profit last year, and Bird — which recently filed to go public through a SPAC at a $2.3 billion valuation — has projected better economics in the years ahead.

Profits are good for investors, of course. And while it’s painful to pay subsidy-free prices for our extravagances, there’s also a certain justice to it. Hiring a private driver to shuttle you across Los Angeles during rush hour should cost more than $16, if everyone in that transaction is being fairly compensated. Getting someone to clean your house, do your laundry or deliver your dinner should be a luxury, if there’s no exploitation involved. The fact that some high-end services are no longer easily affordable by the merely semi-affluent may seem like a worrying development, but maybe it’s a sign of progress.

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What Digital Nomads Need to Know About Taxes Abroad

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It’s risky. Employers need to know where their employees work in case their presence leads to corporate tax obligations abroad. The risk is higher when employees are bringing in revenue for companies, such as in sales positions, said David McKeegan, who co-founded Greenback Tax Services, an accounting firm for U.S. expatriates.

Still, many companies are operating on a “don’t ask, don’t tell” policy. A science writer in his 50s from California, who was granted anonymity because he did not want senior managers to know he had worked from Costa Rica for a few months, said his human resources department discouraged employees from working outside of California, but did not say anything explicit about working abroad. His setup from an Airbnb by the beach worked perfectly until he lost power because of a hurricane and had to work from a bar a few times. He used his company’s Zoom background, but colleagues started asking about where he was when they heard ocean waves and music. “At a restaurant,” he would tell them, without elaborating.

As more people work from abroad, it may be harder for companies to turn a blind eye. About 10.9 million Americans last year described themselves as digital nomads — people who work remotely and tend to travel from place to place — up from 7.3 million in 2019, according to MBO Partners, which provides services for self-employed workers.

“The tax system globally right now is not prepared for what the work force is going through,” Mr. McKeegan said. “I think at some point we’ll see a system where people are asked on the way in or out if they were working and countries will try and get some more tax revenue from this very mobile work force.”

Potentially. If you qualify for the Foreign Earned Income Exclusion, your first $108,700 is exempt from U.S. income tax. But keep in mind that this applies only if you’re a U.S. citizen who resides in a foreign country for more than 330 days within 12 consecutive months, not including time on planes, or if you are a bona fide resident of a foreign country. (You would still have to pay federal and state taxes on unearned income including interest, dividends and capital gains.)

It is important to track the number of days abroad to be able to prove to U.S. tax authorities that you were there.

Paige Brunton, 30, a Canadian website designer based in Hannover, Germany, learned about how complicated the tax rules are for expats the hard way: One year, she had to file tax returns in three countries. The situation was unavoidable, since she had lived and worked in Germany, Canada and the United States during that tax year, but her biggest advice for others who may have complicated situations is to get an accountant who specializes in international tax right away.

“Don’t congregate in Facebook groups and Google, it’ll really stress you out,” she said.

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Stocks Rally but End the Week With a Loss

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Wall Street ended Friday higher at the close of a broad rally, an upbeat conclusion to whipsaw week of buying and selling as signs of a rebounding economy did battle with mounting inflation jitters.

All three major U.S. indexes built on Thursday’s gains, when the S&P 500 notched its biggest one-day percentage bump in over a month.

“It’s a ‘buy everything’ day,” said Chuck Carlson, senior vice president at Wealthspire Advisors in New York.

Still, the indexes suffered their biggest weekly declines since late February.

Big swings this week were stoked by economic data, which fanned concerns that near-term price spikes could translate into long-term inflation, despite assurances to the contrary from the Federal Reserve.

Economic data released on Friday showed retail sales growth stalling and consumer sentiment dipping as prices continue to rise, suggesting that while the demand boom might be taking a breather, inflation has not.

But in an indication that economic activity could return to normal, revised guidance this week from the Centers for Disease Control and Prevention said fully vaccinated people no longer needed to wear masks outdoors and could avoid wearing them indoors in most places.

The S&P 500 gained 1.5 percent on Friday, but ended the week 1.4 percent below last week’s close. The Nasdaq composite jumped 2.3 percent on Friday.

All 11 major S&P sectors ended the session green, with energy, boosted by rebounding crude oil prices, enjoying the largest percentage gain.

Walt Disney Company shares dropped after the subscriber additions to its Disney+ streaming service fell short of expectations.

Airbnb reported a 52 percent jump in bookings, driving its stock higher.

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How to Deal With the Rental Car Crunch

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“These extra steps are annoying,” but essential, he said, especially in Hawaii, where the state’s Department of Commerce and Consumer Affairs told a local television station that it is launching an investigation into the high cost of rentals that have been listed for as much as $600 a day.

In lieu of hunting yourself, you can use AutoSlash, which uses rental car company coupons and discount codes to sort through search results that it says would take consumers considerable time. The free service also uses things like wholesale store and airline frequent flier program memberships and affiliations with organizations like the American Automobile Association and AARP to find deals.

The service then tracks the rental to ensure it remains the best value, emailing travelers to rebook in the event of a price drop.

There are, of course, transit alternatives to renting a car, including ride share services, bike share systems and public transportation.

For those seeking the privacy and control of an auto, Turo acts like Airbnb for cars, allowing individuals to list their vehicles for rent on the platform, where choices range from $20-a-day older subcompacts to luxury cars like a Lamborghini in Miami for more than $1,000 a day. Vehicle owners set the terms for things like daily mileage limits.

“In summer, when we started seeing people getting anxious to get out of their homes, we saw a boom in local travel and local destinations,” said Andre Haddad, the chief executive of Turo. “The local travel boom was advantageous to our hosts because people needed cars to get to these destinations and less so planes.”

For Justin Villa and Meagan Malcolm-Peck, Turo is a side gig through which they rent five Jeeps in the Denver area, which cost between $73 and $98 a day (they also have a heavy-duty pick-up truck for $184). After an initial three-month crash at the start of the pandemic, business has been steady with drivers and rental periods have extended beyond weekends. They encourage guests to rent about a month in advance.

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Restaurants Fought for Covid Survival, With Some Tech Helpers

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The past year has crushed independent restaurants across the country and brought a reality to their doors: Many were unprepared for a digital world.

Unlike other small retailers, restaurateurs could keep the tech low, with basic websites and maybe Instagram accounts with tantalizing, well-lit photos of their food.

For the past decade, Krystle Mobayeni had been trying to convince them that they needed more. Ms. Mobayeni, a first-generation Iranian-American, started her company, BentoBox, in 2013 as a side job. She wanted to use her graphic design skills to help restaurants build more robust websites with e-commerce abilities. But it was a hard sell. For many, she said, her services were a “nice to have,” not a necessity.

Until 2020. The pandemic sent chefs and owners flocking to BentoBox, as they suddenly needed to add to-go ordering, delivery scheduling, gift card sales and more to their websites. Before the pandemic the company, based in New York City, had about 4,800 clients, including the high-profile Manhattan restaurant Gramercy Tavern; today it has more than 7,000 restaurants onboard and recently received a $28.8 million investment led by Goldman Sachs.

“I feel like our company was built for this moment,” Ms. Mobayeni said.

The moment opened a well of opportunity for companies like BentoBox that are determined to help restaurants survive. Dozens of companies have either started or scaled up sharply as they found their services in urgent demand. Meanwhile, investors and venture capitalists have been sourcing deals in the “restaurant tech” sector — particularly seeking companies that bring the big chains’ advantages to independent restaurants.

“A lot of what’s happening is reminiscent of what we’ve seen in the broader retail sector in the past decade,” said R.J. Hottovy, a restaurant industry analyst and an investor at Aaron Allen & Associates. “Covid accelerated the transformation quite a bit. This is a once-in-a-lifetime chance to redefine the experience.”

Part of what Ms. Mobayeni offers restaurants is a one-stop shop and the ability to own their customer data. Many restaurants rely on third-party vendors, such as DoorDash or UberEats, to handle delivery. But those companies charge significant fees and retain customers’ data because the transactions go through their websites. That’s not such a big deal when delivery is 20 percent of a restaurant’s income stream, but it’s a game-changer when delivery becomes 100 percent of income — and you can’t contact any of your customers.

“Restaurants realized they had to think of themselves as larger businesses and brands,” said Camilla Marcus, co-founder of TechTable, which connects the hospitality and tech industries. “You have to expand into other things: e-commerce, delivery, products. You have to think outside the four walls.”

Helping restaurants deepen relationships with customers is where Sam Bernstein saw an opportunity. Before the pandemic he ran a tech start-up that connected students to housing, similar to Airbnb; when universities sent students home last spring, his revenue fell to zero.

He went to his board of directors and offered to return what investment was left and close down. Instead the board suggested he regroup with a smaller team and new vision.

“It was an existential crisis, as you can imagine,” he said.

Mr. Bernstein laid off all but 10 employees and took them for a brainstorming retreat. They considered dozens of business models, looking for the right problem to solve. The more they discussed options, the more the members of the team realized they were all interested in food and hospitality and wanted to help restaurants.

They hit upon the idea for a site that would allow customers to “subscribe” to their favorite restaurants. The new firm, Table22, would help chefs develop and market subscriptions for monthly meal kits and wine clubs, for example, and then manage the sales, recurring billing, scheduling, data analytics and more. In exchange, Table22 takes a percentage of each transaction.

Table22, which is based in New York, went live with its first restaurant in May. Since then, it has grown to more than 150 restaurants in 50 cities. Late last year, the company received about $7 million from investors, who include David Barber, owner of Blue Hill farm and restaurants.

Shelby Allison signed up her Chicago bar, Lost Lake, for the service on a cold email from Table22. She was hesitant at first, planning to listen just long enough to learn how to create a cocktail subscription service herself.

“We get lots and lots of calls from these tech companies trying to help — or prey upon — us struggling businesses,” she said.

But she was impressed by the low service fee and the fact that Table22 shared customer data. She started the service in October, hoping for 30 sign-ups; 100 people joined. Ms. Allison now has 300 subscribers and five employees working on the make-at-home cocktail boxes.

“This will 100 percent stay in the future,” she said. “I love this program. I thought it might cannibalize my to-go business, but it hasn’t at all.”

Ping Ho considered signing up with Table22 to host the wine and meat clubs she offers at her Detroit restaurant and butcher shop, Marrow, and wine bar, the Royce. She decided against it, however, because her existing subscription platform, Zoho, gave her the essential tools.

“It’s a bit more work, but there’s more agency,” she said.

But because her website was mostly informational, she realized she did need help offering online ordering and a delivery system for the butcher shop. So Ms. Ho turned to Mercato, which enables e-commerce for independent grocers. In a bit of fortuitous timing, she had signed up a month before the pandemic struck. When stay-at-home orders were issued, she was able to quickly begin offering grocery items, such as milk and eggs, in addition to meats.

Her sales jumped “tremendously” she said, although they have flattened out in recent months. Still, Ms. Ho intends to maintain the service.

Mercato began in 2015, but 2020 was its year. In February 2020, the service had 400 stores across 20 states; it quickly ramped up to more than 1,000 stores in 45 states. It continues to grow and has added some big-name clients, including the Ferry Building Marketplace on San Francisco’s Embarcadero, with dozens of merchants.

“We’re trying to give independent grocers a sustainable competitive advantage,” said Bobby Brannigan, founder and chief executive of the company, which is based in San Diego.

It’s a mission that he has been training for all his life. Mr. Brannigan’s family owns a grocery store in the Dyker Heights area of Brooklyn, where he started working when he was 8, stocking shelves and delivering groceries.

“It’s ironic that I’m back to doing what I was doing as a kid in Brooklyn,” he said.

Last March and April, Mercato brought on hundreds of new grocers each week — clients that weren’t used to having online orders or weren’t used to the sudden volume of orders. Some stores that were accustomed to 10 orders in a day were flooded with hundreds, Mr. Brannigan said. Thankfully, his dad already had him build tools into the system that would allow grocers to limit the pace of orders and schedule them.

Mr. Brannigan is also adding more data analytics to help his clients better understand what their customers want. They can now see what was bought and what customers searched for.

“You’re amassing a valuable treasure chest of data that lets you sell the products they want today and that they want tomorrow,” he said.

Of course, not all solutions are tech-centric; sometimes, it’s just a grass-roots community of chefs helping chefs. Alison Cayne, for example, has been giving free advice to chefs looking to create packaged goods, like her line of Haven’s Kitchen sauces. Having that extra revenue stream was critical when she shuttered her Manhattan restaurant and cooking school last spring, and she wants others to have the same options.

“This is all very much from my perspective, not the supercapitalized, venture capital-backed, cool-kids business,” she said. “I just want to help them take a brick-and-mortar business and develop a product and build a brand that makes sense and is sustainable.”

In Detroit, the grocer Raphael Wright and the chefs Ederique Goudia and Jermond Booze developed a “diabolical plan,” as Mr. Wright called it, to offer a weekly meal kit cooked by Black chefs during Black History Month.

“Black food businesses are hurting in the city, so we thought, what if we created this meal box in a way that celebrates Black food and Black contributions to American cuisine?” Mr. Wright said.

They named the project Taste the Diaspora Detroit and brought together Black chefs and farmers to create the weekly dishes — like gumbo z’herbes and black-eyed pea masala. The three organized all of the e-commerce and scheduling, which allowed chefs to participate even if they weren’t tech-savvy, and created the packaging and inserts that told the history of the meal. They topped it off with a paired Spotify playlist.

“Being a part of this project woke everyone up and made them think they have a little hope they can push through,” Mr. Wright said.

They hope to reprise the service for Juneteenth and are currently talking to funders to support the effort.

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5 Things to Know About Booking a Summer Rental

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“There are a lot of operators and owners who aren’t accustomed to being fully booked, and it can be tough to make sure they’re sorting out cleaning schedules and things like that,” said Jeremy Gall, a vacation-rentals industry veteran and the chief executive and founder of Breezeway, a property care and cleaning operations platform.

But, he added, “I think it’s all generally good news, especially in the context of the last 12 months. I don’t think there’s an owner, host or manager who would trade off the uncertainty that they felt this time last year for a fully booked summer.”

According to Transparent, a vacation-rentals data company, the countywide average nightly rate for Airbnb vacation rentals in July and August is expected to be around $220. Last year, it was $194; in 2019, it was $185.

At Evolve, a hospitality company that manages more than 14,000 short-term rentals around the United States, nightly rates are up 27 percent in July and 19 percent in August, over those same months in 2019.

“I’d be remiss to say that we didn’t raise our rates significantly,” said Jon Mayo, whose Airbnb in Palm Springs has more nights booked this summer than ever before, despite the sure-to-be-sweltering desert temperatures. “I’m renting at rates I wouldn’t have even dreamed of three years ago.”

Across the 1,000 vacation homes managed by Twiddy & Company, a hospitality and asset management firm in North Carolina’s Outer Banks, weekly summer rates have risen 8 percent since 2019, from $8,406 to $9,152. On StayMarquis, a luxury vacation-property management company, average rates in the Hamptons this summer — around $1,360 a night — are up 12 percent over 2019. Nightly rates across the 270 rentals managed by Hawai’i Life, a luxury brokerage and rental management company in Hawaii, are up 11 percent from 2019.

The elongated travel patterns that emerged last summer, from monthlong stays to four- and five-night “weekends,” are back in full force this year.

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Why Coinbase’s IPO Is a Cryptocurrency Coming-Out Party

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SAN FRANCISCO — Digital currency, once mocked as a tool for criminals and reckless speculators, is sliding into the mainstream.

Traditional banks are helping investors put their money into cryptocurrency funds. Companies like Tesla and Square are hoarding Bitcoin. And celebrities are leading the way in a digital-art spending spree using a technology called an NFT.

On Wednesday, digital or cryptocurrencies will take their biggest step yet toward wider acceptance when Coinbase, a start-up that allows people to buy and sell cryptocurrencies, goes public on Nasdaq. Coinbase shares received a reference price of $250 each on Tuesday evening, which would value the company at $65 billion based on all its outstanding shares.

Call it crypto’s coming-out party. Coinbase, founded in San Francisco, is the first major cryptocurrency start-up to go public on a U.S. stock market. It is doing so at a valuation that tops that of Capital One Financial Corporation or Moody’s, the ratings agency.

plan to “create an open financial system for the world” and “increase economic freedom.”

But so far, cryptocurrency is mostly a vehicle for financial speculation and trading. Few people want to use Bitcoin for everyday purchases like coffee because its price is so volatile. Many early buyers have become wildly rich by simply holding their crypto or “buying the dip” when prices fall. Others ruefully relay tales of the sushi dinner they bought with Bitcoin years ago that would be worth $200,000 today or the million-dollar pizza.

Coinbase eases that trading by acting as a central exchange. Before it and similar services were created, people had to set up their own digital wallets and wire money.

“Can it be anything more than an asset class?” Mr. Tusk asked. “That’s still very much up in the air.”

Silk Road, a marketplace for buying and selling drugs and weapons with Bitcoin until the federal authorities shut it down, and Mt. Gox, a crypto exchange that collapsed under accusations of theft and embezzlement, further tarnished the young industry.

Coinbase tried to change that. The company joined Y Combinator, a prestigious start-up program, and raised money from top venture capital firms including Union Square Ventures and Andreessen Horowitz.

Mr. Armstrong was one of the few people in the industry who seemed prepared to comply with inevitable regulations, rather than cut corners to avoid them, said Nick Tomaino, who dropped out of business school to join Coinbase in 2013.

Coinbase also persuaded well-known retailers to accept Bitcoin. “It was good for credibility when people saw you could actually use a Bitcoin to buy a mattress at Overstock,” Mr. Tomaino, who left in 2016, said. Coinbase earned money on transaction fees.

But Bitcoin’s wildly volatile price and a slow computer network that managed it made transactions difficult, and people began to see the currency as an investment. In 2015, Ethereum, a cryptocurrency network with more tech abilities, was introduced, enticing enthusiasts to build companies and funds around the technology.

Soon after, a flood of “initial coin offerings,” where companies sold tokens on the promise of the technology they planned to build, created a new boom in cryptocurrency trading. But it quickly deflated after many projects were found to be frauds and U.S. regulators deemed the offerings to be securities, requiring that they comply with financial rules.

Tesla to buy $1.5 billion worth of Bitcoin and the payments company Square to spend $170 million. In March, Morgan Stanley began offering its wealthy clients access to three Bitcoin funds, and Goldman announced that it would soon offer similar access. The mayor of Miami has proposed that the city accept tax payments in Bitcoin and invest city funds in the asset.

The stock trading app Robinhood announced that 9.5 million of its customers had traded cryptocurrency in the first three months of the year — up more than fivefold from the previous three months. Venture funding for crypto-related start-ups surged to its highest-ever level in the first quarter to $3 billion, according to PitchBook.

PayPal recently added a crypto trading and shopping feature for its customers in the United States. The company was motivated by consumer interest and advances in the technology that made transactions faster. It plans to quickly expand the offering to customers around the world.

“It feels like the time is right,” said Jose Fernandez da Ponte, head of PayPal’s blockchain, crypto and digital currencies group. “We think this has the potential to revolutionize payments and financial systems in general.”

Still, the so-called revolution faces some challenges. Coinbase has sometimes struggled to keep up with demand, with some customers who lost access to their accounts complaining that the company has been unresponsive. It has also received criticism for its treatment of female and Black employees.

Treasury Secretary Janet L. Yellen has threatened harsher regulation of the currencies, including limiting their use.

And a big drop in prices could again send speculators fleeing. In its financial prospectus, Coinbase warned that its business results would fluctuate with the volatility of crypto assets, “many of which are unpredictable and in certain instances are outside of our control.”

The industry’s biggest issue — fulfilling the promise that the technology is more than just a place to park money — could take another decade to play out.

“There’s no doubt we’re in the latest boom, and I don’t know if that’s going to turn tomorrow or two years from now,” Mr. Tomaino said. “But the busts and booms are always higher than the last.”

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In Empty Amsterdam, Reconsidering Tourism

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Support for the prostitutes and coffee shop owners was echoed in several interviews with Amsterdam residents, including Roy Van Kempen, a 31-year-old marketing manager who has lived in Amsterdam since 2008.

“Paris has the Eiffel Tower, and we have the Red Light District and this idea that everything is possible in Amsterdam. And I would like to keep it like this, actually,” he said.

But Irina, Mr. Helms, Mr. Van Kempen and half a dozen other Amsterdammers interviewed agreed that the city center has a major problem: A tourism “monoculture” has taken root, and residents are being pushed out. Businesses and services that used to cater to locals — high-quality bakeries, butcher shops, and the like — have been replaced by trinket shops, ice-cream parlors and “Nutella shops,” which serve takeaway waffles and other treats smeared in the hazelnut spread, mainly to tourists. Meanwhile, rising housing prices — due, in part, to the rise of Airbnb and other vacation rental platforms — have made the city center unaffordable for many locals.

This monoculture has been thrown into the spotlight over the past year, Ms. Udo said, adding that she had been struck by how deserted the city center has felt during the pandemic, especially compared to other parts of Amsterdam. “That was a real eye-opener,” she said. “There are not enough people living there and working there to get this liveliness back in the neighborhood when the visitors are gone.”

Alongside the restrictions proposed by the mayor’s office, city officials and some residents have also tried softer approaches to tackling the problems associated with tourism, some of which were rolled out with success before the pandemic.

One critical strategy has been to try to reach visitors before they even arrive. Amsterdam’s Enjoy and Respect campaign, which launched in 2018, targeted the primary source of the behavior problems — Dutch and British men between the ages of 18 and 34 — with messages about the fines they could incur by urinating in the street, littering or getting drunk in public areas. A subsequent survey showed that the messages had reached at least part of that audience, but measuring the campaign’s effectiveness has proved to be a challenge.

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With Fewer Ads on Streaming, Brands Make More Movies

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When the N.B.A. shut down its season last year because of the pandemic, one of the first phone calls Chris Paul made was to the Hollywood producer Brian Grazer. Mr. Paul, then a point guard with the Oklahoma Thunder, knew he wanted to chronicle what was going on, and he wanted Mr. Grazer’s help.

“The idea was, basically, film everything that had taken place in that game that night and what was going to come of it,” Mr. Paul said. “We had no clue what would happen next.”

The result was “The Day Sports Stood Still,” a documentary about the shutdown, the N.B.A.’s pandemic bubble and the impact of the Black Lives Matter movement on the league. (Mr. Paul appears in the film and is an executive producer.) It is a portrait of the ways the pandemic convulsed the sports world, but also an example of how Covid-19 has upended the entertainment industry.

The film, which debuts Wednesday on HBO and HBO Max, comes from Mr. Grazer’s Imagine Entertainment and a newer entrant to Hollywood: Waffle Iron Entertainment, Nike’s production entity.

General Electric Theater” television show from 1954 through 1962.

In the past decade, branded filmmaking has only proliferated.

Patagonia funded a feature-length documentary about dams, called “DamNation,” in 2014. Pepsi backed the 2018 movie “Uncle Drew,” which showcased the basketball star Kyrie Irving recreating his septuagenarian character from a popular series of Pepsi Max commercials. The film made $42 million and marked one of the first branded entertainment campaigns to be adapted into a major motion picture. “Gay Chorus Deep South,” a documentary produced by Airbnb, debuted on the festival circuit in 2019. And Apple’s acclaimed “Ted Lasso” began its life as an NBC Sports promotion for its acquisition of the broadcast rights to the English Premier League.

Imagine Entertainment, the production company founded by Mr. Grazer and Ron Howard in 1985, formed Imagine Brands in 2018 to pair companies with filmmakers, hiring Mr. Wilkes and Marc Gilbar, the creator of the “Uncle Drew” Pepsi campaign and an executive producer on the film, to run the group. The division has produced both feature-length documentaries and narrative films with their partners, which have included Unilever, Walmart and Ford.

Imagine is also working with the consumer goods giant Procter & Gamble. The company, which effectively created soap operas when it began to sponsor serial radio dramas in the 1930s to help promote its soap products, is cofinancing a feature-length film with Imagine called “Mars 2080.” It will be directed by Eliza McNitt and begin production later this year. The film, which is scheduled to be released theatrically by IMAX in 2022 before moving to a streaming service, focuses on a family resettling on Mars.

It grew out of a breakfast in New York in 2019, where Mr. Wilkes, Mr. Howard and Marc Pritchard, Procter & Gamble’s chief brand officer, discussed technology in the pipeline. The Imagine team later toured Procter & Gamble’s research labs in Cincinnati, seeing examples of its “home of the future” products and meeting its scientists.

Kimberly Doebereiner, the vice president of Procter & Gamble’s future of advertising division, said the company hoped to do more long-form storytelling, like “The Cost of Winning,” the four-part sports documentary its shaving brand Gillette produced. It debuted on HBO in November.

“We want to be more interesting so consumers are leaning into our experiences and we’re creating content that they want to see as opposed to messages that are annoying to them,” she said. “Finding a way to have content that is in places where ads don’t exist is definitely one of the reasons why we’re leaning into this.”

It’s all part of a deliberate shift by brands to try to integrate themselves more fully into consumers’ lives, the way companies like Apple and Amazon have, said Dipanjan Chatterjee, an analyst with Forrester. And they want to do so without commercials, which, he said, have “zero credibility” with consumers.

“If the right story has the right ingredients and it becomes worthwhile for sharing, it doesn’t come across as an intrusive bit of advertising,” Mr. Chatterjee said. “It feels much more like a natural part of our lives.”

Alessandro Uzielli, the head of Ford Motor Company’s global brand and entertainment division, first met with Imagine Brands in early 2018. He was looking for a way to augment Ford’s advertising campaign for its relaunched Bronco with a piece of entertainment that would reach a younger audience. The result was “John Bronco,” a 37-minute long mockumentary directed by Jake Szymanski (“Mike and Dave Need Wedding Dates”) and starring Walton Goggins (“Justified”) as the greatest fictional pitchman of all time.

The short film earned a slot in the Tribeca Film Festival and is now streaming on Hulu. In addition to featuring guest spots from Tim Meadows, Kareem Abdul-Jabbar and Bo Derek, it helped reintroduce the Bronco, a sport utility vehicle that the automaker pulled in the mid-1990s.

“This helped us speak to an audience that we probably weren’t going to speak to on our own,” Mr. Uzielli said.

“It was Imagine’s project, and we didn’t want to cloud their process, to try to make it feel like too much of a sales job,” he added.

Mr. Szymanski, who has directed both feature films and commercials, including ads for the Dodge Durango starring Will Ferrell’s “Anchorman” character Ron Burgundy, said Ford allowed him a great deal of creative freedom. “I think they could have tried to impose a much larger shadow on it than they did,” he said.

Now, Imagine, Mr. Szymanski and Mr. Goggins are trying to turn John Bronco into the next Ted Lasso — an effort in the early stages of development.

“It’s kind of a win-win,” Mr. Szymanski said of a possible television series based on Mr. Goggins’ character. “I don’t think Ford would have any creative control over it but to have a character named John Bronco in the world, that would be a good thing for them.”

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