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How transportation startups feel about Trump 2.0

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There have been dozens of Tesla Cybertrucks this week in Bentonville, Ark., shuttling startup founders and executives between their private planes and hotels and the row of airplane hangars outside a small, municipal airport where the UP.Summit took place this week.

It’s not every day that so many of the companies I cover actually come to me and the small city I’ve decided to call home. But once a year—when the transportation-focused VC firm UP.Partners hosts this event (this year with Walmart heirs Tom and Steuart Walton as co-hosts)—they do just that. 

I’ve spent the last two days peering into the commercial space station the startup Vast plans to send into orbit next year; doing flight simulations for Joby Aviation’s electric air taxi and Regent’s Seaglider vessel; and sitting across from the son of Robinhood cofounder Baiju Bhatt in a mockup of Blue Origin’s astronaut capsule, which is sending people into space. Tesla’s new Cybercab, and two of its Optimus robots, were here for attendees to gawk at, and Tesla Chief Designer Franz von Holzhausen laughed on stage about the mishap at the initial unveiling of the Cybertruck in 2019, when he threw a steel ball at the window and it broke.

The energy is always high at this annual event—likely in part because of UP.Partners cofounder Cyrus Sigari’s boundless energy and enthusiasm for flying cars and the Jetsons. But there was something else that kept popping up in conversations I had this year: Donald Trump.

If you’ve been paying attention to the transportation and aviation/aerospace industries for any amount of time—flying cars! Mars missions! Autonomous planes!—you know that the enthusiasm around those shiny, cool toys can quickly run dry when you consider the enormous regulatory hurdles that still lie between these companies and many of their products coming to market in the U.S. Here’s an example: Three years ago at this same event, Zipline CEO Keller Rinaudo Cliffton was celebrating his company’s tens of thousands of drone deliveries in Africa. Flash forward to today and I still can’t get anything sent to my house from the company, even though my home is only about a 15-minute drive away from one of their delivery outposts. Executives at transportation companies have long fumbled through questions about certification and product timelines, as there’s so much that is completely out of their control.

But these days, the regulatory piece is actually starting to feel more attainable for many companies that have been playing the waiting game. Adam Woodworth, the CEO of Wing, Alphabet’s drone delivery company, described on stage how his team are in the early stages of scaling up their delivery operations to several cities around the country. I was surprised to hear Walmart innovation executive Greg Cathey be so brazen about Walmart’s plans to bring drone delivery to “most areas that we operate in” due to changes in the regulatory environment. Adam Goldstein, CEO of air taxi startup Archer Aviation, told me about joining the White House’s eVTOL Integration Pilot Program, a group put together after one of Trump’s executive orders pushed the FAA to accelerate the process of getting air taxis into the skies. And Billy Thalheimer, CEO of Regent, a startup building seaglider vessels to shuttle people—and cargo—along the coasts, said that the speed and clarity with which his company has received responses from the Coast Guard has been significant since Trump was elected. 

All this enthusiasm has its limits, of course. Just yesterday, the EV tax credit went away—a notable loss for EV companies like Tesla, Slate Auto, and Scout, which were all present at the Bentonville event. Even for some of the most obvious benefactors of the Trump Administration’s tech agenda, it’s not all milk and roses. Wing CEO Woodworth said he was thrilled to see the new regulation around flying beyond visual line of sight—at first. 

“We were less excited when we started reading it, because there’s a lot of steps back in that rule,” Woodworth said on stage, noting how there had already been a lot of progress made between industry and regulators in the time since the initial rule was drafted.

Politics aside, everyone is excited to talk about what comes next—and the money they still want from investors to make it happen. And I sure got a laugh when, upon arriving on my e-bike— at a transportation conference, no less—there was no place to park my bike, and everyone at the check-in counter seemed bewildered as to what I should do with it.

Until next time,

Jessica Mathews
X:
@jessicakmathews
Email: jessica.mathews@fortune.com

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VENTURE DEALS

Einride, a Stockholm, Sweden-based provider of digital, electric, and autonomous solutions for road freight, raised $100 million in funding from EQT Ventures and others.

Phaidra, a Seattle, Wash.-based developer of AI agents for AI factories, raised $50 million in Series B funding. Collaborative Fund led the round and was joined by Helena, Index Ventures, NVIDIA,

Vibe.co, a New York City-based ad platform designed to bring hyper-targeting to connected TV, raised $50 million in Series B funding. Hedosophia led the round and was joined by Elaia, Singular, and others. 

Baselane, a New York City-based banking and financial platform designed for real estate investors, raised $34.4 million across Series A and B rounds. Thomvest Ventures led the $20 million Series B round and Matrix Partners led the $14.4 million Series A round.

Kanastra, a São Paulo, Brazil-based fintech company for private credit funds and securitizations, raised $30 million in Series B funding. F-Prime led the round and was joined by the International Finance Corporation and others.

Moonlake AI, a San Francisco-based AI research lab, raised $28 million in seed funding from AIX Ventures, Threshold, NVIDIA Ventures, and others.

Predicta Biosciences, a Cambridge, Mass.-based precision oncology company, raised $23.4 million in Series A funding. Engine Ventures led the round and was joined by Illumina Ventures, Lightchain Capital, Mass General Brigham Ventures, and others. 

Remitee, a Buenos Aires, Argentina-based remittance infrastructure provider, raised $20 million in funding. Krealo led the round and was joined by Copec Wind Ventures, Soma Capital, Redwood Ventures, Latitud, and Algorand.

Filament, a New York City-based invite-only connection platform for professionals, raised $10.7 million in seed funding from EQT Ventures, Flybridge Capital, Oceans Ventures, and others.

DJUST, a Paris, France-based business-to-business operations platform, raised €7 million ($8.2 million) in a Series A extension. NEA led the round and was joined by Elaia and Speedinvest.

Mesta, a San Francisco-based global fiat and stablecoin payment network, raised $5.5 million in seed funding. Village Global led the round and was joined by Circle Ventures, Paxos, Canonical Crypto, WTI,  and existing investors Garuda Ventures, Everywhere Ventures, and Inventum Ventures.  

PRIVATE EQUITY

Arlington Capital Partners acquired a majority stake in Concord Biomedical Sciences and Emerging Technologies, a Boston, Mass.-based provider of translational research and product development services for the medical device, pharmaceutical, diagnostic, and biomedical research industries. Financial terms were not disclosed.

Future Standard agreed to acquire the Digital Infrastructure platform of Post Road Group, a Stamford, Conn.-based alternative investment advisory platform. Financial terms were not disclosed. 

Magirus, a portfolio company of Mutares, agreed to acquire Achleitner Fahrzeugbau GmbH, a Radfeld, Austria-based designer and developer of customized vehicles for offroad, police, military, and paramilitary application. Financial terms were not disclosed.

VisuSewer, a portfolio company of Fort Point Capital, acquired MOR Construction Services, a Glen Mills, Penn.-based provider of utility and commercial wastewater infrastructure services. Financial terms were not disclosed.



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What a Walmart CEO contender’s exit reveals about when to move on

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There’s no such thing as a silver medal in a CEO succession race.

In November, Walmart named U.S. chief John Furner as its next CEO, crowning him the sixth leader in the history of the world’s largest retailer. The decision also quietly closed the door on another highly regarded contender for the corner office: Kath McLay, Walmart International’s CEO and a decade-long veteran of the company. On Thursday, Walmart disclosed that McLay would depart, staying on briefly to ensure a smooth transition.

The sequence was swift, orderly, and entirely unsurprising to those who study corporate succession. Boards rarely say it out loud, but experienced executives understand intuitively that once a CEO is chosen, the long-term prospects for previously whispered-about internal candidates dim almost immediately as power consolidates around the new chief executive. 

That’s why many of the most ambitious leaders in American business don’t linger after a succession decision. They move deliberately, and often quickly, because the moment immediately after a board makes its choice is paradoxically when a near-CEO executive’s market value is at its peak. The executive has just been validated at the highest level—close enough to be seriously considered for the top job—without yet absorbing the reputational drag that can follow prolonged proximity to a decision that didn’t go their way.

In that narrow window, the story is still about capability. Search firms and directors see a leader who was trusted with scale, complexity, and board scrutiny, not someone who failed to clear the final hurdle. 

When Jeff Immelt was named CEO of General Electric in 2001, the decision concluded one of the most closely watched succession contests in modern corporate history. Among the executives developed as credible successors was Bob Nardelli, then president and CEO of GE Power Systems. Nardelli didn’t stay to see how it might play out. Within months, he left GE to become Home Depot’s CEO.

A decade later, a different scenario unfolded at Apple, but with a similar outcome. Retail chief Ron Johnson had transformed Apple’s stores into an industry-defining, highly profitable global business and was widely viewed internally as CEO-caliber. Apple’s board had long centered its succession plans on Tim Cook, and when Cook was formally named successor to Steve Jobs, it effectively closed the door on a CEO path for Johnson. He left soon after to take the top job at J.C. Penney.

The executives who leave quickly aren’t being disloyal; they’re being realistic. Remaining too long after a succession decision can quietly erode an executive’s standing, both internally and externally, as the narrative shifts from “next in line” to “still waiting.”

At Ford Motor Co., president Joe Hinrichs was widely viewed as a leading CEO contender. When the board selected Jim Hackett in 2017, Hinrichs left not long afterward. Five years later, he resurfaced as CEO of transportation company CSX. Similarly, several senior Disney executives left or were sidelined after Bob Chapek was chosen as CEO in 2020. Most notably, Kevin Mayer, Disney’s head of direct-to-consumer and international, and a widely assumed CEO contender, departed within months to briefly become CEO of TikTok.

There are exceptions. But they tend to follow a different arc.

Although longtime Nike insider Elliott Hill was not passed over in a formal succession contest, he was widely viewed as CEO-ready when the board opted for an external hire in 2020. Hill stayed on for several years and later retired. Only after performance pressures mounted and the company embarked on a strategic reset did Nike’s board reverse course, asking Hill to return as CEO in 2024. Even then, such boomerangs remain exceedingly rare.

McLay’s departure from Walmart fits the dominant pattern. By exiting promptly while remaining to support a defined transition, she preserves both her reputation and her leverage. She leaves as an executive who was close enough to be seriously considered—not one who stayed long enough to be diminished by the process.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.



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Crypto market reels in face of tariff turmoil, Bitcoin falls below $90,000 as key legislation stalls

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If you don’t like the price of Bitcoin, wait five minutes, and it will change. The major cryptocurrency’s volatility has been on full display to start the year, this time dipping about 7% since last week to its current price of just under $90,000 as of mid-day Tuesday.

Other cryptocurrencies have also slid. Ethereum is down 11% in the last six days to its current price of about $3,000, and Solana is down about 14% during that time to its price of about $127. 

The dip comes as President Donald Trump threatened European nations with tariffs as they pushed back against his plans to take over Greenland, causing markets to scramble. Meanwhile, crypto markets faced an additional headwind as key legislation for the industry, known as the Clarity Act, became stalled after industry giant Coinbase unexpectedly withdrew its support late last week. 

“President Trump’s threat to impose tariffs on Europe has put Bitcoin under pressure,” said Russell Thompson, chief investment officer at Hilbert Group. “The postponement of the Clarity Act in the Senate committee mainly due to concerns from Coinbase eliminated a large amount of positive sentiment in the market.”

Coinbase CEO Brian Armstrong objected to the Clarity Act primarily on grounds that crypto owners would not be able to earn yield from stablecoins. The new uncertainty over the bill, which many assumed was on a smooth path towards a Presidential signature, has shaken the price not just of crypto assets but also the share price of companies exposed to digital assets. 

It’s uncertain whether the current headwinds will fade anytime soon. Trump has made his intentions of taking control of Greenland clear. When a group of European nations expressed solidarity with the Danish, he threatened those countries with tariffs, saying he would not back down until Greenland was purchased. Bitcoin and other risk assets subsequently fell, along with major stock indices, while the price of gold rose.

It’s not all gloom and doom for crypto, at least according to some analysts, who view Bitcoin’s correlation with macroeconomic forces as confirmation that digital assets have finally gone mainstream. 

“Bitcoin’s reactivity is another sign of its increasing integration with broader macroeconomic forces, signaling maturation rather than fragility, even as short-term volatility continues,” said Beto Aparicio, senior manager of strategic finance at Offchain Labs.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.



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The 9 most disruptive deals of Trump’s first year back in the White House

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President Trump lives on deals: “That’s what I do—I do deals,” he once told Bob Woodward. On the one-year anniversary of his second presidency, he’s pushing hard to make his biggest, most disruptive deal ever, one that would bring Greenland under the control of the U.S.—and the global business community is still scrambling to adapt to his approach. Here are nine of Trump’s most unorthodox deals from the past year.

Nine deals that shook the business world

April 2, 2025: Reciprocal tariffs

Trump imposes “reciprocal tariffs” on 57 countries, with each tariff understood as an opening bid in a negotiation. Several countries have since made deals. The one-on-one negotiations, unlike the multilateral system of the past 80 years, can be chaotic for companies and economies

June 13: U.S. Steel “Golden Share”

In return for allowing Nippon Steel to buy U.S. Steel, Trump requires that the U.S. receive several powers over the company, including total power over all the board’s independent directors and vetoes over locations of offices and factories. 

July 10: MP Materials

The U.S. pays $400 million for a large equity share in MP and signs a contract to buy all of MP’s rare earth magnets for 10 years. The reason for the equity stake was not disclosed.

July 14: Nvidia, Part 1

JADE GAO—AFP/Getty Images

Trump reverses the U.S. ban on selling Nvidia H20 chips to China in exchange for Nvidia paying the U.S. 15% of the revenue.

July 23: Columbia University

LYA CATTEL/Getty Images

The Trump administration restores $400 million of canceled federal research funding for the university under an unprecedented multipoint deal. For example, Columbia must supply data to the federal government for all applicants, broken down by race, “color,” GPA, and standardized test performance. A few other schools later make similar deals.

August 6: Apple

Bonnie Cash—UPI/Bloomberg/Getty Images

At a public appearance with Trump, CEO Tim Cook announces Apple will invest an additional $100 billion in the U.S. over four years; Trump announces Apple will be exempt from a planned tariff on imported chips that would have doubled the price of iPhones in the U.S.

August 22: Intel

Justin Sullivan—Getty Images

Intel trades the U.S. government a 9.9% equity stake in exchange for $8.9 billion that might already be owed to Intel under the CHIPS and Science Act. The deal is unusual because the company was not in immediate danger or significantly affecting the economy.

December 8: Nvidia, Part 2:

Trump reverses the U.S. ban on selling powerful Nvidia H200 chips in exchange for Nvidia paying the U.S. 25% of the revenue. Both Nvidia deals are unusual because the payments to the U.S., based on exports, appear to be forbidden by the Constitution. 

December 19: Pharma

Alex Wong—Getty Images

Nine pharmaceutical companies make deals with Trump that are intended to lower drug prices. This is unusual because Trump negotiated separate deals with each company, and the terms have not been released.

All eyes this week will be watching President Trump at the World Economic Forum in Davos, where the president has hinted he’ll announce some high-stakes agreements. Expect the unexpected.

A version of this piece appears in the February/March 2026 issue of Fortune.



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