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Travel guru The Points Guy wants to revamp the luxury travel points system with Journey

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Points fatigue is real. What started as a nice-to-have bonus for traveling has ballooned into a sprawl of rewards programs and arcane conversions that requires an advanced degree in statistics to manage. 

Brian Kelly made a whole career off the cottage industry, parlaying a side hustle of maximizing credit card and travel rewards into a blog, The Points Guy, that became a verifiable franchise. Now he’s arguing that the points system has jumped the shark. Alongside Lerer Hippeau and Slow Ventures, he’s backing the New York-based startup Journey in a $7.7 million seed round to set it back on the right track. 

Maybe this is too much of a first-world problem to care about, but I’m sure plenty of this newsletter’s readers were distraught when Chase announced an abstruse modification of their Sapphire Reserve credit card, or when Marriott acquired Starwood. Who doesn’t love fake internet money that can occasionally give you an airline upgrade or a free hotel night? 

John Sutton, the cofounder and CEO of Journey, thinks the system needs a revamp. A longtime tech entrepreneur, Sutton met Kelly while serving as the chief digital officer at Red Ventures, a media-focused investment firm that owns brands like Bankrate, Lonely Planet, and eventually, The Points Guy. 

When Sutton left his role in 2021, he took a couple of years off to play professional volleyball before figuring out his next venture. After exploring the idea of investing in short-term rentals like Airbnb properties, he had the idea of building out a loyalty program for travelers. After consulting with Kelly, he realized there was a broader problem—not only of short-term rentals and many independent hotels lacking the infrastructure to create rewards systems, but that points in general were increasingly broken. “They’ve been losing the magic of loyalty,” Kelly told me. “There’s a big opportunity to create a program that people are excited about.”

Journey’s website looks like a cross between a travel platform like Booking.com (an online travel agency, in industry parlance) and an Instagram feed, with lush snippets of desert hideouts and jungle treehouses. On the backend, Journey’s small team curates properties, now totaling more than 1,500 from around the world, that want to participate in their loyalty program—a combination of independent hotels and rental properties. Sutton says they’re not looking for certain price points (with properties ranging from several hundred to many thousand dollars per night) or stars, but whether they’ve “created something special that has a story to tell” (you can check out their portal, which just launched, to judge for yourself.)

The upshot for visitors, Sutton and Kelly argue, is that the system is straightforward: You earn five points per dollar spent if you book directly through their platform, with each point worth about two cents, equating to a 10% rebate, which can be instantly redeemed during stays. “Our program is engineered so that you’re not being taken advantage of,” Kelly said.

Journey is the type of consumer-forward, design-first tech product that you don’t see much anymore—a simple concept executed with flair. But this being 2025, there is AI involved, of course. The company has built tools that track visitor preferences and behavior, like whether they’d prefer to be greeted with red wine or mineral water, to help property managers customize the experience. And Journey is also building out a platform for influencers like Kelly that matches them with properties. Eventually, the goal is to build out AI agents that will help tourists. Sutton says it will make platforms like Expedia, where you find a hotel by searching for the top 10 hotels in Paris, look antiquated.

“Travelers will be on a trust journey with us,” he told me.  

Leo Schwartz
X:
@leomschwartz
Email: leo.schwartz@fortune.com

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VENTURE DEALS

Tako, a São Paulo-based developer of AI agents that run payroll and workforce operations, raised $18 million in funding from Ribbit Capital, a16z, and founders.

Raise Robotics, a San Francisco-based developer of a robot designed to complete construction tasks, raised $7.8 million in seed funding. MaC Ventures led the round and was joined by Undivided Ventures and existing investors Cybernetix Ventures, Zacua Ventures, and Union Labs.

Qbeast, a Bellevue, Wash.-based data infrastructure company, raised $7.6 million in seed funding. Peak XV’s Surge led the round and was joined by HWK Tech Investment and Elaia Partners.

Pearl Edison, a Detroit-based general contractor for residential electrification and energy efficiency projects, raised $3.3 million in seed funding. New System Ventures and Commonweal Ventures led the round and were joined by Lightbank and Newlab.

Neurogram, a São Paulo-based neurological diagnostics platform, raised $3 million in seed funding. Headline led the round and was joined by Romero Rodrigues.

PRIVATE EQUITY

Machinify, a portfolio company of New Mountain Capital, agreed to take Performant Healthcare, a Plantation, Fla.-based payments company for the health care industry, private for approximately $670 million.

New Mountain Capital agreed to acquire a minority stake in Wipfli, a Milwaukee-based advisory and accounting firm. Financial terms were not disclosed. 

EXITS

MPLX acquired Northwind Delaware Holdings, a Houston-based sour gas gathering, treating, and processing services business, from Five Point Infrastructure for $2.38 billion. 

Cinven agreed to acquire a majority stake in Smart Communications, a London, U.K.-based cloud-based enterprise customer communications, from Accel-KKR. Financial terms were not disclosed.

NDT Global acquired Entegra, an Indianapolis-based premium integrity and inspection company specializing in Ultra-High-Resolution Magnetic Flux Leakage in-line pipeline inspection services, from Amberjack Capital. Financial terms were not disclosed.

FUNDS + FUND OF FUNDS

Dextra Partners, a New York City-based private equity firm, raised $825 million for its seventh fund focused on middle-market companies.

CRV, a San Francisco and Palo Alto, Calif.-based venture capital firm, raised $750 million for its 20th fund focused on seed and Series A rounds.

This is the web version of Term Sheet, a daily newsletter on the biggest deals and dealmakers in venture capital and private equity. Sign up for free.



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SpaceX to offer insider shares at record-setting valuation

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SpaceX is preparing to sell insider shares in a transaction that would value Elon Musk’s rocket and satellite maker at a valuation higher than OpenAI’s record-setting $500 billion, people familiar with the matter said.

One of the people briefed on the deal said that the share price under discussion is higher than $400 apiece, which would value SpaceX at between $750 billion and $800 billion, though the details could change. 

The company’s latest tender offer was discussed by its board of directors on Thursday at SpaceX’s Starbase hub in Texas. If confirmed, it would make SpaceX once again the world’s most valuable closely held company, vaulting past the previous record of $500 billion that ChatGPT owner OpenAI set in October. Play Video

Preliminary scenarios included per-share prices that would have pushed SpaceX’s value at roughly $560 billion or higher, the people said. The details of the deal could change before it closes, a third person said. 

A representative for SpaceX didn’t immediately respond to a request for comment. 

The latest figure would be a substantial increase from the $212 a share set in July, when the company raised money and sold shares at a valuation of $400 billion.

The Wall Street Journal and Financial Times, citing unnamed people familiar with the matter, earlier reported that a deal would value SpaceX at $800 billion.

News of SpaceX’s valuation sent shares of EchoStar Corp., a satellite TV and wireless company, up as much as 18%. Last month, Echostar had agreed to sell spectrum licenses to SpaceX for $2.6 billion, adding to an earlier agreement to sell about $17 billion in wireless spectrum to Musk’s company.

Subscribe Now: The Business of Space newsletter covers NASA, key industry events and trends.

The world’s most prolific rocket launcher, SpaceX dominates the space industry with its Falcon 9 rocket that launches satellites and people to orbit.

SpaceX is also the industry leader in providing internet services from low-Earth orbit through Starlink, a system of more than 9,000 satellites that is far ahead of competitors including Amazon.com Inc.’s Amazon Leo.

SpaceX executives have repeatedly floated the idea of spinning off SpaceX’s Starlink business into a separate, publicly traded company — a concept President Gwynne Shotwell first suggested in 2020. 

However, Musk cast doubt on the prospect publicly over the years and Chief Financial Officer Bret Johnsen said in 2024 that a Starlink IPO would be something that would take place more likely “in the years to come.”

The Information, citing people familiar with the discussions, separately reported on Friday that SpaceX has told investors and financial institution representatives that it is aiming for an initial public offering for the entire company in the second half of next year.

A so-called tender or secondary offering, through which employees and some early shareholders can sell shares, provides investors in closely held companies such as SpaceX a way to generate liquidity.

SpaceX is working to develop its new Starship vehicle, advertised as the most powerful rocket ever developed to loft huge numbers of Starlink satellites as well as carry cargo and people to moon and, eventually, Mars.



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U.S. consumers are so strained they put more than $1B on BNPL during Black Friday and Cyber Monday

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Financially strained and cautious customers leaned heavily on buy now, pay later (BNPL) services over the holiday weekend.

Cyber Monday alone generated $1.03 billion (a 4.2% increase YoY) in online BNPL sales with most transactions happening on mobile devices, per Adobe Analytics. Overall, consumers spent $14.25 billion online on Cyber Monday. To put that into perspective, BNPL made up for more than 7.2% of total online sales on that day.

As for Black Friday, eMarketer reported $747.5 million in online sales using BNPL services with platforms like PayPal finding a 23% uptick in BNPL transactions.

Likewise, digital financial services company Zip reported 1.6 million transactions throughout 280,000 of its locations over the Black Friday and Cyber Monday weekend. Millennials (51%) accounted for a chunk of the sizable BNPL purchases, followed by Gen Z, Gen X, and baby boomers, per Zip.

The Adobe data showed that people using BNPL were most likely to spend on categories such as electronics, apparel, toys, and furniture, which is consistent with previous years. This trend also tracks with Zip’s findings that shoppers were primarily investing in tech, electronics, and fashion when using its services.

And while some may be surprised that shoppers are taking on more debt via BNPL (in this economy?!), analysts had already projected a strong shopping weekend. A Deloitte survey forecast that consumers would spend about $650 million over the Black Friday–Cyber Monday stretch—a 15% jump from 2023.

“US retailers leaned heavily on discounts this holiday season to drive online demand,” Vivek Pandya, lead analyst at Adobe Digital Insights, said in a statement. “Competitive and persistent deals throughout Cyber Week pushed consumers to shop earlier, creating an environment where Black Friday now challenges the dominance of Cyber Monday.”

This report was originally published by Retail Brew.



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AI labs like Meta, Deepseek, and Xai earned worst grades possible on an existential safety index

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A recent report card from an AI safety watchdog isn’t one that tech companies will want to stick on the fridge.

The Future of Life Institute’s latest AI safety index found that major AI labs fell short on most measures of AI responsibility, with few letter grades rising above a C. The org graded eight companies across categories like safety frameworks, risk assessment, and current harms.

Perhaps most glaring was the “existential safety” line, where companies scored Ds and Fs across the board. While many of these companies are explicitly chasing superintelligence, they lack a plan for safely managing it, according to Max Tegmark, MIT professor and president of the Future of Life Institute.

“Reviewers found this kind of jarring,” Tegmark told us.

The reviewers in question were a panel of AI academics and governance experts who examined publicly available material as well as survey responses submitted by five of the eight companies.

Anthropic, OpenAI, and GoogleDeepMind took the top three spots with an overall grade of C+ or C. Then came, in order, Elon Musk’s Xai, Z.ai, Meta, DeepSeek, and Alibaba, all of which got Ds or a D-.

Tegmark blames a lack of regulation that has meant the cutthroat competition of the AI race trumps safety precautions. California recently passed the first law that requires frontier AI companies to disclose safety information around catastrophic risks, and New York is currently within spitting distance as well. Hopes for federal legislation are dim, however.

“Companies have an incentive, even if they have the best intentions, to always rush out new products before the competitor does, as opposed to necessarily putting in a lot of time to make it safe,” Tegmark said.

In lieu of government-mandated standards, Tegmark said the industry has begun to take the group’s regularly released safety indexes more seriously; four of the five American companies now respond to its survey (Meta is the only holdout.) And companies have made some improvements over time, Tegmark said, mentioning Google’s transparency around its whistleblower policy as an example.

But real-life harms reported around issues like teen suicides that chatbots allegedly encouraged, inappropriate interactions with minors, and major cyberattacks have also raised the stakes of the discussion, he said.

“[They] have really made a lot of people realize that this isn’t the future we’re talking about—it’s now,” Tegmark said.

The Future of Life Institute recently enlisted public figures as diverse as Prince Harry and Meghan Markle, former Trump aide Steve Bannon, Apple co-founder Steve Wozniak, and rapper Will.i.am to sign a statement opposing work that could lead to superintelligence.

Tegmark said he would like to see something like “an FDA for AI where companies first have to convince experts that their models are safe before they can sell them.

“The AI industry is quite unique in that it’s the only industry in the US making powerful technology that’s less regulated than sandwiches—basically not regulated at all,” Tegmark said. “If someone says, ‘I want to open a new sandwich shop near Times Square,’ before you can sell the first sandwich, you need a health inspector to check your kitchen and make sure it’s not full of rats…If you instead say, ‘Oh no, I’m not going to sell any sandwiches. I’m just going to release superintelligence.’ OK! No need for any inspectors, no need to get any approvals for anything.”

“So the solution to this is very obvious,” Tegmark added. “You just stop this corporate welfare of giving AI companies exemptions that no other companies get.”

This report was originally published by Tech Brew.



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