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The changing nature of startup employment, OpenAI’s e-commerce ambitions, and Powell’s future

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It has been, to say the least, a wild week in the private markets. I’m taking you briefly inside my reporter’s notebook. (I do have both a literal notebook, and a Google Doc, for anyone wondering.) Here are some themes I’m watching, thinking, and hearing lots of chatter about: 

Those left behind: If you think about it, joining a startup is a little crazy. In many cases, a startup employee leaves behind a stable job at a longstanding company where their next several years of life can, more or less, be planned. But at a startup, anything can happen, for better or worse. That’s what people sign up for—an adventure. Along with the prospect of some decent financial upside. 

And that’s something that’s come into question in recent days, as the social media ruckus over the Windsurf deal ballooned, followed by Scale cutting 14% of its staff (about 200 employees) Wednesday in the aftermath of its $14 billion Meta deal. Layoffs happen—we all get that—but a deal worth billions that potentially doesn’t account for all early employees is a tough pill to swallow. (To be sure, the full terms of these deals, particularly how they treat employee equity, are not known. It’s possible that the employees, even those laid off, will make out OK. If you have insight, hit me up!). 

Beyond the specific cases of Scale or Windsurf, what I find most interesting is that we’re having a broader conversation about the startup employee social contract. The classic story where an entrepreneur mints hundreds of millionaires by building a generational company, to me, is still the greatest societal good of venture-backed startups. We may be living less and less in a world like that, but I hope not. (If you have thoughts on how deals like Scale and Windsurf will affect conventions for startup employees moving forward, email me! That’s our Friday essay.)

OpenAI buy: It may seem that no one is left at OpenAI given the seemingly ceaseless reports of Meta’s talent poaching, but the $300 billion AI bellwether still has some tricks up its sleeve. The Financial Times reported that OpenAI is working on a checkout system for online sales that would be tied to the LLM and through which OpenAI would take a cut. The search-shopping intersection isn’t a new one, but I do think this is far more interesting and points at the potential for AI business models to expand beyond premium subscriptions (it also strikes me as something I’d be more likely to engage with as a consumer than, say, an OpenAI phone.) As the hunt for revenue in AI continues, don’t be surprised if we see more e-commerce-AI intersections this year. 

Trump’s Powell problem: The markets turned frenetic when reports initially emerged yesterday that Trump may fire Fed Chair Jerome Powell. For years Trump has called Powell a “very stupid person” and a “knucklehead,” so it was a surprise when Trump fired back that it was “highly unlikely” he’d fire Powell. (Per the Supreme Court, Trump does not have unilateral authority to fire Powell, whose term as chair ends in 2026.) Trump wants to see interest rates cut, as does a large swath of the private markets. But would that even be all that good of a thing?

After all, the famed boom of 2021 and 2022 derived its name, the ZIRP (zero interest rate policy) era, from the Fed. An intense bust followed, rescued by AI, where valuations have soared to stratospheric heights. So, the interest rate cut that Trump’s looking for could help the exit environment, but could also have concerning knockdown effects. As always, I would love to know what you think.

See you tomorrow,

Allie Garfinkle
X:
@agarfinks
Email: alexandra.garfinkle@fortune.com
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Venture Deals

Exodigo, a Palo Alto-based AI-powered underground mapping solution provider, raised $96 million in Series B funding. Zeev Ventures and Greenfield Partners the round and were joined by Vintage Investment Partners, Leblon Capital, and existing investors 10D, Square Peg and JIBE.

Exein, a Rome-based cybersecurity company, raised €70 million ($81.3 million) in Series C funding. Balderton led the round and was joined by Supernova and Lakestar, as well as existing investors 33N, United Ventures and Partech. 

Boulevard, a Los Angeles-based client experience platform for appointment based, self-care businesses, raised $80 million in Series D funding. JMI Equity led the round and was joined by existing investors Index Ventures and VMG Partners

One Biosciences, a Paris-based AI-driven driven oncology solutions company, raised €15 million ($17.4 million) in Series A funding. Redmile Group and Blast led the round and were joined by Galion.exe, Invus, Adamed Technology, Sofinnova Partners, Polytechnique Ventures, and Kima Ventures

Gen Phoenix, a recycled leather manufacturer, raised $15 million in funding. Material Impact led the round and was joined by existing investor Tapestry

Empirical Security, a Chicago-based AI-powered cybersecurity company, secured $12 million in seed funding. Costanoa Ventures led the round. 

Retirable, a New York City-based holistic retirement planning platform, raised $10 million in Series A funding. IA Capital Group led the round and was joined by Nationwide Ventures, Western & Southern Financial Group, Clocktower Ventures, and existing investors Primary Venture Partners, Portage Ventures, Vestigo Ventures and SilverCircle.

Billee, a Dallas-based utility management platform, raised $9.15 million in seed funding. RET Ventures led the round. 

BQP, a Syracuse-based quantum-first simulation company, raised $5 million in seed funding. Monta Vista Capital led the round and was joined by New York Ventures, Arc Ventures, Armory Square Ventures, and more.

Coverflow, a San Francisco-based AI insurance platform, raised $4.8 in seed funding. AIX Ventures led the round and was joined by Founder Collective and Afore Capital. 

Kiku, a Copenhagen-based AI-powered recruitment platform, raised €4 million ($4.6 million) in seed funding. Cherry Ventures led the round and was joined by Yellow and others.

Mango, a Mexico-based fintech platform for the construction industry in Latin America, raised $3 million in seed funding. Ironspring Ventures led the round and was joined by Brick & Mortar Ventures, Great North Ventures, and Incisive Ventures

Paypercut, a Bulgarian-based payments aggregation platform, raised €2 million ($2.3 million) in pre-seed funding.  Concentric led the round and was joined by Passion Capital, RTP Global, Tuesday Capital, and more.

Hootology, a New York City-based market research platform, raised $1.1 million in pre-seed funding. JAD Family Revocable Trust led the round. 

Private Equity

Rydoo, backed by Marlin Equity Partners and Eurazeo, acquired Semine, an Oslo-based AI-driven accounts payable automation platform. Financial terms were not disclosed. 

PrecisionX, backed by CORE Industrial Partners, acquired Hudson Technologies, an Ormond, Fla.-based provider of specialty deep and shallow drawn stamping. Financial terms were not disclosed. 

Unity Partners acquired a majority stake in The Byng Group, a Toronto-based residential renovations company. Financial terms were not disclosed. 

KKR acquired a minority stake in ghSMART, a Chicago-based leadership advisory firm. Financial terms were not disclosed. 

Abacus Group and Medicus IT, both backed by FFL Partners, merged to launch a new multi-vertical IT managed services provider exclusively focused on the financial services and healthcare industries. Financial terms were not disclosed. 

Bessemer Venture Partners acquired a minority stake in StayTerra, a Bradenton, Fla.-based vacation rental management platform. Financial terms were not disclosed. 

– CASE, backed by AE Industrial Partners, acquired Ragnarok Technologies, a Reston, Va.-based IT services provider for federal and commercial clients. Financial terms were not disclosed. 

Frontier Growth acquired a minority stake in EPR Fireworks, a Jacksonville, Fla.-based records management and operations software company for fire and emergency medical services agencies. Financial terms were not disclosed. 

Exits

CEA CAPA Education Abroad, backed by Infinedi Partners, acquired CIS Abroad, an Easthampton, Mass.-based provider of education abroad programs, from Global Educators. Financial terms were not disclosed. 

Warburg Pincus acquired a majority stake in Keystone Agency Partners, a Harrisburg, Penn.-based insurance broker and agency network, from Bain Capital, which launched Keystone in 2020. Bain Capital will retain a minority ownership in Keystone through a new investment from Bain Capital Insurance. Financial terms were not disclosed. 

NexPhase Capital acquired Empower Community Care, an Atlanta-based behavioral health organization, from Northlane Capital Partners. Financial terms were not disclosed. 

Other

– Rokt agreed to acquire Canal, a San Francisco-based marketplace growth platform. Financial terms were not disclosed.

FUNDS + FUNDS OF FUNDS

Pantheon, a London-based private equity firm, raised $2.2 billion for its third fund focused on absolute and risk-adjusted returns across a broad and diversified range of credit strategies and investments. 



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Nvidia’s CEO says AI adoption will be gradual, but we still may all end up making robot clothing

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Nvidia CEO Jensen Huang doesn’t foresee a sudden spike of AI-related layoffs, but that doesn’t mean the technology won’t drastically change the job market—or even create new roles like robot tailors.

The jobs that will be the most resistant to AI’s creeping effect will be those that consist of more than just routine tasks, Huang said during an interview with podcast host Joe Rogan this week. 

“If your job is just to chop vegetables, Cuisinart’s gonna replace you,” Huang said.

On the other hand, some jobs, such as radiologists, may be safe because their role isn’t just about taking scans, but rather interpreting those images to diagnose people.

“The image studying is simply a task in service of diagnosing the disease,” he said.

Huang allowed that some jobs will indeed go away, although he stopped short of using the drastic language from others like Geoffrey Hinton a.k.a. “the Godfather of AI” and Anthropic CEO Dario Amodei, both of whom have previously predicted massive unemployment thanks to the improvement of AI tools.

Yet, the potential, AI-dominated job market Huang imagines may also add some new jobs, he theorized. This includes the possibility that there will be a newfound demand for technicians to help build and maintain future AI assistants, Huang said, but also other industries that are harder to imagine.

“You’re gonna have robot apparel, so a whole industry of—isn’t that right? Because I want my robot to look different than your robot,” Huang said. “So you’re gonna have a whole apparel industry for robots.”

The idea of AI-powered robots dominating jobs once held by humans may sound like science fiction, and yet some of the world’s most important tech companies are already trying to make it a reality. 

Tesla CEO Elon Musk has made the company’s Optimus robot a central tenet of its future business strategy. Just last month, Musk predicted money will no longer exist in the future and work will be optional within the next 10 to 20 years thanks to a fully fledged robotic workforce. 

AI is also advancing so rapidly that it already has the potential to replace millions of jobs. AI can adequately complete work equating to about 12% of U.S. jobs, according to a Massachusetts Institute of Technology (MIT) report from last month. This represents about 151 million workers representing more than $1 trillion in pay, which is on the hook thanks to potential AI disruption, according to the study.

Even Huang’s potentially new job of AI robot clothesmaker may not last. When asked by Rogan whether robots could eventually make apparel for other robots, Huang replied: “Eventually. And then there’ll be something else.”



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The ‘Mister Rogers’ of Corporate America shows Gen Z how to handle toxic bosses

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After two decades of climbing the corporate ladder at companies ranging from ABC, ESPN, and Charter Communications (commonly known as Spectrum), Timm Chiusano quit it all to become a content creator. 

He wasn’t just walking away from high titles, but a high salary, too. In his peak years, Chiusano made $600,000 to $800,000 annually. But in June of 2024, after giving a 12-week notice, he “responsibility fired himself” from his corporate job as VP of production and creative services at Charter.

He did it all to help others navigate the challenges of a workplace, and appreciate the most mundane parts of life on TikTok.

@timmchiusano

most people are posting their 2024 recaps; these are a few of my favorite moments from the year that was, but i need to start reintroducing myself too i dont have a college degree, no one in my life knew that until i was 35 when i eventually got my foot in the door in my early 20’s after a few years of substitute teaching and part time jobs, i thought for sure i had found the career path of my dreams in live sports production i didn’t think i had a chance of surviving that first college football season but i busted my ass, stuck around and got promoted 5 times in 5 years then i met a girl in Las Vegas, got married in 7 months, and freaked out about my career that had me travelling 36 weeks a year i had to find a more stable “desk job”, i was scared shitless that i was pigeonholed and the travel would eventually destroy my marriage i crafted a narative for espn arguing they needed me on their marketing team because of my unique perspective coming from the production side i got rejected, but kept trying and a year i got that job the 7 years with espn were incredible, but also exhausting and raised all kinds of questions about corporate america, toxic situations, and capitalism in general why was i borderline heart attack stressed so often when i could see that my ideas were literally generating 2,000 times the money that i was getting paid? in 2012 i had a kid and in 2013 i got the biggest job of my career to reinvent how to produce 20,000 commercials a year for small business it took 12 rounds of interviews, a drug test i somehow passed, and a background check that finally made me tell my wife of 8 years that i didnt have a college degree they brought me in the thursday before my first day and told me what i told grace in that clip the next decade was an insane blur; i saw everything one would ever see in their career from the perspective of an executive at a fortune 100 i started making tiktoks, kinda blacked out at some point in 2019 and responsibly fired myself in 2024 to see what i might be capable of on my own with all the skills i picked up along my career journey now the mission is pay what i know forward, and see if i can become the mr rogers of corporate america cc: @grace beverley @Ryan Holiday @Subway Oracle

♬ original sound – timm chiusano

What started as short-video vlogs on just about anything in 2020 (reviews on protein bars, sushi, and sneakers) later transitioned to videos on growing up, and dealing with life’s challenges, like coming to terms when you have a toxic boss. Today, his platform on TikTok has over 1 million followers

With the help of going viral from his “loop” format where videos end and seamlessly circle back to the beginning, he began making more videos as a side-hustle on top of his day-to-day tasks in the office.

“How can I get people to be smarter and more comfortable about their careers in ways that are gonna help on a day-to-day basis?” Chiusano told Fortune.

Today, he could go by many titles: former vice president at a Fortune 100 company, motivational speaker, dad, content creator, or as he labels himself, the Mister Rogers of Corporate America. 

Just as the late public television icon helped kids navigate the complexities of childhood, Chiusano wants to help young adults think about how to approach their careers and their potential to make an impact. 

“Mister Rogers is the greatest of all time in his space. I will never get to that level of impact. But it’s an easy way to describe what I’m trying to do, and it consistently gives me a goal to strive for,” he said. “There are some parallels here with the quirkiness.”

Firing himself after 25 years in the corporate world

Even with years in corporate, Chiusano doesn’t resemble the look of a typical buttoned-up executive. Today, he has more of a relaxed Brooklyn dad attire, with a sleeve of tattoos and a confidence to blend in with any trendy middle aged man in Soho. During our interview, he showed off one of the first tattoos he got: two businessmen shaking hands, a reference to Radiohead’s OK Computer album.

“This is a dope ass Monday in your 40s,” began one of his videos.

It consisted of Chiusano doing everyday things such as eating leftovers, going to the gym, training for the NYC marathon, taking out the trash, dropping his daughter off at school, a rehearsal for a Ted Talk, eating lunch with his wife, and brand deal meetings. Though the content sounds pretty normal, that’s the point. 

“The reason why I fired myself in the first place was to be here,” he says in the video while picking his daughter up from school.

Today, Chiusano spends his days making content on navigating workplace culture, public speaking, brand deals, brand partnerships, executive coaching, writing a book, and the most important job: being a dad to his 13-year-old daughter Evelyn.

“I’m basically flat [in salary] to where I was, and this is everything I could ever want in the world,” he said. “The ability to send my kid to the school she’s been going to, eat sushi takeout almost as much as I’d like, and do nice things for my wife.”

In fact, when sitting inside one of his favorite New York City spots, Lure Fishbar, he keeps getting stopped by regulars who know him by name. He points out that one of his favorite interviews he filmed here was with legendary filmmaker Ken Burns.

Advice to Gen Z

In a time where Gen Z has been steering to more unconventional paths, like content creation or skill trades rather than just a 9-to-5 office job, Chiusano opens up a lens to what life looks like when deciding to be present rather than always looking for what’s next—a mistake he said he made in his 20s. 

Instead, he wants to teach the younger generation to build skills for as long as you can, but “if you are unhappy, that’s a very different conversation.”

“I think some people will make themselves more unhappy because they feel like that’s what’s expected of a situation,” he said.

“I would love to be able to empower your generation more, to be like somebody’s gonna have to be the head of HR at that super random company to put cool standards and practices in place for better work-life balance for the employees.” 





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Mark Zuckerberg says the ‘most important thing’ he built at Harvard was a prank website

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For Mark Zuckerberg, the most significant creation from his two years at Harvard University wasn’t the precursor to a global social network, but a prank website that nearly got him expelled.

The Meta CEO said in a 2017 commencement address at his alma mater that the controversial site, Facemash, was “the most important thing I built in my time here” for one simple reason: it led him to his wife, Priscilla Chan.

“Without Facemash I wouldn’t have met Priscilla, and she’s the most important person in my life,” Zuckerberg said during the speech.

In 2003, Zuckerberg, then a sophomore, created Facemash by hacking into Harvard’s online student directories and using the photos to create a site where users could rank students’ attractiveness. The site went viral, but it was quickly shut down by the university. Zuckerberg was called before Harvard’s Administrative Board, facing accusations of breaching security, violating copyrights, and infringing on individual privacy.

“Everyone thought I was going to get kicked out,” Zuckerberg recalled in his speech. “My parents came to help me pack. My friends threw me a going-away party.”

It was at this party, thrown by friends who believed his expulsion was imminent, where he met Chan, another Harvard undergraduate. “We met in line for the bathroom in the Pfoho Belltower, and in what must be one of the all time romantic lines, I said: ‘I’m going to get kicked out in three days, so we need to go on a date quickly,’” Zuckerberg said.

Chan, who described her now-husband to The New Yorker as “this nerdy guy who was just a little bit out there,” went on the date with him. Zuckerberg did not get expelled from Harvard after all, but he did famously drop out the following year to focus on building Facebook.

While the 2010 film The Social Network portrayed Facemash as a critical stepping stone to the creation of Facebook, Zuckerberg himself has downplayed its technical or conceptual importance.

“And, you know, that movie made it seem like Facemash was so important to creating Facebook. It wasn’t,” he said during his commencement speech. But he did confirm that the series of events it set in motion—the administrative hearing, the “going-away” party, the line for the bathroom—ultimately connected him with the mother of his three children.

Chan, for her part, went on to graduate from Harvard in 2007, taught science, and then attended medical school at the University of California, San Francisco, becoming a pediatrician.

She and Zuckerberg got married in 2012, and in 2015, they co-founded the Chan Zuckerberg Initiative, a philanthropic organization focused on leveraging technology to address major world challenges in health, education, and science. Chan serves as co-CEO of the initiative, which has pledged to give away 99% of the couple’s shares in Meta Platforms to fund its work.

You can watch the entirety of Zuckerberg’s Harvard commencement speech below:

For this story, Fortune journalists used generative AI as a research tool. An editor verified the accuracy of the information before publishing. 



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