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Joshua Jackson Spotted Holding Hands With Model Olivia Burgess in New York City Outing

Joshua Jackson Spotted Holding Hands With Model Olivia Burgess in New York City Outing

Joshua Jackson enjoyed a lovely day in New York City with model Olivia Burgess.

According to photos obtained by TMZ, Jackson, 47, was spotted out and about with Burgess on Sunday, June 7. The pair were all smiles as they held hands while on a stroll in the Big Apple.

Jackson and Burgess kept it casual for their outing, with the Dawson’s Creek alum rocking a linen button-up shirt and matching pants paired with sneakers and sunglasses. The model, who has walked the runway for the fashion brand Jean Paul Gaultier, donned a black tank top, gray Bermuda shorts and mules. She opted for a messy updo.

Jackson’s day with Burgess comes shortly after the actor made headlines for reconnecting with Katie Holmes. The former costars — and real-life exes — reunited to star in their new movie Happy Hours, which Holmes, 47, wrote and directed. The pair previously worked together on Dawson’s Creek from 1998 until 2003, where they portrayed frenemies turned lovers Pacey Witter and Joey Potter. While filming the beloved teen drama, the duo dated for about one year after the show’s premiere.

Related: Katie Holmes Details Reuniting With Ex Joshua Jackson in New Romance Movie

Katie Holmes opened up about her viral reunion with Dawson’s Creek costar Joshua Jackson for their upcoming film, Happy Hours. “To be honest, it was unexpected,” the actress, 47, said of the fans’ excitement for her and Jackson, also 47, to share the screen again in an interview with Variety published on Friday, June 5. […]

Last summer, Holmes and Jackson were spotted filming in New York City together. It was later revealed that they were collaborating on Happy Hours. The film, which is written to be part one of a trilogy, follows a couple who are contemplating whether their fizzled connection is worth a second chance.

The same day Jackson was spotted with Burgess, he and Holmes attended the Tribeca Film Festival together, posing together and holding hands while on the red carpet. At one point, Jackson gushed about his connection to Holmes after nearly three decades of friendship.

“The time that we spent together when we were young is very precious to both of us,” he told a reporter per a social media clip. “And [it] is like one of the core personal and professional relationships in my life.”

Jackson also applauded Holmes for her creativity and the work she put into Happy Hours, which premiered at the festival.

Joshua Jackson and Katie Holmes' Sweetest Quotes About Their Friendship

Related: Joshua Jackson and Katie Holmes’ Sweetest Quotes About Their Friendship

From teen sweethearts on Dawson’s Creek to lifelong friends who reunited on screen decades later, Joshua Jackson and Katie Holmes have one of Hollywood’s most enduring bonds. The two first met as teenagers when they were cast on the WB teen drama in 1997, and their connection has only deepened through breakups, career milestones and […]

“We had talked about it over the years, and then — I don’t think you’re giving yourself enough credit — because then she creates this beautiful space for the two of us to come back and work together and tell a beautiful story,” Jackson explained. “A hopeful story, a real human story and for me, I was both flattered and very excited to have the opportunity to come back and share this space with you after all of these years.”

Holmes, for her part, added that she takes her and Jackson’s friendship and professional relationship “very seriously.”

“I want to do right by Josh. I have a great deal of respect. So I wanted it to be right,” she said on Sunday. “We’ve often talked about doing something again, but we never knew what. So it was really about that and agreeing to go for it, I suppose. He said yes, and that made me feel very good.”

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Mercor’s Brendan Foody calls out Sequoia over ‘dual-pricing’ valuation tricks | TechCrunch<div> <p id="speakable-summary" class="wp-block-paragraph">In recent days, founders and founders-turned-investors took to X to share <a href="https://techcrunch.com/2026/06/05/founders-share-vc-horror-stories-and-some-are-naming-names/">horror stories</a> about being mistreated by VCs. Their complaints ranged from VCs falling asleep during pitch meetings to investors suggesting a founder fire a co-founder.</p> <p class="wp-block-paragraph">Brendan Foody, co-founder of the AI talent platform Mercor, which was last valued at <a href="https://techcrunch.com/2025/10/27/mercor-quintuples-valuation-to-10b-with-350m-series-c/">$10 billion</a>, went so far as to call out Sequoia, arguably one of the most elite VC firms in the world.</p> <p class="wp-block-paragraph">“The “sequoia scam” is worse than a single horror story,” Foody <a rel="nofollow" href="https://x.com/BrendanFoody/status/2063470286515683759?s=20">wrote on X</a>. “in the last 6 [months] ive seen a half dozen rounds where sequoia invests in 2 tranches. everyone pretends they only did the higher valuation. founders misrepresent this to their employees & then shop it to angels too.”</p> <p class="wp-block-paragraph">TechCrunch has previously <a href="https://techcrunch.com/2026/03/03/why-ai-startups-are-selling-the-same-equity-at-two-different-prices/">reported on VCs</a> investing in the same round at different valuations. Under this mechanism, the lead VC firm invests a significant chunk of its capital at a lower, preferential valuation, while putting a much smaller portion of capital in at a drastically higher price. The massive “headline” valuation that gets announced manufactures the perception of a dominant market winner, masking the fact that the lead investor’s actual average entry price was significantly lower.</p> <p class="wp-block-paragraph">The disparity can be stark. For example, when the AI-driven IT helpdesk startup Serval announced a $75 million Series B at a $1 billion valuation, the announcement didn’t tell the whole story. According to The Wall Street Journal, Sequoia’s actual lowest entry point valued the company at just $400 million — less than half the headline figure. The gap between those two numbers is the gap between perception and reality that Foody is pointing at.</p> <p class="wp-block-paragraph">Serval isn’t alone. At Aaru, a startup that uses AI to simulate user behavior for market research, lead investor Redpoint backed the company at a $450 million valuation despite an announced $1 billion headline price.</p> <p class="wp-block-paragraph">Sequoia’s Shaun Maguire <a rel="nofollow" href="https://x.com/shaunmmaguire/status/2063650964771659790">pushed back</a> on Foody’s characterization directly. “TBH I have seen some of this behavior but I think it’s unfair to call it the ‘Sequoia scam,’” Maguire wrote in response to Foody on X. “This has happened approximately five times during my seven years at Sequoia. What happens is other investors are willing to pay a high price for a hot company — usually AI — at multiples above what we’re willing to pay. So we try to decouple the company-building relationship with our partner from the capital, and this leads to two tranches at different valuations in close succession. </p> <p class="wp-block-paragraph">“I’m not aware of anything shady here,” Maguire continued, “but if you’ve seen it I’d love to know. VC is a repeated game, so it just doesn’t make sense for us to try to mislead people. And if anyone has, I’d love to know. And in general, congrats on the success of Mercor — it was a miss for us.”</p> <p class="wp-block-paragraph">Maguire’s response frames the practice as a market reality rather than a deliberate maneuver — Sequoia, he suggests, is simply unwilling to pay what competitors will pay for the hottest deals, so it structures its participation differently. Whether that explanation fully holds up depends on a question Maguire doesn’t address: what founders are telling the people who don’t already know about the lower tranche.</p> <p class="wp-block-paragraph">Although Sequoia appears to use this pricing mechanism most frequently, Foody acknowledged it isn’t the only firm using this tactic. And while the dual-pricing structures certainly inflate a startup’s perceived worth and help attract top talent, calling the practice a “scam” may be going too far.</p> <p class="wp-block-paragraph">That’s because employee stock options should theoretically be priced based on the blended value of all tranches — not the headline number — according to Jason Woo, partner in valuation and financial modeling at Armanino, whose firm provides the independent 409A appraisals startups use to set option prices. A 409A is supposed to reflect a company’s fair market value, giving employees a strike price that’s insulated from whatever valuation gets announced in a press release.</p> <p class="wp-block-paragraph">There’s a catch: 409A valuations are widely understood to skew low. Because a lower strike price means a smaller tax bill for the company, there is a structural incentive to keep that number down. The appraisal that’s supposed to protect employees from an inflated headline valuation is also, by design, not trying particularly hard to reach the top of the range.</p> <p class="wp-block-paragraph">The angel question is more complicated. Unlike employees, angels are writing checks, not receiving options. There is no independent appraiser standing between an angel investor and whatever number a founder chooses to share.</p> <p class="wp-block-paragraph">The dual-pricing structure is just one of way VCs and founders game the perception of success in a hyper-competitive market. Another, more pervasive tactic involves manipulating or outright overstating annual recurring revenue (ARR). </p> <p class="wp-block-paragraph">The VC Niko Bonatsos, a longtime veteran of General Catalyst who more recently founded Verdict Capital, addressed this issue during one of <a href="https://techcrunch.com/2026/05/30/the-groupthink-boom-what-three-top-vcs-really-think-about-the-ai-frenzy/">TechCrunch’s events</a> in Athens last month. “We [at Verdict] mostly invest before metrics, before product, before the company [has fully taken shape] but I do have a past portfolio, and sometimes the conversations are telling. I’ll get a call or an email with a very high ARR number. I’ll think: I didn’t remember that company doing so well. So I reach out to the founder: ‘What happened? Why are the numbers so strong?’ And the answer is: ‘Oh yeah, it’s 365 times the revenue we made yesterday because one of our campaigns hit.’ So yeah, some of these terms have lost meaning.”</p> <p class="wp-block-paragraph">Foody declined to comment further. Sequoia didn’t immediately respond to a request for comment.</p> <p class="wp-block-paragraph"><em> — With additional reporting from Connie Loizos</em></p> </div><p><em>When you purchase through links in our articles, <a href="https://techcrunch.com/techcrunch-affiliate-monetization-standards/">we may earn a small commission</a>. This doesn’t affect our editorial independence.</em></p>#Mercors #Brendan #Foody #calls #Sequoia #dualpricing #valuation #tricks #TechCrunchMercor,Sequoia Partners,Valuations

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