Much of Silicon Valley has spent years chasing mega-rounds and buzzy AI deals. Meanwhile, Stacy Brown-Philpot is running Cherryrock Capital like a throwback to venture capital’s earlier days, writing smaller Series A and B checks to founders that larger firms routinely overlook.
The former TaskRabbit CEO and decade-long Google veteran launched Cherryrock a year ago after seeing what she calls a persistent gap: access to capital for “underinvested entrepreneurs” building software companies at the crucial growth stage.
“When I left TaskRabbit, I took some time off to figure out what was next and saw this gap in the market, which was access to capital, particularly for underinvested entrepreneurs,” Brown-Philpot told TechCrunch. She’d originally come to the Bay Area 25 years ago, planning to become a VC and even writing her Stanford Business School essay about it. After spending a decade at Google and leading TaskRabbit to a successful exit to IKEA, she’s finally back to that original plan.
She circled back to it for a reason. Before launching Cherryrock, Brown-Philpot was a member of the investment committee for the SoftBank Opportunity Fund, a $100 million vehicle started in 2020 to back underserved entrepreneurs. That experience proved there was no shortage of overlooked founders.
SoftBank itself sold the Opportunity Fund to its leadership team in late 2023, divesting from the diversity-focused initiative. Brown-Philpot, meanwhile, doubled down, and launched her own fund. By the time she closed Cherryrock’s debut fund in February 2025, she already had more than 2,000 companies in her pipeline.
Cherryrock is targeting 12 to 15 investments from its first fund — a concentrated approach and stark contrast to the seed funds that make dozens of bets, or massive funds that write nine-figure checks. Brown-Philpot’s also taking her time; a year after announcing the fund, she and her team, including cofounder Saydeah Howard, who spent nine years at the venture firm IVP, have backed just five companies, putting them about a third of the way toward their goal. In an era when many funds race to deploy capital almost as quickly as it’s raised, Brown-Philpot’s measured pace is another throwback to an earlier generation of VCs.
Brown-Philpot’s focus on “underinvested” founders — a careful choice of words in today’s political climate — means backing entrepreneurs who might not fit the typical Silicon Valley mold.
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When asked directly about the current political environment, where DEI has become a lightning rod, Brown-Philpot is unfazed. “It doesn’t change the pitch at all,” she said. “When we look at the people who decided to back Cherryrock, like JPMorgan and Bank of America…these are financial institutions who expect to generate a return. Our job as investors is to do just that.”
In addition to those investors, Cherryrock’s LP roster includes Goldman Sachs Asset Management, MassMutual, Top Tier Capital Partners, and Melinda Gates’s Pivotal Ventures. Some of these have stepped back from explicit diversity pledges amid pressure from the Trump administration. Yet Brown-Philpot may find herself in an unexpectedly advantageous position.
A new diversity reporting law in California requires VC firms with a California nexus to report demographic data on their portfolio companies’ founding teams, with the first deadline in April. Unlike some corporate diversity initiatives that have faced legal challenges, the law focuses on transparency rather than mandates, requiring reporting but not quotas. For a firm like Cherryrock that’s already tracking and prioritizing investments in diverse founders, compliance is “table stakes,” as Brown-Philpot puts it. “You accomplish what you measure.”
Brown-Philpot’s perspective is informed by her vantage point across multiple institutions. Beyond Cherryrock, she sits on the boards of HP, StockX, and Stanford University — roles that give her insight into both enterprise buyers and the next generation of founders. At Stanford, she’s watching students navigate questions about AI’s impact on employment. “What I see on campus is the students are charting a path and finding a way to create opportunities for themselves,” she said.
Her portfolio reflects her thesis. One investment is Coactive AI, led by Cody Coleman, an MIT grad with advanced degrees in philosophy and engineering from MIT and Stanford. The company provides multimodal AI infrastructure to the media and entertainment industry, a sector now under intense scrutiny following controversies around AI-generated content. Cherryrock led Coactive’s Series B alongside Emerson Collective.
Another bet is Vitable Health, founded by Joseph Kitonga, a Thiel Fellow and Y Combinator alum. The Philadelphia-based company provides on-demand, primary care-based health insurance to employers and hourly workers – the kind of population Brown-Philpot came to know well as the CEO of TaskRabbit during its last years as a standalone company. Kitonga “is the exact kind of founder that we want to back,” Brown-Philpot said. “He does what he says he’s going to do.” Brown-Philpot first invested at the seed stage of Vitable through her work with the SoftBank Opportunity Fund.
When asked about her operating philosophy, Brown-Philpot is pragmatic about exits. “It’s very difficult to go public,” she said. “Most companies don’t go public, they do get acquired.” It’s a refreshingly honest take in an industry that often overpromises on IPO prospects. She points to TaskRabbit’s sale to IKEA as proof that the right acquisition can create lasting value.
As for 2026, Brown-Philpot’s priority is simple: “We are actively deploying capital.” She’s looking for Series A and B companies that have achieved product-market fit at scale, letting founders define what that means. And while the broader venture ecosystem debates the future of diversity initiatives, she is focused on finding great founders, wherever they are.
“I’m from Detroit,” she says. “Hard things are hard, but we know how to do hard things.”
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![OpenAI’s existential questions | TechCrunch
OpenAI has been all over the news recently, whether that news is about acquisitions, competition with Anthropic, or bigger debates about AI’s impact on society.
On the latest episode of TechCrunch’s Equity podcast, Kirsten Korosec, Sean O’Kane, and I did our best to round up all the latest OpenAI news. While the company’s latest acquisitions seem to be classic acqui-hires, Sean suggested they also address “two big existential problems that OpenAI is trying to solve right now.”
First, with the team behind personal finance startup Hiro, the company may be hoping to come up with a product that has “more hooks than just a chatbot, and maybe something worth paying more for.” And with new media startup TBPN, OpenAI could be looking to “better shape its image in the public eye, which lately has not been great.”
Read a preview of our conversation, edited for length and clarity below.
Anthony: [We have] two deals that are worth mentioning, one is that OpenAI acquired this personal finance startup called Hiro. And that comes after another deal that was literally announced when we were recording our last episode of Equity, so we didn’t get to talk about it: OpenAI had also acquired TBPN — a business talk show, like a new media company.
And I think both of these deals are pretty small compared to the scale of OpenAI. These are not things that people expect to really change the course of their business or anything like that, but they’re interesting because it suggests that there’s still this [attitude of,] “Let’s try out different things.”
Especially [with] the TBPN deal […] particularly at this time when it feels like OpenAI, from all the reporting we’re reading, is also trying to really refocus on making ChatGPT and its GPT models really competitive in an enterprise context with programmers.
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Is running a tech talk show, should that really be on the to-do list?
Kirsten: No, this should not be on the to-do list. That’s it.
I do want to mention Hiro because to me, that’s an interesting one, because Julie Bort, our venture editor, super talented, she wrote about this and was I think the first to write about it. She dug in a little bit and basically this looks like an acqui-hire. The company is folding. They basically said, “By this date, you won’t be able to access this anymore.”
This is a personal finance startup. And they only launched two years ago. So this absolutely is about getting talent on board. So I’m very curious to see if OpenAI is going to be just absorbing them into the ether at OpenAI, or if they’re actually interested in some sort of personal finance product that they want to work on. To me, it’s not really clear.
Sean: I think you look at both of these as acqui-hires to a certain extent. I mean, the TBPN acquisition, allegedly they are going to retain their editorial independence on the show that they make every day. And all respect to those guys who’ve put that out there and gotten it off the ground so quickly and grown it into what it has become.
I think any person who follows the media should have a healthy dose of skepticism that when you acquire something like that and you put the people who make the show under the org of the public policy people and comms or marketing adjacent people higher up at the company making the acquisition, that you could have good questions about whether or not saying “editorial independence” is enough. It’s not an incantation that just works.
But you know, what’s interesting to me about these two, while they are similar in their acqui-hire-ness, I think they both represent two major problems that OpenAI is facing.
One is Hiro. OpenAI has a very successful product in ChatGPT. As far as whether or not that will actually ever make them enough money to become a sustainable business that’s not raising the largest private rounds in the world, ever, to keep things going, is a big question. And they also seem to be struggling to keep up on the enterprise side of things where the real money seems to be, so bringing in a team like this seems like taking a shot at, “What else can we do?”
The guy who founded Hiro seems to have a serial entrepreneur streak of creating consumer apps, and so this seems to me like a bet on them being able to come up with something else that may have more hooks than just a chatbot, and maybe something worth paying more for.
And then TBPN is an acquisition made to help better represent what the company does and better shape its image in the public eye, which lately has not been great and certainly is under more questions now than just a few weeks ago, because Ronan Farrow just led a report at The New Yorker that dropped suspiciously right around the time that this and a couple other announcements from OpenAI came out last week.
I think those are two big existential problems that OpenAI is trying to solve right now.
Kirsten: So the thing that you didn’t say is, there’s Anthropic kind of looming in — not in the shadows, I mean, they’re very much taking up a lot of space here — but they’re having a lot of success on the enterprise side of things.
It feels like these guys are competitors and they also feel like very different companies in a lot of ways. Anthony, I’m wondering if you see them as direct competition to OpenAI? Or [are they] just finding their stride in enterprise and in a way, these two companies are clearly going to coexist and they’re really not directly competing with each other — maybe on talent, but not necessarily as we initially thought of them?
Anthony: I think they’re directly competing with each other. There’s definitely a scenario where if AI as an industry, as a technology, is as successful as its proponents hope for, they could both be very successful companies, they could just be the one and two. And the success of one does not necessarily mean that the other will just fade into obscurity.
And again, none of this is official, but there’s just been a lot of reporting around how it seems like OpenAI, more than anyone, is obsessed with and upset about Anthropic’s rise.
Our reporter Lucas [Ropek], he did a great piece over the weekend about the HumanX conference, where he was talking to everyone there and they’re sort of like, “Yeah, ChatGPT is fine, too,” but like they were all about Claude Code. And I think that is exactly what OpenAI is worried about.
Because again, in theory, there could be many other opportunities for generative AI, but it feels like the big growth area, the area where the most money is and where they could at least see a path to having a sustainable business in the future, is in these enterprise and coding tools.
#OpenAIs #existential #questions #TechCrunchAnthropic,Equity podcast,OpenAI](https://i2.wp.com/techcrunch.com/wp-content/uploads/2026/03/GettyImages-2266645295.jpg?w=1024&ssl=1 "OpenAI’s existential questions | TechCrunch
OpenAI has been all over the news recently, whether that news is about acquisitions, competition with Anthropic, or bigger debates about AI’s impact on society.
On the latest episode of TechCrunch’s Equity podcast, Kirsten Korosec, Sean O’Kane, and I did our best to round up all the latest OpenAI news. While the company’s latest acquisitions seem to be classic acqui-hires, Sean suggested they also address “two big existential problems that OpenAI is trying to solve right now.”
First, with the team behind personal finance startup Hiro, the company may be hoping to come up with a product that has “more hooks than just a chatbot, and maybe something worth paying more for.” And with new media startup TBPN, OpenAI could be looking to “better shape its image in the public eye, which lately has not been great.”
Read a preview of our conversation, edited for length and clarity below.
Anthony: [We have] two deals that are worth mentioning, one is that OpenAI acquired this personal finance startup called Hiro. And that comes after another deal that was literally announced when we were recording our last episode of Equity, so we didn’t get to talk about it: OpenAI had also acquired TBPN — a business talk show, like a new media company.
And I think both of these deals are pretty small compared to the scale of OpenAI. These are not things that people expect to really change the course of their business or anything like that, but they’re interesting because it suggests that there’s still this [attitude of,] “Let’s try out different things.”
Especially [with] the TBPN deal […] particularly at this time when it feels like OpenAI, from all the reporting we’re reading, is also trying to really refocus on making ChatGPT and its GPT models really competitive in an enterprise context with programmers.
Techcrunch event
San Francisco, CA
|
October 13-15, 2026
Is running a tech talk show, should that really be on the to-do list?
Kirsten: No, this should not be on the to-do list. That’s it.
I do want to mention Hiro because to me, that’s an interesting one, because Julie Bort, our venture editor, super talented, she wrote about this and was I think the first to write about it. She dug in a little bit and basically this looks like an acqui-hire. The company is folding. They basically said, “By this date, you won’t be able to access this anymore.”
This is a personal finance startup. And they only launched two years ago. So this absolutely is about getting talent on board. So I’m very curious to see if OpenAI is going to be just absorbing them into the ether at OpenAI, or if they’re actually interested in some sort of personal finance product that they want to work on. To me, it’s not really clear.
Sean: I think you look at both of these as acqui-hires to a certain extent. I mean, the TBPN acquisition, allegedly they are going to retain their editorial independence on the show that they make every day. And all respect to those guys who’ve put that out there and gotten it off the ground so quickly and grown it into what it has become.
I think any person who follows the media should have a healthy dose of skepticism that when you acquire something like that and you put the people who make the show under the org of the public policy people and comms or marketing adjacent people higher up at the company making the acquisition, that you could have good questions about whether or not saying “editorial independence” is enough. It’s not an incantation that just works.
But you know, what’s interesting to me about these two, while they are similar in their acqui-hire-ness, I think they both represent two major problems that OpenAI is facing.
One is Hiro. OpenAI has a very successful product in ChatGPT. As far as whether or not that will actually ever make them enough money to become a sustainable business that’s not raising the largest private rounds in the world, ever, to keep things going, is a big question. And they also seem to be struggling to keep up on the enterprise side of things where the real money seems to be, so bringing in a team like this seems like taking a shot at, “What else can we do?”
The guy who founded Hiro seems to have a serial entrepreneur streak of creating consumer apps, and so this seems to me like a bet on them being able to come up with something else that may have more hooks than just a chatbot, and maybe something worth paying more for.
And then TBPN is an acquisition made to help better represent what the company does and better shape its image in the public eye, which lately has not been great and certainly is under more questions now than just a few weeks ago, because Ronan Farrow just led a report at The New Yorker that dropped suspiciously right around the time that this and a couple other announcements from OpenAI came out last week.
I think those are two big existential problems that OpenAI is trying to solve right now.
Kirsten: So the thing that you didn’t say is, there’s Anthropic kind of looming in — not in the shadows, I mean, they’re very much taking up a lot of space here — but they’re having a lot of success on the enterprise side of things.
It feels like these guys are competitors and they also feel like very different companies in a lot of ways. Anthony, I’m wondering if you see them as direct competition to OpenAI? Or [are they] just finding their stride in enterprise and in a way, these two companies are clearly going to coexist and they’re really not directly competing with each other — maybe on talent, but not necessarily as we initially thought of them?
Anthony: I think they’re directly competing with each other. There’s definitely a scenario where if AI as an industry, as a technology, is as successful as its proponents hope for, they could both be very successful companies, they could just be the one and two. And the success of one does not necessarily mean that the other will just fade into obscurity.
And again, none of this is official, but there’s just been a lot of reporting around how it seems like OpenAI, more than anyone, is obsessed with and upset about Anthropic’s rise.
Our reporter Lucas [Ropek], he did a great piece over the weekend about the HumanX conference, where he was talking to everyone there and they’re sort of like, “Yeah, ChatGPT is fine, too,” but like they were all about Claude Code. And I think that is exactly what OpenAI is worried about.
Because again, in theory, there could be many other opportunities for generative AI, but it feels like the big growth area, the area where the most money is and where they could at least see a path to having a sustainable business in the future, is in these enterprise and coding tools.
#OpenAIs #existential #questions #TechCrunchAnthropic,Equity podcast,OpenAI")
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