This week Maya and Priya sit down with Ishan Gupta, CTO and co-founder of Juicebox, who comes on the pod to announce that Juicebox just closed their Series B!!

Juicebox is the AI recruiting platform letting you find your next hire by just describing them in plain English. PeopleGPT searches 800M+ profiles and surfaces the best fits. No boolean filters required.

Ishan grew up in India watching his dad run a business and always knew he wanted to be an entrepreneur, but had no idea he would drop out of college just three months in to build Juicebox.

Before Juicebox, there were two failed pivots. Tune in to hear why they built a music company and marketplace first, and most importantly why they ultimately decided to build Juicebox.

Ishan breaks down why the hiring manager always knows exactly who they want but never has time to find them, and the recruiter has time but less context.

LLMs change the game because they are the first technology that can actually read a resume the way a human would, picking up on someone’s trajectory, company stage, promotion pace, even GitHub contributions.

Ishan talks about

• Finding message market fit and then product market fit
• Why recruiting is a zero sum game
• If the recruiter / sourcer role disappears
• If a human or AI is more biased

Juicebox is hiring across engineering, product, design, sales, and more. The company is high ownership and still operates like a seed stage startup. juicebox.ai/careers.

Now…a word from our sponsors :)

• Lotus Health is an AI doctor you can chat with for free anytime. They just raised $41M, and you can download the app today. The pod tried it, and with just our basic info it pulled up every medication we’ve been on in the last 25 years, sent us relevant studies to our demo, and the app can even refer you to real clinicians when needed.
• Here’s $10 on Kalshi when you trade $10. Kalshi was one of the first believers in the pod, and they let you trade on anything. No seriously anything, you can trade on sports, elections, and even what Taylor Swift will play first at her next concert. DM us on IG if you want to know what markets we are in. Important disclaimer: This is not financial advice. The information shared is for informational and entertainment purposes only and should not be considered investment, financial, or trading advice. Always do your own research and consult with a qualified financial professional before making any financial decisions.

00:00 Series B Fundraising

03:36 Unexpected reason SF is the best city to live in

07:02 Co-founder meet cute <3

09:38 The two ideas that didn’t work

14:32 LinkedIn’s recruiter tool will die

17:43 LLMs change the talent search game

18:37 Juicebox product

26:47 Why recruiting is a zero sum game

28:23 Will recruiters disappear

31:52 Why AI is less biased than humans in recruiting

34:27 How AI impacts recruiting as a founder

38:30 Who Juicebox is hiring

This weekend was the pod’s Season 4 launch party. To celebrate you can give them 5 stars and increase the chance Maya agrees to a Season 5. 

This week the pod starts with with Bitcoin, which is down about 50% from its peak (~120K to ~65K). They walk through why this crash doesn’t have just one culprit. Trump’s tariff uncertainty, Iranian geopolitical tension, and Bitcoin in key ETFs all contributed. On Feb 5, BlackRock’s Bitcoin ETF (IBIT) sold a lot of Bitcoin, seemingly because it had to rebalance alongside a broader US software/tech selloff, which tied Bitcoin even more directly to tech stocks. They also talk about how Bitcoin is failing the “digital gold” test right now (gold is up while BTC is down), even if it’s working as a decentralized currency, it’s not working as a store of value.

Next they unpack the viral “2028 Global Intelligence Crisis” essay by Citrini, which imagines a bearish AI scenario: white-collar automation triggers layoffs, SaaS gets copied and commoditized, and consumer spending weakens because workers don’t have money to spend post layoffs. The pod has hot takes on where Citrini’s assumptions are underbaked.

They close with World Labs, a startup that just raised $1B to build “world models” for spatial intelligence aka AI that actually understands 3D environments. Co-founder Fei-Fei Li is considered the God Mother of AI, since she was one of the first to advocate for data as a way to improve ML models instead of algorithmic improvement. Early use cases include robotics training and game development. Tune in to hear if World Labs would “Get the Check”.

00:00 Season 4 launch party recap

03:54 Why Bitcoin crashes by almost 50%

14:57 Citrini essay hot takes

23:31 The permanent underclass

35:47 Godmother of AI Fei-Fei Li's World Labs raises $1B

It’s another 6AM morning recording and Anika nods off during the recording - just kidding.

The hosts run first discuss Matt Schumer’s viral essay “Something Big Is Happening” (82M+ views on X), which argues AI labs intentionally made coding the focus, that most people don’t realize how advanced models are, and that we’re 1–2 years from AI autonomously building the next generation. They contrast it with Will Mandis’ response essay “Tool Shaped Objects,” arguing LLMs look like powerful tools but headlines focus on spend (GPU clusters, CapEx) more than real output, likening today’s prompting to Farmville-style busywork.

Next, they cover Anthropic’s new funding and model progress: Anthropic raises $30B (from NVIDIA, Microsoft, GIC, among others), bringing total capital raised to $57B and valuing the company at $380B after starting in 2021. They break down Opus 4.6 launching three months after 4.5, with a 4x context window increase and a big “needle-in-a-haystack” retrieval benchmark jump (18% to 76%), which they frame as improving the ability to find issues in large codebases even if core problem-solving hasn’t changed as much.

Finally, they move to AI in finance and AI insurance. Rogo raises a $75M Series C led by Sequoia, and Meridian raises a $17M seed led by a16z; both target finance workflows like deal flow automation, diligence, market research, modeling, and deck/spreadsheet automation. The hosts argue adoption is still early and research-heavy, and debate whether Meridian’s “Cursor for finance” IDE approach makes sense versus keeping Excel as the output layer, citing Microsoft adding Claude models to Copilot in Excel and a view that entrenched formats (Excel, GitHub PRs) won’t change quickly.

They close with AIUC (Artificial Intelligence Underwriting Company), which raised a $15M seed from Nat Friedman (ex-GitHub CEO) and is cofounded by Ro Kitz (ex-Anthropic product, Center for AI Safety board member) and Rajiv Dani (ex-McKinsey partner). AIUC aims to underwrite and standardize risk for AI agents via insurance standards and audits (including red teaming), addressing liabilities like slurs, hacked agents, and data leaks/violations.

00:00 Intro01:46 ‘Something Big Is Happening’: Essay by Matt Schumer14:45 Anthropic’s $380B Valuation + Opus 4.6 Deep Dive28:02 Will AI replace Excel? Meridian’s ‘finance IDE’ debate38:33 AIUC: underwriting AI risk with standards, audits & insurance

You might remember the pod’s tech issues last week. Well this week they are so up. The pod has new, fancy mics and lighting. Priya kicks things off with her last-minute Super Bowl trip after buying tickets Saturday morning.

First up, the hosts break down the Anthropic vs. OpenAI Super Bowl ad beef. Anthropic dropped ads ahead of the game making fun of OpenAI for putting ads into ChatGPT. One featuring a fake therapist pitching a cougar dating site, another recommending shoe insoles to get jacked. The pod debriefs how Anthropic nailed ChatGPT's tone. They also discuss Sam Altman’s clap back that more Texans use ChatGPT than people use Claude in the entire country and if he was valid or not. Anika gives her hot take on why they’re both right and both wrong. OpenAI's actual Super Bowl ad went the wholesome route and the general public loved it, while Anthropic's ad landed in the bottom 3% of Super Bowl ads over the last five years according to Adweek. The trio also gets into Wegovy's Super Bowl push for their new GLP-1 pill, which took 10 years to develop, and Priya’s so down to take it (kidding, kind of).

Then the pod dives into their “Get the Check” segment on Northwood Space, the space infrastructure company founded by former Disney Channel star Bridget Mendler. Northwood just raised a $100 million Series B and landed a $50 million contract with the US Space Force for commanding national security space assets. The hosts walk through why ground networks matter: satellites need to transfer data back to Earth, and right now that means renting time on giant manually-turned dish antennas. Northwood's phased array technology is changing that and the pod is bullish. Maya highlights how Northwood's tech was actually used during the LA fires to get satellite data when traditional systems couldn't transfer it fast enough, and Anika draws a parallel to AT&T and Verizon selling off their infrastructure to companies like American Tower.

Finally, Anika and Priya sit down with Logan, Anika’s next-door neighbor growing up and now a full-time prediction market trader on Kalshi. You can create a Kalshi account to trade here: https://kalshi.com/sign-up?referral=getthecheck. Logan quit his $75K financial risk analyst job after making more from trading on the side, and now has around $450K on Kalshi and $90K on Polymarket, having already made more year-to-date than his old annual salary by February. He walks through his research process, which includes buying a Dutch streaming service to watch Netherland’s election debates live and waking up at 3AM when trading international markets. Logan talks through some of his best plays, including catching a Nobel Prize winner before Kalshi and the public and buying Mark Zuckerberg at 1 cent for Time Person of the Year. Logan describes himself as "vibes-based" versus model-heavy and gives advice for people interested in trading prediction markets.

00:00 Priya goes to the Super Bowl

01:40 Super Bowl tech ads: Anthropic vs. OpenAI, Lays, Him & Hers

11:18 Anthropic releases Claude Opus 4.6, OpenAI released Codex 5.3

16:51 Northwood Space raised $100B Series B

19:37 Northwood Space’s $50M Space Force contract

25:50 Interviewing a full-time trader on Kalshi @LoganPredicts

32:05 Spending 100 hours a week researching

37:14 Figuring out who is going to win Time’s Person of the Year

42:51 Kalshi as a source of truth in a post-truth world

45:03 What prediction market traders say in their group chats

Maya, Anika, and Priya are back. If you notice Maya’s on her phone this week, it’s because she broke her laptop while on FaceTime with Anika and Priya. If you notice Priya’s wavy video, we don’t really know what happened there, but we’ll be so back next week with fixed laptops and cameras. This week they talk about OpenClaw leading to Reddit for AI agents, Trump’s Fed Chair nominee, and Elon’s SpaceX and xAI merger.

First they talk about OpenClaw, which is the viral open source AI personal assistant that's been taking over the internet. Originally called Clawdbot (Anthropic said absolutely not). Created by Austrian developer Peter Steinberger, it's now the fastest growing GitHub project ever with 140K stars. The hosts dive into some of the tasks people have gotten their Clawdbot to do, as well as the security risks that come with giving an agent access to literally everything. The hosts talk about the concerns around prompt injections. The hosts also debrief the biggest gossip in tech, which is Moltbook. It’s a Reddit-style forum where 150,000 AI agents talk to each other. The bots are discussing self-preservation, creating religions (the Church of Molt), and talking about humans like they're their pets. Tune in to hear why the hosts actually don’t think it’s a huge deal the way the internet does.

Next, Trump nominated Kevin Warsh as Fed Chair, and the Senate confirmation odds are sitting at 83%. You can trade on that market here: https://kalshi.com/sign-up?referral=getthecheck. Warsh is a former Fed governor and Morgan Stanley M&A banker, so basically the establishment friendly pick. His big thing is shrinking the Fed's balance sheet (they're holding $4.2 trillion in government debt) and being generally more hawkish than Powell. He was criticized for wanting to raise rates too fast during the financial crisis. This may be the Fed that has to address the impact of AI on unemployment, but at least until now Warsh has been bullish on the impact of AI on the economy.

The last segment is about Elon merging SpaceX and xAI. The pod actually recorded this a couple hours before it was confirmed, which is why they discuss it hypothetically. They dive into how Elon is building an AI empire: Optimus robots, Robotaxis, the Colossus supercomputer, Grok including on X, and eventually data centers on Mars via SpaceX. It looks like SpaceX is headed for an over trillion dollar IPO this year. You can trade on the IPO probability here: https://kalshi.com/sign-up?referral=getthecheck. Anika expresses some concern about one person controlling humanoid robots, brain-computer interfaces (Neuralink), social media, space travel, and AI compute infrastructure.

Finally the hosts say they are going to Known’s Valentine’s Day party. Maya notes that she probably has plans with Adi and can’t go, but also she can say whatever she wants because her boyfriend never listens till the end of the episode anyways…Priya and Anika have zero other plans, so they’ll be there. Let them know if you’re going and check out the interview with Celeste about Known here: https://open.spotify.com/episode/1G3vkS8aqXdVoQrnxeaCr8.

00:00 Maya breaks her work computer

02:01 OpenClaw and Moltbook the first social media for AI agents

20:58 Trump announces Kevin Warsh as his Fed Chair pick

33:36 Elon announces SpaceX and xAI merger valued at $1.25T

This week the pod talks to Celeste the CEO and co-founder of Known. Celeste dropped out of Stanford to build an AI-powered dating app that just raised $10M from Forerunner and NFX. Celeste explains why dating apps are fundamentally broken: they profit when you stay single and are a part of their long tail of retained users. Known flips the business model by monetizing dates instead of monthly subscriptions. Their key metric is introductions leading to people meeting.

Celeste breaks down why the data shows opposites don't actually attract, why 98% of users share their deepest romantic preferences with an AI, and how voice-based onboarding gives Known a matching edge no competitor has because human voice conveys much more than text. Celeste debriefs Known’s beta in SF where 80% of introductions turned into actual dates, which is much higher than legacy players in the space.

Celeste also shares how she accidentally dropped out of Stanford (she and her co-founder missed class enrollment by weeks while white boarding the app until 4am), how she convinced one of Uber's first engineers to join a 22-year-old's startup, and the real reason she's launching in SF instead of New York. The pod ends with the wildest user stories and a speed round of kiss, marry, kill.

You can download Known today: https://www.knowndating.com/

Next week we are covering Ramp’s Super Bowl tailgate at Fort Mason. DM us @getthecheckpod on Instagram, if you want to come and put your Super Bowl trades in today on Kalshi: https://kalshi.com/r/getthecheck

00:00 Introducing Celeste the co-founder and CEO of Known

00:42 Throwing SF’s biggest party in 2 weeks

03:02 The decision to launch in SF

11:01 Why people misunderstand the loneliness epidemic

14:08 What makes Known’s business model different

21:55 Do opposites attract

27:39 Celeste’s craziest set up

30:16 How to ban your ex from Known

31:17 Why Celeste dropped out of Stanford

39:41 Kiss, marry, kill speed round

This week the pod kicks off with Anika's unexpected internet fame after a photo of her and her ex's ex went viral with 11M views. If that sounds really random it’s because it was. Tune in to hear the full story and follow us on X @getthecheckpod. If you just want to see the tweet you can go to @anikamirzaa…

Then they dive into Capital One's $5.15B acquisition of Brex, which is down over 50% from its peak valuation. Maya, Anika, and Priya break down the Brex vs. Ramp rivalry and how Ramp caught up despite a two-year head start. They get into the weeds on revenue multiples, who actually made money on the Brex deal (spoiler: YC got 800x), and why this acquisition might be the right move for Brex given Capital One's unlimited balance sheet. The hosts also debate whether Capital One can compete with Amex for corporate cards by combining luxury lounge perks with Brex's software.

Next, they cover the Davos drama. Trump wants to buy Greenland, Denmark said no, and NATO allies are not happy. The hosts explain why Greenland matters strategically: missile defense from adversaries, rare earth minerals, and trade routes. All of this becomes more important as the Arctic melts. Maya shares her thoughts on Trump, in case you didn't know them already.

Finally, the pod covers Humans&, a new AI lab that raised a $480M seed round at $4B. The founders are ex-every major AI lab and their mission is to build "human-centric" AI. The pod discusses the workplace productivity tools they’re going after like Claude Cowork, Notion, Slack, etc. Maya and Anika get into a full debate about whether this is actually different from what every other lab is doing. The pod ends with them agreeing to disagree.

00:00 Anika goes viral

04:41 Capital One acquires Brex for $5.15B

08:20 The Brex vs. Ramp rivalry

19:00 Davos 2026 and the Greenland crisis

25:00 Why Greenland is so important

34:00 Would Humans& the new AI lab “Get the Check”?

44:30 Anika and Maya debate if Humans& is meeting its mission

This week the pod dives into the AI labs making big moves in healthcare. OpenAI dropped ChatGPT Health, a separate tab for all your medical questions. Hundreds of millions of people a week are already using ChatGPT for health including Priya. Maya roasts OpenAI's enterprise healthcare approach, arguing that their pilot with only 1,000 seats / hospital is a very modest start to cracking a huge problem. Maya’s hot take is a bottoms-up GTM approach makes sense in healthcare, and doctors should control their own tools. They also cover Claude for Healthcare, which is going deep on the admin layer: prior auth, claims, coding, ICD-10, FHIR integrations. The hosts get into the weeds on how prior auth actually works (spoiler: it's a lot of doctors getting on phone calls, which AI can't really fix yet).

Next, the streaming wars continue. Netflix just locked in a $7B Pay-1 deal with Sony. Also, the Warner Brothers acquisition drama is still going on. Paramount wants to outbid Netflix but analysts are calling them "high-levered and risky," because they have a $14B market cap and are trying to make a $95B acquisition. Trump somehow inserted himself into this too because of course he did. Tune in to hear about how.

Finally would insurtech “Get the Check”. The hosts break down why insurance is a $2 trillion industry (bigger than SaaS!) with legacy problems similar to healthcare. They cover Corgi a YC-backed, full-stack AI insurance for startups that has an insane team culture with actual corgis and matching tattoos, and WithCoverage a broker play founded by the Opendoor founder that just raised $42M from Sequoia. Corgi gets the check. Anika thinks full-stack is the way and YC distribution is unbeatable. WithCoverage might get cut out by companies like Corgi that go direct. The hosts compare it to Brex's early strategy of landing every YC company and growing with them.

They wrap by heading to a hotel slumber party in their own city…

Thank you to Kalshi for sponsoring: https://kalshi.com/sign-up?referral=getthecheck. Use our referral code to get $10 when you trade!

00:24 Intro

02:46 OpenAI and Anthropic launch healthcare products

35:12 Netflix and Sony $7B deal

40:51 Warner Brothers acquisition battle continues

49:25 Would Insurtech Get the Check? Corgi (YC) and WithCoverage raises

Get the Check welcomes Florian Juengermann, CTO and co-founder of Listen Labs, to talk about his journey from a small town in Germany to becoming an international mathlete and starting an AI company.

Maya and Priya ask about Florian's origin story from wanting to program his toys to winning IOI medals (the olympics for nerds). They also dig into his path to America: Harvard, Tesla's self-driving team, and the moment he realized he wanted to build after watching a company with no product raise $3M off a pitch deck when he'd actually built the product they pitched.

From there, Listen Labs is born, but v1 was a viral consumer AI image app with 20k users and a scary GPU bill charged directly to their personal credit cards. They still had a positive margin though!

The real insight came when they realize the hardest part of building products is understanding what users actually think, so they flip the model: instead of AI answering questions, they build AI that asks them. Listen Labs becomes the AI interviewer that can talk to thousands of customers at once and turn those conversations into real insights.

Maya and Priya deep dive into how the company found product-market fit, why marketing teams turned out to be the perfect first customers, and how Listen Labs went from scrappy demos to landing massive enterprise clients. Florian shares what it felt like to raise a Series A and then a Series B in rapid succession—and why it finally felt like the market caught up to what they'd believed all along.

The episode also delivers one of Listen Lab’s most memorable moments: the story of the infamous San Francisco billboard. Just a string of numbers. No logo. No explanation. Turns out it's an elaborate puzzle designed to nerd-snipe engineers and recruit talent in the most on-brand way possible.By the end, the conversation zooms out to what it really means to build in Silicon Valley, and Florian's philosophy around AI deepening human connection instead of replacing it.

00:00 Intro

00:18 Learning about programming in a small German town

01:46 Becoming an international mathlete

06:21 The dream of going to Harvard

07:33 Working at Tesla

10:19 Creating a viral app with co-founder Alfred Wahlforss

10:47 Founding Listen Labs

23:19 Finding product market fit

27:40 Fundraising and market validation

28:59 The power of customer insights

37:07 The SF billboard that went viral

44:01 AI and human connection

44:59 Why you should join Listen Labs

Maya woke up to Happy New Years texts from people she hadn’t heard from in awhile. She thought it was really special till she realized she texted them first the night before and forgot. Including Anika and Priya who got 5 Happy New Years texts from her each. Another year, and the same friends.

The pod talks about 2026 as an IPO comeback year and highlight SpaceX, OpenAI, Anthropic, and Cerebras. Maya gives her hot take on why SpaceX’s Starlink numbers look better than they are because their EBITDA hides how much depreciation their satellite business has. Anika explains why she’s still bullish. Next they discuss why OpenAI and Anthropic are considering a 2026 IPO. The trio breaks down why both companies are sprinting toward IPOs and how many $Bs they’re spending each quarter. Priya draws a comparison to Uber IPO-ing pre-profitability, but model technical growth may mean the product catches up with the spend in this case. Lastly, is Cerebras, the AI chip company with a previously attempted IPO. The group explains why having one customer account may be tough in the public markets. They also discuss the recent Groq <> Nvidia deal’s impact on the company.

The episode then pivots into full scale political discourse with the California billionaire tax debate. What started as a policy discussion on X quickly turned into tech billionaires threatening to move to Austin and Ro Khanna who was once their go to guy joking that he doesn’t care if they leave. The pod talks about the right way to tax wealth and if they think there will actually be an exodus to Austin. Priya also debriefs the why behind Austin’s cheap housing.

Finally, this week the “Get the Check” segment goes global with Arya.ag, a company helping Indian farmers store grain, access cheaper loans, and use AI to improve crop yields. Maya and Anika are bias on this one because it reminds them of a Parafin and Fay combo.

00:00 Intro

02:35 Companies that are predicted to IPO in 2026

03:23 SpaceX’s IPO

06:37 Data centers in space

12:05 OpenAI and Anthropic’s race to IPO

22:52 Cerebras take two on an IPO

23:40 Cerebras G42 Controversy

28:06 Debate on X about billionaire tax in California

39:14 SF vs. Austin future tech hub debate

44:09 Would Arya.ag “Get the Check”?