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If you’ve parked a car recently in the U.S. or Canada, there’s a good chance you paid through a startup called Metropolis. Founded in 2017 by CEO Alex Israel and three co-founders in a Santa Monica garage, Metropolis is now the largest parking operator in North America – with 23,000 employees, $5 billion in payments, and 30 million Americans signed up for its ticketless app.
If that sounds unusual for a startup, you’re right. Metropolis got there in unusual fashion, enlisting the help of billionaire Todd Boehly to acquire a legacy player many times its size in a move one banker initially dismissed as “dog catches 747.”
But its CEO doesn’t really see Metropolis as just a parking company. He calls it an applied AI company, one piloting a new “recognition economy” that cuts the wait out of experiences for consumers, from drive-throughs to hotel lobbies.
On The Upstarts Podcast, Israel talks about why merging “ugly, unsexy” businesses with AI has suddenly gained popularity; why Metropolis is all-in on autonomous vehicles, robotaxis, and drones; and why he argues the startup’s opt-in approach avoids the privacy concerns facing surveillance startups.
Plus, he shares his Upstart Moment: Inviting the CEO of his bigger competitor to a seafood buffet to inform him that he planned to take their company private.
Chapters:
00:00 Introduction
Alex's LinkedIn: https://www.linkedin.com/in/alex-israel/?isSelfProfile=false
For more, visit https://www.upstartsmedia.com/
Season 3 of the Upstarts Podcast is presented by Jira by Atlassian: https://www.atlassian.com/software/jira
Produced & edited by Eric Johnson from LightningPod: https://lightningpod.fm/
Neko Health CEO Hjalmar Nilsonne calls it the most valuable hour you can spend on your health. Since opening its first U.S. location in New York last month, more than 50,000 people have joined the waitlist – for one clinic alone.
Co-founded in 2018 with Spotify’s Daniel Ek and valued at $7 billion, Neko offers one-hour scans that map your skin, heart and blood for $499. A clinician then walks you through the results before you leave, complete with a futuristic 3D scan. Already in operation in the U.K. and Sweden, Neko’s now expanding across America, with Miami, Washington, D.C. and San Francisco coming next.
On The Upstarts Podcast, Nilsonne talks about the fateful Twitter DM from Ek that got Neko going; why the doctor visit hasn’t changed much in 100 years; and how to keep a startup team motivated while chasing a long-term “moonshot.”
Plus, he shares his Upstart Moment: a bet-the-company pivot driven by an internal memo he wrote, “Free Is Not Enough.”
Chapters:
00:00 Introduction
Hjalmar's LinkedIn: https://www.linkedin.com/in/nilsonne?originalSubdomain=se
For more, visit https://www.upstartsmedia.com/
Season 3 of the Upstarts Podcast is presented by Jira by Atlassian: https://www.atlassian.com/software/jira
Produced & edited by Eric Johnson from LightningPod: https://lightningpod.fm/
Founder Ben Lamm has found success building startups in gaming, SaaS and AI. But the boldest — and biggest — bet of his career is Colossal Biosciences, a biotech venture working to bring back extinct species like the dire wolf, dodo, Tasmanian tiger and woolly mammoth.
It's a decades-long endeavor so crazy that one investor warned Lamm it would "completely ruin" his career. But so far, it's working. Founded in 2021 by Lamm and famed Harvard geneticist George Church, Colossal has already cloned and raised three dire wolves in a secret location, created woolly mice, and reportedly held talks to raise at a valuation of $23 billion or more.
Still, Lamm faces some basic, persistent questions: Why do all this? And isn't this like Jurassic Park?
On The Upstarts Podcast, Lamm talks about why Colossal made reviving the mammoth its North Star; why building in biology is so different from software; and why he won't consider anything short of reviving every targeted species a success.
Plus: Why Lamm insists Colossal won't bring back the dinosaurs.
Chapters:
00:00 Introduction
Colossal Biosciences: https://colossal.com/
For more, visit https://www.upstartsmedia.com/
Season 3 of the Upstarts Podcast is presented by Jira by Atlassian: https://www.atlassian.com/software/jira
Produced & edited by Eric Johnson from LightningPod: https://lightningpod.fm/
A crisis is happening in accounting that goes far beyond creative bookkeeping or lost receipts: we don't have enough people.
Enough work exists for 30 million accountants to prepare tax returns and audits, restructure data and improve how companies organize. The U.S. has just 3 million, says Basis co-founder and CEO Matt Harpe. "The number is rapidly declining," he says.
Founded in 2023 by Harpe and co-founder Mitchell Troyanovsky, Basis builds AI agents to help. Operating behind the scenes, Basis agents learn a firm's best practices and then automate much of the process, allowing its staffers to review more work for clients. Basis reached a $1.15 billion valuation in February 2026.
Far from eliminating jobs, Harpe believes his startup will help those human accountants get paid more. "It will increase how valuable accountants are, because they will be able to accomplish so much more," he says.
On the Upstarts Podcast, Harpe talks about why Basis shunned a chatbot approach to go all-in on agents from the start; why outcome-based pricing is preferable, but not easily achieved; and how he pitches top AI talent in New York on building in accounting, of all things.
Plus, he shares his Upstart Moment: turning down short-term revenue by not charging for a product until their outcomes could match what they promised.
Chapters:
00:00 Introduction
Matt's LinkedIn
Basis
For more, visit https://www.upstartsmedia.com/
Season 2 of the Upstarts Podcast is presented by Rippling
Produced & edited by Eric Johnson from LightningPod
Doctors are burned out. Patients don’t understand the advice they’re given. And the U.S. healthcare system is drowning each year in $1.5 trillion – with a “T” – in administrative costs.
Abridge co-founder and CEO Shiv Rao thinks he can help. He’s seen the problem on both sides – as a practicing cardiologist who still sees patients, and as a partner who spent years navigating the system to seek fertility treatments with his spouse.
“We’d look at each other and be like, ‘What did they just say?’ And I’m a doctor,” he says.
Founded in Pittsburgh in 2018, Abridge is building what Rao calls the “AI operating system” for healthcare. Abridge’s software automates all the clerical work of a visit, from notes to billing, and increasingly assists with making clinical recommendations, too. Valued at $5.3 billion, Abridge serves more than 300 health systems, reaching 250 million Americans, and recently partnered with Eli Lilly and Nvidia.
But Abridge has faced an uphill journey from day one, when Rao convinced his former employer to take a chance on a fledgling startup. Microsoft’s a big player. Epic Systems looms, and a number of well-funded startups are chasing Abridge’s lead.
On The Upstarts Podcast, Rao talks about how an early bet on AI got Abridge going, before ChatGPT; why reaching scale in healthcare requires years of “eating glass” and “kissing frogs;” and why he thinks Abridge can help doctors and nurses feel like “superheroes.”
Plus, he shares his Upstart Moment: A “YOLO” decision to take on Microsoft head-to-head.
Chapters:
00:00 Introduction
Shiv's LinkedIn
Abridge
For more, visit https://www.upstartsmedia.com/
Season 2 of the Upstarts Podcast is presented by Rippling
Produced & edited by Eric Johnson from LightningPod
The world's big companies are blowing through their AI budgets. At French startup unicorn Pigment, Eléonore Crespo wants to help.
"Our CEO is pressuring us for everybody in the company to use AI, but we don't have any right way to think about it," Crespo says she hears chief financial officers complain. “It’s going to be a big topic for everyone, and it goes beyond just understanding your costs."
Pigment, founded by co-CEOs Crespo and Criteo veteran Romain Nicoli in 2019, fights runaway AI spending with AI. Its agents help CFOs and finance teams at customers like Anthropic, Notion, Coca-Cola and Unilever make faster, better financial decisions.
For analysts, Crespo argues her tools can free up much of the 80% of time they currently spend sifting through data; her (perhaps optimistic) hope is that they can then focus on higher-level decisions, without fearing for their jobs.
On The Upstarts Podcast, Crespo talks about how building in Paris helps Pigment compete; how a culture of “unreasonable hospitality” makes it win; and how careful communication makes a co-CEO setup work.
Plus, she shares her Upstart Moment: landing a key executive hire, with an in-person assist from the actor Tom Cruise.
Chapters:
00:00 Introduction
Eléonore's LinkedIn
Pigment
For more, visit https://www.upstartsmedia.com/
Season 2 of the Upstarts Podcast is presented by Rippling
Produced & edited by Eric Johnson from LightningPod
Materials science hasn’t changed much in 150 years. Radical AI CEO Joseph Krause wants to change that.
In a big new lab in Brooklyn’s Navy Yard, the startup founder is looking to change that. He’s building a “next-gen” approach that he says makes other autonomous labs look like hand-free driving mode on a car, compared to a fully self-driving Waymo.
It’s an approach that plenty of corporate scientists tell Krause must be too good to be true. “How could you really discover more alloys in a week than we have discovered in our company history?” he says they ask.
But since its founding in 2024, Radical AI has already produced valuable, and secret, alloys for customers, Krause insists. And the startup has done it after raising just $55 million in its last funding round, not the $1 billion of well-heeled competitors..
On the Upstarts Podcast, Krause explains how a SpaceX breakthrough helped kick off a category; why cloud labs and deep tech companies often fail; and why concurrent engineering is as important as next-gen lab equipment itself.
Plus, he shares his Upstart Moment: a 100-year-vision to become one of the world’s most important companies: “When we put a civilization on Mars, the habitat that they're living in will be made with Radical materials.”
Chapters:
00:00 Introduction
Joseph's LinkedIn
Radical AI
For more, visit https://www.upstartsmedia.com/
Season 2 of the Upstarts Podcast is presented by Rippling
Produced & edited by Eric Johnson from LightningPod
First at West Point and then as an officer in the U.S. Army Rangers, Brian Elliott always sought out the hardest, highest-impact challenge.
“You can do hard things that don’t have impact, but you can’t do things that have impact that aren’t hard,” he says.
Now Elliott is taking the same approach at Blitzy, the Boston-based startup he co-founded with Harvard Business School classmate Sid Pardeshi in 2023 to overhaul and lead massive code projects for large corporations. Blitzy’s agents can understand 100 million-plus lines of code, automating away work that customers would otherwise pay millions over months to consulting firms to barely crack.
“For eons, we have been limited by how much a human context can hold in their brain,” Elliott argues. Now Blitzy can offload that context to its AI systems: “We can do changes at a size and scale that were previously impossible."
On The Upstarts Podcast, Elliott shares how he built Boston’s newest tech unicorn by becoming a CFO’s friend; why Cursor and Claude Code only see enterprise code through a straw; and what West Point and the Army Rangers taught him about operating with precision under pressure.
Plus, he shares his Upstart Moment: catching the 6am train to New York to close an early customer, with his co-founder’s visa at stake.
Chapters:
00:00 Introduction
Brian's LinkedIn
Blitzy
For more, visit https://www.upstartsmedia.com/
Season 2 of the Upstarts Podcast is presented by Rippling
Produced & edited by Eric Johnson from LightningPod
Writer’s May Habib: On VC Bias, Token Maxing’, And The Customers Anthropic And OpenAI Leave Behind
Fortune 500 boards are in weekend crisis meetings about adopting AI. Many have nothing to show for it, despite spending millions with the big AI labs.
"Anthropic and OpenAI salespeople walk in like heroes, get a contract, and leave to literally never be seen again,” says Writer CEO May Habib.
That’s where her startup, Writer, cleans up. Valued at $1.9 billion, Writer builds for the ‘normal’ people in enterprise, its agents helping customers like Accenture, Cigna and Vanguard with everything from creating morning sales briefings to personalized product invites.
On The Upstarts Podcast, Habib talks about the pivot from Qordoba’s machine translation to Writer’s AI models; ‘token maxing’ and tokenomics’ “absolute insanity”; and why she believes people should start getting fired for buying AI without results.
Plus, she shares her Upstart Moment: facing VC bias first-hand, from Vinod Khosla falling asleep in their meeting, to a rejection from Sequoia that called her running a startup with two kids “inspiring.”
Chapters:
00:00 Introduction
May's LinkedIn
Writer
For more, visit https://www.upstartsmedia.com/
Season 2 of the Upstarts Podcast is presented by Rippling
Produced & edited by Eric Johnson from LightningPod
Salespeople have a problem: they only spend 21% of their time actually selling to customers.
Founder Jaleh Rezaei set out to fix that – and business was booming. Her startup, Mutiny, reached $10 million-plus in revenue for software that helped take some of the busywork out of the sales process.
“When you start a company, the expectation is failure,” she says. “It’s really hard to accept that you’re going to burn it to the ground for the possibility of a better future.”
But the CEO now believes that re-founding Mutiny, including painful layoffs and firing all of its customers, was the best thing she could do. The reborn business now uses AI agents to automate away that pain, allowing sales reps to set custom pricing and share peer case studies with just a prompt. It’s growing 150% month over month.
On The Upstarts Podcast, Rezaei shares why follow-ups are the sales killer; how AI is disrupting software; and how she got over ‘Claude spookies’ about the big labs.
Plus, she shares her Upstart Moment: convincing her co-founder to start over again, on a fateful New York walk.
CHAPTERS
For more, visit https://www.upstartsmedia.com/
Season 2 of the Upstarts Podcast is presented by Rippling
Produced & edited by Eric Johnson from LightningPod
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