Saturday Stories: The Founders Behind Ramp's $60B, Berkshire's Bet and Character.AI's Bankruptcy

Good morning, crowd.

Welcome to Saturday Stories, where we skip the headlines and look at the people behind them. This week: two founders who sold their first startup to a bank and then built a $60 billion company, an Italian app studio Warren Buffett keeps buying, a $2.7 billion AI startup that went bankrupt, and a company that 3D-prints houses for Earth and Mars.

Quick game before we start

Which founder sold his first startup to the same bank that later bought his biggest rival?

A) Eric Glyman, Ramp
B) Noam Shazeer, Character.AI
C) Jason Ballard, ICON

The answer is in story 1.

Read time: 5 minutes

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STORY 1: THE COMEBACK

The short version

• Eric Glyman and Karim Atiyeh sold their first startup, Paribus, to Capital One in 2016

• They started Ramp in 2019. This month it raised $1.85B at a $60B valuation

• Earlier this year, Capital One bought Ramp's closest rival, Brex, for $5.15B

Quiz answer: A, Eric Glyman. The photo above is from 2015, when Glyman and Atiyeh pitched Paribus on the TechCrunch Disrupt stage. Paribus tracked your online purchases and claimed money back when prices dropped. Capital One, one of America's biggest credit card issuers, bought it a year later.

In 2019 they started again with a problem every finance team knows: expense reports and company card spending nobody can control. Ramp launched with a corporate card that helps businesses spend less, then added bill pay, accounting tools and AI that flags waste.

The numbers

• $7.65B → $44B → $60B: Ramp's valuation in April 2024, June 2026 and October 2026

• 70,000: business customers as of June

• $1.5B+: annualized revenue as of June

• $5.15B: what Capital One paid for Brex, Ramp's closest competitor

The twist: the bank that bought their first company ended up buying their rival instead, at about a twelfth of Ramp's price. We covered the $60B round in Thursday's edition.

What to do with this

• Founders: an acquisition isn't the end of the story. Your first company can teach you the industry your second one wins.

• Investors: second-time founders who already know the industry from the inside are among the best bets in venture.

STORY 2: THE BUFFETT BET

The short version

• Berkshire Hathaway agreed to invest another $330M in Bending Spoons, at $33 a share

• That's on top of the $600M Berkshire put in at Bending Spoons' July IPO. Its stake rises to 4%

• Bending Spoons owns Evernote, Vimeo, WeTransfer, Eventbrite and more

Bending Spoons started in 2013 as a small app studio in Milan, co-founded by CEO Luca Ferrari and a group of friends including Francesco Patarnello. Instead of building the next hit app, they found a different game: buy well-known software products that have stopped growing, rebuild them, raise prices where it makes sense, and use the cash to buy the next one.

It works. Revenue went from $387M in 2023 to $671M in 2024 and $1.31B in 2025. The company went public on Nasdaq in July at $29 a share, above its target range, raising about $1.68B. Berkshire's new shares come in at $33. The company says it has never sold a material business it bought.

Buying unloved businesses, running them better and holding them is exactly how Berkshire built its own empire. Bending Spoons is doing it with software.

What to do with this

• Founders: if your product has loyal users but flat growth, you have buyers. Roll-ups like Bending Spoons pay for exactly that.

• Investors: "boring" software with sticky customers can be a better business than a hot startup. Look at cash flow, not hype.

STORY 3: THE CAUTIONARY TALE

The short version

• Character.AI filed for Chapter 11 bankruptcy this week, five years after its founding

• Disney agreed to pay $20M for some of its technology and a license, unless a better bid comes in

• In 2024, Google paid $2.7B to license its models and hired its founders back

Character.AI was one of the hottest AI startups of 2022. Its founders, Noam Shazeer and Daniel De Freitas, were star Google engineers. Shazeer co-wrote the famous "Transformer" paper that powers today's AI. Users chatted with AI characters for over two hours a day on average, and the company hit a $1B valuation within a year.

Then the costs and the risks caught up with it. Every conversation cost money to run, and it was hard to get users to pay. In August 2024, Google paid $2.7B to license its models and brought both founders back to Google. Lawsuits over the safety of teenage users followed, and the company eventually banned minors.

Without its founders and with mounting legal costs, the company is now selling itself in pieces. Disney, which hired its former CEO as its CTO last month, is the opening bidder. The sale is expected to close in late November or early December.

What to do with this

• Founders: usage isn't a business. If every user costs you money, growth can make things worse.

• Investors: in "license and hire" deals, the founders and the big tech company often do well. What's left for shareholders can be very little.

STORY 4: THE BUILDER

The short version

• ICON, the Austin company that builds houses with giant 3D printers, raised a $200M Series D

• BlackRock and Baillie Gifford co-led the round, at a $1.4B valuation according to CNBC

• ICON has now raised $700M in total and is talking about a future IPO

Co-founder and CEO Jason Ballard started ICON with a big idea: print houses layer by layer with robots, using a concrete-like material, to build faster and cheaper. The photo above is NASA's simulated Mars habitat in Houston, which ICON printed for a year-long Mars mission simulation.

The new money is for Titan, ICON's robot that can print buildings more than one story tall. ICON says it can cut costs by 40% and shorten build times by six weeks. It has built 260 homes and other structures this year, partnered with homebuilder Lennar on a 100-home community near Austin, and its homes now qualify for Wells Fargo mortgages.

The market is huge. Zillow estimates the US is short as many as 4.7 million homes.

What to do with this

• Founders: a moonshot project can open doors. Printing a Mars habitat for NASA gave ICON a showcase no ad budget could buy.

• Investors: construction tech is moving from experiments to real volume. Watch how many homes ICON delivers, not how many it announces.

Quick answers

Who founded Ramp?

Ramp was founded in 2019 by Eric Glyman (CEO) and Karim Atiyeh (CTO). They previously founded Paribus, which Capital One acquired in 2016. In October 2026, Ramp raised $1.85 billion at a $60 billion valuation.

How much has Berkshire Hathaway invested in Bending Spoons?

Berkshire Hathaway invested $600 million in Bending Spoons at its July 2026 IPO and agreed in October 2026 to buy 10 million more shares at $33 each, about $330 million, raising its stake to 4%.

Why did Character.AI file for bankruptcy?

Character.AI filed for Chapter 11 in October 2026, citing legal, regulatory and operational headwinds. Its founders returned to Google in 2024 after Google paid $2.7 billion to license its models, and Disney agreed to bid $20 million for some of its assets.

How much is ICON worth?

ICON, the Austin-based 3D-printed construction company, raised a $200 million Series D in October 2026, co-led by BlackRock and Baillie Gifford, at a $1.4 billion valuation according to CNBC.

What These Four Stories Have in Common

Every founder this week bet on something unglamorous: expense reports, old software, a chatbot's server bill, concrete. The winners turned it into a business with customers who pay. The one that couldn't is being sold for parts.

Final round: your call

If you had $10,000 to put into one of these, which would you pick?

A) Ramp at a $60B valuation
B) Bending Spoons stock, alongside Berkshire
C) ICON at a $1.4B valuation

Hit reply with A, B or C and one line on why. The best answers make it into next Saturday's edition.

Tomorrow: the 7 stories that moved private markets this week, ranked.

Track Ramp and the rest of the 100 biggest private companies on our Private Company Index. Or listen to the Founderscrowd podcast.

Hunt accordingly.

Jose, Alberto & the Founderscrowd Team

Sources

• TechCrunch: Character.AI files for bankruptcy

• TheWrap: Disney readies $20 million bid for Character.ai assets

• Pulse 2.0: Berkshire Hathaway invests additional $330 million in Bending Spoons

• The Next Web: Bending Spoons prices $1.68 billion Nasdaq IPO

• Bisnow: BlackRock invests in 3D-printing construction startup valued at $1.4B

• Bloomberg: Ramp hits $60 billion valuation in $1.85 billion funding round

• Wikimedia Commons: Paribus founders at TechCrunch Disrupt NY 2015

Photos via Wikimedia Commons. Ramp founders: Noam Galai/Getty Images for TechCrunch (CC BY 2.0). Warren Buffett: U.S. International Trade Administration (public domain). Disney Studios: Coolcaesar (CC BY-SA 4.0). Mars habitat: NASA/Bill Stafford (public domain).

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