Irza Waraich – Observer https://observer.com News, data and insight about the powerful forces that shape the world. Sun, 05 Oct 2025 16:38:21 +0000 en-US hourly 1 https://wordpress.org/?v=6.8.3 168679389 Where the ‘PayPal Mafia’ Is Today: Founders, Fortunes and Feuds https://observer.com/2025/10/paypal-cofounders-today/ Sun, 05 Oct 2025 16:38:21 +0000 https://observer.com/?p=1562799

In 2007, Fortune magazine reimagined a classic mafia scene with a Silicon Valley twist: 13 male founders and early employees of PayPal, all long gone from the company, posed at a San Francisco café with slicked-back hair, poker chips and dozens of whiskey glasses. The crowd included some of the most recognizable names in today’s tech scene, like Elon Musk, Peter Thiel and Reid Hoffman. The magazine dubbed them the “PayPal mafia,” not for their time at the fintech company, but for their outsized impact on Silicon Valley through the companies they launched afterward.

PayPal went public in early 2002 and was acquired by eBay for $1.5 billion the same year. Most of its early employees left the company after the acquisition. They went on to found YouTube, SpaceX and LinkedIn, among other legendary names in Silicon Valley. However, like their cinematic namesake, the group hasn’t avoided controversy. These former colleagues have built billion-dollar businesses while also finding themselves in the crosshairs of public criticism.

For instance, Thiel has faced controversy over his political affiliations and, most notably, for funding Hulk Hogan’s 2012 lawsuit against Gawker Media with $10 million — a case that ultimately drove the online media company into bankruptcy. Musk has also faced criticism for his takeover of Twitter and his prior role in the Trump administration, where he led widespread federal employee firings.

Here’s what they are up to these days:

Peter Thiel: venture capitalist 

Peter Thiel speaking at the 2022 Bitcoin Conference
  • Position at PayPal: co-founder, CEO from 1998 to 2002
  • Companies later founded: Palantir, Clarium Capital, Founders Fund, Valar Ventures, Mithril Capital
  • Net worth: $26 billion

Peter Thiel, Max Levchin and Luke Nosek founded PayPal in 1998, originally as a software security company. After merging with Elon Musk’s X.com (unrelated to the social media platform he owns today), PayPal shifted its focus to digital payments.

Thiel served as CEO from 1998 until 2002, leaving after the company was sold to eBay. He then co-founded Palantir Technologies, a major U.S. government contractor providing data analytics services. The company now has a market capitalization of $439 billion.

Thiel is also known as a prolific angel investor. He co-founded Clarium Capital, Founders Fund, Valar Ventures and Mithril Capital. In 2004, Thiel became Facebook’s first outside investor after acquiring a 10.2 percent stake in the company for $500,000.

Thiel is among the many former PayPal employees who have entered political and high-profile public arenas. An active donor to the Republican Party, Thiel supported Donald Trump’s 2016 presidential campaign but withheld donations during the 2024 election. He is also credited with helping JD Vance reach the Vice Presidential ticket.

Elon Musk: entrepreneur, the world’s richest person

Elon Musk gesturing at a press conference in the Oval Office of the White House in May 2025.
  • Position at PayPal: co-founder, CEO from February 2000 to September 2000
  • Companies later founded: Tesla, SpaceX, The Boring Company, Neuralink, xAI
  • Net worth: $482 billion

Elon Musk briefly served as PayPal’s CEO before being ousted by the board in 2000. He went on to build one of the most influential portfolios in technology, spanning electric vehicles, space exploration, social media and A.I.

Musk founded SpaceX in 2002 and has led Tesla since 2008. He also founded Neuralink and The Boring Company, expanding his reach into brain-computer interfaces and infrastructure. In 2022, Musk gained global attention for acquiring Twitter for $44 billion, later rebranding it as X.

His ties to A.I. run deep: Musk co-founded OpenAI with Sam Altman in 2015 but left in 2018 over strategic disagreements. In 2023, he returned to the field by launching xAI, a research venture focused on building A.I. that is more understandable for humans.

Today, Musk is the richest person in the world, with an estimated net worth of $400 billion. He is also perhaps the only PayPal alumnus to ascend into direct political influence. During the Trump administration, he led the Department of Government Efficiency (DOGE)—a name shared with his cryptocurrency venture—before stepping down in May after clashing publicly with the President.

Max Levchin: computer scientist 

Max Levchin speaking at a FOX Network show in 2019.
  • Position at PayPal: co-founder, chief technology officer from 1998 to 2002
  • Companies later founded: Affirm
  • Net worth: $1.8 billion

As PayPal’s chief technology officer, Max Levchin helped lead the company’s anti-fraud efforts by co-creating the Gausebeck-Levchin test—the foundation for the widely used CAPTCHA security tool. After leaving PayPal, he launched the media-sharing platform Slide in 2004, which was acquired by Google in 2010. Levchin briefly served as Google’s vice president of engineering until Slide was shut down the following year.

In 2012, he co-founded Affirm, a leading “buy now, pay later” (BNPL) company, where he continues to serve as CEO. Today, Affirm has a market capitalization of $27.5 billion, with 21.9 million consumers and more than 350,000 merchant partners on its platform.

Levchin has also held board positions at Yahoo and Yelp. In 2015, he became the first Silicon Valley executive appointed to the U.S. Consumer Financial Protection Bureau’s advisory board, emphasizing the importance of collaboration between companies and regulators.

Reid Hoffman: entrepreneur, investor

Reid Hoffman speaking at event for WIRED's 30th anniversary.
  • Position at PayPal: chief operating officer
  • Companies later founded: LinkedIn, Greylock Partners
  • Net worth: $2.5 billion

Before joining PayPal, Hoffman worked as a senior user experience architect at Apple, contributing to the company’s online social network eWorld. He later became director of product management at Fujitsu. After his online dating startup, SocialNet, folded, Hoffman joined PayPal in 2000 as chief operating officer.

In 2003, he co-founded the career networking site LinkedIn. Following Microsoft’s $26.2 billion acquisition of LinkedIn in 2017, Hoffman joined Microsoft’s board, a move that greatly increased his wealth.

Over the years, Hoffman has served on the boards of Airbnb and OpenAI, where he was also an early investor. Through the venture capital firm Greylock Partners, he has backed dozens of A.I. startups. In 2022, he co-founded Inflection AI with Mustafa Suleyman, who now serves as CEO. Earlier this year, he teamed up with cancer researcher Siddhartha Mukherjee to launch Manas AI, a startup focused on drug discovery.

David Sacks: investor, White House A.I. and Crypto Czar

David Sacks being photographed on a red carpet in Los Angeles.
  • Position at PayPal: chief operating officer from 1999 to 2002
  • Companies later founded: Craft Ventures
  • Net worth: $200 million

Since leaving PayPal, David Sacks has built a career spanning film, tech, investing and politics. In 2005, he produced and financed a political satire that earned two Golden Globe nominations. The following year, he founded Geni.com, a genealogy-focused social network that later spun off Yammer, one of the earliest enterprise social networking platforms. He went on to co-found Craft Ventures, the startup Glue, and the podcast platform Callin.

Today, Sacks serves as the White House’s Special Advisor for A.I. and Crypto, a role created by the Trump administration to guide policy on artificial intelligence and cryptocurrency.

Jeremy Stoppelman: engineer, Yelp CEO 

  • Position at PayPal: vice president of engineering
  • Companies later founded: Yelp
  • Net worth: $100 million

Jeremy Stoppelman joined Musk’s X.com in 1999 and became vice president of engineering after its transition to PayPal. In 2004, he co-founded Yelp, where he has served as CEO ever since. Under his leadership, the company turned down a 2010 acquisition offer from Google and went public two years later. Stoppelman’s net worth is estimated at more than $100 million.

Ken Howery: investor, U.S. ambassador

  • Position at PayPal: chief financial officer from 1998 to 2002
  • Companies later founded: Founders Fund
  • Net worth: estimated $1.5 billion

Ken Howery served as PayPal’s chief financial officer from 1998 to 2002. After PayPal’s sale to eBay, he became eBay’s director of corporate development until 2003. He later joined Peter Thiel at Clarium Capital as vice president of private equity and went on to co-found Founders Fund as a partner. Beyond investing, he is a member of the Explorers Club, a nonprofit dedicated to scientific exploration, and an advisor to Kiva, the micro-lending nonprofit founded by former PayPal colleague Premal Shah.

Howery is also among the former PayPal executives who have moved into politics. He has donated at least $1 million to Donald Trump’s campaign through Elon Musk’s political action committee. During Trump’s first term, Howery was appointed U.S. ambassador to Sweden and today serves as the U.S. ambassador to Denmark.

Roeloth Botha: venture capitalist

Roelof Botha joined PayPal as director of corporate development shortly before graduating from Stanford University. He later became vice president of finance and went on to serve as chief financial officer until the company’s acquisition by eBay.

After leaving PayPal, Botha joined Sequoia Capital, where he oversaw investments in YouTube and Instagram. He currently sits on the boards of MongoDB, Evernote, Bird, Natera, Square, Unity and Xoom.

Russel Simmons: entrepreneur 

  • Position at PayPal: software architect from 1998 to 2003
  • Companies later founded: Yelp, Learnirvana

Russel Simmons helped design PayPal’s payment system as a software architect. After leaving the company, he and fellow PayPal alum Jeremy Stoppelman set out to build a platform for restaurant reviews. With a $1 million investment from Max Levchin, they launched Yelp in July 2004. Simmons served as chief technology officer until his departure in 2010. At the time, Yelp said he would remain a “significant” shareholder, though the size of his stake—and whether he still holds it—remains unclear.

In 2014, Simmons co-founded Learnirvana, an online learning platform.

Andrew McCormack: entrepreneur

  • Position at PayPal: assistant to Thiel from July 2001 to November 2002
  • Companies later founded: Valar Ventures

Andrew McCormack began his career as an assistant to Peter Thiel at PayPal and followed him into subsequent ventures. From November 2002 to April 2003, he oversaw operations at Thiel’s hedge fund, Clarium Capital.

In 2010, McCormack co-founded Valar Ventures with Thiel and James Fitzgerald, focusing on fintech investments. He remains a general partner at the firm.

Luke Nosek: investor 

  • Position at PayPal: co-founder and vice president of marketing and strategy from 1998 to 2002
  • Companies later founded: Founders Fund, Gigafund

In 2005, Luke Nosek joined Peter Thiel and Ken Howery to launch Founders Fund, a San Francisco–based venture capital firm that has backed companies such as Airbnb, Lyft and SpaceX. While his exact net worth is unclear, Nosek has made substantial investments through his venture firms. At Founders Fund, he led one of the firm’s earliest major deals with a $20 million investment in SpaceX, later serving on its board.

In 2017, Nosek left to co-found Gigafund, which went on to invest $1 billion in SpaceX, according to the company. He also sits on the board of ResearchGate.

Premal Shah: entrepreneur 

  • Position at Paypal: product manager
  • Companies later founded: Kiva

Three years after leaving PayPal, Premal Shah co-founded Kiva, a nonprofit that provides loans to entrepreneurs in underserved communities worldwide. He also serves on the boards of other nonprofits, including the Center for Humane Technology, the Change.org Foundation, Watsi and VolunteerMatch.

Keith Rabois: investor

  • Position at PayPal: executive vice president of business development

After leaving his executive role at PayPal, Keith Rabois became an active investor, backing companies including Slide, YouTube and Palantir. He also invested in LinkedIn, where he served as vice president of business and corporate development, and Square, where he was chief operating officer.

Rabois joined venture capital firm Khosla Ventures from 2013 to 2019 and was a partner at Founders Fund from 2019 to 2024.

]]> 1562799
 Reddit’s A.I. Tools Drive 78% Revenue Surge in Best Quarter Since IPO https://observer.com/2025/08/reddits-ai-tools-drive-ad-revenue-growth/ Fri, 01 Aug 2025 21:50:30 +0000 https://observer.com/?p=1568924

Reddit’s recently launched A.I. marketing tools are already fueling strong advertising growth. In the latest quarter ended June, the social media company reported a 78 percent year-over-year revenue increase to $500 million, with 93 percent coming from advertising, the company reported yesterday (July 31). Touting the momentum, CEO Steve Huffman told analysts on an earnings call that one major advertiser plans to feature Reddit’s A.I. tools in a Super Bowl ad next year and another client said the tools uncovered a previously untapped customer segment.

Introduced in June, the new products—Reddit Insights, which tracks user engagement across posts and comments, and Conversation Summary Add-ons, which incorporate real user commentary into ads—have been warmly received.

“We’ve just gotten them out the door and I think they’ve been very well received,” Reddit chief operating officer Jen Wong rang an optimistic bell on yesterday’s earnings call. “We’re really excited to see more broad based adoption and impact from them.” Wong added that Reddit’s number of advertising accounts grew by 50 percent in the April–June quarter.

Beyond advertising, Reddit brought in $35 million primarily from A.I. licensing deals, including a partnership with Google. The agreement, signed last year, allows Google to train its Gemini A.I. models using Reddit’s vast archive of human-generated content. In return, Reddit gains access to Google’s Vertex AI platform, which has boosted the visibility of Reddit posts in Google Search results.

Reddit has also been building its own A.I.-driven tools. Last year it rolled out Reddit Answers, a search assistant that uses Vertex AI to summarize community discussions in response to user questions. As of the end of June, Reddit Answers had grown to six million weekly users—five times more than a year earlier.

That growth has also helped Reddit better understand the depth of its content and the opportunity it presents. “On our own product, we’re seeing that the corpus is deeper and broader, that I think even we realized before we built Reddit Answers,” Huffman said. “There’s a huge opportunity to provide users with broad and varied viewpoints on subjective questions, which I think is an important category of questions that users have on the internet.”

To make Reddit Answers more central to the user experience, the company plans to replace its existing interest boxes with a dedicated Reddit Answers search bar on the app’s homepage. “What we’re building towards this year is to have a product that starts personalizing instantly, removing as many barriers as we can for a new user to start finding their home on Reddit,” Huffman said. 

While Reddit’s A.I. tools and ad business are driving short-term success, some analysts remain cautious. Redburn Atlantic warned that Reddit’s reliance on Google could eventually limit its growth potential, including its ability to attract new users.

For now, the platform’s user base continues to grow. At the end of June, Reddit had 110 million daily active users, up 21 percent from the same period last year.

]]> 1568924
 From Hops to Orbit: A Fiery History of SpaceX’s Starship Program https://observer.com/2025/07/spacex-starship-test-timeline/ Wed, 23 Jul 2025 13:00:58 +0000 https://observer.com/?p=1561445

On June 19, a Starship prototype exploded on the launch pad at SpaceX’s Starbase facility in Texas during preparations for what would be its tenth test flight. After three consecutive failed orbital attempts this year, the upcoming launch is shaping up to be a pivotal moment in Elon Musk’s vision to send humans to Mars and beyond.

Since its first orbital test flight in April 2023, Starship has made notable progress but has also suffered high-profile setbacks, keeping the project under close scrutiny. To date, Starship has completed nine orbital test flights, following a series of ground-based trials. Current tests are focused on demonstrating the rocket’s ability to recover its booster, reach target altitudes, deploy payloads and execute controlled landings. All these goals are key to making the vehicle reusable.

Standing 403 feet tall when fully stacked, Starship costs an estimated $100 million per launch, according to the Reason Foundation. SpaceX aims to eventually reduce that figure to $10 million. By comparison, NASA’s Space Launch System (SLS)—also designed for deep space missions but built as an expendable rocket—costs about $2 billion per launch.

Every Starship prototype built and tested to date:

April 3, 2019: The Starhopper prototype climbed one foot in a tethered test hop.

April 5, 2019: Starhopper rose three feet in a tethered hop, using the full length of the tether.

July 25, 2019: Starhopper jumped to 65 feet (20 meters) in an untethered test flight.

Aug. 27, 2019: Starhopper flew even higher, reaching 500 feet (150 meters), slewing sideways before descending slowly to a nearby landing pad.

The Starhopper rocket at a test site. A woman standing in front of the MK1 prototype of Starship.

Nov. 20, 2019: A larger prototype, Mk1, was built but blew its top off during a cryogenic proof test (also known as a pressure stress test), rendering it unusable for flight.

May 29, 2020: After earlier prototypes SN1 and SN3 exploded during ground tests, SpaceX found success with SN4, which completed five static fire tests before exploding during the final one.

Aug. 5, 2020: SN5 successfully performed a 500-foot (150-meter) flight and landed on a nearby pad.

Sept. 3, 2020: SN6 completed another 500-foot test flight.

Dec. 9, 2020: SN8, the first prototype with fins and a nose cone, was designed to reach higher altitudes. It ascended to 7.8 miles (12.5 kilometers) but descended too fast and exploded upon landing.

Feb. 2, 2021: SN9 flew to 6 miles (10 kilometers) but crashed on landing after one engine failed to ignite.

March 3, 2021: SN10 nearly completed a 6-mile flight but crushed its landing legs, causing it to tip and explode minutes after touchdown.

March 30, 2021: SN11 successfully reached 6 miles but exploded mid-air during descent.

(SpaceX skipped SN12, SN13, and SN14.)

May 5, 2021: SN15 successfully completed a high-altitude flight and landed intact.

The Starship rocket taking off for its first test flight

Nov. 18, 2023: The second orbital test flight reached 93 miles (150 kilometers) and became the first Starship to reach outer space, but it exploded before completing its mission.

March 14, 2024: The third orbital test flight reached approximately 1,515 feet (462 meters) before destructing ahead of a planned splashdown.

June 6, 2024: The fourth orbital flight achieved a full ascent burn and completed a landing burn, concluding with a gentle splashdown in the Gulf of Mexico.

Oct. 13, 2024: The fifth orbital flight marked the first successful booster recovery, with the booster returning to the launch tower. The flight completed its mission with no engine failures and ended in a planned splashdown in the Indian Ocean.

Nov. 19, 2024: During the sixth orbital test, the booster latched onto the catch tower but had to divert for a splashdown in the Gulf of Mexico. The ship ignited one of its six engines in space, successfully reentered the atmosphere, and splashed down in the Indian Ocean.

Starship during its sixth test, taking off from the launch pad.

Jan. 16, 2025: The seventh orbital test launched successfully with all six engines ignited, but a fire eight minutes in caused the rocket to explode.

March 6, 2025: The ship lost several engines during ascent, leading to a loss of altitude control and communication. It diverted into a controlled area to prevent debris from falling into public spaces.

May 27, 2025: The ninth orbital test flight marked the first reuse of a Super Heavy booster. However, the booster exploded unexpectedly, and the ship lost an engine due to a fuel leak. After abandoning its payload deployment attempt, Starship exploded over the Indian Ocean when it failed to properly reposition for reentry.

]]> 1561445
 Sam Altman’s Startup Portfolio: 14 Companies Backed by the OpenAI CEO https://observer.com/2025/06/sam-altman-startup-investments/ Wed, 25 Jun 2025 19:48:28 +0000 https://observer.com/?p=1560722

The overnight success of ChatGPT in late 2022 made Sam Altman, the CEO of OpenAI, the public face of A.I. But a lesser-known aspect of Altman’s career is his long-standing role as a prolific angel investor in early-stage tech startups. Before co-founding OpenAI with Elon Musk in 2015, Altman spent eight years leading the startup incubator Y Combinator from 2011 to 2019, during which he oversaw 280 investments across a wide range of startups.

Altman continued backing many of these companies with his own wealth after departing Y Combinator. As of June 2024, he had invested in nearly 400 companies, according to an analysis of company filings by The Wall Street Journal.

Although OpenAI is currently valued at a staggering $300 billion, Altman has stated he holds no equity in the company and receives only a modest annual salary of about $76,000. This makes it difficult to determine his overall net worth. Forbes estimates the value of Altman’s equity stakes in the companies he has backed to be around $2 billion. According to the Wall Street Journal, he finances many of these investments with loans from JPMorgan Chase.

Here are 14 Altman-backed companies that are valued at over $100 million:

Reddit: social media

  • Founded in: 2005
  • Market cap: $27 billion
  • Altman’s first investment: 2014
  • Altman’s role: former board member

Under Altman’s leadership, Y Combinator became a significant early backer of Reddit. In 2014, Altman led Reddit’s $50 million Series B funding round that valued Reddit at half a billion dollars. Y Combinator continued its support by participating in the company’s $200 million Series C round in July 2017, which raised Reddit’s valuation to $1.8 billion.

After leaving Y Combinator, Altman personally invested $50 million in Reddit’s Series E round in 2021, pushing its valuation to $10 billion. Reddit went public in March 2024. Since then, its market value has climbed to nearly $27 billion. Altman served on Reddit’s board from 2014 until January 2022. The company was originally founded in 2005 by Steve Huffman and Alexis Ohanian.

Neuralink: brain-computer interface

  • Founded in: 2016
  • Valuation: $9 billion
  • Altman’s first investment: 2021
  • Altman’s role: investor

Altman joined as an investor in Elon Musk’s brain implant startup Neuralink in July 2021, participating in the company’s $205 million Series C funding round. Neuralink is developing a wireless implantable device designed to connect the human brain directly to computers. The startup was most recently valued at $9 billion following a Series E round in May 2024.

Helion Energy: nuclear fusion energy

  • Founded in: 2013
  • Valuation: $5.4 billion
  • Altman’s first investment: 2015
  • Altman’s role: investor

Helion Energy is developing what it hopes will be the world’s first fusion power plant by 2028. The company has become a cornerstone of Altman’s investment portfolio. In 2021, Altman invested $375 million in Helion’s Series E round, his largest personal investment to date, when the company was valued at $2.5 billion. In January 2024, Altman and a group of investors invested an additional $425 million in a Series F round, bringing Helion’s valuation to $5.4 billion. David Kirtley, Helion’s co-founder and CEO, told GeekWire that Altman has remained deeply involved in the company’s “hyper growth,” pushing it to move faster and test more aggressively.

Coalition: insurance and cybersecurity 

  • Founded in: 2017
  • Valuation: $5 billion
  • Altman’s first investment: 2018
  • Altman’s role: investor

Coalition, a San Francisco-based cybersecurity insurance provider, offers tools and policies to help companies defend against cyber threats. Altman participated in its $10 million seed round in 2018. The company, founded in 2017 by Joshua Motta and John Hering, reached a $5 billion valuation after its Series F round in 2022.

Asana: productivity management

  • Founded in: 2008
  • Valuation: $3.37 billion
  • Altman’s first investment: 2016
  • Altman’s role: investor

Asana, a work management platform designed to help teams organize and track tasks, also counts Altman as a major early backer. He led the company’s $50 million Series C round in March 2016 and later participated in its $75 million Series D in January 2018. Asana was founded by Dustin Moskovitz, one of Facebook’s co-founders.

Wave Mobile Money: fintech

  • Founded in: 2018
  • Valuation: $1.7 billion
  • Altman’s first investment: 2021
  • Altman’s role: investor

Wave Mobile Money is a fintech startup focused on expanding access to financial services across Africa through mobile apps for money transfers and borrowing. In September 2021, Altman participated in the company’s $200 million Series A round, which brought its valuation to $1.7 billion. Wave was founded by Drew Durbin and Lincoln Quirk, who previously launched the remittance startup Sendwave before selling it to WorldRemit.

Patreon: content creation

  • Founded in: 2013
  • Valuation: $1.2 billion
  • Altman’s first investment: 2014
  • Altman’s role: investor

Patreon, a platform that enables creators and artists to offer subscriptions and sell digital products directly to fans, also attracted early backing from Altman. In 2014, he and a group of investors raised $15 million in Patreon’s Series A round. The platform’s valuation peaked at $4 billion in 2021 before dropping 70 percent to around $1.2 billion. Patreon was co-founded in May 2013 by Jack Conte and Sam Yam. Notably, Yam previously worked with Altman on the social networking app Loopt, which Altman co-founded with Nick Sivo in 2005.

Hermeus: supersonic aviation

  • Founded in: 2018
  • Valuation: $538 million
  • Altman’s first investment: 2022
  • Altman’s role: investor

Hermeus is a defense technology company aiming to develop the world’s fastest supersonic jets. Altman was a lead investor in the company’s $100 million Series B round in March 2022. Following a subsequent funding round in 2024, Hermeus reached a valuation of $538 million, according to Forge Global.

Rescale: cloud software

  • Founded in: 2011
  • Valuation: between $500 million and $1 billion
  • Altman’s first investment: 2012
  • Altman’s role: investor

Rescale is a cloud platform that helps engineers and scientists in fields like aerospace and energy build and run custom applications. Altman has invested in the company five times since its seed round in 2012. He later participated in a $32 million Series B round in 2018, a $55 million Series C in November 2021 and most recently, a $115 million Series D round in April 2024. Following the latest funding, Rescale’s valuation is estimated to be between $500 million and $1 billion.

Meter: internet infrastructure

  • Founded in: 2015
  • Valuation: $365 million
  • Altman’s first investment: 2015
  • Altman’s role: investor

Meter provides companies with reliable network infrastructure by integrating hardware, software and operational support. Altman has invested in Meter three times. He led the company’s $4 million seed round in December 2015 and participated in a $38 million Series B round in May 2022. He later co-led another $35 million Series B round alongside Lachy Groom, a solo tech investor and former Stripe executive. That round brought Meter’s valuation to $356 million.

Alt: sports card trading

  • Founded in: 2020
  • Valuation: $325 million
  • Altman’s first investment: 2021
  • Altman’s role: investor

Alt is an alternative asset platform that lets users trade and store sports cards. Altman participated in the company’s $75 million Series B round in November 2021, which valued the startup at $325 million.

Oklo: nuclear energy

  • Founded in: 2013
  • Valuation: $300 million
  • Altman’s first investment: 2014
  • Altman’s role: former chair

Oklo is another nuclear energy startup currently building a commercial power plant in Idaho, designed to operate for up to 10 years without refueling. It was one of the earliest companies backed by Altman during his time at Y Combinator, where he invested $120,000 in its 2014 seed round. A Series B round in 2021 brought Oklo’s valuation to $300 million. In May 2024, the company raised over $300 million by going public through a reverse merger with AltC Acquisition Corp, a SPAC backed by Altman. He stepped down as Oklo’s chair in April to focus on potential partnerships between the company and OpenAI. Oklo was founded in 2013 by Caroline Cochran and Jacob DeWitte.

Humane: software and hardware

  • Founded in: 2018
  • Valuation: $116 million
  • Altman’s first investment: 2020
  • Altman’s role: investor

Humane developed the A.I. Pin, a wearable virtual assistant. Altman invested in the company three times: leading its $30 million Series A in 2020 and joining its $100 million Series B and C rounds in 2021 and 2023. In February 2024, Humane sold all assets to HP for $116 million, ending A.I. Pin sales. Co-founder and former CEO Bethany Bongiorno now serves as a senior vice president at HP.

Apex: cybersecurity

  • Founded in: 2023
  • Valuation: $105 million
  • Altman’s first investment: 2024
  • Altman’s role: investor

Apex is an Israeli cybersecurity startup helping companies mitigate A.I. risks. Altman joined a group of investors in a $7 million seed round in 2024. In May, the company was acquired by Tenable at a $105 million valuation. Founders Matan Derman and Tomer Avni told Globes they continue to consult with Altman.

]]> 1560722
 From Snoo to Subreddits: How Reddit’s Look and Features Evolved Over 20 Years https://observer.com/2025/06/reddit-branding-logo-evolution/ Mon, 23 Jun 2025 12:00:09 +0000 https://observer.com/?p=1560676

In the spring of 2005, University of Virginia students Steve Huffman and Alexis Ohanian pitched the business idea of a text message-based food delivery service to the then-nascent startup incubator Y Combinator (YC). The concept failed to win over investors, but YC co-founder Paul Graham saw promise in the duo and encouraged them to develop something that could become the “front page of the internet.” That summer, Huffman and Ohanian turned that idea into Reddit and were admitted into YC’s inaugural startup batch with $12,000 in seed funding.

Fast forward 20 years, Reddit is now a $24.8 billion social media giant boasting 108 million daily active users. Over the past two decades, Reddit has kept its original name and orange alien mascot, but has made subtle branding tweaks to reflect shifting market trends and user tastes.

Here’s how Reddit’s face has changed over the years:

2005-2006: The debut of “Snoo”

A phone screen shows the 2005 reddit logo placed in front of a laptop.

The original Reddit logo was simple, with just a hint of orange in the eyes of its alien mascot, Snoo. The site’s name came from the phrase “I read it,” a nod to its purpose: a place where users could discover, share, and upload new information. Snoo—originally named “S’new,” short for “What’s new?”—was meant to embody the spirit of exploration across Reddit’s many communities.

Huffman coded the site in just three weeks, while Ohanian handled pretty much everything else, including designing Snoo. Initially, the site was so empty that Huffman and Ohanian decided to create hundreds of fake accounts to simulate user activity.

Fortunately, the site quickly became a hit, attracting 70,000 daily visitors in its first year, Huffman and Ohanian told TechCrunch in a 2006 interview. Later that year, they sold the company to Condé Nast for $10 million. In 2009, both founders stepped away from their leadership roles to pursue new ventures.

2007-2016: Quiet improvements under the surface

During Condé Nast’s ownership from 2006 to 2011, Reddit saw no major rebranding or integration with its parent company. But things changed when Reddit became an independent subsidiary of Advance Publications, Condé Nast’s parent company. The move gave Reddit more operational freedom and brought in a new CEO: Yishan Wong, a former PayPal engineer.

New features rolled out during and after this period reshaped how users interacted on the platform and helped Reddit grow its user base by the millions.

In 2008, Reddit introduced “subreddits”–individual communities dedicated to specific topics—a feature credited with driving the site’s popularity. That year, Reddit reached 2.6 million users that year, according to SEO solutions firm SEO.AI. In 2013, it launched “multireddits,” which let users view top posts from multiple subreddits in one feed.

Wong stepped down as CEO in 2014 and was succeeded by Ellen Pao, a corporate lawyer known for spotlighting sexism in Silicon Valley. Her tenure lasted just eight months.

Huffman returned as CEO in 2015. He introduced formal content policies and a safety team to oversee moderation. That included a new anti-harassment policy and the replacement of shadowbans with transparent account suspensions.

In 2016, Reddit launched its official mobile app. It also began allowing images and videos to be uploaded directly, eliminating the need for third-party hosting sites. According to SEO.AI, Reddit’s user base grew to 170 million that year.

An example of a user getting permanently banned from participating in a subreddit thread for certain behavior.

2017-2022: More orange and a site overhaul

The 2017 reddit logo on a phone screen.

In 2017, Reddit updated its logo, turning Snoo entirely orange while keeping the Reddit wordmark in black. The following year, the company rolled out its first major website redesign—a shift away from what Huffman once described as a “dystopian Craigslist.” The overhaul introduced new viewing options, streamlined navigation and a more prominent blue button for creating posts.

2023-2025: Going full orange and public

The 2023 Reddit logo in the orange-red color.
Courtesy of Reddit

In 2023, ahead of its IPO, Reddit unveiled a refreshed logo featuring a fully orange, three-dimensional version of Snoo. The update also gave the mascot a wider range of poses, expressions and reactions.

That same year, Reddit released its custom typefaces, Reddit Sans and Reddit Display, on GitHub and Google Fonts to make its “clear, understandable letterforms” freely accessible across the web.

The company went public in March 2024. Recently, it launched a set of A.I. tools to help advertisers better understand which trends and campaigns are gaining traction on the platform.

]]> 1560676