Technology
Anagram takes a gamified approach to employee cybersecurity training

Despite employers requiring their employees to complete yearly cybersecurity training courses, human-driven cybersecurity breaches still happen. The problem could even get substantially worse as generative AI increases the scale and personalization of social engineering campaigns.
Anagram, formerly known as Cipher, is taking a new approach to employee cybersecurity training that the company hopes can keep up with the changing nature of these campaigns.
The New York-based company built a platform that contains hands-on security training for enterprises. The training includes bite-sized videos and personalized interactive puzzles to teach employees how to spot suspicious emails and communication. These trainings are designed to be more frequent, and more engaging, than the current standard of a once yearly, lengthy training session.
Harley Sugarman, the co-founder and CEO of Anagram, told TechCrunch that these activities include tasks like having employees create their own personalized phishing emails to teach them how to spot sophisticated campaigns against themselves.
“We took very little, in fact, basically no inspiration from the existing stuff out there,” Sugarman said regarding existing cybersecurity training. “What we really took was lessons from TikTok, and lessons from Duolingo and Khan Academy. We looked at these platforms that have done really, really well engaging and changing user behavior outside of the security space and we said, OK, how can we apply those lessons within security?”
Building gamified cybersecurity training wasn’t what Sugarman, a former VC at Bloomberg Beta, set out to do when he initially launched the company.
Sugarman’s first idea was a way to take the cybersecurity industry’s “capture the flag” training approach to upskill enterprise cybersecurity employees. This training approach involves building software with vulnerabilities and having security researchers go into the software to find the bugs and figure out how to write code without falling into the same traps.
That company launched as Cipher in 2022 and gained some traction. But chief information science officers (CISOs) started telling Sugarman that their businesses actually had a bigger security issue they were looking to tackle: their non-security employees. Sugarman said that CISOs describe their employees as their weakest cybersecurity link.
“What sort of surprised me was actually just the amount of hopelessness that I heard in their voices,” Sugarman said. “This was an unsolvable problem for them.”
Cipher then pivoted in January 2024 to focus on solving that problem. Now the startup is changing its name to Anagram to reflect its new focus and is in the process of winding down its original product. Anagram has seen strong growth since its pivot and landed customers including Thomson Reuters, MassMutual, and Disney, among others.
Anagram recently raised a $10 million Series A round led by Madrona with participation from General Catalyst, Bloomberg Beta, and Operator Partners, among others. The company plans to use the funds to build out its sales team and continue to improve the product. Sugarman said that so far they have been able to bring company’s phishing failure rates from 20% down to 6%, but he thinks they can continue to get closer to zero.
Sugarman said Anagram launched its product at a really interesting inflection point for the cybersecurity industry. With the advancements of generative AI, social engineering campaigns can be more personalized than ever, which will make it increasingly hard for people to tell what is real and what isn’t.
“I think the sort of side effect of that is that traditional email security platforms are actually going to have a much harder time detecting these AI-generated phishes,” Sugerman said. “That ability to generate and randomize is just so strong, and it’s really, really difficult, from an engineering perspective, to defend against that.”
Anagram is also working to develop an AI agent that will sit in enterprise employees’ emails and will be trained to flag potential cybersecurity slip-ups before they happen. Sugarman said the agent would do things like pop up to ask someone if they really want to send their credit card information over email and other similar safeguards.
In the meantime, Anagram hopes its puzzles and TikTok-like training videos will continue to move the needle.
“Humans are not dumb, we built skyscrapers we can do space travel,” Sugarman said. “We can figure out how to not click on a suspicious link in an email.”
Technology
Pintarnya raises $16.7M to power jobs and financial services in Indonesia

Pintarnya, an Indonesian employment platform that goes beyond job matching by offering financial services along with full-time and side-gig opportunities, said it has raised a $16.7 million Series A round.
The funding was led by Square Peg with participation from existing investors Vertex Venture Southeast Asia & India and East Ventures.
Ghirish Pokardas, Nelly Nurmalasari, and Henry Hendrawan founded Pintarnya in 2022 to tackle two of the biggest challenges Indonesians face daily: earning enough and borrowing responsibly.
“Traditionally, mass workers in Indonesia find jobs offline through job fairs or word of mouth, with employers buried in paper applications and candidates rarely hearing back. For borrowing, their options are often limited to family/friend or predatory lenders with harsh collection practices,” Henry Hendrawan, co-founder of Pintarnya, told TechCrunch. “We digitize job matching with AI to make hiring faster and we provide workers with safer, healthier lending options — designed around what they can reasonably afford, rather than pushing them deeper into debt.”
Around 59% of Indonesia’s 150 million workforce is employed in the informal sector, highlighting the difficulties these workers encounter in accessing formal financial services because they lack verifiable income and official employment documentation.
Pintarnya tackles this challenge by partnering with asset-backed lenders to offer secured loans, using collateral such as gold, electronics, or vehicles, Hendrawan added.
Since its seed funding in 2022, the platform currently serves over 10 million job seeker users and 40,000 employers nationwide. Its revenue has increased almost fivefold year-over-year and expects to reach break-even by the end of the year, Hendrawn noted. Pintarnya primarily serves users aged 21 to 40, most of whom have a high school education or a diploma below university level. The startup aims to focus on this underserved segment, given the large population of blue-collar and informal workers in Indonesia.
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“Through the journey of building employment services, we discovered that our users needed more than just jobs — they needed access to financial services that traditional banks couldn’t provide,” said Hendrawan. “We digitize job matching with AI to make hiring faster and we provide workers with safer, healthier lending options — designed around what they can reasonably afford, rather than pushing them deeper into debt.”

While Indonesia already has job platforms like JobStreet, Kalibrr, and Glints, these primarily cater to white-collar roles, which represent only a small portion of the workforce, according to Hendrawan. Pintarnya’s platform is designed specifically for blue-collar workers, offering tailored experiences such as quick-apply options for walk-in interviews, affordable e-learning on relevant skills, in-app opportunities for supplemental income, and seamless connections to financial services like loans.
The same trend is evident in Indonesia’s fintech sector, which similarly caters to white-collar or upper-middle-class consumers. Conventional credit scoring models for loans, which rely on steady monthly income and bank account activity, often leave blue-collar workers overlooked by existing fintech providers, Hendrawan explained.
When asked about which fintech services are most in demand, Hendrawan mentioned, “Given their employment status, lending is the most in-demand financial service for Pintarnya’s users today. We are planning to ‘graduate’ them to micro-savings and investments down the road through innovative products with our partners.”
The new funding will enable Pintarnya to strengthen its platform technology and broaden its financial service offerings through strategic partnerships. With most Indonesian workers employed in blue-collar and informal sectors, the co-founders see substantial growth opportunities in the local market. Leveraging their extensive experience in managing businesses across Southeast Asia, they are also open to exploring regional expansion when the timing is right.
“Our vision is for Pintarnya to be the everyday companion that empowers Indonesians to not only make ends meet today, but also plan, grow, and upgrade their lives tomorrow … In five years, we see Pintarnya as the go-to super app for Indonesia’s workers, not just for earning income, but as a trusted partner throughout their life journey,” Hendrawan said. “We want to be the first stop when someone is looking for work, a place that helps them upgrade their skills, and a reliable guide as they make financial decisions.”
Technology
OpenAI warns against SPVs and other ‘unauthorized’ investments

In a new blog post, OpenAI warns against “unauthorized opportunities to gain exposure to OpenAI through a variety of means,” including special purpose vehicles, known as SPVs.
“We urge you to be careful if you are contacted by a firm that purports to have access to OpenAI, including through the sale of an SPV interest with exposure to OpenAI equity,” the company writes. The blog post acknowledges that “not every offer of OpenAI equity […] is problematic” but says firms may be “attempting to circumvent our transfer restrictions.”
“If so, the sale will not be recognized and carry no economic value to you,” OpenAI says.
Investors have increasingly used SPVs (which pool money for one-off investments) as a way to buy into hot AI startups, prompting other VCs to criticize them as a vehicle for “tourist chumps.”
Business Insider reports that OpenAI isn’t the only major AI company looking to crack down on SPVs, with Anthropic reportedly telling Menlo Ventures it must use its own capital, not an SPV, to invest in an upcoming round.
Technology
Meta partners with Midjourney on AI image and video models

Meta is partnering with Midjourney to license the startup’s AI image and video generation technology, Meta Chief AI Officer Alexandr Wang announced Friday in a post on Threads. Wang says Meta’s research teams will collaborate with Midjourney to bring its technology into future AI models and products.
“To ensure Meta is able to deliver the best possible products for people it will require taking an all-of-the-above approach,” Wang said. “This means world-class talent, ambitious compute roadmap, and working with the best players across the industry.”
The Midjourney partnership could help Meta develop products that compete with industry-leading AI image and video models, such as OpenAI’s Sora, Black Forest Lab’s Flux, and Google’s Veo. Last year, Meta rolled out its own AI image generation tool, Imagine, into several of its products, including Facebook, Instagram, and Messenger. Meta also has an AI video generation tool, Movie Gen, that allows users to create videos from prompts.
The licensing agreement with Midjourney marks Meta’s latest deal to get ahead in the AI race. Earlier this year, CEO Mark Zuckerberg went on a hiring spree for AI talent, offering some researchers compensation packages worth upwards of $100 million. The social media giant also invested $14 billion in Scale AI, and acquired the AI voice startup Play AI.
Meta has held talks with several other leading AI labs about other acquisitions, and Zuckerberg even spoke with Elon Musk about joining his $97 billion takeover bid of OpenAI (Meta ultimately did not join the offer, and OpenAI denied Musk’s bid).
While the terms of Meta’s deal with Midjourney remain unknown, the startup’s CEO, David Holz, said in a post on X that his company remains independent with no investors; Midjourney is one of the few leading AI model developers that has never taken on outside funding. At one point, Meta talked with Midjourney about acquiring the startup, according to Upstarts Media.
Midjourney was founded in 2022 and quickly became a leader in the AI image generation space for its realistic, unique style. By 2023, the startup was reportedly on pace to generate $200 million in revenue. The startup sells subscriptions starting at $10 per month. It offers pricier tiers, which offer more AI image generations, that cost as much as $120 per month. In June, the startup released its first AI video model, V1.
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Meta’s partnership with Midjourney comes just two months after the startup was sued by Disney and Universal, alleging that it trained AI image models on copyrighted works. Several AI model developers — including Meta — face similar allegations from copyright holders, however, recent court cases pertaining to AI training data have sided with tech companies.
Got a sensitive tip or confidential documents? We’re reporting on the inner workings of the AI industry — from the companies shaping its future to the people impacted by their decisions. Reach out to Rebecca Bellan at [email protected] and Maxwell Zeff at [email protected]. For secure communication, you can contact us via Signal at @rebeccabellan.491 and @mzeff.88.
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