Tech and startups: 20th May 2025

• Work-Bench raised $160M for its Fund IV, focusing on seed-stage enterprise software companies in New York City, targeting AI, cybersecurity, and developer tools.
• Redpoint Ventures secured $650M for its 10th early-stage fund, maintaining its previous fund size despite overall venture capital funding decreases, while DFJ Growth closed a $1.2B flagship fund focusing on AI, robotics, aerospace, and biotech.
• In AI funding news, Cognichip raised $33M to enhance chip design productivity using its Artificial Chip Intelligence model, Moonvalley secured $53M for its advanced AI video generation technology, and Pathos AI closed a substantial $365M investment to enhance its platform processing multimodal oncology data.
• The VC landscape showed positive signals with seven new unicorns emerging in April, including healthcare and data startups, while startups displayed optimism with IPOs and acquisitions, including Chime's IPO filing and Databricks' $1 billion acquisition of Neon.
• Rippling raised $450 million at a $16.8 billion valuation amid accusations of corporate espionage against rival Deel, who denies the claims and counters with its own lawsuit involving secret crypto payments and decoy Slack channels.

How HelloBetter Designed Their Interview Process Against AI Cheating (newsletter.eng-leadership.com, 2025-05-18). HelloBetter revamped its technical interview process to combat AI cheating, focusing on real-world skills with a new structure including pair programming and a questionnaire to align candidate expectations

Interruptions, skip levels, and good handbooks 💡 (refactoring.fm, 2025-05-19). AI tools are misdirected; 53% of developers face daily knowledge gaps, while Carlson's and Illich's laws stress work flow continuity for productivity. Skip-level 1:1s and handbooks are key for effective feedback and team integration

How Jit overcame developer resistance to shift to Cursor (leaddev.com, 2025-05-15). Jit, an Israeli startup, transitioned from JetBrains to the AI-powered coding assistant Cursor, overcoming developer resistance by enhancing automation and productivity through tailored rules and the effective use of AI tools

The future of long-term hiring: the Nintendo way? (aman-agarwal.com, 2025-05-18). Aman Y. Agarwal discusses adopting a membership-based hiring strategy inspired by Nintendo's specialized career tracks, focusing on adaptability, innovation, and problem-solving over traditional job-based criteria in the tech industry

“The Pope was chosen in 2 days. Your remote hire doesn’t need 5 rounds of interviews.” (globalnerdy.com, 2025-05-13). Benedikt Becker's post emphasizes that hiring processes, especially for remote roles, can be streamlined significantly, arguing that five rounds of interviews are unnecessary, akin to the swift choosing of a Pope in two days

Decoding delivery and leading tech teams (madetech.com, 2025-05-19). Sade Onile-Ere shares her transition from software engineer to delivery manager, emphasizing Agile methodologies, strategic project management, people-first leadership, and fostering team dynamics for meaningful project outcomes

How Do You Make a Safe Hiring Decision? (jrothman.com, 2025-05-13). Diverse hiring decisions lead to longer employee retention, improved team collaboration, and better products. Emphasizing varied experiences prevents groupthink and fosters a culture of learning, driving effective software development

When to build an in-house engineering team and when to hire an agency (feed.thoughtbot.com, 2025-05-16). Evaluate when to build an in-house engineering team versus hiring external expertise, considering factors like rapid delivery needs, specialized tools (e.g., Ruby on Rails, Hotwire, Terraform), and the balance of in-house culture with external capabilities

Launching is the Second Hardest Part (dillonshook.com, 2025-05-19). Launching presents significant challenges, including backend monitoring with Honeycomb, API error handling, and navigating Chrome and Firefox extension submissions. Key issues also involved DNS setting, CSP errors, and deployment automation

How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product) (lennysnewsletter.com, 2025-05-15). Dmitry Zlokazov explains Revolut's 'local CEO' model, prioritizing raw intellect over experience, fostering a culture of ownership, and delivering 'wow' products through unique organizational approaches and rigorous product quality practices

O(n) vs. O(n^2) Startups (rohan.ga, 2025-05-14). Explore the distinction between $O(n)$ and $O(n^2)$ startups, focusing on growth rates, funding, talent acquisition, and operational dynamics, emphasizing how these factors impact long-term success and founder earnings

Why Romanticizing PLG is Dangerous (mostlymetrics.com, 2025-05-17). Romanticizing Product-Led Growth (PLG) as a sales-free strategy is misguided; significant challenges include capped revenue potential, hidden credit card fees, and the necessity of a dedicated sales team for growth beyond $25M ARR

Waste in Software (belowwaterlevel.com, 2025-05-16). Research indicates that 75% of software products fail, while 80% of developed features go unused, often due to misguided priorities and inefficient methods impacting ROI and stakeholder relations

Why VC and software have PE envy (notes.mtb.xyz, 2025-05-13). VCs are increasingly adopting private equity strategies, moving beyond traditional minority investments to enhance returns through vertical software applications, AI, and tools like embedded fintech and marketing, while navigating a saturated market

Podcast: Inside the Platform Powering +$125B in Private Capital, with AngelList CEO Avlok Kohli (lex.substack.com, 2025-05-19). AngelList CEO Avlok Kohli discusses the platform's evolution from a startup connector to a comprehensive fintech entity, revealing innovations like Rolling Funds, syndicates, and AI applications in the private capital markets

[GE] What I learned working at a high-growth crypto startup (aletteraday.substack.com, 2025-05-16). Parth Chopra shares insights from scaling OpenSea, emphasizing adaptability, the importance of specific knowledge, and the role of product usage in startup success within the rapidly evolving crypto industry

Microsoft CPO: If you aren’t prototyping with AI you’re doing it wrong | Aparna Chennapragada (lennysnewsletter.com, 2025-05-18). Aparna Chennapragada emphasizes AI prototyping's importance for PMs, discussing concepts like prompt sets, natural language experience (NLX), and the evolving role of PMs amidst rapid AI adoption and development frameworks like Microsoft's Frontier

Quoting Katie Parrott (blog.lmorchard.com, 2025-05-14). Katie Parrott discusses 'vibe coding', AI tools, and democratizing software development for non-engineers, emphasizing the importance of empowering writers, designers, and domain experts to solve specific problems

Applying Stephen King’s Rules to Software Development: Crafting Digital Experiences (aman-agarwal.com, 2025-05-13). Aman Y. Agarwal draws parallels between Stephen King’s writing process and software development, emphasizing the importance of crafting engaging digital experiences rather than mere tools, using concepts like storyboarding and user participation

Anchor between two positioning from Tinybird (markepear.dev, 2025-05-17). Exploring developer marketing with Tinybird's effective anchoring strategy, leveraging familiar tools like ClickHouse, Supabase, and Postgres to convey impactful messaging tailored for a developer audience

How I Approach Feature Requests (jakeworth.com, 2025-05-14). Feature requests are essential in software development; they require careful handling through empathy, documentation, and management decisions while employing tools like the 'Five Whys' technique to clarify customer needs

The New Creator Economy: The 'Vibe Revolution' Democratizing Software Creation (blog.jordanurbs.com, 2025-05-16). The 'vibe revolution' in software creation empowers everyone, from seasoned coders with AI tools like Cursor to non-coders leveraging YouTube and git to build apps efficiently and cost-effectively, democratizing creation

Purchasing White Elephants (funcall.blogspot.com, 2025-05-13). A software engineer warns against the pitfalls of custom software projects, emphasizing the cost and inefficiency compared to existing solutions, while leveraging LLMs to provide management with project estimates and breakdowns

Joe Marshall: Purchasing White Elephants (funcall.blogspot.com, 2025-05-13). Joe Marshall discusses the challenges of custom software projects, advocating for existing solutions while leveraging LLMs for project planning estimates, highlighting cost and time discrepancies in management's expectations

Developer Tooling is a Lousy Business (avdi.codes, 2025-05-15). Building a developer tools startup is challenging due to high user expectations and low prices, emphasizing the importance of offering real value to customers, as noted by Slava Akhmechet and Avdi Grimm

Unapologetically Technical Episode 20 – Shane Murray (jesse-anderson.com, 2025-05-13). Shane Murray, Field CTO at Monte Carlo Data, discusses digital transformation, data observability, the hub-and-spoke model for team management, and innovations such as AI-powered troubleshooting agents during an interview with Jesse Anderson

My Engineering Craft Regressed (lemmy.ml, 2025-05-15). An engineer reflects on the regression of their programming skills amid job market challenges, transitioning from open source contributions to focusing on Leetcode for better financial opportunities, despite losing passion for coding

Week 20, 2025 - Consolidate and Move (peterszasz.com, 2025-05-16). Péter Szász discusses upcoming Hungarian tech conference engagements, site enhancements, and insights on AI Security, team dynamics, document feedback techniques, leadership mistakes, and significant operational shifts like 37Signals’ migration from AWS to a more cost-effective solution

What's next for Supervised (supervised.news, 2025-05-16). Matthew Lynley discusses ending his full-time role with Supervised due to a back injury, plans to write for free about the modern data stack, and the recent consolidation in the tech industry

Am I Part of the Cure or the Disease? (itfossil.com, 2025-05-16). Reflections on the software industry, grappling with scope creep, ineffective tools, and burnout while developing an Excel-like data entry experience illuminated the feeling of being part of the disease rather than the cure

Pros and Cons of Going from Individual Contributor Back to Manager (code.dblock.org, 2025-05-18). Daniel Doubrovkine shares his journey from individual contributor to manager, discussing the stresses of management, organizational dysfunctions, and his work on the open-source tool Roast within Shopify's Developer Productivity organization

The Company Closed, I'm Unemployed Again (en.smallyu.net, 2025-05-15). Backend developer reflects on a month at Tantin Chain, where they built a transaction aggregation service for crypto wallets before the company unexpectedly laid off all employees on the day of the planned release

Whether AI is a bubble or revolution, how does software survive? (stackoverflow.blog, 2025-05-15). AI investment surpasses $100 billion, disrupting software through acquisitions, innovation, and shifts in development as found in tools like the Crunchbase AI-powered Prediction Engine and Model Context Protocol

Practical Considerations for Advancing AI Collaboration in Software Development (blog.vanillajava.blog, 2025-05-15). Explores AI collaboration in software development, emphasizing tools like GitHub Copilot, Ai for enhancing documentation, and engaging in complex tasks to evolve software engineering practices and challenge AI's boundaries

What Does AI Do to The Craft of Software and Data Engineering? (joereis.substack.com, 2025-05-17). Joe Reis explores how AI influences software and data engineering craftsmanship, emphasizing the importance of depth, expertise, and the value of high-quality content amidst the rise of AI-generated materials and tools like ChatGPT

Lessons from the AI Trenches: Building, Breaking, and Learning Weekly (novice.media, 2025-05-17). Exploring AI's potential, insights from building tools like tinylandingpage.com and Scoutzie, and adopting strategies to effectively manage AI's complexities showcase the rapid evolution in product development and user engagement

When AI Injects Liquidity Into Skills: What Happens to the Middle Tier? (unmitigatedrisk.com, 2025-05-17). AI tools like GitHub Copilot and ChatGPT transform the software skill market by increasing accessibility, shifting the value from mid-tier developers to juniors and seniors, creating both challenges and opportunities in team structures

Things I Currently Believe About AI and Tech Employment (skamille.medium.com/things-i-currently-believe-about-ai-and-tech-employment-3e712df1dc51, 2025-05-13). Camille Fournier explores the impact of AI, particularly low-code tools, on tech employment, advocating for the continued necessity of junior engineers while emphasizing specialization in engineering careers amidst evolving demands

What we in the open world are messing up in trying to compete with big tech (berthub.eu, 2025-05-18). Open tech must prioritize user experience and offer services prominently to compete with big tech, avoiding pitfalls like unclear sign-up processes and unnecessary tracking, while integrating relevant features to be genuinely useful

Ditching Obsidian and building my own (amberwilliams.io, 2025-05-18). Amber Williams details her transition from commercial PKM tools like Obsidian to building a self-hosted solution using Directus, focusing on privacy, security, and long-term sustainability for personal knowledge management

Build Your Own Gumball (tedium.co, 2025-05-16). Gumroad's shift to an MIT license enhances user control and flexibility, promoting open-source collaboration while navigating self-hosting complexities with tools like Docker, Redis, and MySQL for a more technical user base

Dev Therapy, part 4: Tending the narrative gardens (melatonin.dev, 2025-05-16). Solo developers face unique challenges in maintaining narratives while working on long-term projects. The author reflects on balancing personal identity, innovation, and the pressure of market expectations in building a software synthesizer

An app of one's own (contraption.co, 2025-05-16). Philip I. Thomas discusses building a personal app, 'Junk Drawer,' using APIs and AI for life automation, showcasing features like indexing Gmail and automating accounting, highlighting the potential of vibe coding

194 / What the Comfort Class Doesn’t Get (arne.me, 2025-05-18). Arne Bahlo discusses persuasion techniques in engineering, shares insights on childhood programming preferences, and highlights new scheduling algorithms impacting user feedback and content interaction

A Case for Pragmatic Engineering Leadership (cacm.acm.org, 2025-05-13). Pragmatic engineering leadership emphasizes validating user needs over trendy technologies, prioritizing risk management and team well-being, as demonstrated by case studies from Digg and Zillow, highlighting the importance of thoughtful decision-making

Software_Engineering_Practices = Morals+Theology (shape-of-code.com, 2025-05-18). Software engineering intersects with moral theology, emphasizing teamwork, moral rules, and methodologies like Agile and Waterfall, while questioning its classification as a true engineering discipline due to human variability

Approximation (exple.tive.org, 2025-05-14). The shift towards stochastic approximation in tech reflects a changing perception of value, emphasizing computational tools over human talent, questioning the essence of innovation and data utility in AI and machine learning