AI Startup Playbook For $100M ARR, Grammarly Doubles Down on Classrooms

Bessemer Venture Partners has published its 2025 State of AI report, redefining what "great" looks like for AI startups. The study of 20 high-growth companies shows "Supernovas" averaging $40M ARR in their first commercial year and $125M in year two.

The report contrasts these breakneck players with "Shooting Stars" that reach roughly $3M ARR in year one, quadruple annually, and maintain 60% gross margins. Supernovas run on about 25% gross margins yet post a striking $1.13M ARR per employee, four to five times typical SaaS efficiency.

Bessemer states classic SaaS yardsticks such as T2D3 are obsolete, substituting a "Q2T3" pattern—quadruple, quadruple, triple, triple, triple—to mirror AI's faster cycles. It concludes that the market will be shaped less by a handful of Supernovas and more by hundreds of Shooting Stars that combine rapid growth with sturdier retention.

Researchers led by MIT’s Nataliya Kosmyna asked 54 participants to write essays with either AI assistance, search engines, or no tools. Those using large language models produced fact-dense papers but struggled to recall their own content and claimed less authorship.

EEG scans showed up to 55% lower neural connectivity in the AI group compared with brain-only writers, indicating reduced executive function and attention activity during the task. Essays from AI users were more homogenous, while brain-only writers generated a wider variety of arguments.

The authors conclude that external support tools reshape both task performance and the underlying cognitive architecture. Opinion columnist David Brooks frames the findings as evidence that outsourcing thinking to bots sacrifices genuine learning for speed.

Casanova AI analyzes live dating chat app conversations and offers tailored replies without leaving the app. The software works across all popular dating apps on both Android and iOS.

Casanova AI dissects the intricacies of user chats, ensuring that messages resonate deeply. It's not just about what the user says; it's about expressing it in a way that's both authentic and engaging.

The integrated design removes the need to switch apps. Users can edit, ignore, or regenerate every suggestion, keeping full control of their chats. With over 5,000 reviews, users are increasingly turning to AI to boost their dating success.

Q4 is fast approaching, which means it’s time to start calculating the payoff of this year’s AI investments to get the budget again next year. But measuring AI ROI requires a fundamentally new way of thinking about success – so Section is gathering 11 of the best minds in AI to give you their own winning strategies.

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Five CIO-level leaders from Ordnance Survey, Snowflake, HPE, The AA, and Happy Socks detail how they are embedding AI agents into daily operations. They emphasize clear guidelines, continuous human dialogue, talent development, deliverable audits, and treating AI as a “perfect intern.”

Ordnance Survey runs Microsoft Copilot with strict usage rules, Snowflake demands permission-based data access, and HPE uses agents to multiply senior developers’ output. The AA tracks agent performance like staff, while Happy Socks frames agentic AI as an intern automating discrete workflow tasks.

Across all five cases, AI is viewed as augmenting rather than replacing employees, with governance and auditing ensuring trust. The executives agree that disciplined oversight keeps automation productive without derailing workforce growth.

Grammarly has rolled out a lineup of task-specific AI agents inside its new “AI-native” Docs writing surface. The tools handle everything from estimating grades to scanning for plagiarism and come at no additional cost for Grammarly Free and Pro users.

Students gain an AI grader, reader reactions predictor, proofreader, paraphrase assistant, citation finder, and expert review agent. Educators receive plagiarism and AI detector agents, which are limited to Pro accounts at launch with wider Enterprise and Education access promised later this year.

Head of Grammarly for Education Jenny Maxwell says the agents enhance student work without undermining learning. The company positions the rollout as preparation for a workplace where AI literacy is essential.

Uber. Airbnb. eBay. Venmo. What do they have in common? The early backers for these companies all invested in Pacaso.

Pacaso was started by a former Zillow exec and is disrupting a $1.3 trillion market with breakthrough tech. And it’s been a hit. They’ve made $110M+ in gross profits to date. Now they’re expanding to 10 new international markets. They’ve even reserved their Nasdaq ticker.

Now you can join 10,000+ everyday investors as a Pacaso shareholder. But you can’t wait. This opportunity ends on September 18.