The decision to move from Arc to Dia was less about Arc's limitations and more about the founders' profound conviction that AI was a fundamental platform shift they had to build for from scratch. The pull of the new technology was a stronger motivator than the push from the existing product's challenges.

Redpoint Ventures' Erica Brescia describes a shift in their investment thesis for the AI era. They are now more likely to back young, "high-velocity" founders who "run through walls to win" over those with traditional domain expertise. Sheer speed, storytelling, and determination are becoming more critical selection criteria.

The motivation to start Blue Jay wasn't just market opportunity, but a powerful personal exercise in avoiding future regret. The founder envisioned himself decades from now, knowing he saw the AI freight train coming for his industry but chose not to act. This imagined feeling of "profound regret" created the urgency to change his professional trajectory.

Low-cost AI tools create a new paradigm for entrepreneurship. Instead of the traditional "supervised learning" model where VCs provide a playbook, we see a "reinforcement learning" approach. Countless solo founders act as "agents," rapidly testing ideas without capital, allowing the market to reward what works and disrupting the VC value proposition.

During a fundamental technology shift like the current AI wave, traditional market size analysis is pointless because new markets and behaviors are being created. Investors should de-emphasize TAM and instead bet on founders who have a clear, convicted vision for how the world will change.

While technical founders excel at finding an initial AI product wedge, domain-expert founders may be better positioned for long-term success. Their deep industry knowledge provides an intuitive roadmap for the company's "second act": expanding the product, aligning ecosystem incentives, and building defensibility beyond the initial tool.

In rapidly evolving markets like AI, founders often fall into psychological traps, such as feeling they are too late or that funding has dried up. However, the current environment offers unprecedented organic user demand and technological leverage, making it an ideal time to build if you can ignore the noise.

The hardest transition from entrepreneur to investor is curbing the instinct to solve problems and imagine "what could be." The best venture deals aren't about fixing a company but finding teams already on a trajectory to succeed, then helping change the slope of that success line on the margin.

There's a growing belief in venture that experienced, second-time founders may be at a disadvantage in the AI era. Younger founders who grew up natively with new tools can move faster because they don't have to unlearn established, but now obsolete, ways of working.