Chime IPO, Private Markets & Startup Lawsuits

You got to pick your wedge AI entry point for that 2 or 3 years where there's kind of magic AI premium... but you've got to operate on the assumption that 3 to 5 years from now, the core thing you do is going to be commodified.

• Choose a specific market entry point where AI adds significant value.
• Plan for future commodification by building defensible advantages.
• Continuously innovate to stay ahead in a rapidly evolving market.

I had two portfolio companies recently that got offers to buy them at $500 million... But they didn't step up in the way I would expect.

• Be aware that M&A opportunities may not always meet expectations.
• Timing your exit requires understanding market dynamics and buyer motivations.
• Set realistic valuation expectations based on current market conditions.

If MCP really works... we won't even really need these applications... I might not even, you know, what is HubSpot gonna be worth to me?

• Recognize that AI can enable new solutions that bypass traditional software.
• Prepare to adapt your product offerings in response to AI-driven changes.
• Stay ahead by integrating AI capabilities into your products.

You have to be very granular on what works... you have to be aligned around that. And then you have to be really honest, are you delivering?

• Focus on unique value propositions that set your AI product apart.
• Demonstrate clear metrics of success to investors.
• Continually assess and validate your product's effectiveness in the market.

...the longer you hold the company, the more compounding takes place, the more dispersion takes place, the big get bigger and the shitty ones are crap. It's just math.

• Recognize that extended private growth can amplify exit valuations.
• Plan your fundraising to support longer growth trajectories before exit.
• Understand that compounding benefits companies that can scale effectively over time.

If they have full ratchet... you didn't raise money at $25 billion. You thought you raised money at $25 billion. But in fact, if you go public at 12, you raised money at 12 and you just didn't know it.

• Understand the implications of terms like full ratchet on your fundraising rounds.
• Price protection can safeguard investors but may lead to unexpected dilution.
• Carefully negotiate terms to balance immediate capital needs with future equity considerations.

If you're presented with an exit opportunity at 5 billion... statistically 80% of the time you should sell...

• Analyze market data to understand typical outcomes for companies at your stage.
• Consider the potential for future growth versus current exit value.
• Align the decision with your long-term vision and risk tolerance.

The basic vibe was everyone recognized 20 to 30% of their team's gonna be replaced with AI and they're happy for it.

• Evaluate which roles can be enhanced or replaced by AI to improve productivity.
• Embrace AI as a tool to optimize team performance, not just a cost-cutting measure.
• Prepare your workforce for changes by investing in AI training and development.

Settle everything, especially when you're not in the wrong... It's never worth it for either, like, it's almost never worth it.

• Avoid prolonged legal disputes that can harm your company's focus.
• Even if you're in the right, settling may be the best strategic move.
• Consult legal advice but weigh the business impact over principles.

I think they were smart. They had their S1 on file...Now everything's back. What it just shows is when policy changes that quickly, you really can't triangulate on that.

• Keep your IPO documents updated to be ready when the market turns favorable.
• Market conditions can change rapidly; being prepared allows you to seize opportunities.
• Assess if your company's scale and growth make IPO timing advantageous.