The Big Picture: The macro is challenging, and this too shall pass. Redwood has built a competitive moat, positioning itself to capitalize on two long-term, undeniable trends: electrification and onshoring. While the EV market has recently swung in favor of…

We’re investing in OCN via Deepwater Venture Fund II based on the potential for dramatic growth as the company enables gig workers to flourish throughout the Americas.  We believe OCN will become a large and diversified financial services platform, initially…

Bezos wrote, “Given a ten percent chance of a 100 times payoff, you should take that bet every time.” That’s venture in a nutshell, although you’re looking at more like a 1-2% chance of 100x rather than 10%. If there’s…

Deepwater is an investor in xAI's Series B round. Despite the lofty $24B valuation for what is effectively a startup, we are confident in the investment for four reasons: 1. Foundation Models will power the world, 2. Model competence is a competitive advantage, 3. Unique training data and 4. Elon Musk. In the end, we believe xAI has the potential to be one of the twenty most important tech companies.

Would You Die for Your Life’s Work? There’s a 500-year-old chapel outside of Edinburgh in Scotland that’s rumored to be the burial site of the Knights Templar and the Holy Grail. Dan Brown featured Rosslyn Chapel in his 80-million-copy book, The…

What’s my company worth? What makes you special? The two questions are inextricably intertwined. The more special your value add, the more your company’s potential value. It’s true at the individual level too. The value of your time or effort…

We’re investing in Digs via Deepwater Venture Fund II based on the fact that most people’s largest asset has been left behind while the rest of the world has been digitized. Software is eating the world, but it hasn’t yet gobbled up…