What I’ve Been Up To Lately

Hey folks, short letter today.

Ever since I started this newsletter, one unexpected benefit has been the signaling.

I’m generally a private person, but writing publicly about what I’m thinking and working on has created useful conversations. I’ve met and talked with a lot of interesting people — each with their own perspective on investing, risk, and how capital should be deployed over time.

As part of that, I’ve spent more time around investors who specialize in a fairly niche area: angel investment tax credits, particularly the resale of those credits.

Because of that focus, they naturally see a large volume of startups. And some of those startups are actively looking for funding.

That’s created an opportunity I didn’t fully appreciate at first:
access to private deals, earlier than most people see them, with information advantages that don’t really exist in public markets.

Of course, investing in startups comes with a hard truth attached.

They’re risky. Very risky.
Many — perhaps most — individual angel investments go to zero.

That reality forced me to slow down and ask an important questions.

A question more important than “Is this a good deal?

How do you approach this as a system — one designed to survive losses and still produce strong long-term outcomes?

So next week, I’m going to write about how I’m thinking about angel investing — not as a one-off bet, but as part of a broader, long-term strategy.

More on that soon.

— Dakota

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