4 Comments

this is a very thoughtful post-and excellent. People underestimate the amount of work and time it takes to create good deal flow let alone great deal flow. This post also ignores ancillary costs like legal. If you don't do the legal right in the beginning, you won't have access to the deal if it gets hot even though you are on the cap table.

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Excellent post. I’ve invest in over 100 startups and 25 funds over the past 2.5 decades. Have gotten some great co-investments through the funds and also allowed to diversify across stages and sectors.

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Love this post. Charlie - how do you feel about Angel groups and syndicates in terms of diversifying deal flow and access? You reference some of the costs (carry, SPV, etc.), do you also see upside and those costs being mitigated by the improved flow. Curious for you to expand on your POV here.

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I think you have to pick exposure to both very carefully. In some geos, angel groups are the only game in town--but in highly competitive geos and sectors, they don't provide the same kind of user experience for founders. They often take too long to make decisions for deals that go quickly. So, they could be good to participate in to make connections, but it doesn't guarantee you flow or exposure to build a portfolio with. Syndicates are interesting. A lot of people have them, and I think it goes back to what I said. If the person is known in the ecosystem and working hard at it with a good chunk of their time, could be good--but it still takes a lot of time to build up flow.

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