Investing/Angel investments

Small checks, close to operators.

Alongside the rest of the firm, we keep a portfolio of angel checks in early-stage companies we know well. We invest small, we invest in operators we've worked with or whose work we've followed closely, and we invest because being close to founders is one of the highest-bandwidth ways to understand what's actually happening at the edge of an industry before it shows up in public-market data.

We're not running a venture fund. Angel investing is adjacent to everything else we do: it gives us exposure to ideas earlier than we'd otherwise have it, it keeps us in the deal flow within our network, and it surfaces the growth-stage companies that mature out of that network.

Early-stage companies Milton Maxwell principals have backed as angels, each with a short thesis on why we invested.

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User: confirm the full list, investment years, and that public listing is acceptable to each company before launch. Theses marked placeholder need a one-to-two-sentence draft from Charlie or Alex.

  • Tribe AI

    Charlie

    Applied-AI consulting and engineering, a network of senior practitioners building AI systems for enterprise. A bet that, in the early innings of AI adoption, the binding constraint for most companies is implementation talent, and the team that aggregates it captures durable demand.

  • Fleetworks

    Charlie

    An AI-native operations platform automating the back office of trucking and freight. Freight brokerage runs on phone calls and manual coordination; applying AI to that workflow is a clear case of cheap, scalable input replacing an expensive manual one.

  • Marathon Fusion

    Charlie, Alex

    Builds tritium fuel-cycle systems, the unglamorous but essential plumbing every fusion power company needs. A picks-and-shovels bet on fusion: it wins if the field advances, without having to pick which reactor design succeeds.

  • Triply

    Charlie
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    Confirm what Triply does, then write a one-to-two-sentence thesis.

  • VGroup Ventures (VClub)

    Charlie, Alex
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    Confirm description and write thesis.

  • PathOn AI

    Charlie, Alex
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    Confirm description and write thesis.

  • SwiftLane

    Charlie, Alex

    Touchless access control and video intercom for buildings. A bet on hardware-plus-software replacing legacy badge/buzzer systems.

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    Confirm and refine thesis.

  • Giga Next (Giga AI)

    Charlie, Alex
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    Confirm description and write thesis.

  • Alex's remaining angel positions

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    Alex has angel-invested in 20+ companies. List the ones acceptable to show publicly, each with a short thesis.