Will Robbins

Who they are

Will Robbins is a software engineer and investor at Contrary — joined the fund at ~$2M AUM in 2017 and built Dinkbase, a pickleball court and tournament finder, as a side project.

Person

Will Robbins started early: he built an app that reached 100,000+ users by age 17, somewhere in the 2011–2017 window — a signal that he was writing production software long before most people finish high school. His background is in machine learning and infrastructure, and he moved through tech companies in that vein before landing at Contrary in 2017, when the fund had roughly $2M under management. He's been there through its growth to $250M+ AUM across 4 funds, with the portfolio generating $10B+ in market cap from seed investments — a run that spans enterprise software, fintech, and healthtech bets including DOSS ($18M Series A, April 2025), Moment ($36M Series B in fixed income tech), and DualEntry ($90M Series A, which he framed publicly as an ERP disruption signal). Possibly — he currently holds an engineering role at Bigeye, a data observability company, in parallel with his Contrary work. He writes on LinkedIn about enterprise software, ERP disruption, AI, fintech, and healthtech, and keeps a site at notes.willrobbins.org covering data observability, data reliability engineering, and data quality — he's also spoken at DRE-Con. Side projects include Dinkbase, the pickleball court and tournament finder, and on the personal side he makes music with hardware synthesizers, drum machines, and samplers. The through-line is someone who moves between building and backing — an engineer who uses a technical lens to pick investments and a side-project habit to stay sharp.

Network

No direct relationship edges are available from the data. His public endorsements point to portfolio founders at DOSS, Moment, Carda Health (partnered with Humana), and DualEntry as the closest named connections — all Contrary portfolio companies he has championed publicly.

How they likely show up

  • Built an app to 100,000+ users as a teenager → he self-directs early and doesn't wait for institutional permission to ship.
  • Joined Contrary at ~$2M AUM and stayed through $250M+ → comfortable with long arcs and building conviction before the crowd arrives.
  • Writes publicly on LinkedIn about ERP disruption, fintech, and healthtech while also maintaining a technical Substack on data reliability → operates across both the investor and engineer registers, not just one.
  • Possibly holds an engineering role at Bigeye alongside Contrary work → high agency, likely runs parallel tracks rather than sequencing them.
  • Side projects include Dinkbase (a functional product) and hardware synthesizer music → ships things for their own sake, not just for résumé signal.
  • Spoke at DRE-Con on data reliability engineering → willing to go deep in public on technical topics, not just high-level takes.

Conversation tips

  • → Reference a specific portfolio bet — DOSS, Moment, or DualEntry — and ask what the underlying thesis was; he's gone on record framing each one and will engage with the reasoning.
  • → His framing of DualEntry as an 'ERP disruption signal' is a stated view, not just a deal announcement — ask him where he thinks the next ERP unlock is and you'll get a real answer.
  • → If the conversation touches data tooling, he has a practitioner's view from Bigeye and DRE-Con, not just an investor's view — treat him as an engineer first.
  • → Dinkbase is a real product he built and shipped; it's a good temperature check on how he thinks about consumer utility vs. enterprise bets.
  • → Don't skip the early app story — 100k users at 17 is formative context and he's likely proud of it.

Toolbox

Openers

  • Open on the DualEntry $90M Series A — he publicly framed it as an ERP disruption signal, which is a specific and contrarian thesis worth unpacking given how entrenched SAP and Oracle are.
  • Mention Dinkbase — he built a pickleball court and tournament finder as a side project, which is a pointed choice for someone who also backs enterprise software; it says something about how he thinks about product and distribution.
  • Reference his notes.willrobbins.org writing on data reliability engineering — he spoke at DRE-Con and writes technically, which is unusual for someone also doing seed-stage investing.

Discovery questions

  1. You framed DualEntry's Series A as an ERP disruption signal — where do you think the wedge actually is, and which incumbent do you think cracks first?
  2. You came up through ML and infrastructure before moving into investing — how much does your technical background shape which deals you're willing to push for at Contrary?
  3. Your Substack covers data observability and reliability engineering at a practitioner level — is that primarily to stay sharp as an engineer, or are you actively using it to find companies to back?

Avoid

Don't treat him as a pure investor or a pure engineer — he operates both tracks simultaneously, and collapsing him into one role will make the conversation feel shallow.

Make it yours

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Sources

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Generated by briefthecall.com from public web sources on September 7, 2026. Each claim is linked to its source above.

Automatically generated by AI from public sources. May be inaccurate or out of date. Remove or correct this profile →