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Pre/Seed, Control Points, and Frenemies with Jackie DiMonte of Grid Capital

  • Joe Magyer
  • Oct 29
  • 2 min read

Jackie DiMonte is the Cofounder and General Partner of Grid Capital. We talked about power laws, investing with conviction, how to help founders in their earliest stages, small funds vs. big funds, and whether pre-seed valuations really are mental.


The episode is now available on Apple Podcasts, Spotify, Amazon, and YouTube Music.


Chapters from Pre/Seed, Control Points, and Frenemies with Jackie DiMonte of Grid Capital


00:00 Introduction to Jackie DiMonte and Grid

02:03 The Shift from Chicago to New York

10:51 Understanding Product-Market Fit

13:41 Navigating Frenemy Dynamics in Industry

18:21 Founder Archetypes and Marketplaces

19:49 Vertical AI and Its Impact

24:13 Current Market Valuations and Trends

30:16 Expectations for Seed Rounds

33:04 Outperformance in Venture Capital


Takeaways from Pre/Seed, Control Points, and Frenemies with Jackie DiMonte of Grid Capital


  • Thesis & geography: Grid Capital focuses on tech for industrials—manufacturing, construction, and supply chain—with deep networks across Chicago, Austin, and the NYC–Atlanta corridor (LA also rising).

  • Concentrated at pre-seed: Grid runs a concentrated, lead-investor strategy so every check “matters to the fund” and there’s a true owner who helps define milestones to the next round.

  • Why lead matters: Early “party rounds” often lacked clear milestones and accountability; leading creates ownership, signals, and hands-on help.

  • Stage model: Jackie sees three early phases—pre-PMF, PMF, and “get ready to scale”—and prefers investing “before it’s obvious.”

  • Scientific method at pre-seed: Start with a market/product hypothesis, define success metrics, and be willing to change the hypothesis quickly rather than hiding from feedback.

  • Go-to-market clarity: At pre-seed, “de-risking” = finding PMF; de-risking looks very different post-PMF.

  • Founder traits: No bias on solo vs. teams; strongest signal is deep customer empathy, often from industry experience + high-growth tech exposure.

  • Marketplaces in industrials: Network effects are powerful, but entrenched relationships and behavior change make industrial marketplaces hard to ingrain.

  • Vertical AI lens: Two durable “buckets” attract them—(1) core systems (ERP/MES) that own workflows/data, and (2) tech-enabled services that remove whole functions and deliver outcomes. Middle-layer “bolt-ons” face durability risk.

  • “Control points” test: They back wedges with fast time-to-value and measurable ROI that can expand into other use cases; absent a clear control point, they pass.

  • Logistics AI “agent” wave: Despite obvious efficiency gains, they expect a noisy, customer-acquisition bloodbath across overlapping point solutions—and are sitting it out.

  • Seed timing: Raise when momentum is at a local maximum—seed can still be narrative-driven; once metrics show up, investors judge on those.

  • Valuations are “mental”… and bifurcated: The power law now applies to fundraising; the highest-consensus teams/markets see extreme pricing gaps vs. everyone else.

  • Process dynamics: Headlines highlight overnight, high-price rounds, but most founders face slower, tougher processes despite similar sticker prices.

  • On mega-funds: Don’t underestimate large, multi-stage firms—given the higher ceiling (e.g., AI), they can still generate outlier-like outcomes; outperformance is hard for everyone.



The content here is for informational purposes only and should not be construed as investment, legal or tax advice. The opinions expressed by guests are their own and do not reflect the views of Seaplane Ventures. Our host, guests and clients may hold investments discussed in this podcast. Please invest responsibly.

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