E41: Pre/Seed, Control Points, and Frenemies with Jackie DiMonte of Grid Capital

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. We spoke in depth about:    - Why Pre/Seed (not just “pre-seed”). Jackie sees pre/seed as a continuum and optimizes for investing “before it’s obvious”—pre-PMF and before scale playbooks kick in.    - Concentrated by conviction. Grid leads rounds so every check matters; “party rounds” left no owner, unclear milestones, and shaky odds—so she backs fewer, deeper and sets explicit experiment plans.    - The pre-PMF playbook. Start with a market hypothesis, define the signals that prove or disprove it, and don’t hide from feedback—iterate fast on product, pricing, and business model.    - Control points > features. In crowded industrial/logistics AI, she looks for wedge use cases with fast time-to-value and durable leverage; otherwise it devolves into a customer-acquisition bloodbath.    - “Frenemies” in supply chains. Competitors often integrate and overlap; Grid underwrites only when the entry point creates credibility to crowd out others—important for a small, high-ownership fund.    - Founder archetype. Best fit: builders with industry roots and high-growth tech chops who show real customer empathy; solo vs. teams can both be superpowers.    - Marketplaces & vertical AI (reality check). Network effects are unmatched, but in industrials behavior change and trust make embedding hard; Jackie favors either core systems of record or AI-enabled services that deliver outcomes, not middling bolt-ons.    - Valuation dispersion & speed. The “power law” now shows up in fundraising: a few rounds price mental and close overnight on relationships, while most processes remain slow and illiquid.    - Geo lens. Grid’s industrial thesis maps to Chicago/Austin and the Atlanta-to-NY corridor; LA is emerging in manufacturing—where domain roots meet tech talent.   Investing in Startups is a Seaplane Ventures production and hosted by Joe Magyer.