The Operator’s Edge: Inside Grit Capital’s High-Conviction Bet on Applied AI
By Valentin Saitarli
As venture capital shifts toward operational value over brand hype, one investor stands at the intersection of grit and execution: Mike Flannery. The founder of Grit Capital Partners is helping redefine early-stage investing by bringing operator credibility to an industry often dominated by spreadsheet theory. Through a focused thesis on Applied AI and a playbook forged in enterprise trenches, Grit Capital is quietly constructing a high-leverage portfolio with long-term implications for B2B SaaS.
“You can’t just write a check anymore. You need to sit on the board, help them sell, build hiring plans, and find product-market fit. That’s how you reduce risk in early-stage AI.”
– Mike Flannery, Founder, Grit Capital Partners
From Health IT to High-Stakes VC
Before founding Grit Capital, Flannery was a founder himself—co-founding and scaling Sagacious Consultants, a healthcare IT firm that helped hospitals implement enterprise systems. After leading it to a $270 million acquisition by Accenture, Flannery turned his playbook into a venture strategy. That exit wasn’t just a liquidity event; it was a thesis in disguise: operators build differently, and they back differently too.
The Applied AI Sweet Spot
Grit Capital’s focus on Applied AI isn’t generic. Rather than betting on broad language model platforms, the firm hones in on B2B applications where AI solves narrow but critical workflow problems—automating compliance in fintech, optimizing ad delivery in martech, or detecting fraud in e-commerce logistics. Grit’s typical check size ranges from $500K to $1.5M, with a sharp eye on pre-seed and seed rounds where founder coaching matters most.
The firm’s portfolio includes several stealth-stage SaaS platforms, many of which deploy foundational models but are engineered around proprietary datasets and fine-tuned customer integrations—core to maintaining defensibility as AI commoditizes.
Why Founders Choose Grit
“When Mike invests, you get a board member, a hiring partner, and a product strategist in one,” says a founder from Grit’s portfolio who asked to remain anonymous while in stealth. “It’s like getting a mini-operating system for scaling.”
Beyond capital, Grit provides operational support on go-to-market motion, enterprise sales playbooks, and capital structuring. With Flannery’s team including ex-operators in finance and product management, Grit offers what founders describe as “full-stack help.”
Backing Builders and Equity
Flannery’s impact extends beyond his term sheets. As a board member at iFundWomen, he’s publicly supported increasing access to capital for underrepresented founders. Grit Capital is intentionally sourcing deals from beyond the typical coastal echo chambers—focusing instead on founder resilience, market pain, and technology execution over social capital or trend-chasing.
Redefining Venture Discipline
In a post-ZIRP venture world, Grit Capital stands as a case study in operator-driven investing. With a focus on applied outcomes over abstract vision, Flannery is building a different type of portfolio—one that reflects not just capital, but conviction rooted in lived experience. As AI matures and early-stage liquidity tightens, this style of venture discipline might just become the blueprint for the next great generation of VCs.
About the Author
Valentin Saitarli is a contributing editor at StockBurger.news and a partner at AI Media Miami, covering the intersection of emerging tech, venture capital, and policy. His reporting focuses on real-world impact in AI, crypto, and finance.
