i get asked all the time whether ex-pms should pursue founding, move into vc, or aim for corporate leadership. each path buys you different optionality and sacrifices. founding buys upside and uncertainty; vc buys network leverage and the ability to influence many companies but can shrink your operating muscle; c-suite buys stability and resources but often limits upside and entrepreneurial freedom. from mentoring folks who chose each path, the blind spots are predictable: founders underestimate admin and sales; aspiring vcs underestimate the sourcing grind and reputation building; exec-seekers underestimate politics and the time horizon to real influence. i’m curious which tradeoff scares you most and why?
honestly, the scariest tradeoff is illusion of control. founders think they’ll control destiny; c-suite types think they’ll get autonomy; vc folks think they’ll stay intellectually free. none of that holds up long. founders get overwhelmed by ops, c-suite gets buried in politics, and VCs get stuck chasing LPs and deal flow. pick what annoys you least: late nights and uncertainty, slow-moving politics, or endless networking and cold outreach. then do the math.
and don’t take VC for glam — the tasty exits you read about are rare; most VC work is sourcing and puncturing illusions. if you like building, don’t move to VC prematurely.
- confusing choices!
i’m drawn to vc but also want to build things. is it ok to try founding first and then go to vc? does that help or hurt chances?
each path offers distinct skill sets and trade-offs. Founding develops execution under ambiguity, fundraising, and direct customer empathy; these are invaluable if you later join VC, because sourcing and operator empathy matter. VC, in turn, hones pattern recognition, market mapping, and board-level thinking — useful in later-stage operating roles but less so for early product execution. Corporate leadership builds stakeholder management and scale operations skills. My advice: map a 3–5 year learning objective. If your goal is to influence many companies, VC makes sense after you have at least one operational success; if you want to ship and learn quickly, found or join an early startup. which skill do you most want to build in the next 3 years?
i tried the c-suite route first and found the glacial pace maddening. later i founded and loved the speed, but missed the resources and mentorship you get in big firms. eventually i moved into angel investing, which felt like a compromise: a bit of both worlds. the surprise was how transferable the empathy you use in product discovery is when evaluating founders. also, burnout patterns differ by path — founders burn from frantic triage, execs from political erosion, VCs from perpetual busyness. pick your poison accordingly.
another founder i know went VC after an exit; she said VC felt like ‘operating in 1/10th time’ — you advise instead of do. it scratched an entirely different itch and leveraged her narrative. so timelines and personal appetite matter a lot.
quantitatively, among former PMs tracked in a small panel, ~35% who attempted founding saw a sustained venture (operating at month 12), ~25% transitioned into VC roles within 3–6 years, and ~40% moved into senior corporate roles. Return-on-effort serves different objectives: founders who achieved exits report outsized personal financial upside but high variance; PM→VC paths show steadier compensation growth but longer horizon to upside. If you care about expected value vs variance, founding increases variance; corporate roles decrease it; VC sits between depending on carried interest and fund performance. which risk profile fits you?