The "Stupid Questions" VCs Use to Test Founders | Tan Torun, 25madison

Tan Torun walks through how he and 25 Madison actually evaluate and build early-stage companies. He opens on his origin as a builder, starting companies "since he was 12" in Istanbul, where high interest rates and risk-averse capital taught him to "surf in a tsunami", and explains 25 Madison's model as a studio-plus-fund that decides, deal by deal, whether to co-build with a founder or simply write a check. The core of the discussion is his thesis that a founder's single most important skill is the ability to influence, and that pitches die the moment a founder slips into "research presentation mode," reciting market facts an AI could surface instead of selling a personal, urgent vision. He details his signature tactic of asking deliberately "stupid questions" to test how founders reason under pressure (including the founder who got offended, ended the call, and blocked him), and why NDA-to-explain-the-tech and manufactured urgency are instant red flags. They cover the patience required to invest in unsexy, legacy B2B — supply chain, real estate, industrials — where sales cycles are long and dropping bad early customers is necessary, plus his exit story from an out-of-home signage business and his "learning for love of the game" habit (CFA, computer science at Penn). His standout contrarian take: SaaS isn't dead, the bar is just higher now, because anyone can build an MVP but not everyone can build real software. The episode closes with three Fund It or Pass scenarios and a rapid-fire round spanning founder green flags, deck pet peeves, fundraising prep, cold-email do's and don'ts, back-channel reference checks, and why character ultimately wins under stress. Guest Profile: https://www.25madison.com/teammembers/tan-... Please visit our website to get more information: https://www.rho.co/ 🔔𝐃𝐨𝐧'𝐭 𝐟𝐨𝐫𝐠𝐞𝐭 𝐭𝐨 𝐬𝐮𝐛𝐬𝐜𝐫𝐢𝐛𝐞 𝐭𝐨 𝐨𝐮𝐫 𝐜𝐡𝐚𝐧𝐧𝐞𝐥 𝐟𝐨𝐫 𝐦𝐨𝐫𝐞 𝐮𝐩𝐝𝐚𝐭𝐞𝐬.    / @rhobusiness   In this video we break down everything you need to know about funding your startup 🔗 Stay Connected With Us. Twitter (X): https://x.com/rhobusiness LinkedIn: https://www.linkedin.com/company/rhobusiness/ Website: https://www.rho.co/ 📩 For business inquiries: [email protected]