How do you actually sell to enterprises? Why do most startups fail at it? In this episode, we talk to the founder of DataColor.ai — a serial entrepreneur who built and sold his last company and is now building in the enterprise AI space. We dive deep into how enterprise sales really work, how to tap into communities for feedback, and the mindset shift between your first and second startup.💡 Learn about:Enterprise sales psychologyHow to build with feedback loopsWhat most founders get wrong about VC moneyHow second-time founders think differentlyTimestamps:00:00 – Intro: From Bing to DataColor.ai01:15 – What is DataColor.ai building?02:00 – Role of community for startup founders04:00 – How to extract value from founder communities06:00 – The real way to reach out cold (and get replies)08:50 – What excites him about AI in enterprise10:30 – The real enterprise AI opportunity12:15 – What a Chief Data Officer really does13:30 – Selling to enterprise vs SMBs – explained with a car analogy15:00 – Why product matters the least in enterprise sales17:00 – Should startups even try selling to enterprise?19:00 – Smart marketing and how to build trust early21:00 – Second-time founder mindset: What he’s doing differently24:00 – The startup trap: Solving tomorrow’s problem today26:00 – Fundraising strategy: Not all money is equal29:00 – Should you avoid VCs early on?32:00 – Real stories: Founders who raised too soon34:00 – Why he chose strategic angels only37:00 – Is cap table dilution really a problem?39:00 – What’s holding back growth today?40:00 – Favorite tools, tech stack & startup habits41:00 – His big lesson from the first startup42:00 – The question every founder should answer

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“What did the council decide on item 42?” — answered with the speaker and the moment.