The Costliest AI Mistake in Startups | Protik Mukhopadhyay - E61
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 psychology
- How to build with feedback loops
- What most founders get wrong about VC money
- How second-time founders think differently
Timestamps:
00:00 – Intro: From Bing to DataColor.ai
01:15 – What is DataColor.ai building?
02:00 – Role of community for startup founders
04:00 – How to extract value from founder communities
06:00 – The real way to reach out cold (and get replies)
08:50 – What excites him about AI in enterprise
10:30 – The real enterprise AI opportunity
12:15 – What a Chief Data Officer really does
13:30 – Selling to enterprise vs SMBs – explained with a car analogy
15:00 – Why product matters the least in enterprise sales
17:00 – Should startups even try selling to enterprise?
19:00 – Smart marketing and how to build trust early
21:00 – Second-time founder mindset: What he’s doing differently
24:00 – The startup trap: Solving tomorrow’s problem today
26:00 – Fundraising strategy: Not all money is equal
29:00 – Should you avoid VCs early on?
32:00 – Real stories: Founders who raised too soon
34:00 – Why he chose strategic angels only
37:00 – Is cap table dilution really a problem?
39:00 – What’s holding back growth today?
40:00 – Favorite tools, tech stack & startup habits
41:00 – His big lesson from the first startup
42:00 – The question every founder should answer
