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