Episode 62

The Costliest AI Mistake in Startups | Protik Mukhopadhyay - E61

Published on: 14th June, 2025

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 β€” 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.

πŸ’‘ 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

All Episodes Previous Episode
Show artwork for Funds and Founders: Untold Journeys Behind Their Breakthroughs

About the Podcast

Funds and Founders: Untold Journeys Behind Their Breakthroughs
Welcome to "Funds & Founders: Untold Journeys Behind Their Breakthroughs," where we dig deep into the stories of successful Austin founders. Instead of focusing on their successes though, we dive into their journeys, particularly the struggles and obstacles they had to overcome.

This weekly podcast is tailored for Austin founders navigating the early stages of their entrepreneurial journey and hosted by fellow Austinite Abhinav Sinha. Here’s what to expect by tuning into Funds & Founders:

πŸš€ Embark on a Journey to Success
Join Abhinav as he takes you behind the scenes, exploring the highs and lows of building a company. This isn't your typical success story – we dive into the failures, the struggles, and those pivotal breakthrough moments that define a founder's path.

🌟 Real Conversations, Real Insights
Abhinav's approach is refreshingly different. Rather than dwelling on success, he crafts casual conversations that unravel the untold stories. Identify the setbacks that helped them grow, the lessons learned from failures, and the breakthrough moments that fueled these founders.

πŸ€” Why Didn't They Quit? Learn and Apply.
At the heart of each episode, Abhinav delves into the 'why' behind the perseverance. Why didn't they throw in the towel during tough times? And, most importantly, how can you apply their insights to your own journey? Get ready to be inspired and equipped with practical takeaways for your entrepreneurial adventure.

🀝 Decoding Venture Capital
Ever wondered what goes on in the minds of Austin's venture capitalists? Abhinav sits down with local VCs to decode their criteria for investing in early-stage companies. Gain valuable insights into the world of venture capital, understand what investors look for, and appreciate the vital factor of founder-investor compatibility.

πŸŽ™οΈ Meet Your Host, Abhinav Sinha:
Abhinav's soft-spoken yet inquisitive style creates an intimate atmosphere, allowing guests to share their authentic stories. His genuine curiosity and insightful questions make each episode a captivating journey into the minds of Austin's most successful founders.

If you're a budding Austin entrepreneur seeking the inspiration and insight needed for building a successful company, "Funds & Founders" is your go-to podcast.