Bob is a serial entrepreneur who founded MobileIron, grew it to $150M in revenue, and took it public. Now, he's back with his fourth startup, BlueRock, tackling the next massive wave: agentic AI security.

In this episode, Bob breaks down the distinct difference between finding Product-Market Fit and finding Go-To-Market Fit—and why confusing the two can kill your company.

He shares the exact questions he asked early customers to pivot from a generic mobile idea to a billion-dollar enterprise solution, the painful transition from founder-led sales to a repeatable playbook, and why he believes agentic AI is the "mobile wave" all over again.

Why You Should Listen

• Why asking "what else is bothering you?" can uncover real pain points.
• Why finding Product-Market Fit might actually increase your burn rate.
• Why founder-led sales often fail to scale and what to do about it.
• How to use a "Deal Grind" session to turn anecdotal sales wins into a scientific Go-To-Market machine.
• Why identifying the right tech wave matters more than your initial idea.

Keywords

startup podcast, startup podcast for founders, product market fit, go to market fit, enterprise sales, founder led sales, mobileiron, agentic AI, cybersecurity startup, bob tinker

00:00:00 Intro
00:03:17 Talk to Customers Before Writing Code
00:15:28 Why Finding PMF Can Increase Burn Without Growth
00:17:51 The Founder "Magic Pixie Dust" Trap
00:25:34 The Deal Grind Exercise
00:31:43 From 1M to 80M ARR in 4 Years
00:32:54 Why Agentic AI is the Next Mobile Wave
00:38:30 The Famous Sequoia Tombstone Meeting
00:40:17 The Magic Question: What Else is Bothering You?

Send me a message to let me know what you think!