How AI Is Changing Growth, Teams, and Startup Strategy with Jon Mest #244

Jon Mest is the CEO of ChatRank and JustReachOut, where he operates at the intersection of data, growth, and marketing. Throughout his career, he has worked across companies like Thomas Weisel Partners, 1010data, and Sika Health, building a strong foundation in using data to drive scalable growth strategies.

At ChatRank, Jon is focused on helping businesses win in the era of AI-driven search, where relevance and quality matter more than ad spend. He also leads JustReachOut, a PR platform that enables companies to secure media coverage through targeted outreach, analytics, and proven frameworks. With a background in applied mathematics from Johns Hopkins University and an MBA from Wharton School, Jon brings a data-driven perspective to helping businesses amplify their visibility and compete more effectively in evolving digital landscapes.

In this episode we cover:

• 00:00 - Intro
• 01:24 - Jon's Journey Through Data, Growth, and Startups
• 03:16 - Building ChatRank and JustReachOut
• 05:21 - How AI Is Reshaping Startup Teams
• 07:55 - Why Jon Chose Bootstrapping Over Venture Capital
• 10:51 - Building the Product You Actually Need
• 14:35 - How AI Search Is Changing Brand Discovery
• 16:56 - The New Rules for Startup Growth in 2026
• 21:38 - Building an AI-First Startup Team
• 26:26 - Jon's Favorite Activity To Get Into a Flow State
• 27:23 - Jon's Piece Of Advice For His Younger Self
• 28:55 - Jon's Biggest Challenges at ChatRank and JustReachOut
• 31:03 - Instrumental Resources For Jon's Success
• 33:46 - What Does Success Mean for Jon Today
• 35:37 - Get In Touch With Jon

Get In Touch With Jon:

Jon's Email

ChatRank Website

Mentions:

Joe Delgado

Yelp

G2

Trustpilot

Healthgrades

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