Intro - Tim the Legacy AI guy
December 02, 2025
by a professional from Liberty University in New Smyrna Beach, FL, USA
Hi everyone! I recently joined and am looking forward to joining more conversations here. I started my career in big tech (Google, Facebook) before founding a fintech company that I ran for 8 years, learning many lessons through failure, eventually hit #777 on the Inc 500 list, stalled during economic changes, and I finally sold in early###-###-#### I now occasionally share some of those lessons via HowNotToFounder.com.
Since exiting, I fell into consulting for small businesses, recently delivering custom AI agents and revenue operations automation for a few different SMBs. I have also met a few different search funders over the last couple of years, and have a few friends acquiring businesses.
I've been thinking a lot about the intersection of the Silver Tsunami (so many aging business owners who have uncertain exit plans) and the new AI Tsunami (the step-function change we're all experiencing with AI allowing us to click "skip" in our digital work). It has really perplexed me to think how about how Baby Boomers, who started in business before EMAIL, might be able to communicate and hand off their operation effectively to an AI-dependent young buck.
That line of thinking has led me to a new business experiment aiming to ease that transfer process, and make it really easy for aging owners to prepare their knowledge base for a successor through the power of... phone calls! Some of the least organized and documented small business operations are led by driven owners with a keen sense for the business, but no patience for writing SOPs, recording client account history, and the like, but they'll TALK all day. Why not talk with an AI agent which absolutely EXCELS at taking unstructured information and processing it into useful artifacts?
So that's the idea, it's still being formed into a fully fledged product, but I have a couple of requests for those in the community that may be interested in this sort of thing:
1. Check out the newly launched DEMO at https://LegacyAI.dev. Feel free to make up a fake business and pretend you're the owner, my AI voice agent won't mind!
2. If you've scoped a profitable small business (figure $250k-$5 Million EBITDA) and thrown the deal in the scrap heap due to Key Person Risk or Documentation Gaps, please, I would greatly appreciate a referral to that owner or broker!
I really love feedback, so if this is thought provoking for you in any way, feel free to comment or DM me. I'd love to connect with more of you. Thank you!
from Virginia Polytechnic Institute and State University in Charlottesville, VA, USA
from Liberty University in New Smyrna Beach, FL, USA