Most acquisitions fail because founders obsess over the price — not the people. Monica Kocher built and exited two companies by doing the opposite. In this episode, Carrie sits down with Monica, a rare founder who bootstrapped and sold twice — once through a strategic partnership that became an acquisition, and once through an advisory relationship that turned into a buyer.

This is a masterclass in what most founders get wrong: thinking exits are transactions, not long-term relationships. Monica breaks down why partnering before you sell can be the difference between a smooth exit and a cultural disaster, and why letting a potential acquirer see your company up close is not weakness, it’s leverage.

01:00 Meet Monica Kocher

02:15 First Exit: Building And Selling Gugu Chew

04:08 How The Acquisition Came Together

07:15 Looking Back On The Gugu Chew Exit

08:56 Second Company: The Smart Gift Idea

11:04 Partnering With 1-800-FLOWERS

13:16 Why Advisory Boards Matter More Than You Think

13:57 Aligning Vision With Advisors Early

14:47 How COVID Changed Corporate Gifting Forever

15:15 Scaling Fast Without Losing Control

16:08 Inside The Acquisition Process

16:44 When Advisors Become Acquirers

20:34 Advice For Women Building Toward An Exit

23:43 Final Takeaways + How To Find Monica