I Sold My $5,000,000 Business… Here’s How | 045

Sep 12, 2024

Join Cathryn Lavery, an entrepreneur and founder of BestSelf Co., as she recounts her fascinating journey of selling and buying back her business. She shares invaluable insights on the challenges entrepreneurs face during sales, including negotiation tips and emotional hurdles. Discover her experiences with a major theft and how she's leveraging AI to boost efficiency. Cathryn also discusses adjusting business strategies post-COVID and the significance of reclaiming control instead of relying on external management.

Ask episode

AI Snips

Chapters

Books

Transcript

Episode notes

INSIGHT

PE vs. Founder Nuance

Private equity firms often over-rely on spreadsheets and lack the nuanced understanding of small businesses.
This can lead to mismanagement and create opportunities for founders to repurchase their businesses.

ANECDOTE

Buying Back BestSelf

Cathryn Lavery bought back her business after selling it, a decision partly inspired by the desire for a good story.
This "hanging around the hoop" strategy involves selling to private equity, waiting for them to fail, then repurchasing at a lower price.

ANECDOTE

The Sale of BestSelf

Cathryn decided to sell after an unsolicited offer while postpartum and tired.
A casual conversation in a Slack group led to a much better offer from a private equity firm.

Get the Snipd Podcast app to discover more snips from this episode

Get the app

Thinking about selling your business? Here’s everything you need to know.

In this episode, I sit down with the amazing Cathryn Lavery to hear the incredible story of how she sold her business—and then bought it back.

We chat about the real challenges entrepreneurs face when selling a business, the must-know tips to protect yourself from making expensive mistakes, and how to secure the best deal.

Cathryn also shares how $230,000 was stolen from her business, and we dig into how she's using AI and tech solutions to stay ahead, especially in a post-COVID world.

Timestamps:
00:00 Introduction: Key Takeaways from This Business Journey
00:58 What 'Hanging Around the Hoop' Means for Your Business Strategy
03:44 How to Decide Whether to Sell Your Business
08:33 Adapting Your Business Strategy During COVID
10:25 How to Navigate the Business Selling Process: Proven Tips and Negotiation Strategies
13:59 What to Expect After Selling Your Business
17:29 Things to Know Before Selling Your Business
23:05 How to Approach Rebuying Your Business
27:57 Negotiation Tips
34:48 Starting Over: Essential Lessons and Strategies for Success
37:48 Best Ways to Use AI to Optimize Business Operations
50:10 How AI Can Improve Both Personal and Business Efficiency
55:44 How to Combat and Prevent Counterfeit Issues in Your Business
58:21 Dealing with Embezzlement: Protect Your Business from Theft
01:09:28 Advantages and Challenges of Hiring Remote Talent
01:12:21 Effective Personal Productivity Systems and Life Hacks
01:16:29 Closing Thoughts

If you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one.

Learn more about The Nathan Barry Show: https://nathanbarry.com/show

Follow Nathan:
Instagram: https://www.instagram.com/nathanbarry/
LinkedIn: https://www.linkedin.com/in/nathanbarry/
Twitter: https://twitter.com/nathanbarry
Website: https://nathanbarry.com/

Follow Cathryn:
YouTube: https://www.youtube.com/@LittleMight
Twitter: https://twitter.com/cathrynlavery
TikTok: https://www.tiktok.com/@cathrynlavery
LinkedIn: https://www.linkedin.com/in/cathryn-lavery/
Instagram: https://www.instagram.com/cathryn.lavery/

Featured in this episode:
Michael Girdley - https://www.girdley.com/
BestSelf Co. - https://bestself.co/
ConvertKit (soon to be Kit) - https://convertkit.com/
ChatGPT - https://chat.openai.com/
Claude (AI assistant) - https://www.anthropic.com/
Fiverr - https://www.fiverr.com/
Final Loop - https://finaloop.com/
Super Whisper - https://superwhisper.com/
Sagan Passport - https://saganpassport.com/
Quick Hire VA - https://quickhireva.com/
Online Jobs - https://www.onlinejobs.ph/
Alexa - https://www.amazon.com/alexa
Little Talk - https://bestself.co/products/little-talk-deck
Tropical MBA - https://tropicalmba.com/
"Before the Exit" - https://a.co/d/dzlXNcH

Highlights:
03:14 Decision-Making Framework
34:48 The Struggle of Founders and Blank Slates
35:42 Nathan’s Major Shift in Management Strategy
44:42 Joining a Team Without Context: Lessons from Apple University
01:06:08 Embezzlement and Taking Vacations