Bill D'Alessandro: The Hard Thing(s) About HoldCos - Outside Insights Permanent Podcast: Real Talk About Private Equity and Buying, Selling, and Operating Small Businesses

Why did one of the biggest holdco owners & operators sell his holdco? Bill D’Alessandro talks about what led to the decision to sell all but one of his companies, having to let go of being “the Holdco Guy,” advice for entrepreneurs thinking about operating & owning multiple companies, insights on online marketing, & how he sees AI changing the world forever.
 
LINKS & MENTIONS FROM THIS EPISODE
Bill’s Natural Dog Company https://naturaldog.com/
Acquisitions Anonymous podcast https://www.acquanon.com/ 
Join the list for Main Street Summit https://www.mainstreetsummit.com/
Read the Messy Marketplace (or go to episode 1 of the Permanent Podcast feed to listen) https://www.permanentequity.com/the-messy-marketplace
 
CONNECT
Bill on twitter https://twitter.com/BillDA 
Bill on LinkedIn https://www.linkedin.com/in/billda/
Brent on twitter https://twitter.com/BrentBeshore
Brent on LinkedIn https://www.linkedin.com/in/brentbeshore 
Visit https://www.permanentequity.com/ for more
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TIMESTAMPS
0:00 Bill Fills Dead Air Time
4:48 HoldCos: A Mailbox Full of Money?
11:19 Letting Go of the HoldCo
16:14 Hitting Rock Bottom & Losing the Plot
25:01 How to Build a Holdco the Right Way
31:54 From HoldCo to OneCo
34:55 When to Go Fast vs. When to Be Patient
41:30 Don’t Buy a Business That’s Too Small
47:50 Handling Layoffs
52:12 Being Vulnerable: Handling Anxiety & Loss
1:08:26 The Additive Effect of Subtracting 
1:15:12 Lightning Round: Advice for Small Business Owners & Operators
1:16:16 Lightning Round: Hiring
1:16:38 Lightning Round: Marketing Doesn’t Work
1:18:24 Lightning Round: When to Take on Capital
1:19:13 Lightning Round: How to Sell a Company
1:21:14 Lightning Round: How Much Debt is too Much?
1:21:50 Lightning Round: Stop Using Slack
1:23:51 Lightning Round: Cutting Costs While Increasing Quality
1:24:28 Lightning Round: AI is the Singularity
1:32:26 Advice for Your 25-Year-Old Self: Be Deliberate
1:34:28 Why Brent Can’t Sleep: Main Street Summit
 
EPISODE CREDITS
Produced by David Cover 
Additional editing & mastering by Ryan Lipman
Intro music by David Cover, Andy Freeman, Rhett Johnson, & Andrew Luley
Outro music by Jees Guy
 
WE STEWARD COMPANIES THAT CARE WHAT HAPPENS NEXT 
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LEGAL DISCLAIMER
This podcast is made available solely for educational purposes, and the information presented here does not constitute investment, legal, tax or other professional advice, and should not be construed as an offering of advisory services, or as a solicitation to buy, an offer to sell, or a recommendation of any securities or other financial instruments. The thoughts and opinions expressed by or through this podcast are those of the individual guests and speakers and do not necessarily reflect the views of Permanent Equity. The discussion on this podcast of any entity, product or service does not imply an endorsement thereof, and the guests may have a financial interest, whether through investment or otherwise, in one or more of any such entities, products or services. This podcast is presented by Permanent Equity and may not be copied, reproduced, republished or posted, in any form, without its express written consent.