Bill D'Alessandro: The Hard Thing(s) About HoldCos - Outside Insights
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 Sign up for our weekly newsletter for operators, Permanent Playbook: https://www.permanentequity.com/newsletter Sign up for a new daily newsletter from Tim Hanson, Unqualified Opinions: https://www.permanentequity.com/unqualified-opinions 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 Visit https://www.permanentequity.com/ for more Sign up for Permanent Playbook, our newsletter for operators in the field: https://www.permanentequity.com/newsletter Sign up for Unqualified Opinions, a new daily newsletter from our very own Tim Hanson: https://www.permanentequity.com/unqualified-opinions Check out our other podcast episodes here: https://www.permanentequity.com/audio 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.