Michael Houlihan: Angel Investing SECRETS from Legendary Barefoot Wine Mogul

Today, I welcome Michael Houlihan to The Gould Mine.

Michael is the co-founder of Barefoot Wine, the best-selling wine brand in the U.S. for decades. Since selling the company to E. & J. Gallo in 2005, Michael has turned his focus to angel investing, mentoring founders, and helping businesses build toward successful exits. In this episode, he brings a no-nonsense, cash-flow-first mindset to the table and completely flips modern startup myths on their head.

Michael shares why he only invests in founders planning to sell, how today’s tech culture has warped real business fundamentals, and why message-to-market fit matters more than product. He walks us through the real-world lessons he learned while scaling Barefoot - including the merchandising failures, distributor chaos, and “wine cops” he hired to protect his shelf space.

Later in the episode, Michael gives us a checklist of what every investor should look for before cutting a check - how much overhead is too much, why you should never outsource your sales, and the shocking truth about margins when you scale. Whether you’re building a tech startup or selling cases of wine, this is a masterclass in practical entrepreneurship.

Welcome Michael, to The Gould Mine.

Follow Michael:
Website: https://bit.ly/4mLieUv
LinkedIn: https://bit.ly/4laJCtJ
Email: michael@thebarefootspirit.com

Follow Me:
LinkedIn: https://bit.ly/3L2sTc7
Instagram: https://bit.ly/3soYxtW

Looking to build lasting wealth through alternative investments? You’re in the right place.

If you’re new here, my name is Danny Gould. I’m the founder and CEO of Gould Capital, a private equity firm specializing in exclusive commercial real estate and other alternative investments. We connect investors with elite opportunities - investments that aren’t public, aren’t cookie-cutter, and most importantly, aren’t what your financial advisor is pitching.

Here’s how I got here…

1) Started as a pre-med student at Stanford University, but a lifelong dream of building the biggest hotel-casino on the Las Vegas Strip ignited my passion for real estate.
2) Transitioned to residential real estate, driving over a quarter billion dollars in sales, and became an industry leader in one of the most competitive markets in the world.
3) Decided to finally pursue my Hotel dreams and founded GMS Ventures alongside two experienced Hoteliers, with a total Hotel Portfolio Size of over $300M
4) Leveraged my expertise and relationships to build Gould Capital - which empowers investors to access transformative commercial real estate deals and alternative investments.

FULL DISCLOSURE
I create content to connect with ambitious investors - people who want to take control of their financial futures. If that’s you, let’s build something extraordinary together - I invite you to take the first step by connecting with me via a 20 minute Zoom Call.  Here’s my calendar: https://bit.ly/3rVfqwn