Authority in the Wild #149 - From Selling Private Jets to Solving Grocery Poverty w/ Andy Ellwood
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What if the biggest problems are the ones everyone's ignoring?
In this episode, I sit down with Andy Ellwood, Founder and CEO of Stretch, to talk about building companies that solve real human problems, not just convenient tech problems.
Andy shares how he went from selling life insurance and private jets to building startups acquired by Facebook and Google, why his pandemic-era company Basket didn't survive, and what he learned about falling in love with problems instead of solutions.
Whether you're a founder trying to find product-market fit or someone who believes technology should serve everyday people, this conversation will challenge how you think about building businesses.
🟪 Timestamps
(00:00) Introducing Andy Elwood
(00:49) From Selling Private Planes to Entrepreneur
(02:38) Lessons from Life Insurance
(04:25) The Grocery Problem and Stretch’s Mission
(08:25) Challenges and Lessons from Basket
(10:23) How Stretch Works
(17:36) Building and Validating a Startup
(25:48) The Business Idea Test
(27:17) Understanding Your Customers with Surveys
(29:57) The CEO’s Role
(33:51) Fundraising and Maintaining Control
(38:49) Facing Competition from Major AI Players
(42:20) Balancing Life and Work as A Founder
(46:10) Solving Grocery Industry Inefficiencies
🟪 Key Topics Discussed
The "run into the roar" philosophy and why hard things signal opportunityWhy Basket failed during the pandemic and what Andy would do differentlyThe painkiller vs. multivitamin test for business ideasHow 17% of Americans are skipping meals to feed their familiesWhy Stretch is building for shoppers, not retailers (and why that matters)The CEO's only 3 jobs: vision, money, and unblocking the teamHow to launch before you're ready without destroying your reputationWhy falling in love with the problem is more important than the solution
🟪 About the Guest
Andy Ellwood is the founder of Stretch, a new AI platform reimagining how families navigate the grocery aisle. A serial entrepreneur behind companies acquired by Facebook and Google, Andy has built everything from global learning communities to purpose-driven tech startups. His philosophy, Make Room For Many, guides his work as he uses technology to create more access, clarity, and opportunity for everyday consumers.
🟪 Connect with Andy Ellwood
- Website: https://stretchformore.com
- LinkedIn: https://www.linkedin.com/in/andyellwood/
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Pura Vida!
Gabe Marusca