Andy Ellwood

Andy Ellwood is a technology entrepreneur, executive coach, and founder of Stretch, a company focused on bringing transparency and empowerment to grocery shoppers.

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Hosted by

Hilmarie Hutchison

About this Episode

In this episode, Hilmarie sits down with Andy Ellwood to explore resilience, entrepreneurship, and what it means to rebuild after losing everything. From selling private jets for Warren Buffett’s company to founding multiple technology ventures, Andy’s journey is a powerful lesson in courage, accountability, and purpose-driven innovation.

Andy shares the Green Pill moment that changed the trajectory of his life when a successful client challenged him to stop “limo driving” his way through life and start building something of his own. That conversation pushed him out of a comfortable career and into the uncertain world of startups. The discussion dives deep into the rise and fall of his previous venture, Basket, where an unexpected tragedy, the loss of a key investor and board chairman, triggered a chain of events that ultimately led to the company’s collapse. Through those experiences, Andy learned some of leadership’s hardest lessons about responsibility, resilience, and the reality that no one is coming to save you.

The conversation also explores Andy’s latest venture, Stretch, a platform designed to bring transparency to grocery shopping and help families make better decisions about one of their largest household expenses. He explains why he waited for a long time before returning to the grocery technology space and how advances in AI finally made it possible to solve a problem he has been passionate about for years. Along the way, Andy discusses the emotional burden many families carry when trying to stretch their budgets, the importance of building solutions around real human problems, and why founders must stay focused on serving users rather than chasing investor expectations.

At its core, this episode is about integrity. It’s about choosing purpose over prestige, staying true to your values when shortcuts appear tempting, and finding the strength to begin again after failure. Andy’s story is a reminder that some of life’s greatest opportunities emerge not from success itself, but from how we respond when everything falls apart.

Andy Ellwood

Founder & CEO of Stretch | Entrepreneur | Executive Coach

→ Read the executive analysis inspired by this conversation

Andy Ellwood is a technology entrepreneur, executive coach, and founder of Stretch, a company focused on bringing transparency and empowerment to grocery shoppers. His career spans finance, aviation, Silicon Valley startups, and consumer technology, giving him a unique perspective on leadership, innovation, and business growth.

Before becoming a founder, Andy worked in private aviation, selling jet programs owned by Warren Buffett to athletes, celebrities, and business leaders. He later transitioned into technology startups, where he built and led ventures aimed at solving meaningful real-world problems. His previous company, Basket, sought to bring clarity to grocery pricing and consumer purchasing decisions, providing valuable lessons that ultimately shaped his next chapter.

Today, through Stretch, Andy is focused on helping families navigate rising grocery costs by providing greater visibility into product availability and pricing. Alongside his entrepreneurial work, he serves as an executive coach, helping founders and leaders make better decisions, build resilience, and stay aligned with their mission. His work reflects a commitment to solving everyday problems while leading with authenticity, empathy, and long-term integrity.

“No one else is gonna come to save you.”

Andy Ellwood

“Don’t settle for being close to cool people. Go be the cool people.”
Andy Ellwood

Show highlights

The challenges that happened, you know, they really test you. -Andy Ellwood Click To Tweet

“ The opportunity of a lifetime must be seized within the lifetime of the opportunity. By the time you see that there’s an opportunity, if you’re not ready to seize it, it will pass you by.”

Andy Ellwood