Ashish Gupta didn’t set out to become the Chief Strategy Officer of a company using AI to teach kids how to read. But in hindsight, the path makes a certain kind of sense.
Today, two-thirds of U.S. fourth graders are not reading at grade level. For children from low-income or non-English-speaking households, the numbers are even more stark. Literacy isn’t just a skill—it’s a gatekeeper. It shapes graduation rates, lifelong health, and economic mobility.
The son of immigrants. A UT honors grad. An investor trusted with over a billion dollars in capital. A two-time fund founder. And now, a builder of tools designed to change the literacy landscape for millions of children. Ashish saw this problem not just as a social challenge, but as a systems failure. And he realized that with the right tools, we could do better. The son of immigrants. A UT honors grad. An investor trusted with over a billion dollars in capital. A two-time fund founder. And now, a builder of tools designed to change the literacy landscape for millions of children.
Underneath all those titles is a pattern that goes deeper: a man who has never stopped asking what matters most—and who continues to shape his life around the answer, even as it evolves.
In this episode of Uncharted: Your Sidekick for Life, we talk about the long arc of reinvention; how failure and fatherhood, risk and restlessness, shape the version of us that shows up in the world. We explore how systems shape stories, how education links to equity, and how capital can become a lever for meaningful change.
Ashish shares what it was like growing up in Texas, shaped by parents who lived their values through hard work and curiosity. He watched his mother give relentlessly to the community without expecting anything in return, and his father pursue deep learning as a lifelong habit.
Those early lessons seeded a tension that would return later in life: success vs. meaning.
He shares the experience of raising two daughters in a different generation—one that’s more digital, more distracted, but no less full of potential.
And he opens up about what it means to trust your gut when the world sees your value one way—but your heart pulls you in another.
After years of investing in markets, Ashish felt a growing disconnect.
“There came a point where I asked myself: am I still learning? Am I still growing?” “And if not—what am I really doing this for?”
That internal question marked the beginning of a deeper shift. A movement away from financial returns and toward human returns.
“I realized I wanted to work on something that helped communities like the one I grew up in,” "Something with real, measurable impact."
That clarity led him to Amira Learning, a company that combines artificial intelligence with the science of reading to help students gain fluency in English and Spanish.
The impact is measurable: faster literacy growth, stronger student outcomes, and broader access to high-quality tutoring at scale.
But the story isn’t just about AI or education reform. It’s about legacy.
Ashish reminds us that legacy isn’t built in a boardroom.
“It’s what you do daily,” “It’s how you show up when no one is watching."
Legacy, to him, is less about prestige and more about participation. Less about what you leave behind, and more about what you build alongside others.
He doesn’t present his choices as easy. But he does make them feel possible—for any of us brave enough to question what we’re really building.
Who are we building for? What do we want to be remembered for? And what happens when we stop trying to impress—and start trying to contribute?
Tune in to Ashish’s story now on Uncharted: Your Sidekick for Life.
Ashish Gupta is the Chief Strategy Officer at Amira Learning, an AI-powered edtech company revolutionizing childhood literacy. A former venture capitalist and two-time fund founder, Ashish has led investments across technology, education, and healthcare. His career spans over a billion dollars in capital managed—but his true focus today is on creating human impact at scale. A UT Austin graduate and father of two, Ashish is passionate about equity in education, systems change, and building tools that matter.
Natalie Peyton studied theatre and film in Australia, New York and LA and performed stand-up on the “three coasts.” She honed her podcast executive skills over the last 4 years developing and producing dozens of podcasts and even hosts a children’s mindfulness bedtime program
Leon Vanstone: Leon brings his curiosity and sharp interviewing skills to the table, facilitating insightful discussions with our mentors, extracting valuable lessons and insights to empower listeners on their own path to growth and achievement.
Dan Dillard: Dan, with his thoughtful approach and engaging style, delves into the minds of our mentors on the podcast, crafting compelling interviews that uncover the wisdom and experiences driving their success and impact.
This blog was written by Anais Schmidt, one of the hosts of the Uncharted Podcast. Anais is also an aspiring musician. When not in her studio, she tours Europe with Monte Mai.
If you would like to join the conversation email us at anais@foundingup.com
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