When you meet Cliff Weitzman, founder and CEO of Speechify, his magnetism is immediate. He knows exactly where he’s headed, and he’s willing to think harder and work smarter to get there. It’s the same energy that’s made Speechify the #1 text-to-speech app used by over 55 million people.
But this episode isn’t about Speechify. It’s about the family that built him.
Cliff grew up one of five siblings in a home fueled by ambition and unconditional love. His parents pushed the couches back on weekends for dance parties, spent time explaining how the world works, and invited the whole family into big decisions.
When the Weitzmans decided to move from Israel to the U.S., his parents didn’t make it about sacrifice. They used story to set the vision and framed it as an adventure: “If you write a book in Hebrew, seven million people can read it. In English, seven billion can.”
It’s also why Cliff describes his upbringing as maximizing the surface area for serendipity.
If something sparked your curiosity, you were encouraged to chase it — to muck out stables for a free horseback ride, to learn gymnastics from YouTube, to code, to build, to explore.
And when one sibling applied to college, the whole family pulled up chairs around the dining table, red pens in hand, turning Thanksgiving week into a group edit session. In the Weitzman family, nobody goes at it alone.
The message we are taking away is clear: High standards + High support + Shared purpose.
In Cliff’s words: “You can’t fail unless you quit.” With a family like he has behind him, quitting seems very unlikely.