Many of us feel like we know Lenny Rachitsky because we see him everywhere. He’s on our commutes, in our ears as we do weekend chores, or with us at work as we’re trying to get better at our jobs.

The First Round Review got a rare opportunity to profile Rachitsky, spending hours with him at his home to understand the person behind the screen. What motivates him is far more interesting than what you might think. 

Rachitsky was born in Ukraine to Jewish parents who applied to emigrate but were denied exit, being labeled “refuseniks.” Wanting to leave the country was itself an act of treason, and Rachitsky says his parents had a difficult time once their application was denied. He watched his parents navigate a lack of choice — as they figured out how to live in Ukraine and also when they finally did make it to the US, establishing their careers here. 

Rachitsky says he always had a chip on his shoulder and wanted to show people what he could do. Starting a company was the ultimate form of autonomy, so that’s what he did (which he eventually sold to Airbnb). 

Once Rachitsky became “Lenny,” he was driven by creating value for his audience. He dedicates between 5 - 100 hours to each newsletter, poring over it 50 times before it’s published. And as he adds new things to his network — a conference, other podcasts, his Product Pass — he always views these through the lens of value delivery.

Now that he’s built one of the most influential platforms in tech, what motivates him to keep doing it?

“I’m very afraid of moving into a place of just talking about things that aren’t real and just sound true, but aren’t true at all,” he says. He doesn’t want to pontificate or become a talking head, being so far removed from the day-to-day work of a PM that he loses grounding with what his audience wants.