The ROI of Generosity: Aaron Schwartz @Orita.ai on Luck, Boundaries, and Building People

Aaron Schwartz has built and scaled companies you know — Modify Watches, Passport, Loop Returns — and now Orita.ai, helping 100+ brands land in inboxes instead of spam. But ask anyone who’s worked with him, and they’ll tell you his real superpower isn’t just building businesses. It’s building people.

In this conversation, we dig into:

- Why sharing problems faster leads to better solutions (and stronger relationships).

- The inner circle of advisors that Aaron has relied on for years, and how you can build one too.

- His personal framework for paying it forward without burning out.

- Why he only advises founders he’d be willing to work for himself.

- The surprising ROI of generosity (including the story of how a casual meeting in Bryant Park turned into co-founding Orita).

- How to be authentic without oversharing, and the boundaries that protect trust.

- Balancing the weight of being a founder with the realities of family, guilt, and joy.

- The books Aaron rereads to stay focused and grounded when life gets loud.

This one’s about generosity, luck, boundaries, and the human side of building. I walked away with a new perspective on who I help, how I help, and what I say yes to. And I think you will too.

Full episode is live now on Spotify, Apple Podcasts, and YouTube.