Sasha Cayward was a nationally ranked junior tennis player — good enough to turn pro, until she decided that wasn't the life she wanted and walked away from the sport that had been her whole identity. A decade later, she did it again: she left the startup she'd spent a year building, with no plan for what came next. Sri caught her mid-jump — reinventing in public, betting on herself, and strangely at peace with not knowing.

This one's less a career story than a field guide to reinvention. Sasha and Sri get into choosing a career over a job, why joy (not discipline) is the real engine of high performance, and her core claim: you can't build self-belief on a dysregulated nervous system. With degrees in psychology and neuroscience — and a decade spanning founder, investor, and community builder — she ties the confidence to chase big opportunities straight to a felt sense of safety in the body, then gets practical about how founders and operators actually build it.

In this episode:
- Why to choose a career, not a job — and how the two differ
- Why joy, not discipline, drives real performance
- The link between self-belief and a regulated nervous system — and the tools that build it (breathwork, EFT tapping)
- How to "borrow" belief from the people around you until it's your own
- The "six-pack mind, muffin-top thoughts" trap that hits the most disciplined people hardest

If you're between chapters — or too scared to start the next one — this one's for you.

Sasha spent the past year building community at Hubble, a place for founders to get the advice they need. Sasha has unique insights having been a founder but also as an elite athlete. She was a nationally ranked junior on the tennis circuit.

She and Sri together document reinvention while it's happening—not the highlight reel.

📌 Want to crush 2026? Book a free clarity call with Sri to get your priorities in order and start getting unstuck.

📩 Get free elite performance tools weekly through the Warrior Poet newsletter 👉 join ✅

_____

Follow Sri for elite leadership tips:
➡️ LinkedIn.com/in/andrewsridhar

Connect on Instagram: @andrewsridhar + @sri_actually

Intro and/or outro music in most episodes is by Paul Sridhar. 🎧

Disclaimer: Any audio clips are included with every intent and steps taken to abide by Fair Use and serve the purpose(s) of illustration, education, augmentation, or promotion of source content.

Sri talks with Adam Rossi, who set a 2-year clock on founding a company after he graduated college. At 24 he started his entrepreneurial journey along with his young wife Laila. They eventually sold to a public company, achieving the exit every founder dreams of—but only after immense struggle.

Adam tells the raw, unvarnished story: not being sure about making payroll—or even groceries.

And about how to choose a life partner and what entrepreneurship can do to a marriage.

Sri and Adam also talk about zero-to-one startups vs. acquisition, the flaws in our education system, and how younger generations should prepare for AI.

📌 Want to crush 2026? Book a free clarity call with Sri to get your priorities in order and start getting unstuck.

📩 Get free elite performance tools weekly through the Warrior Poet newsletter 👉 join ✅

_____

Follow Sri for elite leadership tips:
➡️ LinkedIn.com/in/andrewsridhar

Connect on Instagram: @andrewsridhar + @sri_actually

Intro and/or outro music in most episodes is by Paul Sridhar. 🎧

Disclaimer: Any audio clips are included with every intent and steps taken to abide by Fair Use and serve the purpose(s) of illustration, education, augmentation, or promotion of source content.

From the San Francisco 49ers to $4M Seed Round: Kevin Jurovich on Surviving "The Desert"

Kevin Jurovich's NFL career ended with a dropped pass in the fourth quarter. Seven years later, he and his cofounder closed a $4 million seed round for Hubble, his expert marketplace for founders.

This isn't a highlight reel. Kevin talks about the brutal middle years—failed launches, 14 months of uncertainty, and why most people quit right before things work. Sri and Kevin dig into how writing on LinkedIn during his lowest point accidentally became his breakthrough, why conviction comes from user feedback (not delusion), and the journey through the desert that every entrepreneur faces.

You'll learn:

• What a true 'aha' moment feels like (Kevin's Limitless moment)
• How to stay in the game when nothing's working
• Why iterative processes beat perfect plans
• Where real conviction actually comes from
• Kevin's 2025 goals (written before Hubble launched—he crushed them)

If you're in your own desert right now, this one's for you.

📌 Want to crush 2026? Book a free clarity call with Sri to get your priorities in order and start getting unstuck.

📩 Get free elite performance tools weekly through the Warrior Poet newsletter 👉 join ✅

_____

Follow Sri for elite leadership tips:
➡️ LinkedIn.com/in/andrewsridhar

Connect on Instagram: @andrewsridhar + @sri_actually

Intro and/or outro music in most episodes is by Paul Sridhar. 🎧

Disclaimer: Any audio clips are included with every intent and steps taken to abide by Fair Use and serve the purpose(s) of illustration, education, augmentation, or promotion of source content.