The Warrior Poet

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 ✅

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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 ✅

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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.

Harvard Business School professor and behavioral scientist Mike Norton breaks down why rituals—small, often “irrational” actions—carry outsized emotional weight. From his own black binder “totem” for teaching, to sports routines and workplace team practices, Mike explains how rituals can reduce anxiety, create belonging, and add meaning to relationships and family life. 

Mike and Sri also explore the line between habits (get it done) and rituals (it matters how it’s done).

Some of the examples Mike cites will shock you. Others will melt your heart. 

Michael Norton is author of the book The Ritual Effect (highly recommended). 

Visit michaelnorton.com to take the fun and insightful quiz on your own rituals. 

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Key takeaways

• Anything can become a “totem.” Objects (a binder, a pen, a mug) can anchor confidence and readiness.  
• Rituals are a belonging engine: doing something in sync (even a made-up stomp/clap) bonds groups fast.  
• Top-down rituals can backfire—but even shared “eye-roll unity” can create camaraderie (sometimes against the boss 😅).  
• Rituals help manage performance anxiety, but they’re not magic; sometimes anxiety is simply too high for rituals alone.  
• In relationships, rituals are often tiny and adorable, and they correlate with satisfaction—especially when both partners experience them as meaningful.  
• Family rituals don’t need to be elaborate: simple, values-based practices beat “perfect dinner every night.”  
• Habits vs. rituals: same action, different meaning—what matters is whether it’s “check the box” or emotionally loaded/presence-driven.  
• Watch the danger zone: rituals can become the thing you do in order to do the thing, and then start interfering with life (OCD as the extreme case).  

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📌 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.

Phil Neil scaled a business to $70M in ~8 months—then watched a warehouse fire erase uninsured inventory. 

Phil is a serial entrepreneur and former pro football player. 

He currently coaches founders on "the middle layer" between intellect and tactics. 

Sri and Phil tackle founder-mindset essentials:

• Overcoming fear
• Balancing family and a startup
• Finding a great cofounder
• Recovering from loss
• How to be strategic

Key takeaways

• Speed can hide fragility. Scaling fast doesn’t mean the foundation is stable.
• Risk isn’t just financial. There’s “risk of purpose” and “risk of identity,” too.
• Shadow patterns show up under pressure (burnout, reactivity, ego defense, avoidance).
• Frameworks reduce drama. Naming thinking styles (DISC / color archetypes) creates shared language.
• The “Courage Compass” idea: create a gap before action so intuition can speak.
• Rock bottom can be a reset—especially when your nervous system stops cooperating.
• Sales = human connection + precision. Listening and situational questions beat scripts.
• Influence vs persuasion: some deals are closed in a day; others are earned until they ask you.

Keywords

entrepreneurship, startup scaling, business pivot, decision making, courage, fear of failure, imposter syndrome, shadow work, cognitive preferences, DISC personality, leadership under pressure, emotional mastery, risk tolerance, identity, purpose, cofounder, partnerships, negotiation, sales psychology, listening skills, situational questions, persuasion vs influence, founder burnout, resilience

📌 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 Chris Eversley, former professional basketball player and expert on resilience. Chris reinvented himself after sports through an arduous journey learning to walk again at the age of 33. 

He gives you the secrets of elite performance that high-stakes decision makers pay him for. You won't want to miss this. 

Learn more about Chris: website | insta 

📌 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 and Gregory Russell Benedikt talk about how to find your true calling and follow through on action. 

They also discuss romantic relationships, life after finance, and whether Sri should be a Civil-War reenactor. 

Gregory is a life and leadership coach who has helped over 170 clients feel alive again. 

Here's Gregory's TEDx talk. 

📌 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 and Gregory Russell Benedikt talk about how to find your true calling and follow through on action. 

They also discuss romantic relationships, life after finance, and whether Sri should be a Civil-War reenactor. 

Gregory is a life and leadership coach who has helped over 170 clients feel alive again. 

💬 Have a question? Shoot us a text!

📌 FEELING STUCK?

LIMITED TIME: 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: @sri_the_warrior_poet + @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 takes the show to Oslo, Norway 🇳🇴, where he and Rachel Wilson Rugelsjøen talk all things culture and leadership through the lens of Human Resources. 

🙉 They have the realest debate on psychological safety you'll find anywhere. 

Plus everyone's favorite topic: cold plunges 🥶

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Rachel is the founder and managing director of LevelUp HR, which "help[s] global corporates, SME’s and scale-up’s achieve, through your most valuable asset - your people."

Her experience spans over 20 years leading human capital at top-tier companies like Bank of America/Merrill Lynch, the Norwegian Oil Fund, Cognizant, and Barclays Capital — where she and Sri overlapped without knowing it! 

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highlights

"The leadership game has changed."

• How founders can build an effective culture
• Role of values in leadership
• Amazon's leadership principles
• Ownership and accountability
• Norwegian vs. UK vs. American perspectives on ownership
• Human nature and leadership challenges
• The evolution of leadership through history
• How to navigate instability 
• Nuances of team dynamics
• Cold showers and dopamine regulation
• Psychological safety: just a buzzword? 
• Trust as the foundation 

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📌 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.

"Your work does not have a voice. You have to share what you're doing." —Jill Avey

Get the results you deserve — not the ones you hope for. Sri and Jill Avey discuss how to lead in complex corporate environments -- in ways that are authentic, moral, yet tangibly rewarding. 

Topics: 

• How to self-promote (in a non-cringy way 😬)
• Gender differences in leadership
• Positive intelligence theory 
• Navigating office politics 
• Networking productively
• How to build confidence
• 'Mental saboteurs' that hinder your progress

Jill is a successful corporate marketing executive formerly at Timberland and Propet USA. She has an MBA from Columbia Business School and is the founder of SisterSmart, which aims to help women succeed in attaining the executive positions they deserve.  

Find Jill here: 

• https://sistersmart.com/
• https://www.linkedin.com/in/jillavey/

keywords: leadership, women in leadership, workplace relationships, radical candor, self-promotion, career development, communication skills, networking, personal branding, professional growth, leadership, courage, fear, positive intelligence, saboteurs, gender differences, women in leadership, self-awareness, emotional intelligence, collaboration

📌 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.