Serial Entrepreneur: When Someone Tells You Your Energy Is Bringing Them Down | Soul Toll S1E5

DON'T HIRE SAD PEOPLE

It sounds harsh until you sit with it. You can't change what's heavy in someone else's life. It's not your job to. And the people you build with, work with, live with — their energy ends up shaping yours, and yours shapes theirs. So who are you bringing close, and what are you bringing into the room when you walk in?

If you've been thinking about the energy you bring, and the energy you're surrounded by, this is the conversation.

ABOUT THE EPISODE

In this episode of Soul Toll, host Anusia Gillespie sits down with serial entrepreneur Tivan Amour for a conversation about a philosophy he built a company on — don't hire sad people — and what happened when he had to apply it to himself.

Tivan and his co-founder once had a stretch of bad hires. When they looked closely at the pattern, the people they were letting go all had something heavy outside of work pulling them down. They couldn't fix it, and they realized it wasn't theirs to fix. That insight became a philosophy. They got intentional about who they brought close, and the business got stronger. Tivan walks Anusia through how he holds it now, how he interviews for it, and why he thinks every interaction is a chance to set the tone rather than inherit one.

Then the conversation turns. A few of his closest pickleball partners told him his energy was bringing them down on the court. He could have shrugged it off. Instead he started walking onto the court with intention, deciding to be a nine before he opened the gate. He started winning more. And he started to see that no matter how steady you are on average, you can be the heavy one in any given room and a philosophy is only as good as the rooms you carry it into.

ABOUT THE GUEST

Tivan Amour is a serial entrepreneur who has spent his career founding and scaling companies across manufacturing, e-commerce, real estate, and B2B software. He sold his last startup to a $2B company, where he built and led a global sales and support team of more than 140. He now serves as Founder and CEO of Upwind, a sales growth firm helping companies accelerate revenue through better outreach, stronger systems, and smarter execution. Outside of work, he spends time with his family, plays pickleball, and kiteboards.

Learn more about Upwind: https://upwindcompanies.com/

CHAPTERS

[00:00] Don't Hire Sad People

[01:04] Lifestyle design as the frame

[03:35] Why the philosophy works

[05:09] The hires we had to let go

[06:36] How do you interview for it

[10:02] The word people flinch at

[12:01] The conversation with my wife

[13:11] What raising money actually costs

[15:16] Turning 40 and chasing 30

[17:43] I wonder how sad people sleep

[18:55] When you don't get to choose who's around you

[19:50] Southern hospitality and what gets mirrored back

[22:27] The pickleball partners who told me

[25:00] The energy it takes to build something

[26:30] You can be the heavy one at any moment

[28:00] My version of gratitude

[29:25] Everything is a game

[31:20] How much control we actually have

[32:34] Stop trying to change them

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CONNECT

Website: https://soul-toll.com

Instagram: https://instagram.com/anusiagillespie

LinkedIn: https://linkedin.com/in/anusiagillespie

Facebook: https://facebook.com/anusia.gillespie.5

Business inquiries: hello@soul-toll.com

READ THE BOOK

Soul Toll by Anusia Gillespie: https://www.amazon.com/Soul-Toll-Anusia-Gillespie/dp/B0FN9PSS2N

PRODUCTION

Director: Michael Dynice Writers and Producers: Anusia Gillespie, Lady Unicorn Executive Producers: Johnny Ray, Richard Messinger Lighting and Scenic Design: We Roadie and Grip Inc. Post Production and Editing: Streamography Produced for Warwick TV at Johnny Ray's Music Emporium

WITH SPECIAL THANKS

Eat Well Kitchen of Marblehead Johnny Ray's Music Emporium We Roadie and Grip Inc. Chic Streets Mabel of Marblehead The Yoga Loft Marblehead Ghislain Viau of Creative Publishing Book Design

#SoulToll #TivanAmour #Energy #Entrepreneurship #LifestyleDesign #Upwind #Founders #IntentionalLiving #Pickleball #MindsetShift #AnusiaGillespie

In the season one premiere, Anusia Gillespie talks with Scott Westfahl, Harvard Law School Faculty Director of Executive Education, about conviction, courage, and the cost of ignoring what you see wrong.

DROP ANCHOR

There's something important bothering you. Something you feel strongly about and want to change. But something is in your way. This episode is about what happens when you stop waiting and drop anchor in what you actually believe.

If you've been carrying something you want to fix, this is the conversation that gives you permission to start.

ABOUT THE EPISODE

In the season one premiere of Soul Toll, host Anusia Gillespie sits down with her longtime mentor and friend Scott Westfahl, a Harvard expert in leadership development and Faculty Director of Harvard Law School Executive Education, for a conversation about conviction, courage, and the cost of ignoring what you see wrong.

Scott has spent his career closing the leadership gap in law, training the most influential leaders in the profession. In this episode, he walks Anusia through the inflection points of a career — what someone is really thinking at the start, in the middle, and as a seasoned executive — and what universally separates the people who follow their conviction from the ones who keep it on the periphery.

ABOUT THE GUEST

Scott Westfahl is a world-renowned expert in leadership development. He is a Professor of Practice at Harvard Law School and Faculty Director of Harvard Law School Executive Education, where he designs and leads programs for senior leaders across law firms, in-house legal departments, and government. His work has shaped how the legal profession thinks about leadership, talent, and the long arc of a career.

Scott's Book Recommendation

Four Thousand Weeks: Time Management for Mortals by Oliver Burkeman

https://www.amazon.com/Four-Thousand-Weeks-Management-Mortals/dp/0374159122

In this episode, you'll learn:

• What conviction looks like
• How we lose our own compass
• The cost of maximizing productivity
• The achieving brain vs. the awakened brain
• When extrinsic success swallows the intrinsic
• Why the change you keep trying to make at work isn't landing
• What we're really avoiding when we stop reflecting
• Conviction at the start, the middle, and the senior arc of a career
• What success looks like when you finally stop to look
• What to start, what to stop

Follow Soul Toll on your favorite podcast app for new episodes weekly.

CONNECT

Website: https://soul-toll.com

Instagram: https://instagram.com/anusiagillespie

LinkedIn: https://linkedin.com/in/anusiagillespie

Facebook: https://facebook.com/anusia.gillespie.5

Business inquiries: hello@soul-toll.com

PRODUCTION

Director: Michael Dynice

Writers and Producers: Anusia Gillespie, Lady Unicorn

Executive Producers: Johnny Ray, Richard Messinger

Lighting and Scenic Design: We Roadie and Grip Inc.

Post Production and Editing: Streamography

Produced for Warwick TV at Johnny Ray's Music Emporium

WITH SPECIAL THANKS

Johnny Ray's Music Emporium

We Roadie and Grip Inc.

Chic Streets

Eat Well Kitchen

Mabel of Marblehead

The Yoga Loft Marblehead

Creative Publishing Book Design

READ THE BOOK

Soul Toll by Anusia Gillespie: https://www.amazon.com/Soul-Toll-Anusia-Gillespie/dp/B0FN9PSS2N

Tags: Soul Toll, Scott Westfahl, leadership, Harvard Law, executive education, mentorship, career, personal leadership