The Founder Mindset

Leah Sarich interviews Jenn Hunter, Co-Founder of PayShepherd, a contractor management platform for heavy industry. They discuss Jenn's journey into entrepreneurship, the challenges of digitizing workflows in heavy industry, and how PayShepherd has transformed contractor-client interactions. They also touch on the experiences of working in a male-dominated field and the changing landscape for women in heavy industry.

Jenn shares her journey of balancing entrepreneurship and motherhood while prioritizing personal wellness. She discusses transformative changes she implemented, including better nutrition, sleep, and physical movement, which enhanced her productivity and well-being. Jenn also emphasizes fostering a healthy work culture at PayShepherd, highlighting flexibility, team support, and the value of life’s big moments. She explains how the company’s approach positively affects clients and their communities, offering valuable lessons for entrepreneurs and business leaders.

About Jenn Hunter

Jenn Hunter is a Co-Founder of PayShepherd, a contractor management solution that automates contract compliance, resulting in real-time cost reporting, shared accountability, and effective risk management, providing clients with improved operating margins. PayShepherd is ranked #13 in “Forbes 2024 Best 200 Canadian Startup Employers” and “2024 Products That Count” winner in the category of AI & Data.

Jenn's focus is on customer outcomes. She brings deep domain expertise from her background in heavy industry and has navigated every phase of the customer journey, from solutions and delivery to end-user support. Jenn is an EY Entrepreneur Of The Year 2024 finalist, an associate member of the A100, as well as mother to 3 boys under the age of 5.

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Contact Thin Air Labs:

• Website: ThinAirLabs.ca
• LinkedIn: Thin Air Labs
• X: Thin Air Labs
• YouTube: Thin Air Labs

Contact Jenn Hunter:

• Website: payshepherd.com
• Linkedin: Jenn Hunter

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Transcript

Jenn 00:02

It's all personal to me. It's my baby, like I've sacrificed so much personally for this, and this has afforded me so much personally as well. And so the blend to me is just, it's just my time. And you know, whatever is the highest priority in the moment, gets my time.

Leah 00:19

Hi, thanks for being here. And welcome to Season Two of The Founder Mindset, brought to you by ATB. I'm Leah Sarich, your host, and I'm super excited to talk to more founders about the human experience of being an entrepreneur. In this podcast, we're digging into what it really feels like to build a company from nothing. I was a broadcaster for over 20 years. So, I've interviewed thousands of people, but entrepreneurs, not that many, and yet they have the best stories. They're solving big problems, and they're creating an incredible impact. But it is hard work. So, why would they do this? Let's find out.

Leah 01:06

Joining me in studio today is Jenn Hunter, co-founder and director of operations for PayShepherd, a contractor management platform for heavy industry. Hey, Jenn.

Jenn 01:14

Hey, Leah.

Leah 01:16

Thanks so much for doing this.

Jenn 01:17

Of course happy to.

Leah 01:19

So fun to have you in the studio. Let's go right back to the beginning, as we do with all of these conversations, how did you actually get into entrepreneurship?

Jenn 01:27

I wouldn't have thought that I would be an entrepreneur. It definitely wasn't something I thought about growing up. But it wasn't something I was exposed to a lot. But a colleague that I'd worked with for many years had, you know, left the company that we were both at, and he was starting something and he asked if my husband and I wanted to invest. And so I actually got to kick the can without taking a lot of risk. I still had a full-time job, I didn't have to, you know, lose that financial security for my family. But I was able to kind of join the hustle and see what that was like. And it was a really great stepping stone for me to actually take it on full-time, which I would consider kind of the real baby as PayShepherd.

Leah 02:01

Okay, cool. So, you dipped your toe in the water with this first operation? And how did you feel about it? Even from the get-go? What did it feel like to you?

Jenn 02:10

I mean, it felt really natural for me like the hustle, you kind of like picking up the evenings and...

“It’s been 13 years... and the way she talks about the future, the way that she talks about how the opportunity has never been greater, she’s never been more excited... It’s easy to understand why we’d make an investment in a person like this.” —James Lochrie on Orpyx CEO Breanne Everett

In this episode of The Founder Mindset, Dr. Breanne Everett, Founder and CEO of Orpyx, chats with Leah about:

• Why she went from surgeon to entrepreneur
• How she navigated the premature birth of her first child and fundraising at the same time
• Why the opportunity for impact keeps her going through the inevitable challenges

BONUS CONTENT

At the end of the episode, Leah gets reaction to her conversation with Breanne from James Lochrie, Managing Partner of Thin Air Labs which invested in Orpyx.

Learn more about how James deeply admires Breanne’s growth as a leader, her emotional resilience and her drive to create meaningful human impact with her company.

“Through and through, one of the most competitive entrepreneurs that we’ve invested in, and that’s saying a lot because the bar is pretty high for the competitive average for our entrepreneurs, yea this guy, he will not quit.” —James Lochrie on Provision CEO Erik Westblom

• In this episode of The Founder Mindset, Erik Westblom, Co-founder and CEO of Provision, chats with Leah about:
• Why he wants people to really understand the stress of being a founder
• How he thinks about shame as motivation
• Why he’ll always be obsessed with the bank balance

BONUS CONTENT

At the end of the episode, Leah gets reaction to her conversation with Erik from James Lochrie, Managing Partner of Thin Air Labs which invested in Provision.

Hear how James relates to Erik’s candid truths about the impact entrepreneurship can have on families. Find out what James has learned about processing the stress of being a founder, and how that’s helped him become a better investor and mentor to founders like Erik. And hear what led James to offer a rare investment on the spot into Provision.

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“This is a guy, an accidental entrepreneur, with a low risk tolerance - a guy who stumbled into entrepreneurship because someone opened a door for him, and now he talks about it like a north star. He’s got it.” —James Lochrie on ZayZoon CEO Darcy Tuer

In this episode of The Founder Mindset, Darcy Tuer, Co-founder and CEO of ZayZoon, chats with Leah about:

• Why he’s continually drawn to being a founder
• How he thinks about rejection
• What he’s learned from facing several ‘go or no go’ points in his startup journey

BONUS CONTENT

At the end of the episode, Leah gets reaction to her conversation with Darcy from James Lochrie, Managing Partner of Thin Air Labs.

Hear how James deeply respects Darcy’s desire to make a meaningful difference in people’s lives, how he shares Darcy’s low risk tolerance and love of problem-solving as risk mitigation. And learn more about James and Darcy’s love of the Calgary innovation ecosystem.

“She believes in a future we can’t see. She believes in challenging herself and creating autonomy for herself. She wants fulfillment that only she can deliver as an entrepreneur to herself” — James Lochrie on AltaML Co-CEO Nicole Janssen

In this episode of The Founder Mindset, Nicole Janssen, Co-founder and Co-CEO of AltaML chats with Leah about:

• How she was a terrible employee and what she loves about being an entrepreneur
• What it feels like to learn a major investor is pulling out while you’re on your first vacation in years, and what she learned from that experience
• How a life-changing diagnosis has made her a better entrepreneur

BONUS CONTENT

At the end of the episode, Leah gets reaction to her conversation with Nicole from James Lochrie, Managing Partner of Thin Air Labs.

Find out why James thinks Nicole is the ultimate professional, how he deeply admires her ability to create trust with her candor and why he thinks more entrepreneurs should take on a leadership role like Nicole has to educate and inspire stakeholders in their sectors.