What Small Businesses Taught These Founders About Trust, Grit & Tech with Sam Pillar and Forrest Zeisler of Jobber

In this episode of Tank Talks, we’re joined by Sam Pillar and Forrest Zeisler, co-founders of Jobber, a platform that’s changing the way small service businesses operate. Jobber brings everything, quoting, scheduling, invoicing, and payments, into one simple, powerful system, making it easier for service professionals to run and grow their businesses.

Sam and Forrest share how what began as late-night coding sessions and casual coffee shop chats evolved into a company helping thousands of tradespeople work more efficiently and take back control of their time. They talk about the early lessons learned, the importance of staying relentlessly focused on real customer needs, and how they’ve embraced AI to help entrepreneurs future-proof their businesses.

From turning 56-hour workweeks into tasks handled in minutes, to giving business owners the freedom to manage operations from anywhere, even a hospital room or beachside cabana, Jobber is proving that small businesses don’t have to sacrifice their well-being for success.

We explore the big questions:

* Can AI finally give small business owners their "5 to 9" back?

* What happens when you build software by listening, not dictating, to your customers?

* Will AI become the most indispensable "employee" for millions of tradespeople?

The Coffee Shop Origins of Jobber (00:01:43)

* Meeting over code at Remedy Coffee in Edmonton

* Building software to bring order to small business chaos

* Learning from real customers instead of leading with assumptions

The Power of Listening to Small Business Pain Points (00:04:31)

* How a $430 phone bill inspired Jobber's early product

* Focusing on relationship-driven problem discovery

* Why the best solutions come from understanding, not pitching

Early Hustle and Near-Impossible Odds (00:08:19)

* Maxed-out credit cards, mice in the office, and toaster oven hacks

* The role of naive optimism in surviving the startup grind

* Asking parents for investment in an “idea” that wasn’t worth much (yet)

Building Trust with Small Business Owners (00:11:27)

* Overcoming skepticism of the cloud and digital tools

* Why authenticity, empathy, and asking the right questions matter

* The “bullsh*t meter” of tradespeople and how Jobber earned credibility

Impact Stories: Reclaiming the '5 to 9' Life (00:18:24)

* A customer's ability to run his business from a hospital bedside

* Empowering entrepreneurs to pursue dreams, not drown in paperwork

* Emotional success stories from Jobber customers

The 'Gateway Drug' of Entrepreneurship (00:22:02)

* The surprising role of poop scooping businesses

* Why low-barrier industries ignite entrepreneurial ambition

* Jobber’s commitment to serving all small businesses, no matter how niche

Scaling with Purpose: Jobber as the Shopify of Home Services (00:23:43)

* Prioritizing customer stories over founder fame

* Embedding customer obsession into every team and meeting

* How Jobber fosters an internal culture rooted in small business success

The Future of AI for Trades & Small Business (00:26:07)

* AI as a “most trusted employee” for entrepreneurs

* Real-world automation reducing 56-hour tasks to minutes

* Why tradespeople stand to benefit most from AI efficiency

* Building trust before AI can fully run their business

Co-Founder Chemistry & Fun Facts (00:34:16)

* Forrest’s love for right-hand drive sports cars

* Sam’s vintage Mercedes obsession and former bike courier skills

* The role of carpentry, farming, and hands-on hobbies as a founder escapes

As entrepreneurial life splinters under pressure, platforms like Jobber illuminate a better path: one where smart technology and strong relationships meet. They’re not just building software—they’re cultivating trust, reclaiming freedom, and reimagining what it means to succeed in small business. Whether you're buried in paperwork or dreaming of the next simple service, Jobber could be the partner you didn't know you needed.

About Sam Pillar

Co-founder & CEO of Jobber, passionate about empowering small service businesses. Former freelance developer turned tech leader driven to help entrepreneurs succeed.

Connect with Sam Pillar on LinkedIn: https://ca.linkedin.com/in/sampillar

About Forrest Zeisler

Co-founder & CTO of Jobber, software engineer by trade with a deep belief in building practical solutions for real-world problems. Known for his car obsession and mechanical watch collection.

Connect with Forrest Zeisler on LinkedIn :https://ca.linkedin.com/in/forrestzeisler

Visit Jobber Website: https://www.getjobber.com/

Connect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1

Visit the Ripple Ventures website: https://www.rippleventures.com/

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