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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