Explore every episode of the podcast The True North Pod

Mike and Dave Wessinger turned a handshake during a 1997 snowstorm into PointClickCare, a $5 billion software company, without ever leaving Canada. 

In this episode of The True North Pod, the brothers break down the exact playbook they used to build a billion-dollar business from Mississauga, Ontario, dominate their market one state at a time, and refuse to move to the US.

This is the founder story most Canadians have never heard: two brothers, four years of nearly missing payroll 36 times in a row, and a disciplined go-to-market strategy that turned a dated, low-tech industry into a category-defining empire.

If you're a founder trying to figure out how to scale a SaaS company, find product-market fit, or build something world-class, this is the tactical breakdown you've been looking for.

→ They bootstrapped with friends-and-family money and almost died making payroll for four years 

→ They used Geoffrey Moore's "Crossing the Chasm" and "Inside the Tornado" as a literal operating manual 

→ They ran the "bowling pin" strategy: win one state completely, then move to the next 

→ They turned away their biggest customers, on purpose, to protect product-market fit 

→ There were years they didn't lose a single deal

 → And they did all of it from Canada

We started The True North Pod to tell the stories of the country's greatest founders and prove to the next generation that you can build a world-class company right here. This one is a masterclass.

🎧 Subscribe for more Canadian founder stories → youtube.com/@TheTrueNorthPod

0:00 The $5 Billion Company Canada Never Talks About

3:24 Build It in Canada, or Move to the US?

8:43 The 1997 Blizzard Handshake That Started It All

13:48 From Reselling Software to Building Their Own

17:25 Almost Dying: 36 Payrolls in a Row

21:08 The Muddy Moose: Where the Team Was Forged

25:18 Fighting Like Brothers (and Why It Worked)

28:54 The People Who Saved the Company

34:01 The Book That Built a $5B Company: Crossing the Chasm

36:55 The Bowling Pin Playbook: Dominating One State at a Time

43:22 Why They Turned Away Their Biggest Customers

48:45 Building the Product + Is SaaS Dead?

52:43 The Silver Tsunami and AI in Healthcare

1:02:30 Handing Over the CEO Chair

1:04:59 Why They Refuse to Leave Canada

1:11:58 The Brothers' Origin + Their Father's Escape from Germany

1:18:43 Their Mom, Sheila, and the Nursing-Home Connection

1:22:34 What Building a $5B Company Really Cost Them

1:26:33 Their Message to Every Canadian Founder

IN THIS EPISODE YOU'LL LEARN 

→ How to find and dominate a beachhead market before scaling (the bowling pin strategy) 

→ Why turning away customers can be the most disciplined growth move you make 

→ How to apply "Crossing the Chasm" to a real go-to-market plan 

→ What bootstrapping a SaaS company through four brutal years actually looks like 

→ Why they grew profitably instead of burning cash to chase growth 

→ Why the Wessingers choose to keep PointClickCare headquartered in Canada 

→ Where AI and the "silver tsunami" are taking healthcare technology next

ABOUT MIKE & DAVE WESSINGER 

Mike and Dave Wessinger are the co-founders of PointClickCare, the leading cloud-based software platform for the long-term and post-acute care industry, serving 27,000+ long-term care providers and 2,800+ hospitals across North America. Dave Wessinger is CEO; Mike Wessinger co-founded PointClickCare and served as its longtime CEO before Dave took over.

ABOUT THE TRUE NORTH POD 

The True North Pod tells the untold stories of Canada's greatest founders, the failures, the near-death moments, and the comebacks, to inspire the next generation of Canadian builders. Hosted by Gregory Foran. 

→ Subscribe: youtube.com/@TheTrueNorthPod] 

→ Follow on LinkedIn: www.linkedin.com/in/gregory-foran/

→ Follow on Instagram: www.instagram.com/thetruenorthpod/

Proud partner of True North Fund 🇨🇦 #TeamTrueNorth

#CanadianFounders #PointClickCare #SaaS #FounderStory #TheTrueNorthPod

What if everything you've been told about WINNING is wrong?

Cathy Priestner Allinger influenced 105+ Olympic medals across 4 countries—more than any coach or leader in history. She took Canada from ZERO gold medals at home to 14 golds and an Olympic record.

Then did it 3 more times: USA, Russia, China. Every time: record-breaking results.

Her secret? An 8-step system for going from good to world-class that works for ANYTHING—building startups, leading teams, dominating your field.

Cathy Priestner Allinger is the architect of Own The Podium. Olympic silver medalist at 19. First Canadian woman to medal in speed skating. First woman in Olympic history to lead sports at Olympic Games.

Her track record: USA 2002 (21 medal increase), Canada 2010 (14 gold medals, Olympic record), Russia 2014 (most gold/total medals), China 2022 (best ever).

In this episode, Cathy reveals:

◼️ The 8-step framework for peak performance (applicable to sports, business, life)◼️ Why "if you want to be the best, you have to have the best" transforms team building◼️ How to identify high-potential people and ruthlessly focus resources on them◼️ The strategic planning system used across 4 Olympic Games◼️ Why declaring goals publicly (even when mocked) creates accountability◼️ Top Secret 2010: The innovation program that gave Canada a competitive advantage◼️ How independent reviews reveal blind spots killing your performance◼️ Why "pretty good" is the enemy of world-class excellence◼️ The mindset shift that took Canada from settling to dominating

Key Lessons - Leadership & High Performance:

- "If you want to be the best, you have to have the best." Look around. Are your people "pretty good"? Not good enough.- "Surround yourself with people better than you." Never be threatened—that's how winning teams are built.- "Say your goal out loud." If you don't know what you want, you can't design a system to achieve it.- "Targeted focus beats trying to do everything." Half will be unhappy. But clear goals demand ruthless prioritization.- "Monitor progress rigorously." Plans without measurement lead to failure. Adjust based on data.

Topics:

00:00 Intro07:00 The Night Before Olympic Silver15:46 The "Is It Worth It?" Moment21:18 Bonnie Blair: "Don't Bother With Her"35:40 Canada's 0 Gold Medal Problem38:04 "We're Going to Own the Podium"44:04 The Crosby Golden Goal46:13 8-STEP FRAMEWORK FOR WINNING47:08 Step 1: Analyze Historical Data54:38 Step 2: Independent Review55:49 Step 3: Identify Opportunities56:55 Step 4: Ruthless Focus59:30 Step 5: Bet on High-Potential People1:05:03 Step 6: Establish Goals Publicly1:06:31 Step 7: Strategic Planning1:13:39 Step 8: Monitor & Adjust1:16:16 Top Secret 2010 Innovation Program1:20:46 Message for Canadians1:29:00 Applying Own The Podium to Business

This episode is part of The True North Pod—telling the real stories of Canadian founders and leaders who are building world-class companies and organizations in Canada. Raw, unfiltered, and real. We need more people building and fewer people complaining.

Subscribe to be part of moving this country forward. 🇨🇦

The True North Podcast:YouTube: https://www.youtube.com/@TheTrueNorthPodSpotify: https://open.spotify.com/show/6VRZwP5JMkzKSjfHsxFcNX?si=ad7eaad8a68543a4Instagram: https://www.instagram.com/thetruenorthpod/TikTok: https://www.tiktok.com/@thetruenorthpodX: https://x.com/TheTrueNorthPod

Gregory Foran:Website: https://foundersnorth.coLinkedIn: https://www.linkedin.com/in/gregory-foran/Instagram: https://www.instagram.com/thegregoryforan/TikTok: https://www.tiktok.com/@thegregoryforan

Backed by True North Fund:Website: https://www.truenorthfund.com/Chris Albinson: https://www.linkedin.com/in/albinson/

How do you build a billion-dollar company in Canada without moving to Silicon Valley?

Jeff Shiner, former CEO of 1Password, proves Canadian tech startups can compete globally. He bootstrapped a $75 password manager app in Toronto into a $6.8 billion cybersecurity business—profitable for 14 years before raising $920 million in venture capital.

With celebrity investors like Ryan Reynolds, Scarlett Johansson, and Robert Downey Jr., and sponsoring Oracle Red Bull Racing in Formula One, Jeff's message is clear: Canadian entrepreneurs don't need to leave Canada to build world-class companies.

This is the ultimate startup founder advice for anyone wondering whether to stay or go.

Under his leadership, the company grew from 20 people in a basement office in Toronto to 1,500 employees and became a global leader in cybersecurity. In this conversation, Jeff breaks down:

◼️ Why every business leader needs to find their tractor

◼️ The dinner conversation that sparked a $6.8B pivot to B2B

◼️ How his dad's table saw taught him everything about leadership

◼️ Why he was hired as CEO without telling anyone for 6 months

◼️ The exact moment he knew they raised money too late

◼️ When to raise venture capital (and when to stay bootstrapped)

◼️ How to scale a startup from 20 to 1,500 employees

◼️ Why "a leader leads" changed his entire approach to management

◼️ His message for young Canadians thinking about leaving

Key Lessons from Jeff:

• "A leader leads" - You don't need a title to lead. If you want to lead, just start leading.

• "Promote the result, not the opportunity" - Promote people who've already done the work, not those hoping to.

• "Build a good product. Support the heck out of your customers." - Jeff's simple formula for success.

• "Find your tractor" - Every leader needs something that takes their mind completely off work.

• "Have a non-financial reason for fundraising" - Know WHY you're raising beyond just the money.

• "Companies are humans" - Every problem a consumer has at home, an employee has at work.

• "Enjoy the ride" - It's not what you accomplish, it's the people you meet and opportunities you get.

• "We have it all in Canada" - Universities, talent, businesses. We just need our folks to know it.

Topics:

00:00 Intro

03:28 Why Every Business Leader Needs to Find Their Tractor

06:27 The Mind-Clearing Power of Building Things

09:25 Epic Sweet Tooth: Jelly Beans & The CEO Who Lives on Candy

17:12 Holding the Board for Dad: Fear, Intimidation, and Love

25:37 The Manager Who Said: "A Leader Leads"

26:11 Six Months as CEO Without the Title

29:48 Promote the Result, Not the Opportunity

33:14 The Lightning Bolt Moment at a Quebec Conference

35:39 Companies Are Humans: The Insight That Changed Everything

44:14 The Problem with Pride: When Bootstrapping Hurts You

47:03 The Non-Financial Reason for Every Fundraise

53:58 Humanizing Big Problems: The Scheiner Approach

56:10 Tailoring Your Message to What Each Person Cares About

59:20 Hire Someone You Want to Work With

1:06:51 The $200M Raise: Making Noise to Attract Talent

1:09:24 Fear, Pride, and Hindsight

1:25:58 Enjoy the Ride: The One Thing He Wishes He Knew in 2012

1:27:49 His Message for Canadians: We Have It All

1:28:38 Stop Thinking You Have to Leave Canada

This episode is part of The True North Podcast—telling the real stories of Canadian founders who are building world-class companies in Canada. Raw, unfiltered, and real.

Subscribe to be part of moving this country forward. 🇨🇦