The True North Pod

How do you raise $2 billion and build a $5 billion company in Canada without moving to Silicon Valley?

Jack Newton and Rian Gauvreau, co-founders of Clio, built the world's leading legal technology company from Burnaby, BC.

Today Clio is valued at $5 billion, serves over 400,000 legal professionals across 130+ countries, and has raised more than $2 billion in venture capital. They never left Canada.

They launched in 2008, in the worst financial crisis in 80 years, pitched more than 100 investors, and heard a wall of no's. And a $1 million email that saved the company sat unread in their spam folder.

Eighteen years later, they closed the largest Canadian tech financing on record and the largest acquisition in legal tech history.

Their story proves Canadian founders don't need to leave Canada to build world-class companies.

Jack Newton is the CEO and co-founder of Clio. Rian Gauvreau co-founded Clio, served as COO and Chief People Officer, and is now founder and CEO of Aeon Health. The two have been best friends since growing up together in Edmonton.

In this episode of The True North Pod, Jack and Rian break down:

■ Why their first investor's $1M email sat unread in the spam folder for two weeks
■ The "lifestyle business" plan that accidentally became a $5 billion company
■ Why they swore off venture capital entirely, and what changed their minds
■ What happened inside Clio the week Anthropic entered legal tech
■ The $1 billion acquisition bet Jack made a year before the AI panic hit
■ The four steps to product-market fit that most founders skip
■ Why Rian modeled Clio's customer service on a shoe company
■ The predatory term sheets that would have killed Clio
■ The trip to Barcelona that changed how Jack runs the company
■ Their answer to founders who say you can't raise capital in Canada

Topics:

00:00 Intro
03:53 Welcome to Clio HQ: Would You Build It Here Today?
07:52 Can You Raise Venture Capital in Canada?
10:07 Canadian Term Sheets at 50% of US Valuations
14:05 Making Canada the Most Obvious Place to Build
16:57 "Capital Will Find You": Advice for Founders Who Can't Raise
20:50 Two Kids From Edmonton: Snow Shoveling, LAN Parties, First Businesses
24:34 Newton Gauvreau Aerospace: The Company That Never Existed
27:08 The $100K Lifestyle Business That Became $5 Billion
32:02 Anthropic Enters Legal Tech: The Week Thomson Reuters Dropped 16%
32:20 The $1 Billion vLex Bet: A Billion Legal Documents as the Moat
34:06 Why Doesn't Claude Eat Clio's Lunch?
35:48 Competing With Thomson Reuters and LexisNexis
40:16 Will AI Eliminate Legal Jobs? The Accountant Parallel
43:58 Steve Blank's Four Steps to the Epiphany
45:03 Why Most Companies Jump Straight to Step Four
49:37 Education as Go-to-Market: Building a Movement Around Clio
51:59 Sell Work, Not Software: The $1 Trillion Market
55:09 The Zappos Playbook: Fixing Legal Software's Customer Service
59:24 Why Lawyers Turned Out to Be Incredible Customers
1:03:18 2008: Pitching 100+ Investors in the Financial Crisis
1:06:18 The $1M Email in the Spam Folder
1:08:33 "The First Million Is the Hardest": The $900M Series F
1:10:44 Swearing Off VCs: 37signals, Bootstrapping, and the Decision to Swing Big
1:15:12 Bootstrapping Is Just Rate Limiting Your Growth
1:17:05 The Sagrada Família: When the Founder Becomes the Bottleneck
1:22:08 "Of Course You Are": Rian's Answer
1:23:31 What Actually Has to Change in Canada
1:28:51 "You're Wrong": The Final Question
1:30:29 A Message for Canadian Founders

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.

We need more people building and less people complaining.

Follow the show to be part of moving this country forward.

How do you build a $5.2 billion company from Waterloo, Ontario, when Silicon Valley keeps asking you to leave?

Marcelo Cortes, co-founder and CTO of Faire, said no every time. He landed in Canada from Brazil in 2001 with enough money for one month of English school, worked two full-time jobs while earning his degree at the University of Waterloo, and helped build Cash App at Jack Dorsey's Square—then walked away from the equity to start Faire.

When Square offered him the job and asked when he could move to San Francisco, he told them he was staying in Waterloo. Faire is now a $5.2 billion wholesale marketplace with hundreds of thousands of retailers, and its engineering team was built in Canada from day one.

This is the ultimate founder playbook for anyone trying to find product-market fit when customers hate what you're selling.

Marcelo Cortes is the co-founder and CTO of Faire. Before Faire, he was an engineer at Google and one of the small team at Square that built Cash App. He has lived in Waterloo, Ontario since 2005.

In this conversation, Marcelo breaks down:

■ The word he banned from Faire—and why retailers wouldn't even talk to them until it was gone

■ Four days at a New York trade show that produced $3,500 in sales

■ How Try Before You Buy unlocked 200% month-over-month growth

■ Why growing that fast almost killed the company

■ The board meeting they moved so investors wouldn't see the office

■ Why no Canadian investor would back Faire for years

■ What he actually thinks about the SaaS apocalypse

■ How an engineer's job changes when AI writes the code

■ Why he turned down Silicon Valley more than once

■ His answer to whether he'd still build it in Canada in 2026

Key Lessons from Marcelo:

- "Why would I compromise on that?" - He had the life he wanted in Canada. No job offer was worth trading it.

- "I am the curator of my store. No computer is going to tell me what my customers want." - The customer objection that rebuilt Faire's entire product.

- "As a founding team, you need complementary skills." - Two engineers is not a founding team.

- "You need to build something that people are telling other people about." - Press is not product-market fit.

- "Believe in yourself. Believe in the country." - His message to Canadian founders.

Topics:

00:00 Intro

03:18 The State of Canadian Entrepreneurship in 2026

05:26 Would You Build It in Canada or the US?

07:03 Growing Up Outside São Paulo: The Video Rental Store

08:47 The Intel 286 That Changed His Life

12:05 Landing in Canada With One Month of English School

13:39 Meeting Adrienne

20:01 Quitting Google Less Than Two Years In

21:27 Why His First Startup Failed

23:12 The Partner Who Made It Possible

24:59 Why He Took a Job at Square Instead

27:28 "When Can You Move to San Francisco?"

29:57 Building Cash App at Jack Dorsey's Square

33:51 The Venmo Problem and the 1% Fee That Fixed It

36:32 The WhatsApp Message That Became Faire

38:17 Applying to Y Combinator on the Last Day

44:19 Why He Built Faire's Engineering Team in Waterloo

45:47 996 and Worse: The Intensity It Took

47:26 Faire's First Trade Show: Four Days, $3,500

50:46 Try Before You Buy: The Full Playbook

56:43 Founder-Market Empathy Beats Data

58:13 Brute Force, Brand Backlash, and Doubt

1:01:06 Losing 50 Cents on Every Dollar

1:03:55 Is the SaaS Apocalypse Real?

1:05:55 How an Engineer's Job Changes When AI Writes the Code

1:09:07 What AI Actually Changes in Retail

1:10:58 Building for People Like His Parents

1:15:18 "Why Are You Leaving?" The Cost of Building

1:17:33 Do You Regret the Time You Missed?

1:20:05 Why No Canadian Investor Would Back Faire

1:21:32 His Message for Canadian Founders

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. We need more people building and fewer people complaining.

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

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. 🇨🇦