Owners & Experts

CollectiveXP
  • 0.0 (0)
  • Entrepreneurship
  • Weekly

Owners & Experts is a weekly podcast for Canadian business owners running a $5–20M company. Your hosts, John Ling and Victor Wong, spent a decade on the team that built Flipp from nothing to 60 million users and a nine-figure exit. Now, at CollectiveXP, they help Canadian owners scale what comes next. Every week they sit down with an owner, operator or expert who has solved one hard part of growing a business in Canada: marketing and pipeline, hiring and leadership, pricing, AI, operations, or getting out of the day-to-day. You get the specifics, not the highlight reel: what they did, what it cost, what didn’t work, and what you could try on Monday. If you bought your business through ETA, took over the family company, or grew your own past the startup stage, this show is for you. New episodes every Wednesday.

Episodes

  1. 6d ago ·  Video

    Owners & Experts: Ep 4 Jason Cole | Get Sales Out of Your Head

    Is your sales process still in your head? Start a conversation with us → collectivexp.io/podcast Most $5–20M owners are their sales process: the relationships, the follow-up and the forecast all live in their head. Jason Cole ran business development for Schawk, LYFT Visual and Flipp. He explains how to get sales out of your head and into a process you can test. Jason started in operations, as an on-site production manager at SGS, before leadership talked him into sales. Today he runs his own creative production shop, 3 Apples High. John Ling and Jason talk about: • Why business is built on relationships, and why golf and lunches don't turn into sales • Make the NDA your first small win, and watch who signs it • Close the gap between sales and operations: your own team is your first customer • From the production floor to sales: the bet that changed his career • Run a process ten times before you judge it • Work your pipeline math backwards: 20, 40, 60, 80, close • What AI changes in sales, and why you should never go in cold Three things to try this week: 1. Write down what success looks like and where you are today. The gap is your sales plan. 2. Break the path into five steps and run them ten times before you change them. 3. Make your first win small and concrete, like a signed NDA, and notice who signs it. That tells you who actually decides. Disclosure: John and Jason worked together at LYFT Visual and then at Flipp. This episode isn't sponsored. ABOUT OWNERS & EXPERTS We scaled Flipp past $100M US by finding the best person in the market for each hard problem and learning from them. Owners & Experts brings that network to Canadian owners growing a $5–20M business: candid conversations, a new episode every week, from the team at CollectiveXP. CHAPTERS 0:00 Intro 1:21 Business is built on relationships 3:12 How do you get a sales team to care? 4:41 Make the NDA your first small win 7:22 Whoever signs the NDA shows you who decides 8:40 Close the gap between sales and operations 13:14 Your own team is your first customer 15:22 From the production floor to sales 25:10 Sales is a numbers game. Process is how you win it 26:09 When your sales leader stops prospecting 29:43 Run a process ten times before you judge it 31:15 What great sales managers do differently 34:18 Work your pipeline math backwards 35:41 When relationship turns into pressure 40:03 What AI changes in sales 42:35 Never go in cold: three points per prospect 47:01 Your Monday move: define success, then five steps 50:03 What to do this week LINKS Watch on YouTube: youtu.be/xJtTX5Lixfo Jason Cole on LinkedIn: linkedin.com/in/jasonvcole 3 Apples High: 3appleshigh.com CollectiveXP: collectivexp.io

    Owners & Experts: Ep 4 Jason Cole | Get Sales Out of Your Head

  2. Oct 30

    Owners & Experts: Ep 3 John Rebello | Fix the Process Before You Hire

    Quality slipping as demand grows? Start a conversation with us → collectivexp.io/podcast Demand is up, quality is slipping, and the reflex is to hire. John Rebello, former Director of Continuous Improvement at Flipp, explains why that takes about six months to pay off and still doesn't fix the process. He says to build a KPI tree first. John learned continuous improvement on a GM assembly line and later built the continuous-improvement team on a Bombardier aircraft line, where, he says, moving inspections to where problems were caused cut defects by about 75%. Victor Wong and John talk about: • Why adding headcount is a band-aid, and what to check before you open a job posting • Bombardier: find where a problem is caused, not just where it's caught • Why leaders stop at the top-line number, and how KPIs should link up and across teams • When the top number lies: two regions that cancel each other out • 30,000 support tickets, and the team only ever saw 3,000 • The dashboard nobody looks at, and how fast your business really moves • How to build your first KPI tree in 10 minutes Three things to try this week: 1. Before you hire to fix a quality problem, find where it's caught and where it's caused, then move the check upstream. 2. Break revenue into price × volume, then one level further for your business. That's your first KPI tree. 3. Put one scoreboard where every team can see it, and look at it on a set rhythm. Disclosure: Victor and John worked together at Flipp. This episode isn't sponsored. CHAPTERS 0:00 Cold open 0:24 Welcome to Owners & Experts 1:39 Why hiring won't fix your quality problem 3:55 From The Goal to the GM assembly line 7:56 Why fast growth leaves so much to fix 9:13 Bombardier: 1,000 snags per aircraft 16:40 Why leaders stop at the top-line number 20:50 When the top number lies: Arizona vs Ontario 24:27 Your first KPI tree will be wrong 25:26 30,000 tickets, and the team saw 3,000 28:03 The dashboard nobody looks at 31:52 How fast does your business really move? 33:16 Build your first KPI tree in 10 minutes 37:00 Find what changed, then share what you learn 39:28 Give your team a scoreboard LINKS Watch on YouTube: youtu.be/kOAKzkRejlc John Rebello on LinkedIn: linkedin.com/in/johnrebello CollectiveXP: collectivexp.io

    Owners & Experts: Ep 3 John Rebello | Fix the Process Before You Hire

  3. Oct 27

    Why Owners Stall When They Build a Product | Chris Chae, Fractional CPO

    Building a product inside your business, and it's stalling? Start a conversation with us → collectivexp.io/podcast Last episode, Justin Wood told $5–20M owners to just build a product. Chris Chae has spent 15 years building them, and he's watched owners hire engineers, hand them "what to build" a couple of hours a week, and stall. Chris ran product inside a venture studio, ran Sportsbook Review after it was acquired, and led product at Neo Financial. Today he's a fractional chief product officer. In this episode of Owners & Experts he covers: • Why every product person should own a number • Rebuilding an acquired business for a new market: picking a new customer and turning the old community into evangelists • Growing a new line without cannibalizing the core • Why the customers you turn away tell you what to build next • Whether every $5–20M business should build a product • What product is for now that AI has made building cheap • Why owners stall, and when to bring in product help Three things to try this week: 1. Look at the customers you're turning away. They're telling you what to build next. 2. Build something small yourself, even in a tool like Lovable, to learn how product works. 3. If you hire engineers, don't give "what to build" two hours a week. That's where owners stall. Disclosure: Chris and I worked together at Flipp, and he's been advising us at CollectiveXP this year. This episode isn't sponsored. CHAPTERS 0:00 Cold open: just build it? 0:25 Welcome to Owners & Experts 0:54 Every product person should own a number 3:01 Sportsbook Review: rebuilding an acquired business for a new market 6:58 The first big call: pick a new customer 8:02 Turning the old community into evangelists 10:26 Grow without cannibalizing the core 12:39 Neo: adding product lines around the customer 15:20 Listen to the customers you turn away 19:45 Should every $5–20M business build a product? 22:37 AI made building cheap. So what's product for? 26:31 Never touched AI? Start by building 31:04 Where to start: get in the ring 34:55 Why owners stall, and when to bring in product help 39:43 The question owners should ask: what's possible? 42:26 What to do this week LINKS Watch on YouTube: https://youtu.be/1GZQmQ4Iza4 Episode 1, Justin Wood: https://www.collectivexp.io/cxplive/owners-and-experts/justin-wood?utm_source=podcast&utm_medium=shownotes&utm_campaign=owners-experts-ep02 Chris on LinkedIn: https://www.linkedin.com/in/chrischae/ Owners & Experts is a weekly podcast for Canadian business owners growing a $5–20M company, hosted by John Ling and Victor Wong of CollectiveXP, part of the team that built Flipp. CollectiveXP: https://www.collectivexp.io/?utm_source=podcast&utm_medium=shownotes&utm_campaign=owners-experts-ep02

    Why Owners Stall When They Build a Product | Chris Chae, Fractional CPO

  4. Oct 21

    Content Marketing in the Age of AI: Why Your Business Needs a Product | Justin Wood, Produktiv

    Thinking about building a product around what your business knows? Start a conversation with us → collectivexp.io/podcast AI just made your expertise cheaper. So what's left for a $5–20M business? Justin Wood, founder of Produktiv, says it's trust, and that owners should build a product around it. Justin has spent 16 years building marketing engines in-house, at agencies and at startups. He says his own podcast, The Katalog, brought in about 20% of his agency's revenue in one year. We talk about: • Why the $2–5M stage is a "valley of death", and the difference between a business owner and an entrepreneur • How a podcast built his sales pipeline, and why it only works if you're curious rather than selling • The Wealthsimple test: why a $5–20M firm needs a product, and why the product is the marketing • How to tie every dollar of marketing spend to a dollar of revenue • Why "boring" AI is good news for owners Three things to try this week: 1. Write down the five questions clients ask you every week. That's your content, and maybe your first product. 2. Tag every link and QR code so you can tie a dollar spent to a dollar made. 3. Record one real conversation with a client or a peer, and put it out. Disclosure: Justin and I worked together back in his KRFTWRK days, and we've traded notes on our businesses ever since. This episode isn't sponsored. CHAPTERS 0:00 Cold open 0:36 Welcome to Owners & Experts 1:26 The playbook changed: from craftsperson to director 6:03 The $2–5M "valley of death": owner vs entrepreneur 9:45 AI can outthink you. It can't out-trust you 12:18 How a podcast built his pipeline 19:45 Two kinds of owners on AI 27:39 Why a $5–20M firm needs a product 29:49 The product is the marketing (the Wealthsimple test) 32:58 Tie every dollar spent to a dollar made 38:32 Turn the questions you answer every week into a product 41:57 Why "boring" AI is good news 47:30 The fundamentals haven't changed 50:30 Build the audience, then the product 53:17 What to do this week LINKS Watch on YouTube: https://youtu.be/c3fTQK1bs04 Produktiv: https://produktiv.agency/?utm_source=podcast&utm_medium=shownotes&utm_campaign=owners-experts-ep01 Trakt: https://trakt.pro/?utm_source=podcast&utm_medium=shownotes&utm_campaign=owners-experts-ep01 The Katalog (Justin's podcast): https://thekatalog.co/?utm_source=podcast&utm_medium=shownotes&utm_campaign=owners-experts-ep01 Justin on LinkedIn: https://ca.linkedin.com/in/jwoodisgood Owners & Experts is a weekly podcast for Canadian business owners growing a $5–20M company, hosted by John Ling and Victor Wong of CollectiveXP, part of the team that built Flipp. CollectiveXP: https://collectivexp.ai/?utm_source=podcast&utm_medium=shownotes&utm_campaign=owners-experts-ep01

    Content Marketing in the Age of AI: Why Your Business Needs a Product | Justin Wood, Produktiv
  • 4 Episodes

About

Owners & Experts is a weekly podcast for Canadian business owners running a $5–20M company. Your hosts, John Ling and Victor Wong, spent a decade on the team that built Flipp from nothing to 60 million users and a nine-figure exit. Now, at CollectiveXP, they help Canadian owners scale what comes next. Every week they sit down with an owner, operator or expert who has solved one hard part of growing a business in Canada: marketing and pipeline, hiring and leadership, pricing, AI, operations, or getting out of the day-to-day. You get the specifics, not the highlight reel: what they did, what it cost, what didn’t work, and what you could try on Monday. If you bought your business through ETA, took over the family company, or grew your own past the startup stage, this show is for you. New episodes every Wednesday.

Information

  • Creator
    CollectiveXP
  • Years Active
    2026
  • Episodes
    4
  • Rating
    Clean
  • Copyright
    © 2026 CollectiveXP
  • Show Website
    Owners & Experts

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