The StartWell Podcast

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Conversations with our members, partners and associates - recorded on campus in downtown Toronto.

  1. The Founder OS - Talent, Culture, and Why Startups Plateau - Joseph Fung

    2D AGO

    The Founder OS - Talent, Culture, and Why Startups Plateau - Joseph Fung

    *Recorded at StartWell - Toronto's campus for corporate meetings & events: https://startwell.co Joseph Fung is a 5x founder and CEO with a simple obsession - building places where great people can do their best work. In this conversation, Joseph walks through the real arc of entrepreneurship: bootstrapping companies to the brink, learning how exits actually happen, and why the hardest part isn’t 0-to-1 - it’s building something with longevity. We dig into his journey from an early white-label CMS business (built while in engineering at Waterloo) to TribeHR’s acquisition, and the lessons he learned inside a much bigger machine afterward. Then we get into the messy reality of workforce development and talent - why most companies underinvest in employee growth, why “culture” only matters if it speeds up decisions under stress, and why software companies live or die by alignment and knowledge transfer. We also unpack Uvaro’s pivot from tooling to outcomes, the challenge of government procurement cycles, and how 2025’s macro uncertainty created a sudden squeeze between banks and delayed contracts. And yes - after shutting down a 60+ person company, Joseph went to China for two months of Shaolin-area kung fu training to reset his body, his mind, and his relationship with productivity.

    1h 7m
  2. How Sherpa Built the Infrastructure Behind Global Travel - Max Tremaine

    4D AGO

    How Sherpa Built the Infrastructure Behind Global Travel - Max Tremaine

    *Recorded at StartWell - Toronto's campus for corporate meetings & events: https://startwell.co Max Tremaine is the cofounder and CEO of Sherpa - the travel infrastructure company helping millions of travellers every week understand what they need to cross borders, apply for eVisas as an add-on inside travel bookings, and validate documents for airlines and travel operators. In this conversation on the StartWell Podcast, Max breaks down how a painful personal travel problem turned into a global B2B platform - and why the travel world is shifting from “visa-free” to “pre-clearance everywhere” (eVisas, ETAs, and arrival systems). We also dig into the COVID-era inflection point that helped Sherpa scale from a couple airline integrations to dozens, the realities of selling into airlines and travel ecosystems, and why “hiring a bunch of people” is rarely the shortcut founders think it is. We also get practical about AI - not as hype, but as a real operational advantage. Max shares how Sherpa uses LLMs to spot changes in government systems earlier and reduce response times from weeks to hours, while still keeping humans accountable for architecture and trade-offs.

    58 min
  3. Public Policy for Founders - A Conversation with Morva Rohani

    MAR 4

    Public Policy for Founders - A Conversation with Morva Rohani

    In this StartWell Podcast episode, lobbyist Morva Rohani breaks down public policy for founders, the reality of regulation in Canada, and why understanding government priorities can become a competitive advantage.

    55 min
  4. Why Big Law Is Broken - And How Goodlawyer Is Fixing It

    MAR 2

    Why Big Law Is Broken - And How Goodlawyer Is Fixing It

    Goodlawyer CEO Brett Colvin explains why Big Law incentives are broken, how fractional general counsel works, and how scaling companies can modernize legal support with embedded in-house talent.

    1h 6m
  5. Why Founders Hate Sales (and Why It’s Usually Not a Sales Problem) - Collin Stewart

    FEB 26

    Why Founders Hate Sales (and Why It’s Usually Not a Sales Problem) - Collin Stewart

    Collin Stewart has spent the last decade-plus helping founders find customers - but in this conversation, he’s not selling tactics. He’s selling sequence. We talk about Collin’s book, The Terrifying Art of Finding Customers, and why he wrote it in the first place: he didn’t want to regurgitate another “sales development playbook.” Instead, he wanted to name the part founders don’t want to face - that the hardest, most terrifying work isn’t outreach. It’s discovering whether a real, urgent, expensive pain actually exists in the market. Collin shares the classic founder failure mode in one phrase: “show up and throw up” - demoing everything you built before you’ve earned the right to talk about solutions. He learned this the hard way building Voltage CRM: plenty of people told him the idea was “cool,” then none of them would pay. That mistake becomes the foundation for the book’s thesis: the deeper the pain and dissatisfaction you uncover, the easier selling becomes downstream. Then comes the proof point that reframed everything for him: product-market fit strength is a multiplier. Collin tells the story of running campaigns for Uber and seeing performance so extreme it couldn’t be explained by tactics alone - it was demand. From there, we explore product-market fit as a spectrum (not a checkbox), and how founders confuse product-customer fit with product-market fit - finding “Bob,” the one buyer who loves you, instead of a market that needs you. We finish with practical selling discipline (buyer-verified pipeline stages, MEDDICC-style qualification), plus where AI actually helps today: research, signals, and internal enablement - not mass-generated messaging.

    1h 19m
  6. Why Leaders Need a “Third Space” - Christine Song on Building 5 to 9 Society

    FEB 19

    Why Leaders Need a “Third Space” - Christine Song on Building 5 to 9 Society

    What if “networking” is broken - and leadership is lonelier than we admit? In this episode, Christine Song (Founder, 529 Society) breaks down why big conference rooms and name tags don’t create real relationships - and why she believes leaders need a third space outside of work to talk honestly, pressure-test decisions, and build trust without politics. Christine shares how a single LinkedIn post led to 600 applicants in 30 days, why she chose to keep 529 Society intentionally small (and vetted), and how she designs intimate, high-trust dinners and operator-founder-investor cohorts across Canada. We also dig into what founders often miss when they only spend time with other founders, how “character” becomes a business advantage, and why IRL connection is becoming more valuable as online trust erodes. If you’re a founder, exec, operator, investor, or builder who’s tired of performative networking and wants a more real peer network - this one will land and you'll probably want to join her community.

    1h 21m
  7. Smart Girl, Dumb Questions: Why Curiosity is Important for Podcasters - with Nayeema Raza

    FEB 19

    Smart Girl, Dumb Questions: Why Curiosity is Important for Podcasters - with Nayeema Raza

    Nayeema Raza believes that success comes from embracing authentic curiosity rather than chasing algorithms. For this episode of the StartWell Podcast, Nayeema joined us in studio in Toronto to discuss her lens on hosting her own show (Smart Girl, Dumb Questions), and what the modern media landscape looks like from her perspective as a journalist, filmmaker and podcaster.

    1h 19m
  8. PR vs Marketing: How Founders Really Build Trust in 2026 – with Katie Zeppieri

    11/20/2025

    PR vs Marketing: How Founders Really Build Trust in 2026 – with Katie Zeppieri

    In this episode, Qasim sits down with Katie Zeppieri, founder and CEO of The Mic Drop Agency, a PR and marketing firm working with venture-backed tech startups, reality TV talent and authors across North America. From her new base in Austin, Katie helps founders and executive teams tell their stories, earn trust, and grow faster. The conversation starts by untangling a common misconception: PR is not a guaranteed lead machine. Katie positions PR clearly in the brand awareness and reputation bucket. One launch or one media hit won’t move the needle on its own. Instead, PR is about showing up consistently in the right places so your market becomes familiar with you—and that familiarity compounds into trust. AI has changed the game too. Drafting a press release or basic content can now be done with tools like ChatGPT, but that only gets you part of the way. The real value of an agency lies in strategy and execution: crafting the right angle, timing the announcement, pre-pitching journalists, and tying earned coverage into broader marketing and paid efforts. Katie also talks about the rise of founders as media channels. People often discover a company through its leaders first, so she walks through how to choose your thought-leadership pillars and pick formats that suit you—whether that’s video, newsletters, op-eds, or podcasts. Through a case study with insurtech entrepreneur James Benham, Katie shows how long-term PR, speaking, and owned content can help a founder successfully enter a new vertical and become a recognized authority. The episode closes on a powerful theme: treat content as a sales and relationship engine, not just a broadcast. Repurpose every shoot, test formats using data, and think like an investor about where your time and marketing dollars go.

    43 min
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About

Conversations with our members, partners and associates - recorded on campus in downtown Toronto.

Information

  • Creator
    StartWell
  • Years Active
    2018 - 2026
  • Episodes
    77
  • Rating
    Clean
  • Copyright
    © 2021 StartWell Holdings Inc.
  • Show Website
    The StartWell Podcast