Between Two Brunettes

Thirty Two Media
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Welcome to Between Two Brunettes, a show dedicated to amplifying Canadian voices. Every other week, we dive into real conversations with entrepreneurs, operators, creators and leaders who are shaping what’s next. From scaling companies and raising capital to relationships, resilience and the moments that changed everything - nothing is off limits. New full-length episodes drop every other Wednesday, with clips and shorts throughout the week. Hit SUBSCRIBE so you never miss a conversation with Canada’s innovators. We hope you enjoy the show!

  1. Oct 21

    Jon Love on Building KingSett, Selling Oxford & Why He’s Betting on Canada

    Jon Love has spent more than four decades building, investing and leading through some of the biggest cycles in Canadian real estate. After rising through Oxford Properties and becoming CEO during one of the industry’s most difficult periods, he helped take the company public and ultimately sold it to OMERS. Then, instead of retiring, he disappeared for six months, came back with a new idea and founded KingSett Capital, which has grown into one of Canada’s leading private real estate investment firms. In this episode, we get into: What Jon learned from growing up around business and the advice from his father that shaped his career How he built credibility at Oxford while being the founder’s son The intensity behind Oxford’s sale to OMERs How he raised KingSett’s first fund and built the original team Why he describes entrepreneurship as a constant “wheel of terror” The investment philosophy behind finding assets that are mispriced, mismanaged or misunderstood Why Jon would rather see people make mistakes than avoid making decisions How he thinks AI will change real estate and white-collar work Why he believes Canada has an opportunity to become a global leader in technology, energy, finance and agriculture What Canada needs to change to attract more investment and build at greater scale How Jon spent years preparing KingSett to survive beyond its founder Why delegating responsibility without giving up authority creates a “toxic” leadership dynamic The case for consensus-driven leadership  Why Jon believes more Canadian business leaders need to speak publicly about the country’s future ___ Between Two Brunettes Youtube: https://www.youtube.com/@betweentwobrunettes Instagram: https://www.instagram.com/betweentwobrunettes Tiktok: https://www.tiktok.com/@betweentwobrunettes LinkedIn: https://www.linkedin.com/company/betweentwobrunettes X: https://x.com/twobrunettespod Samantha Miller Instagram: https://www.instagram.com/samanthaj_miller Tiktok: https://www.tiktok.com/@samanthaj_miller LinkedIn: https://www.linkedin.com/in/samanthamiller111 X: https://x.com/samantha_btbpod Germana Kazazi Instagram: https://www.instagram.com/germanakazazi Tiktok:https://www.tiktok.com/@germanakazazi LinkedIn: https://www.linkedin.com/in/germana-kazazi X: https://x.com/GermanaKazazi Jon Love LinkedIn: https://www.linkedin.com/in/jonlovekingsett KingSett Capital LinkedIn: https://www.linkedin.com/company/kingsett-capital ___ Produced by Thirty Two Media Inc.

  2. Oct 7

    Felix Health’s Rise to $200M+ : Co-Founder Emma Stern on Taking Big Bets

    Emma Stern didn’t set out to become an entrepreneur. After starting her career in investment banking and moving into the startup world, she co-founded Felix Health. Eight years into the journey, Emma joins us to unpack what happens between starting a company and reaching real scale, including the decisions that worked, the expensive ones that didn’t, and the lessons she wishes more founders understood earlier. In this episode, we get into: The uncomfortable conversations every co-founder should have early How one wrong hire can cost a growing company far more than expected Why Felix chose to build healthcare differently instead of simply putting the traditional doctor’s visit online How trust, regulation and patient safety shaped the way Felix grew The thinking behind bringing pharmacy operations in-house and why it became one of their hardest lessons How Felix decides which new healthcare categories are worth entering When data matters, when intuition matters, and why founders need both Why Felix stayed close to profitability while continuing to grow The reason Emma has turned down higher valuations for the right investor How her role changed from operating almost everything herself to leading a large executive team Why Emma still sees Felix as being in the early innings of what it can build in Canadian healthcare ___ Between Two Brunettes Youtube: https://www.youtube.com/@betweentwobrunettes Instagram: https://www.instagram.com/betweentwobrunettes Tiktok: https://www.tiktok.com/@betweentwobrunettes LinkedIn: https://www.linkedin.com/company/betweentwobrunettes X: https://x.com/twobrunettespod Samantha Miller Instagram: https://www.instagram.com/samanthaj_miller Tiktok: https://www.tiktok.com/@samanthaj_miller LinkedIn: https://www.linkedin.com/in/samanthamiller111 X: https://x.com/samantha_btbpod Germana Kazazi Instagram: https://www.instagram.com/germanakazazi Tiktok:https://www.tiktok.com/@germanakazazi LinkedIn: https://www.linkedin.com/in/germana-kazazi X: https://x.com/GermanaKazazi Emma Stern LinkedIn: https://www.linkedin.com/in/emmaainleystern Felix Health LinkedIn: https://www.linkedin.com/company/felixhealthca Instagram: https://www.instagram.com/felixhealthca TikTok: https://www.tiktok.com/@felixhealth ___ Produced by Thirty Two Media Inc.

  3. Sep 24

    What Makes a Founder Investable? Neil Grunberg on Building Companies and Raising Capital

    After helping build AlayaCare, Neil Grunberg crossed to the other side of the table and launched Storytime Capital, an early-stage fund investing in the future of work. In this candid conversation, Neil shares what he has learned from reviewing hundreds of companies each year, and why a compelling pitch is never enough on its own. The conversation explores: Why Storytime won’t write a cheque unless its network can genuinely help the founder The subtle behaviours that reveal co-founder chemistry, coachability and integrity Why Neil believes some entrepreneurs are “playing founder” instead of building real businesses What makes founders stand out Why young parents, siblings and married co-founders can be overlooked strengths The case for building meaningful companies without obsessing over unicorn valuations How founders must learn to relinquish control as their companies grow The lesson Neil hopes to pass on to his three daughters about treating people well It’s an honest look at venture capital from someone who remembers worrying about payroll, product-market fit and whether the next round would come together. ___ Between Two Brunettes Youtube: https://www.youtube.com/@betweentwobrunettes Instagram: https://www.instagram.com/betweentwobrunettes Tiktok: https://www.tiktok.com/@betweentwobrunettes LinkedIn: https://www.linkedin.com/company/betweentwobrunettes X: https://x.com/twobrunettespod Samantha Miller Instagram: https://www.instagram.com/samanthaj_miller Tiktok: https://www.tiktok.com/@samanthaj_miller LinkedIn: https://www.linkedin.com/in/samanthamiller111 X: https://x.com/samantha_btbpod Germana Kazazi Instagram: https://www.instagram.com/germanakazazi Tiktok:https://www.tiktok.com/@germanakazazi LinkedIn: https://www.linkedin.com/in/germana-kazazi X: https://x.com/GermanaKazazi Neil Grunberg LinkedIn: https://www.linkedin.com/in/neilgrunberg Storytime Capital LinkedIn: https://www.linkedin.com/company/storytime-capital X: https://x.com/StorytimeVC ___ Produced by Thirty Two Media Inc.

  4. Sep 2

    Disrupting the Legacy Art World With a DTC Playbook: How Nuria Grew Tacit Collective From a $15K LOC

    Nuria Madrenas started Tacit Collective with a $15,000 personal line of credit and has never raised outside capital since. Seven years and 100+ represented artists later, she still runs it that way, by choice. She discusses: Why moved away from the traditional gallery model to build a direct to consumer art marketplace Only 2% of art sold at auction globally is by women artists, and why that shaped Tacit's entire focus How their team leverages back end sales data to make decisions on representation and artwork Why the middle of the art market is disappearing Her prediction on the coming $83 trillion generational wealth transfer’s impact on the art world Why she's skeptical of fractional ownership and art as an alternative asset class, and the liquidity problem she thinks buyers overlook Running five and a half years of the business solo before hiring her first team member Preparing her team to run without her ahead of her due date ___ Between Two Brunettes Youtube: https://www.youtube.com/@betweentwobrunettes Instagram: https://www.instagram.com/betweentwobrunettes Tiktok: https://www.tiktok.com/@betweentwobrunettes LinkedIn: https://www.linkedin.com/company/betweentwobrunettes X: https://x.com/twobrunettespod Samantha Miller Instagram: https://www.instagram.com/samanthaj_miller Tiktok: https://www.tiktok.com/@samanthaj_miller LinkedIn: https://www.linkedin.com/in/samanthamiller111 X: https://x.com/samantha_btbpod Germana Kazazi Instagram: https://www.instagram.com/germanakazazi Tiktok:https://www.tiktok.com/@germanakazazi LinkedIn: https://www.linkedin.com/in/germana-kazazi X: https://x.com/GermanaKazazi Nuria Madrenas LinkedIn: https://www.linkedin.com/in/nuriamadrenas Instagram: https://www.instagram.com/nmadren Tacit Collective Instagram: https://www.instagram.com/tacitcollective TikTok: https://www.tiktok.com/@tacitcollective LinkedIn: https://www.linkedin.com/company/tacitcollective ___ Produced by Thirty Two Media Inc.

  5. Aug 19

    From Big Law to Bootstrapping: Why Building a Resale Marketplace Was Her Best Career Move

    Devyn Olin left a law career to build Cache, an influencer-led resale marketplace, and has raised exactly one round of outside capital to date. Everything else has come from revenue, starting with $40,000 in gross merchandise value from in-person pop-ups in her first four months, without spending a dollar to acquire a customer. She discusses: Why she walked away from practicing law to build in resale The two existing resale models and where each one breaks down for sellers How pop-ups became her proof of demand Building an app with zero technical background Why Cache runs on a drop model and how she decides which influencers get invited to sell The $1,000 origin of Cache's brand identity and why she sees it as the company's real moat What fundraising for a consumer startup looks like in Canada vs. the US ___ Between Two Brunettes Youtube: https://www.youtube.com/@betweentwobrunettes Instagram: https://www.instagram.com/betweentwobrunettes Tiktok: https://www.tiktok.com/@betweentwobrunettes LinkedIn: https://www.linkedin.com/company/betweentwobrunettes X: https://x.com/twobrunettespod Samantha Miller Instagram: https://www.instagram.com/samanthaj_miller Tiktok: https://www.tiktok.com/@samanthaj_miller LinkedIn: https://www.linkedin.com/in/samanthamiller111 X: https://x.com/samantha_btbpod Germana Kazazi Instagram: https://www.instagram.com/germanakazazi Tiktok:https://www.tiktok.com/@germanakazazi LinkedIn: https://www.linkedin.com/in/germana-kazazi X: https://x.com/GermanaKazazi Devyn Olin LinkedIn: https://www.linkedin.com/in/devyn-olin Instagram: https://www.instagram.com/devynolin Cache Substack: https://cacheinyourcloset.substack.com Instagram: https://www.instagram.com/cacheinyourcloset TikTok: https://www.tiktok.com/@cacheinyourcloset LinkedIn: https://www.linkedin.com/company/cacheinyourcloset ___ Produced by Thirty Two Media Inc.

  6. Jul 30

    Building Clutch: A Story of Grit, Resilience and Return to Profitability

    The used car market in Canada hasn't changed much in decades. Dealers control inventory and buyers have limited options. Steve Seibel (Founder & President) started Clutch believing there had to be a better way. Dan Park (CEO) joined in 2019, fresh from venture capital and Uber, to help him build it. Seven years later, they're running Canada's fastest-growing online used car marketplace. But getting here required navigating one of the most capital-intensive and operationally complex industries you can start: automotive retail. This is a conversation about hitting rock bottom, the hard decisions that followed, and how they built their way back. Together, they discuss: Why starting a used car business was the dumbest first venture Steve could have chosen The partnership dynamic between a founder and an operator: who does what and why it works How strong product-market fit kept them alive through capital shortages and scaling chaos The moment people were "competing like a sport" just to buy a car from Clutch Why investors were terrified of physical retail while Clutch was fundraising Building a real product vs. pure software: why Clutch chose the harder path How much inventory, people, and operational intensity it takes to move that fast Making tough decisions that weren't popular but were right ___ Between Two Brunettes Youtube: https://www.youtube.com/@betweentwobrunettes Instagram: https://www.instagram.com/betweentwobrunettes Tiktok: https://www.tiktok.com/@betweentwobrunettes LinkedIn: https://www.linkedin.com/company/betweentwobrunettes X: https://x.com/twobrunettespod Samantha Miller Instagram: https://www.instagram.com/samanthaj_miller Tiktok: https://www.tiktok.com/@samanthaj_miller LinkedIn: https://www.linkedin.com/in/samanthamiller111 X: https://x.com/samantha_btbpod Germana Kazazi Instagram: https://www.instagram.com/germanakazazi Tiktok:https://www.tiktok.com/@germanakazazi LinkedIn: https://www.linkedin.com/in/germana-kazazi X: https://x.com/GermanaKazazi Dan Park LinkedIn: https://www.linkedin.com/in/danpark1 X: https://x.com/parkdan Steve Seibel LinkedIn: https://www.linkedin.com/in/stephen-seibel-aa800726 X: https://x.com/stephenseibel Clutch Instagram: https://www.instagram.com/clutch.ca LinkedIn: https://www.linkedin.com/company/clutch-canada X: https://x.com/clutchcanada ___ Produced by Thirty Two Media Inc.

  7. Jul 15

    How Tofu Discovered a $96B Fraud Problem by Listening to Customer Feedback

    Jason Zoltak had already pivoted his company once when a strange pattern in customer feedback made him pivot again. Names on resumes didn't match the voices answering the phone. With just three people on the team, he and his co-founder started calling candidates themselves with no caller ID, and what they found led straight into government warnings about state-sponsored fraud targeting hiring teams across North America. Jason is the Co-Founder of Tofu, an AI-native fraud and security platform tackling a $96 billion problem in talent attraction. What started as a marketplace for rerouting rejected job candidates went through two pivots before landing on fraud, and the second one came directly from a signal nobody else was paying attention to. He discusses: The original talent marketplace model, why it was nearly impossible to scale, and his blunt advice to founders considering something similar The full spectrum of fraud his platform catches, from candidates using AI to mass-apply beyond their qualifications to organized state-backed operations like North Korea Why fraud felt like the right category to bet on instead of joining the crowd building more AI recruiting tools His timing rule for pivots and the costs of doing it too late What "blue ocean" means when you're carving out space inside an already saturated market How Tofu landed its seed round by showing traction first, and his view on when founders should actually start fundraising ___ Between Two Brunettes Youtube: https://www.youtube.com/@betweentwobrunettes Instagram: https://www.instagram.com/betweentwobrunettes Tiktok: https://www.tiktok.com/@betweentwobrunettes LinkedIn: https://www.linkedin.com/company/betweentwobrunettes X: https://x.com/twobrunettespod Samantha Miller Instagram: https://www.instagram.com/samanthaj_miller Tiktok: https://www.tiktok.com/@samanthaj_miller LinkedIn: https://www.linkedin.com/in/samanthamiller111 X: https://x.com/samantha_btbpod Germana Kazazi Instagram: https://www.instagram.com/germanakazazi Tiktok:https://www.tiktok.com/@germanakazazi LinkedIn: https://www.linkedin.com/in/germana-kazazi X: https://x.com/GermanaKazazi Jason Zoltak LinkedIn: https://www.linkedin.com/in/jasonzoltak Tofu LinkedIn: https://www.linkedin.com/company/tofu-id X: https://x.com/hiretofu ___ Produced by Thirty Two Media Inc.

  8. Jul 1

    The Operator Behind Wealthsimple's Growth: Brand Bets, Blitz Hiring, and 125 Billion in AUA

    Most financial institutions in Canada built trust the same way: slowly, through branch relationships, decades of presence, and the assumption that people had nowhere else to go. Wealthsimple decided to build it differently, betting on brand and on product experience at a moment when fintech was still trying to prove it could be trusted with people's money. Paul Teshima is Wealthsimple's Chief Commercial and Chief Marketing Officer. He came to the company in 2020, with no background in financial services. What he brought instead was a startup operator's instinct, a gritty approach to growth, and a willingness to figure things out in real time. He has since helped lead Wealthsimple through one of the most aggressive growth periods in Canadian fintech history, from somewhere around 5 to 10 billion in assets when he joined to over 125 billion today, and from under a million clients to nearly four million. This is a conversation about what it takes to build a growth and marketing engine inside a company moving that fast.  He discusses: Selling a company two weeks before Covid hit, and what made him say yes to Wealthsimple Why not coming from financial services turned out to be the point, not the problem The blitz scaling moment in early 2021 when Wealthsimple hit its year-end customer number in 30 days The "bright spots" framework from Made to Stick, and how it shaped decisions when everything was on fire The early brand bet that counterintuitive VC math couldn't easily support, and why it worked How Wealthsimple shifted from spending millions with Facebook and Google to paying customers directly What naive ambition looks like as a real operating value, not just a thing on a wall Wealthsimple Predictions and the case for launching it Recruiting Canadian talent back from San Francisco with ketchup chips and a North Star event Why Canada is the third-largest financial services market in the world, and what that means for what's still possible here ___ Between Two Brunettes Youtube: https://www.youtube.com/@betweentwobrunettes Instagram: https://www.instagram.com/betweentwobrunettes Tiktok: https://www.tiktok.com/@betweentwobrunettes LinkedIn: https://www.linkedin.com/company/betweentwobrunettes X: https://x.com/twobrunettespod Samantha Miller Instagram: https://www.instagram.com/samanthaj_miller Tiktok: https://www.tiktok.com/@samanthaj_miller LinkedIn: https://www.linkedin.com/in/samanthamiller111 X: https://x.com/samantha_btbpod Germana Kazazi Instagram: https://www.instagram.com/germanakazazi Tiktok:https://www.tiktok.com/@germanakazazi LinkedIn: https://www.linkedin.com/in/germana-kazazi X: https://x.com/GermanaKazazi Paul Teshima LinkedIn: https://www.linkedin.com/in/paulteshima X: https://x.com/paulteshima Wealthsimple Instagram: https://www.instagram.com/wealthsimple LinkedIn: linkedin.com/company/wealthsimple X: https://x.com/Wealthsimple ___ Produced by Thirty Two Media Inc.

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About

Welcome to Between Two Brunettes, a show dedicated to amplifying Canadian voices. Every other week, we dive into real conversations with entrepreneurs, operators, creators and leaders who are shaping what’s next. From scaling companies and raising capital to relationships, resilience and the moments that changed everything - nothing is off limits. New full-length episodes drop every other Wednesday, with clips and shorts throughout the week. Hit SUBSCRIBE so you never miss a conversation with Canada’s innovators. We hope you enjoy the show!

Information

  • Creator
    Thirty Two Media
  • Years Active
    2025 - 2026
  • Episodes
    19
  • Rating
    Explicit
  • Copyright
    © 2026 Thirty Two Media Inc.

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