The Real.TO Podcast

We’re three Toronto-based real estate professionals with over 20 years of combined experience in sales, marketing, and homeowner relations. After meeting countless inspiring women in the industry, we created The Real.To Podcast to bring their voices to the mic. Expect real stories, fresh insights, and plenty of laughs. Follow us @thereal.topodcast or email therealtopodcast@gmail.com.

The Real.TO Podcast is a business podcast hosted by Heather, Kaleigh, Kendal, with 22 episodes on record and a Required Pod Score of 80.

Heather, Kaleigh, Kendal hosts The Real.TO Podcast, a business show with 22 episodes published.

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  The Real.TO Podcast

  Switching the Narrative with Riva Finkelstein

  Sep 22, 202646 min

  ️ Episode 18 — Riva Finkelstein, Principal & Founder of Switchboard Strategic CommunicationsShe started in Journalism and found her calling in PR. Riva Finkelstein has spent 15+ years in strategic communications and marketing — building brands and reputations across the development industry, from condo launches to city-building conversations that shape entire neighbourhoods.In this episode of The Rea.TO Podcast, we talk about: Her career path from journalism into PR, and what that shift taught her about storytelling The opportunities and stories she's passionate about and what we need to be talking about. The launch of her own company, Switchboard Strategic CommunicationsRiva has a gift for taking complex real estate and city building stories and making them land — with media, with communities, with the public. If you've ever wondered how a background in journalism becomes a launchpad for a PR career (and eventually your own company), this one's for you.https://www.linkedin.com/in/rivafinkelstein/

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  The Real.TO Podcast

  Foundation First: Homes, Hammers, and Finding Her Fit with Ene Underwood

  Sep 1, 202643 min

  Episode 17 | Ene Underwood, CEO Habitat for Humanity, GTA From strategy consulting to leading one of the GTA's most impactful nonprofits — Ene Underwood's career journey is proof that sometimes the perfect fit finds you when you least expect it. On the the eve of their Women's Build we sat down with Ene, to chat about: ✨ Her path to Habitat — and why it just clicked The many moving pieces that make Habitat's work possible How the organization has evolved to keep pace with a shifting housing market ‍♀️ A first look at our upcoming Women Build — and how you can get involved Whether you already know about Habitat or are hearing about them for the first time, our chat with Ene was both inspiring and educational. Affordable homeownership doesn't happen by accident. It takes vision, adaptability, and people like Ene who show up for the long haul. https://www.linkedin.com/in/eneunderwood/ https://habitatgta.ca/

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  The Real.TO Podcast

  Crepes, Contracts and Courage with Vanessa Oliver

  Aug 18, 202642 min

  Episode 16 | Vanessa Oliver Principal and Broker of Record with Regent Street Commercial Corp. It all started with crepes. Before becoming one of Toronto's most respected voices in commercial real estate, Vanessa Oliver had a very different dream — bringing the art of Parisian crepes to the city. While searching for the perfect restaurant space, she fell in love with retail leasing, and that unexpected detour changed everything. In this episode, we chat with Vanessa Oliver, Principal and Broker of Record with Regent Street Commercial Corp, about: How a search for a restaurant location launched a 15+ year career in restaurant leasing Taking the leap from leasing agent to founding her own boutique brokerage The mindset behind betting on yourself — even when it feels a little scary ❤️ Her passionate charitable work with JDRF and raising over $4 million for juvenile diabetes research Vanessa is proof that the moments we almost talked ourselves out of are often the ones that define us most. This is exactly the kind of conversation Real.TO was built for. https://www.linkedin.com/in/vanessa-oliver-02288427/ Special thanks to our Sponsor: Bratty's LLP in Trust (www.Bratty.com)

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  The Real.TO Podcast

  Leading with the Greatest Capital - People and Purpose featuring Natasha Rubin-Coupland

  Jul 6, 202647 min

  Episode 14 | Natasha Rubin-Coupland | The Real.to Podcast She's shaping how one of Canada's biggest banks shows up for real estate coast to coast — and she's coaching leaders to do the same in their own lives. Natasha Rubin-Coupland leads strategic real estate partnerships across Canada for TD Bank and brings a rare combination of institutional expertise and human-centered leadership to everything she does. As a certified leadership coach, she doesn't just understand the systems — she understands the people inside them. In this episode we cover: 🏦 Her 3 decade career with one of Canada's largest financial institutions. 🧭 What authentic leadership really looks like. 💪 The importance of telling people where you see there value and how investing in yourself is the greatest professional move you can make. Whether you're a real estate professional or someone navigating your own leadership journey — this conversation is sure to leave you inspired and shift the way you think about what's possible. https://www.linkedin.com/in/nrcoupland/ Special Thanks to our Sponsor: Bratty's LLP in Trust //www.bratty.com/

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  The Real.TO Podcast

  People over Profit with Danielle Olivierre

  Jun 15, 202638 min

  She Built a Community and a Career — Our 13th Episode features Danielle Olivierre Danielle is a Real Estate Agent with Royal LePage Signature, Co-Founder of Girlies in the 6ix — a community redefining what it means for women to connect, grow and thrive together. Born and raised in Ireland 🍀, Danielle made the leap to Toronto and never looked back. In this conversation, she shares the real story behind her journey — the wins, the lessons, and the belief systems that have guided her along the way. In this episode we cover: What drove Danielle to get into real estate; The founding story of Girlies in the 6ix and why community is everything; Financial knowledge as a tool for women's independence and power; and Why she puts people over profit — always. 🏡 Her upcoming live event: Buying Her First Property is coming up on June 20th! Details below. Whether you're a first-time buyer, a woman in real estate, or someone who believes that doing business with heart is the only way to do it — you are going to love this conversation. Danielle's Linked In https://www.linkedin.com/in/danielle-olivierre-b15270b1/ Details to her upcoming Event: https://luma.com/f1sn3prd Instagram: @girliesinthe6ix

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