Episode 17: Marketing, Community and the Power of Local with Wendy Smith | Like A Bos
EPISODE INFO
In this episode, we’re cutting through the noise. The market might feel unpredictable, but we’re here to make it make sense. With real-world insights, smart strategies, and timely advice, we’re equipping buyers, sellers, and agents with the clarity and confidence they need to move forward.

Jason Friesen
With over 20 years of experience and $2 billion in managed mortgage originations, Jason Friesen is a Managing Partner at Outline Financial. A former senior underwriter, he co-founded Outline to simplify the mortgage process through high-touch customer service. He is also an avid cyclist and philanthropist.
To demystify the legal risks facing buyers, sellers, and agents in today’s real estate market by sharing real-life examples, warning signs, and preventative strategies from an experienced real estate lawyer. Listeners will gain the knowledge to protect their interests, avoid costly mistakes, and approach transactions with greater confidence. Equip consumers with insights on how to spot and prevent fraud, understand the fine print, and safeguard their investment — while giving agents the tools they need to better guide and protect their clients in the current market.
In this episode, we take a look at home staging through the lens of a family-run business. You’ll hear how smart, intentional staging can shape buyer perception, create emotional connection, and help homes sell faster. We’ll dive into real-life transformations, generational takes on design, and where the industry is headed, all while highlighting the unique dynamic of a mother-daughter duo.
This episode explores how a purpose-driven culture, supportive atmosphere, and collaborative leadership can create an environment where agents feel empowered to grow and succeed. Through Patrick Burke’s perspective, listeners will gain practical insights into cultivating an office culture where trust, alignment, and support fuel success through change—demonstrating how the right environment can elevate both individual performance and overall team impact.
Enjoyed the conversation? Follow and subscribe, share this with a colleague who needs a mindset reset, and leave a review to help more listeners find the show.Join us as we explore the defining characteristics of high-performing real estate professionals and uncover why those differences matter to today’s buyers and sellers. Leveraging Dan Elzer’s decades of training expertise, this episode goes behind the scenes to reveal the DNA of top producers. We dive deep into the mindset, leadership, and skill-building required to succeed in today’s market, showing how elite preparation leads to better client outcomes and a more professional industry overall.
This episode explores the partnership between Bosley Real Estate and Trillium West, marking the expansion and bridging the market areas. Listeners will hear the story behind the collaboration, why it was such a natural fit, how it builds on shared values and strengths, and what it means for agents, clients, and the communities they serve. Together, they’ll discuss the why, the what, and the what’s next. A vision anchored in culture, leadership, and purpose-driven growth.
This episode cuts through the noise to reveal what happened in the market this past year, what mattered, what didn’t, and what most people got wrong. With David Fleming’s unfiltered perspective, we break down the key shifts, surprises, and signals shaping both buyers and sellers. Our goal is to give listeners clear, honest insight into where the market stands now and what to watch for next, so they can move forward with confidence (and a little humour).
This episode gives consumers and agents a clear look at what it really takes to invest beyond Toronto, whether in Ontario’s secondary markets or internationally in places like Barbados. It breaks down why people look outside the GTA, how to spot strong opportunities, what changes in the buying process, and the key mistakes to avoid. For consumers, the goal is to build confidence in exploring new markets. For agents, it’s about strengthening their ability to guide clients and evaluate opportunities.
Social media doesn’t build trust by accident, it builds it through intention. In this episode, Anya shares how her approach to social media has evolved over time and why she doesn’t see herself as a “creator” first, but as a trusted REALTOR. By showing up online with authenticity she’s been able to attract the right clients, shape expectations before the first meeting, and cut through the noise in an increasingly crowded space.
Confidence comes from understanding the full picture. This episode provides valuable insight into the home inspection process, helping consumers understand what findings truly matter, what is common, and how inspections can influence their decisions and confidence when buying or selling. At the same time, it supports agents in their role as trusted advisors by offering perspective and language to help guide clients through inspection findings, manage expectations, and navigate with clarity, professionalism, and reassurance.
Estate sales are often emotional and complex, and most people don’t know what to expect until they are in the middle of one. In this episode, Christan sits down with an experienced agent to break down the process, from probate and timing to preparing the home and supporting families through the transition. The goal is to provide clarity, set expectations, and help both consumers and agents understand what it takes to navigate an estate sale with care and confidence.
This episode is designed to give both first-time buyers and real estate professionals a clearer understanding of what’s actually happening in today’s market. It explores how the mindset of first-time buyers is evolving, the common misconceptions and emotional barriers they face, and what a realistic path into home ownership looks like right now. Through real experiences and practical insight, the conversation highlights how buyers can approach the process with more confidence, and how agents can better guide, support, and build trust with this next generation of clients.
Gregory Balian | REALTOR®
Coming from his award-winning background in financial sales, Gregory has seamlessly integrated his ambitious, driven attitude to his blossoming career in real-estate. Attention to detail, strategic negotiation, and a keen understanding of market dynamics are the pillars that underpin his approach to real estate transactions. It’s not just about closing deals; it’s about strategically guiding clients towards informed and impactful investments. He firmly believes that understanding the individual behind the transaction is a necessity in building lasting relationships.
We’re turning the tables and putting our host, Christan Bosley, in the guest seat for conversation about the experiences, challenges, lessons, and values that have shaped her journey. From growing up in a real estate family to leading one of Toronto’s most respected independent brokerages.
We’ll go beyond the title to explore the person behind the Bosley name, what drives her today, and the impact she hopes to have on the people around her.
Because behind every leader is a story, and today, we’re telling hers.
Christan Bosley
President & Broker of Record at Bosley Real Estate
In 2020, Christan took over as President & Broker of Record at Bosley, becoming one of the youngest in her position within the industry. With a passion for creativity and ingenuity, and a commitment to innovation, she’s determined to steer the business in a new direction to ensure the brokerage remains influential in the market, and a top-producing firm—while continuing to develop highly-capable industry professionals.
Canada is full of stories hiding in plain sight. In this episode we uncover the history behind the streets, neighbourhoods, landmarks, and everyday places we often pass without a second thought. More than a history lesson, this conversation explores how understanding the past helps us appreciate where we live and why knowing the story of a place can deepen our sense of connection, community, and home.
Explore the growing impact of generational wealth transfer and what it means for Canadian families, homeowners and the next generation. The conversation will look beyond inheritance to explore how wealth is already being transferred through real estate, down-payment assistance, gifting and estate planning, while addressing the financial, tax and family considerations that come with it.
The goal is to help consumers start better conversations and make more informed decisions, while giving real estate professionals greater insight into the financial and family dynamics that may increasingly influence their clients’ real estate decisions.

JoAnne Martin, CFP®
Co-Founder & Partner at Empowered Path Wealth Planning
As a CERTIFIED FINANCIAL PLANNER® professional and co-founder of Empowered Path Wealth Planning, JoAnne brings both technical expertise and lived experience to guiding individuals through major life transitions. In the financial services industry since 2016, she is known for turning complex topics—like estate planning, corporate finances, and tax strategies—into clear, simple conversations.
In a business built on relationships, standing out isn’t always about marketing more, it can be about making more meaningful connections. This episode explores how our past experiences, personal strengths and community relationships can shape the way we market to build a business and earn trust.
We’ll also look at the value of supporting local, collaborating with other businesses and creating experiences that strengthen the communities we serve.

Wendy Smith
REALTOR®
As a Toronto native, Wendy has an intimate knowledge of Toronto neighbourhoods and welcomes the opportunity to help people find a place to call home in our beautiful, vibrant city. Wendy began her career as a marketing professional at some of the top advertising agencies in Toronto. With over a decade of invaluable corporate experience, Wendy decided to lean into her entrepreneurial roots and launch a business in the printing and design field. After the sale of her business, Wendy followed her long-time passion for real estate and joined the team at Bosley.













