The SYPE Show

Hosted by SYPE

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Sep 2026

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About the show

Welcome to 'The SYPE Show’. Featuring Saskatchewan Young Professionals and Entrepreneurs as we aim to connect, engage and inspire our business community and listeners. Grab your favourite local beverage and get to know the leaders in Saskatchewan as we deep dive into personal journeys, biggest lessons, current events, hopes and aspirations, etc. Recorded at the Sound Lounge and hosted by SYPE board member, co-founder of Local Companies That Care, and owner of Sik Pics Productions, Chris Sikorsky.

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17 recent

September 14, 2026Episode 449 min

SYPE Show - Season 2, Ep. #4 - Shayla Romanyshyn

We are back from Summer and that means we have another episode for you! This is the SYPE Show, Season 2. And this season has one through-line: SYPE is over 25 years old. Twenty-five years of connecting young professionals and entrepreneurs across Saskatchewan. Twenty-five years of people walking into a room not knowing anyone and walking out with a business partner, a mentor, a friend. Probably a few drinks in between. We are telling that story one conversation at a time. Each guest this season played a different role in building this organization. Some were there at the very beginning. Some kept it alive through the hard years. Some brought the energy that pulled a whole new generation in the door. And our guest this time is one of the longest serving SYPE Board members of all time. She came into the organization at a low point in the Saskatchewan economy, stewarded it through the pandemic, and helped bring it all back as the Events Chair post-COVID before taking over as President to end her tenure. For a total of 8 years, she was at the beating heart of SYPE and you are going to love hearing her story. Shayla Romanyshyn Shayla Romanyshyn is an Investment Director with Equitable, leading Investment Sales across Manitoba and Saskatchewan by helping financial advisors grow their practices through tailored investment and marketing strategies. Backed by a strong background in private equity, venture capital, and advisor development, she is recognized for her relationship-first, people-centered leadership. Beyond her corporate role, Shayla is a dedicated community leader, serving on the SYPE Board for 8 years and earning the 2024 Wanda Hunchak Leadership Award for her outstanding impact. Outside of work, she is passionate about mentorship and enjoys spending time at the lake with her partner Logan and their dog Sadie, fishing through every Prairie season This Season is brought to you by Chartered Asset Management of Canada, iA Private Wealth. Chartered Asset Management is dedicated to tirelessly working for your wealth and your legacy. While they’re proud to support this podcast, please note that the views and opinions shared by the hosts and guests are their own and do not necessarily reflect those of Chartered Asset Management of Canada, iA Private Wealth Inc., or any of their affiliates. iA Private Wealth Inc. is a member of the Canadian Investor Protection Fund and the Canadian Investment Regulatory Organization. iA Private Wealth is a trademark and business name under which iA Private Wealth Inc. operates. And our guest sponsor - Road Coffee - who are on a mission to revolutionize the coffee industry by fostering direct relationships, ensuring fair compensation, and delivering unparalleled quality to your cup. Check them out for your morning brew.

April 23, 2026Episode 31 hr 9 min

SYPE Show - Season 2, Ep. #3 - Kyle Drever

We’re back. It has been a few months since the last episode dropped. Life gets busy. The calendar fills up fast. But the stories did not go anywhere, and this season, the stories are too good to sit on. This is the SYPE Show, Season 2. And this season has one through-line: SYPE is over 25 years old. Twenty-five years of connecting young professionals and entrepreneurs across Saskatchewan. Twenty-five years of people walking into a room not knowing anyone and walking out with a business partner, a mentor, a friend. Probably a few drinks in between. We are telling that story one conversation at a time. Each guest this season played a different role in building this organization. Some were there at the very beginning. Some kept it alive through the hard years. Some brought the energy that pulled a whole new generation in the door. Today’s guest falls squarely in the middle category. He is an engineer. He has an MBA. He now runs enterprise software systems that touch 50,000 healthcare workers across this province. And for four years, from 2015 to 2019, he showed up for SYPE Saskatoon, year after year, as board member, president, and past president. Not because anyone asked him twice. Just because that is who he is. Kyle RJ Drever A transformational leader who bridges the gap between strategy and operational excellence, Kyle brings a rare combination of an MBA’s business acumen and an Engineer's precision to every challenge he tackles. He is a "player-coach" who earns the trust of executive boards and front-line teams alike. Kyle strives to inspire people to rethink what is possible, turning complex, high-pressure transitions into seamless success stories driven by accountability, innovation, and a tireless commitment to the people he serves. This Season is brought to you by Chartered Asset Management of Canada, iA Private Wealth. Chartered Asset Management is dedicated to tirelessly working for your wealth and your legacy. While they’re proud to support this podcast, please note that the views and opinions shared by the hosts and guests are their own and do not necessarily reflect those of Chartered Asset Management of Canada, iA Private Wealth Inc., or any of their affiliates. iA Private Wealth Inc. is a member of the Canadian Investor Protection Fund and the Canadian Investment Regulatory Organization. iA Private Wealth is a trademark and business name under which iA Private Wealth Inc. operates. And our guest sponsor - Road Coffee - who are on a mission to revolutionize the coffee industry by fostering direct relationships, ensuring fair compensation, and delivering unparalleled quality to your cup. Check them out for your morning brew.

November 19, 2025Episode 245 min

SYPE Show - Season 2, Ep. #2 - Mark Smith-Windsor

SYPE Show – Season 2, Episode 2: Mark Smith-Windsor A pillar of the Saskatoon business community as well as our title sponsor for the new season, Mark Smith-Windsor joins us for an engaging conversation on our second episode. You will hear all about his work happening at Chartered Asset Management and how the time he spent with SYPE shaped the foundation for his current career. We also talk about the importance of building real relationships, practicing leadership, and so much more! Whether you’ve been part of SYPE since the beginning or are just now discovering the community, this is a great episode to learn more about how SYPE got going and the importance of building community! Please enjoy the second episode in our latest season, one focused on the history of SYPE over the past 25 years. You will hear episodes from Saskatoon and Regina, we look forward to sharing them with you.

October 31, 2025Episode 146 min

SYPE Show - Season 2, Ep. #1 - Janae Dineo

SYPE Show – Season 2, Episode 1: Janae Dieno From global adventures to financial mastery, Janae Dieno joins us for an in‑depth conversation tracing her journey from member of the Jr. Chamber before it became SYPE in 2002 to entrepreneur and financial advisor with Brightrock Financial. In this episode, she shares behind‑the‑scenes stories from the early days of SYPE, her leadership roles, and the lessons she’s carried forward into her 17+ years in business. We also talk about the importance of youth networks, meaningful connections, and how Saskatchewan’s future is shaped by its young professionals. Whether you’ve been part of SYPE since the beginning or are just now discovering the community, this episode offers inspiration, practical takeaways, and an inspiring look at how one person’s passion helped build something lasting. Please enjoy the first episode in our latest season, one focused on the history of SYPE over the past 25 years. You will hear episodes from Saskatoon and Regina, we look forward to sharing them with you.

October 17, 20251 hr 19 min

SYPE Show - Special Episode - Engaging Local Leaders: Hot Ones w/ Mayor Cynthia Block

Recorded back in April, join us for a special episode of The SYPE Show as Saskatoon President, Jesse Wiebe, is joined by her worship, Mayor Cynthia Block. While proving her mastery of things spicy, Mayor Block answers questions on the state of Saskatoon and what she hopes to accomplish as Saskatoon's First Female Mayor. With plenty of laughs and some special guests, this is an episode you will enjoy! This special episode also marks the beginning of a new season of The SYPE Show with brand new episodes coming soon. In the meantime, enjoy this special episode of The SYPE Show !

March 31, 2025Episode 41 hr 11 min

SYPE Show EP #12 Jason Aebig

Jason Aebig, CEO of the Greater Saskatoon Chamber of Commerce, joins us for an engaging and insightful conversation. In his very first podcast appearance, Jason dives into international trade, buying local, board governance, his journey through business, the Chamber’s role in Saskatoon, partnerships, and supporting SYPE and the next generation of community leaders. This special episode also marks Chris’ final show as host as he graduates from the SYPE Board. Jason’s dynamic background brings thoughtful insights, along with plenty of humuor. As business-savvy as he is playful, he makes this candid conversation both entertaining and informative. Enjoy episode #12 of The SYPE Show !Please enjoy episode #12 of the SYPE Show!

March 22, 2024Episode 21 hr 21 min

SYPE Show EP #11 Joshua MacGowan

Joshua MacGowan joins SYPE for episode #11. Josh is the Founder of Supplement World Canada and talks about launching and growing a supplement brand, expansion into new markets, connecting with community, educating customers on products, as well as adventuring to the Arnold Classic. Josh also breaks down what's contributed to the man he is today, and his thoughts on nature vs nurture. Josh and Chris also recap Swinging with the Stars and their friendly rivalry that brought in nearly $250,000 between the two of them for the Saskatoon City Hospital Foundation. Enjoy this episode on life in business as a young entrepreneur in the supplement industry.

December 21, 2023Episode 21 hr 2 min

SYPE Show EP #10 Alisha Esmail

Founder of Road Coffee, Alisha Esmail is one of the Saskatchewan’s most inspiring entrepreneurs. She shares her origin story, what drives her and her passion to tackle unethical business practices in the coffee industry. She opens up on business challenges, setting big goals, putting ego aside, as well the power of mentors or advisors. Alisha is a SYPE SilverSpades awards winner and reflects on SYPE helping propel her career. Alisha updates us on her international travels, a brand new MCT product line, a documentary in the works, and the exciting launch of Solstice. We discuss scary things, surf, superpowers, and so much more. More than any other episode this show really heats up the further we go, so grab your favourite blend of Road Coffee and turn it up! Special thanks to our show sponsors Road Coffee for keeping us fuelled with ethically sourced, delicious coffee, & Prairie Proud for producing quality casual wear showcasing the beautiful prairies.

November 22, 2023Episode 91 hr 3 min

SYPE Show EP #9 Talitha McCloskey

The SYPE Show second half of Season 1 kicks off with Talitha! Talitha is the co-founder of RaiseHER Co, an inclusive circle of change-makers in Regina designed to connect, support and raise women and girls to become leaders in their communities. She also happens to be the SYPE Regina President, and an absolute force when it comes to building relationships and supporting others. 'Dare to Lead' certified, Talitha addresses heavy topics with grace, and provides insight on how to invite other circles into these conversations for the greatest impact. Talitha shares her journey, a Silver Spades recap, her hopes and dreams for the city of Regina, favourite Halloween candy, the books she is reading and so much more!

June 15, 2023Episode 843 min

SYPE Show EP #8 Megan Douglas

The SYPE Show welcomes Megan Douglas to the club in EP #8 to chat about Saskatchewan's health literacy and resources for a healthy lifestyle. Megan is the Senior Vice President, Chief Brand and Commercialization Officer at Saskatchewan Blue Cross and has strategic oversight of Sales, Product, Marketing, External Relations, Communications, Corporate Social Responsibility and Client Experience. Megan’s leadership experience has spanned Canada, Europe and Asia in the financial services, telecommunications, fast-moving consumer goods, outsourcing, attractions, oil and gas, community development and charitable sectors. Chris & Megan talk healthcare, forging new connections, contributing to community and the race to visiting more countries than your age! Special thanks to our to show sponsors Road Coffee for keeping us fuelled with ethically sourced, delicious coffee, & Prairie Proud for producing quality casual wear, showcasing the beautiful prairies.