The SYPE Show

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

Wed, 22 Apr 2026 21:00:00 -0400

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.

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

Tue, 18 Nov 2025 21:00:00 -0500

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.

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

Fri, 31 Oct 2025 11:00:00 -0400

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.

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

Fri, 17 Oct 2025 08:00:00 -0400

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!

SYPE Show EP #12 Jason Aebig

Mon, 31 Mar 2025 00:34:19 -0400

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!

SYPE Show EP #11 Joshua MacGowan

Fri, 22 Mar 2024 08:00:00 -0400

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.

SYPE Show EP #10 Alisha Esmail

Thu, 21 Dec 2023 06:00:00 -0500

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.

SYPE Show EP #9 Talitha McCloskey

Wed, 22 Nov 2023 07:00:00 -0500

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!

SYPE Show EP #8 Megan Douglas

Thu, 15 Jun 2023 08:00:06 -0400

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.

SYPE Show EP #7 Cynthia Block

Fri, 07 Apr 2023 09:00:13 -0400

Saskatoon City Councillor Cynthia Block joins Chris to answer all the burning questions regarding Saskatoon's potential Downtown Events & Entertainment District (DEED), and what the heart of Saskatoon could look like in the coming years. Cynthia addresses possible funding strategies, timelines, design ideas, inspiration, Bus Rapid Transit, parking questions, and most importantly WHY the DEED is an important part of Saskatoon's future. Cynthia paints a picture and highlights that it's not just an arena, it's a district. We tackle all the hot topics and Cynthia provides everything we need to know about Saskatoon's DEED.

SYPE Show EP #6 Heather Morrison

Fri, 24 Feb 2023 01:01:22 -0500

Public Speaking Coach Heather Morrison of Deliver Your Best deep dives into preparation, performance, and everything it takes to be a confident public speaker, a crucial skill for young professionals and entrepreneurs. Heather shares her journey through theatre and broadcasting, some stumbles, and how she has learned to be okay with being bad when trying new things. She also chats about growing an online audience from scratch, community relationships leading to opportunities, a healthy relationship with nerves, running marathons, and a unique run in with James Corden. Heather is a true Sasky gem with contagious energy you want to bottle up. This episode is a must hear!

SYPE Show EP #5 Kendal Netmaker

Wed, 21 Dec 2022 07:00:53 -0500

Canada's Top 40 under 40, Kendal Netmaker sits down with host Chris Sikorsky and shares his story of poverty to podium. Owner of apparel company Neechie Gear, an Indigenous consultant, and a Public Speaker, Kendal has had success throughout several industries as a young Entrepreneur. In a rare podcast appearance, Kendal opens up about struggles as an indigenous youth, but how hard work paved the way for success in business. Kendal talks about battling through nerves, business challenges, writing his first book, the important of Truth & Reconciliation, setting and attaining goals, the power of your personal story, his experience with the Prime Minister during a trip to Ottawa, and more. Kendal also recalls his big SYPE moment as a 2013 Silver Spades Award Winner!

SYPE Show EP #4 Ashlyn George

Tue, 04 Oct 2022 08:00:54 -0400

Ashlyn George takes SYPE for a TRIP on EP #4 as she shares her passion for the great outdoors and adventure travel. Since graduating from the University of Saskatchewan, Ashlyn has had an incredibly unique journey through business, traveling to over 60 countries, working with huge international brands, and essentially influencing before it was cool. She is an award winning travel writer, photographer, content creator, and speaker, who chooses to make Saskatoon home. Ashlyn's blog, The Lost Girl's Guide to Finding the World, educates and inspires nearly 100,000 engaged followers to seek out adventure. Ashlyn talks tourism industry in Saskatchewan, the value of a blog, and how you have to stand up for yourself and go after what you want.

SYPE Show EP #3 Nykea Behiel

Wed, 08 Jun 2022 08:00:54 -0400

EP #3 of The SYPE Show talks all things branding with Nykea Behiel, Director of Brand at Vendasta, a tech company based right in the heart of Saskatoon, Saskatchewan. Nykea is a brand storyteller and marketer specializing in writing, leadership, and content creation focusing on creativity. Strong branding is crucial now more than ever in the modern world, and Nykea tells us why. Nykea also shares her non-traditional professional journey, the power of doing the thing that scares you to position yourself for growth, and how your story is your superpower.

SYPE Show EP #2 Travis Low

Thu, 24 Feb 2022 17:00:00 -0500

Host Chris Sikrosky sits down to talk biz with Travis Low, a young Saskatchewan entrepreneur and owner of Blue Moose Media, a team of social media educators based in Saskatchewan. Travis has a passion for business and his community and is a former SYPE Silver Spades Entrepreneur of the Year winner. Travis shares stories from his incredibly successful charity fundraiser event ‘Lows In Motion’ that celebrated 10 annual events raising significant amount of awareness and funding for Parkinson’s Canada. Travis also gets into innovative ways to come up with business ideas, travel stories, and what shaped his entrepreneurial journey.

SYPE Show Episode #1 Stephanie Yong

Tue, 08 Feb 2022 16:59:57 -0500

Welcome to the ‘SYPE Show’. SYPE - Saskatchewan Young Professionals and Entrepreneurs, is exactly who we feature as we aim to connect, engage and inspire our business community and listeners. In our inaugural first episode, Stephanie Yong, a local celebrity and a leader in the Saskatoon business community, discusses SYPE's impact on her career, her teachings on design thinking principals, thriving through the pandemic, and current events.