Learn from Canada's top business leaders

Join some of Canada's most successful founders and business leaders to learn how they started and scaled their companies.

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OneEleven HQ, Toronto
November 8, 2022

Welcome to The Peak's Bet On Canada Summit

Bet On Canada is a one-day summit where some of Canada's top business leaders will:

  • Share the most important lessons they have learned building and scaling a business in Canada.
  • Teach the practical strategies and tactics they use to start and scale businesses.
  • Go behind-the-scenes to share their wins and losses.

What to expect

The Bet on Canada Summit is a one day event jam-packed with practical insights, tactics, and lessons from over a dozen top Canadian business leaders and founders, including people building Canada's most promising businesses right now.

  • 16 different keynotes, panels, Q&As, and ignite presentations focused on real-world lessons and insights.
  • Facilitated networking opportunities with some of the country's top business leaders, decisionmakers, and entrepreneurs.
  • Live recording of The Peak Daily podcast followed by an evening social.

Who should come

You should come to Bet On Canada if:

  • You want to learn how to start a new business from people who have done it before.
  • You want to learn how to scale a company from some of the top business leaders in the country.
  • You want practical tactics for operators you can use to grow, hire, sell, and more.
  • You want to learn about raising capital in Canada from top VCs.
  • You want to learn about how to drive innovation inside big companies.

Meet our 2022 speakers

Jason Goldlist

VenueCEO and Co-Founder

Fatima Zaidi

QuillCEO and Founder

Jake Karls

Mid-Day SquaresCo-Founder

Erin Bury

WillfulCEO and Co-Founder

Rob Khazzam

Float CardCEO and Co-Founder

Rachel Zimmer

Entrepreneur FirstPartner and General Manager, Toronto

Mark MacLeod

Former CFO, ShopifyAdvisor, Investor

Mallory Greene

EireneCEO and Founder

Anshul Ruparell

ProperlyCEO and Co-Founder

Dan Park

ClutchCEO

Sheryl Song

RynaCEO and Co-Founder

Lee Silverstone

UMAMA House of FundsCEO

Mohannad El-Barachi

WrkCEO and Co-Founder

Josh Domingues

FlashfoodCEO and Founder

Swish Goswami

SurfCEO and Co-Founder

Yvonne Pilon

WEtech AlliancePresident and CEO

Jesse Abrams

HomewiseCEO and Co-Founder

Mike Pinkus

ConnectCPACEO and Co-Founder

Reuven Gorscht

DeededCEO

Saeid Fard

DimensionalCEO and Founder

Daniel Goldgut

EpilogueCEO and Co-Founder

Tobi Oluwole

ShopifySales Lead

Shawn Qanun

Float CardAccount Executive

Joel Zien

ConnectedManaging Director

Markus Sturm

Tim HortonsSVP & Head of Digital, Loyalty and Consumer Goods

Jonah Midanik

Forum VenturesCOO

Dani Lipkin

TMX GroupDirector, Global Business Development

Emma Stern

Felix HealthCo-Founder and COO

Anthony Lacavera

Serial Entrepreneur, VC, and Founder of Globalive

Braden Dennis

The Canadian Investor PodcastCo-Host

Prashant Matta

Panache VenturesPartner

Eric Leblanc

RBCxDirector, Banking

What they're saying

"Bet on Canada is like an entire semester of business school packed into one day. And considerably less expensive!"

"I've never been to a business event that packs this much concrete information and knowledge into one day. There was literally zero fluff, which was so refreshing."

"I don't know where else you'd go to learn from this number of high-calibre people. The speakers on Bet On Canada are operators at the top of their game. Learning from them was a massive value-add for my career."

Agenda

8:00am - 9:00am

Registration + Networking Breakfast

Join The Peak starting at 8 am for coffee, snacks and networking.

9:00am - 9:30am

All In On Canada

Who understands the challenges and opportunities of scaling a global business in Canada? Jason Goldlist does, and that’s why the CEO’s of Slack, Remote, and Squarespace just placed a big bet on him.

Fresh of raising a $4 million seed round the Venue CEO and TechTO co-founder will make the case why Canada is the best place in the world to build a business …and why sometimes it’s not.

9:30am - 9:40am

Most unsolicited advice is bad advice... except this

We live in a culture of unsolicited advice. Everyone wants to tell you about the right way to do things and how to be successful. Too much advice can be overwhelming and make us feel inadequate.

And at its worst can lead us to a life we don't want. Understanding the psychology of advice can help us decide what paths to take. Saeid Fard, CEO of Dimensional, will dive into the psychology of advice-giving. Why do people offer it up, why do people look for it, and why it matters if the advice is generic and specific.

9:40am - 10:10am

Going All The Way To Solve Canada’s Unicorn Problem

Canada is falling behind. With only about 20 unicorn startups, we the north are punching well below our weight compared to the United States where over 600 startups are valued at over $1 billion.

Prashant Matta Partner, Panache Ventures, and Rachel Zimmer, Partner and General Manager, Entrepreneur First, are confident Canada can and should be a unicorn green field by thinking bigger, acting quicker, and resisting the urge to cash out before reaching their full potential.

10:10am - 10:20am

How and when to leave your stable job

The difference between a startup and a side hustle is how you’re paying rent.

If you want to scale a business, you have to quit your day job and go all in. But how do you know when the time is right in your personal life, your financial life, and your budding business’ life? Daniel Goldgut left his stable job as a corporate lawyer to start Epilogue. He’ll explain how he knew it was the right time to make the jump. If you want to scale a business, you have to quit your day job and go all in. But how do you know when the time is right in your personal life, your financial life, and your budding business’ life? Daniel Goldgut left his stable job as a corporate lawyer to start Epilogue. He’ll explain how he knew it was the right time to make the jump.

10:20am - 10:30am

Break

Take a quick break, stretch your legs, and meet your neighbour.

10:30am - 11:00am

Disrupting a boring industry

As our parents like to say nothing is certain in life but death and taxes. Along the way, you might buy a house, see a doctor for good measure and eventually start planning for death.

Here’s the thing: Each stop in the game of life hasn’t changed much since our parents’ day or even our parents’ parents' day. Let’s be honest when things don’t change, people get comfortable, and comfortable people don’t like competition. Luckily, there’s a new wave of entrepreneurs challenging the way things have always been done in buying a home, seeing a doctor, and even planning for death. Jesse Abrams (Homewise), Mallory Greene (Eirene), and Emma Stern (Felix Health) will share their perspectives on what it takes to disrupt boring, established industries.

11:00am - 11:15am

How to reach the top of Canada's podcast charts

Braden Dennis co-hosts The Canadian Investor Podcast which is Canada's most listened to finance podcast bringing in 2.5 million listens per year.

Braden Dennis co-hosts The Canadian Investor Podcast which is Canada's most listened to finance podcast bringing in 2.5 million listens per year. Braden will share every trick he has learned to grow a podcast that will help you build an audience and personal brand

11:15am - 11:30am

How The Peak grew to 100,000 subscribers in two years

The Peak is Canada’s top business newsletter, reaching over 100,000 readers daily.

CEO Brett Chang will share the playbook that his team used to quickly scale cost efficiently while maintaining an industry-leading 50% open rate.

11:30am - 12:00pm

Hands-on or hands-off: What’s the right way to build an accountability culture?

Can you define your organization’s culture? If not, that’s a problem.

But before a culture is defined, you have to know what type of culture is right for your team. Float’s high-performance accountability culture might be what drives your leadership team or Willful’s work-from-anywhere flexible hours could be the key to recruiting and retaining talent. Hear from the CEOs of both of the companies to inform your corporate culture decisions.

12:00pm - 12:40pm

Lunch + Peak News Trivia

Stick around for lunch (included with your ticket), meet some new people and test your news knowledge with Peak News Trivia hosted by Peak writer Quinn Henderson.

12:40pm - 12:50pm

Bringing Star Power to VC

Adrian Grenier, along with dozens of other household names are investors and believers in Umana...

...a house of funds and family office that focuses on achieving outsized financial returns and positive impact. Investment money may not be as accessible as it was a year ago, but with investors still clamouring for deals and promising “value add” there may be no better value add than a celebrity co-signing your startup. Hear from Umana CEO Lee Silverstone about the ins and outs of raising capital from some of the world’s most recognizable faces.

12:50pm - 1:20pm

The Sales Level Up

A great product? Must have. A healthy pipeline? Need it.

An honest to god connection between the salesperson and the prospect? A challenge. Getting your prospects to fall in love with you and your product takes skill, ingenuity and a lot of heart. Hear the secrets that Fatima Zaidi (Quill Podcasting), Shawn Qanun (Float), and Jonathan Siadat (Shopify) use day in and day out to close deals.

1:20pm - 1:50pm

The Journey from Founder to CEO

Since 1999 Mark MacLeod sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker.

As the CFO of Shopify and Freshbooks, he experienced outright failures, wildly profitable exits, and everything in between. Mark will be sharing the invaluable lessons he learned about what it takes to be a founder and what it takes to be a CEO. Get a peek into life in the C-suite with Mark’s keynote to hear how founders can transition to be effective CEOs, or when they need to replace themselves at the top.

1:50pm - 2:20pm

Outlook: 24 Months Ahead

Fingers crossed we can confidently say the next two years won’t be anything like the past two.

But, what’s in store for the 24 months ahead? We’re once again heading into newly uncertain times that includes an economy faltering in some measures, while remaining strong in others. Jonah Midanik (Forum VC), Dani Lipkin (TMX Group) and Dan Park (Clutch) will share their predictions for what’s ahead for Canadian businesses at home and abroad.

2:20pm - 2:30pm

Break

Take a quick break, stretch your legs, and meet your neighbour.

2:30pm - 3:00pm

Building to Scale and Survive when Everything is on Fire

Scaling a business can sometimes feel like putting out a million little fires all over the place, all at once.

If you don’t have a plan to survive, you won’t. To scale when everything is on fire business leaders need to: Put systems in place and trust them as you scale. Adopt the right mindsets to push through and stay focused. At the Bet on Canada Summit Josh Domingues (Flashfood), Mohannad El-Barachi (Wrk), Sheryl Song (Ryna) will share their actionable tips, strategies and lessons learned to build and scale when it feels like everything is on fire.

3:00pm - 3:25pm

Canada’s Path to Prosperity: Competition Drives Innovation

Anthony Lacavera is fighting to bring competition to Canada’s telecoms.

The founder of Wind Mobile, which became Freedom Mobile, is attempting to buy back the company he founded as part of the proposed Rogers-Shaw merger agreement. He brings the perspective that a lack of competition in Canada is hurting our innovating and prosperity.

3:25pm - 3:55pm

What it takes to raise money at home and abroad

Raising money is a full-time job. Unfortunately, one typically needs a full-time job - running a company - in order to raise money in the first place.

Learn how to manage the fundraising process from start to finish with expert insights from pros who have raised and advised on hundreds of millions of dollars of investor money. Anshul Ruparell (Properly), Reuven Gorscht (Deeded), Mike Pinkus (ConnectCPA) and Yvonne Pillon (Wetech) will dive into the nitty gritty and the picture big picture of everything you need to know about raising money in Canada and abroad.

3:55pm - 4:05pm

How Tim Horton’s is disrupting from within

Believe it or not, one of Canada’s most iconic brands, Tim Horton’s, has embraced innovation.

Learn from Markus Sturm, Senior Vice President of Consumer Goods, Digital and Loyalty at Tim Hortons, about how the company has embraced innovation and is going all in on technology to create personalized and experiential ways to engage with its guests.

4:05pm - 4:30pm

Building a Personal Brand for Success

Swish Goswami has a lot to brag about.

He’s built six high-impact ventures, raised over $5 million from investors including several NBA players, and made deals with Netflix, L’Oreal and Electronic Arts. Here’s the thing, Swish isn’t bragging, he’s building a personal brand, a flywheel of success that allows him to win and win again. Learn Swish’s playbook for personal branding in entrepreneurship at the Bet on Canada fireside chat.

4:30pm - 4:45pm

How To Build Fans Rather Than Customers

Jake Karls has sold over 11 million chocolate bars. He’s sometimes known as “the modern-day Willy Wonka.”

Despite being a fictional character, Willy regularly goes viral. Jake is the real deal, and he goes viral all the time. How? Jake goes hard, approaching his business with unrivalled intensity. Living by the motto Get comfortable being uncomfortable, he throws himself into entertaining and delighting his fans - better known as his customers, partners, vendors and the wider business community. Jake’s Let’s F-ing Go attitude powers his brand and his company. Learn his secrets firsthand at the Bet on Canada Summit.

5:00pm - 5:15pm

The Peak Daily Podcast - Live Recording!

Canada's most listened to daily business podcast is coming to you live to close out The Bet on Canada Summit.

Hear hosts Jay Rosenthal and Brett Change break down the biggest news stories of the day.

5:30pm - 9:00pm

The Commons x Peak Bet on Canada Social

The Commons & The Peak are hosting a social for business + tech leaders, investors and innovators.

If you're looking to make new connections across business & tech, this one's for you. We promise candid connections with ambitious professionals, because that's what The Commons & The Peak are all about. Rsvp to save your spot: https://par.tf/wVRc

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