What does it really take to build a global business, become one of the world's most influential podcasters, and inspire millions of entrepreneurs?

In this episode of How to Make It in Toronto, we explore the incredible journey of Steven Bartlett—entrepreneur, investor, bestselling author, and host of The Diary of a CEO.

From dropping out of university to co-founding Social Chain, launching FlightStory, investing in groundbreaking companies, and building one of the world's most successful business podcasts, Steven's story is a masterclass in resilience, curiosity, and long-term thinking.

In this episode you'll discover:

• How Steven Bartlett got started in business
• Why he chose entrepreneurship over university
• How he built Social Chain into a global company
• The challenges and failures he faced along the way
• How he launched FlightStory and transformed Diary of a CEO into a worldwide phenomenon
• The mindset, habits, books, mentors, and resources that helped him succeed
• Actionable lessons every entrepreneur can apply to their own journey

Whether you're building your first business, growing your personal brand, or searching for inspiration to take the next step, Steven Bartlett's journey proves that success isn't about having all the answers—it's about continuously learning, adapting, and taking action.

🎙 Subscribe to How to Make It in Toronto for more interviews, success stories, and practical strategies from world-class entrepreneurs, innovators, and industry leaders.

Artificial Intelligence is transforming the future of education and careers faster than ever. So how should students and families prepare?

In this episode of How to Make It, returning guest Howard Freedman, financial aid professional and college planning expert, shares powerful insights on how AI is reshaping a student’s academic path, career opportunities, and the college experience.

Howard explains why it's never too early to start planning for college, how families can reduce financial stress, and what students can do today to build a strong foundation for the future.

We also discuss practical strategies to help students manage the emotional pressure of college planning, navigate uncertainty, and make confident decisions about their education.

Whether you're a student, parent, or young professional thinking about higher education, this conversation will give you the tools to plan smarter in a rapidly changing world.

In this episode we cover:

• How AI will impact future careers and college majors
• Why early college planning can save families thousands
• Hidden financial aid opportunities many families miss
• How students can reduce college stress and pressure
• The mindset students need to succeed in an AI-driven future

🎧 Subscribe to How to Make It for conversations with entrepreneurs, leaders, and experts sharing real strategies for success.

In today’s crowded digital world, attention is everywhere — but connection is rare.

In this episode of How to Make it in Toronto, we sit down with John Elbing, Chief Storybuilder Officer and creator of the Storybuilding methodology, to break down how founders and entrepreneurs can build brands that actually connect, convert, and grow.

With experience coaching over 150 startups and companies, John shares why most businesses get storytelling wrong — and how shifting your focus from your story to your customer’s story can completely transform your marketing.

We dive into:

• The 3-step framework every customer goes through before buying
• Why niching down is the fastest way to grow
• The difference between attention vs. real engagement
• Common storytelling mistakes founders make
• How to create messaging that drives emotion, trust, and action

If you’re an entrepreneur, content creator, or business professional looking to stand out in a competitive market, this episode will give you practical tools to refine your message and grow your brand.

🎯 Whether you're building a startup, scaling a business, or growing a personal brand — this conversation will change how you think about marketing.

Connect with John:
Website: standpoint.ch
Linkedin: linkedin.com/in/elbing