The Hard Part with Evan McCann

Neha Khera is a General Partner at 2048 Ventures, known for her focus on early-stage investments. She shares insights from her journey, including her foundation in engineering at the University of Waterloo. Neha discusses being an early investor in Mejuri and contrasts Canadian and American startup cultures, highlighting the need for diversity in venture capital. She emphasizes the importance of research and team dynamics in investment decisions, alongside the challenges of being an emerging manager in a fast-paced tech landscape.

Kaylee Astle, Founder and CEO of Blanka, discusses her background and learnings at Deloitte, SAP, MobSquad, and Spocket. She shares insights on building for the Shopify App Store and the potential of platform businesses. Kaylee explains why they chose to be more vertically integrated with Blanka and how the beauty industry is evolving. She also discusses the shift in strategy from bootstrapping to raising capital and the importance of building a strong network of founder friends.

Elizabeth Yin is the Co-Founder and General Partner of Hustle Fund. Hustle Fund is a venture capital fund investing in founders at the pre-seed and seed stages. They also have Angel Squad, a vetted community of angel investors, who get radical access to Hustle Fund's deals and investor education. Takeaways Learnings from working for Tony Hsieh (LinkExchange and Zappos). Being in Silicon Valley provides a unique environment for networking and learning from peers. Why Canadian founders should consider spending time there. How Toronto's tech ecosystem has changed over the last few years. Differences between Canadian and American founders. A great angel investor is someone who understands their purpose and has a clear portfolio construction strategy. Things that Hustle Fund looks for in founders at the earliest stages. What it was like raising Hustle Fund I. If you have the desire to start a business, now is the best time in history to pursue that opportunity. Chapters 00:00 Getting into Tech and Working at Google 04:16 Learning from Tony Hsieh 07:24 Starting LaunchBit 08:30 What Made LaunchBit Different 12:15 Working at 500 Startups 14:35 Starting Hustle Fund 17:40 The State of Pre-Seed Market 20:48 Geography and Investing in Toronto 23:16 Mindset of Toronto Founders 26:46 The Importance of Being in Silicon Valley 30:12 Qualities of a Great Angel Investor 35:25 The Purpose of Angel Squad 43:42 Favorite Book: Buy Back Your Time 45:45 Excitement for 2024 47:24 Dealing with Hard Times 47:52 Recognizing Privilege and Gratitude 49:18 The Opportunities of the Post-Pandemic World 50:46 Inspiration and Encouragement My podcast supporter! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fasken's Emerging Tech and Venture Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada. Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns! 

Yvette Wu is the Co-Founder and CEO of Yield Exchange. Yield Exchange is a B2B SaaS platform for organizations to access competitive GIC rates with speed, transparency, and ease. Their platform acts as an online GIC marketplace for investors such as Canadian municipalities, universities, school boards, hospitals, and large corporations to access competitive rates directly from their partnering financial institutions. Takeaways Building a double-sided marketplace requires addressing the needs of both sides: depositors and financial institutions. How Yvette solved the Cold Start Problem with Yield Exchange's marketplace. Deeply listening to users' feedback and understanding their pain points is crucial for product development and iteration. Hiring should be job-dependent, with a focus on potential and diversity of perspectives. Maintaining focus and work-life balance is essential for long-term success as a founder. Finding support from fellow founders, mentors, and advisors is valuable for personal and professional growth. Chapters 00:00 Yvette's Background and Journey 06:08 Internal Consulting and Skillset as a Founder 07:36 Enterprise Risk Management and the Genesis of Yield Exchange 10:15 GICs and their Use in Innovative Ways 13:17 Creating a Marketplace for GICs 17:36 Building the Initial Marketplace for Yield Exchange 22:18 Product Development and Feedback from Users 26:45 Digging Deeper and Asking the Right Questions 30:29 Hiring and Building a Diverse Team 33:53 Growth Strategies and Prioritization 37:02 Finding Support as a Founder 40:36 Maintaining Focus and Work-Life Balance 44:28 Favorite Book and Excitement for the New Year 46:51 Dealing with Hard Times 48:03 Message to Listeners My podcast supporter! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fasken's Emerging Tech and Venture Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada. Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns! 

Dan Belostotsky is the Founder of HonestDoor. HonestDoor is an Edmonton-based, VC-backed company that combines real estate data with data science to produce estimated values of houses and condos. In addition to the estimated HonestDoor price, it contains property taxes, transaction data, permit data, and neighbourhood growth rates for over 16M properties in Canada. By creating the most comprehensive source of commercial and residential real estate information in Canada, it empowers existing and potential homeowners to make more informed decisions. Takeaways Founding his first business in the digital sign space. Seeking advice is important, but it's crucial to filter advice and trust your own knowledge and instincts. Interesting ways Dan made money in the real estate space. Transparency is essential in the real estate market, and platforms like HonestDoor aim to provide consumers with access to information. Raising VC money for a B2C PropTech company can be challenging, but with the right product and market fit, success is possible. Consider alternative options in real estate transactions. Explore new possibilities and challenge traditional practices. New product launches for HonestDoor. Chapters 00:00 Starting Bellonet Media and the Inspiration from Jim Pattison 01:14 The Journey of Bellonet Media and the Acquisition Process 04:25 Lessons Learned in Entrepreneurship in Early 20s 06:41 Seeking Advice and Sticking to Your Guns 07:44 Finding Mentors and Filtering Advice 09:16 Venture Partnerships and Angel Investing 13:10 Investing in Real Estate and Creative Ways to Make Money 17:44 The Opaque Nature of Real Estate and the Birth of Honest Door 19:18 The Data Play and the Addition of Listings on Honest Door 21:10 Copying Successful Models and Adapting to the Canadian Market 23:00 Adding Listings and Challenging the Traditional Commission Structure 26:40 Raising VC Money for a PropTech Company 38:10 Expanding into B2B Products and Services 43:40 The Challenges of Raising VC Money for B2C PropTech 43:43 Favorite Books and Reading Habits 45:02 Looking Forward to 2024 46:14 Dealing with Hard Times 47:20 Final Message from Dan My podcast supporter! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fasken's Emerging Tech and Venture Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada. Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns! 

Rashel Hariri is a seasoned marketing professional, startup consultant, and podcast host. With over 14 years of experience leading marketing strategies and teams at Global organizations. She created award-winning marketing campaigns for some of the largest brands in the world, like McDonald’s, Shopify, and ING Direct/Tangerine Bank.  After leaving the corporate world in 2021, she established Rashel Hariri Inc., specializing in leading holistic marketing and business strategies for startups, including creating transformative go-to-market strategies, brand partnerships, and product launches. She has worked with startups and founders across North America and the Middle East.  This fall, Rashel launched She's Interesting, a podcast community changing the narrative around entrepreneurship and highlighting the powerful stories of women entrepreneurs and investors.  Rashel is deeply committed to the success of startups and offers guidance to career-driven individuals. As a career and entrepreneurial coach, she assists clients in unlocking their potential and shaping careers that resonate with their missions. Takeaways Understand the consumer and their buying decisions to effectively market your product or brand. Be scrappy and resourceful, regardless of budget or company size, to connect with your target audience. Focus on channels where your customers are spending the most time and tailor your content to their preferences. Build a strong network and leverage personal connections to generate leads and opportunities. Embrace deep conversations and curiosity to uncover unique stories and perspectives. Choosing a podcast topic that you are passionate about and that has an audience is crucial for success. Thorough research and preparation before each podcast episode can help you create high-quality content. Effective interviewing techniques, such as active listening and asking open-ended questions, can lead to engaging conversations. Editing and post-production are important steps in creating a polished and professional podcast. Promoting and growing your podcast requires a strategic approach, including utilizing social media and networking with other podcasters. Chapters 00:00 Interest in Marketing 02:08 Influential Brands 04:07 Marketing Experience at Tangerine and McDonald's 06:28 Working with Limited Budgets 08:17 Marketing at Shopify 12:40 Analyzing Data and Feedback 16:12 Thinking about Marketing Channels 19:11 Creating Valuable Content 25:37 Starting a Consulting Practice 29:27 Common Marketing Mistakes by Founders 32:10 Starting the She's Interesting Podcast 35:22 Goals for She's Interesting 40:44 Guest Composition on the Podcast 44:37 Dealing with Hard Times 46:00 Final Message 05:30 Choosing a Podcast Topic 15:45 Research and Preparation 25:10 Interviewing Techniques 35:20 Editing and Post-Production 42:50 Promoting and Growing Your Podcast 46:15 Conclusion My podcast supporter! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fasken's Emerging Tech and Venture Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada. Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns! 

Tyler Rooney was the Co-Founder of Format (acquired by Zenfolio). Format has been offering creatives solutions to showcase, manage and grow their business since 2010. Takeaways The dot-com era at Waterloo was a formative time for Tyler, where he learned valuable lessons and worked at startups a few of which ultimately flamed out. Tyler's early work experiences at companies like Infusion Development and Amazon taught him what he did and did not want to do, and helped him discover his strengths. The inspiration from 37Signals and Basecamp influenced Tyler's approach to building Format, focusing on sustainable business models and creating value for customers. Tyler's obsession with SaaS and business metrics. Format experienced early traction and growth, and Tyler emphasizes the importance of staying true to bootstrapping and not getting caught up in the hype of raising venture capital. The acquisition of Format and the change in pace it created for Tyler. Throughout his journey, Tyler has learned the importance of meaningful relationships and the support of people in both personal and professional life. Chapters 00:00 Tyler's Time at Waterloo and Startups 03:00 Early Work Experiences and Lessons Learned 09:50 Inspiration from 37signals and Basecamp 13:29 The Idea for Format and Building the Business 21:29 Early Traction and Maintaining Momentum 25:59 Reflections on the Journey and Staying True to Bootstrapping 35:05 Transitioning from Format and Future Excitement 46:08 Dealing with Hard Times and the Importance of People 48:20 Closing Thoughts on Meaningful Relationships My podcast supporter! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fasken's Emerging Tech and Venture Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada. Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns! 

Nadia Barbosa is the Co-Founder and CEO of Tandem Experiences. Tandem Experiences is a woman-led, purpose-oriented company making date night easy. They bundle the best local events with great food and activities so that couples can focus on spending quality time together, instead of sweating the details. Takeaways Tandem Experiences aims to solve the problem of fragmented planning and lack of support for couples in finding and evaluating experiences. User feedback and engagement are crucial for improving the platform and providing value to users. Organic growth through social media and partnerships with community organizations can help amplify the reach of Tandem Experiences. The company focuses on unique local experiences and aims to support small to medium-sized businesses in the food, beverage, and arts industries. Nadia emphasizes the importance of a supportive community, continuous learning, and celebrating both small and big accomplishments as a founder. Tandem is a platform that connects people through shared experiences in their city. The app provides recommendations for activities and events, allowing users to discover new things to do. Tandem helps people form impactful memories and reconnect with friends and loved ones. Chapters 00:00 Background and Motivation for her MBA 02:01 Connecting with Co-Founder and Pivoting the Idea 03:05 Genesis of the Idea: Personal Experience with Dating Apps 05:31 Focus on Nurturing Relationships 08:04 The Fragmented Nature of Planning Experiences 10:12 Balancing Unique and Recurring Experiences 12:28 Measuring Success: User Satisfaction and Growth 16:14 Collecting and Prioritizing User Feedback 17:45 Organic Growth and Social Media Strategy 20:04 Expansion Strategy to Other Cities 22:12 Different User Groups and Tailoring Experiences 24:08 Partnership Strategy and Value for Partners 26:25 Balancing Efficiency and Quality with Technology 28:31 Support System and Learning from Other Founders 31:09 Product Development and Lean Approach 32:57 Gathering Feedback and Improving Recommendations 35:05 Engaging Users and Driving Engagement 37:02 Viral Growth and Referral Strategy 39:51 AI and the Flywheel Effect 42:03 Favorite Business Books and Continuous Learning 43:40 Excitement for the Future and Growth Opportunities 45:48 Pitching Advice and Celebrating Accomplishments 47:03 Dealing with Hard Times and Having a Supportive Community 49:10 Societal Impact and Mission of Tandem Experiences My podcast supporter! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fasken's Emerging Tech and Venture Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada. Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns! 

Shane Murphy is the CEO of Ownr. Ownr is an RBCx company. They are making it simpler and more affordable for businesses to start and succeed. They know that starting and running a business takes a huge effort. By simplifying and automating business formation and everyday legal work, they help SMBs thrive. Takeaways Ownr aims to democratize access to incorporation and provide ongoing support for small businesses. Building product within RBCx allows Ownr to leverage existing RBC products and create an embedded experience for users. Shane emphasizes the importance of surrounding oneself with good people, engaging in physical activity, and listening to customer feedback. The future of Ownr includes expanding services and addressing the needs of entrepreneurs at different stages of their business journey. The acquisition of Founded Technologies by Ownr/RBCx. Transitioning from COO to CEO. Shane's thoughts on competition. Hints of potential future products from Ownr. Chapters 00:00 Shane's Interest in Law 01:27 Master's Degree in Political Theory 03:24 Starting Founded Technologies 06:03 Transition to Owner 08:28 Acquisition by RBC Ventures 12:46 Transition from COO to CEO 13:22 RBCx and the Focus on Tech and Innovation 17:09 Democratizing Access to Incorporation 19:37 Building Product within RBCx 22:20 Gathering Feedback from Customers 24:01 Creating a Deeper Relationship with Customers 26:57 Competition in the Market 29:39 Growth and Partnerships 32:23 RBCx and its Focus 34:10 Future of Ownr 36:40 User Journey for Different Types of Businesses 39:07 Favorite Book: Scaling People 41:01 Excitement for the New Year 41:51 Dealing with Hard Times 42:53 Closing Remarks My podcast supporter! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fasken's Emerging Tech and Venture Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada. Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns! 

Jesse Abrams is the Co-Founder & CEO of Homewise. Homewise is a national consumer end-to-end homeownership platform, centered around its digital mortgage experience that uses data intelligence to match and secure clients with their best mortgage from 30+ banks and lenders in minutes. Homewise then connects clients to their in-house Real Estate solution (Homewise Real Estate) and partners at each step of the process from there, such as insurance and real estate law. Homewise Real Estate Listings Jesse’s Twitter Takeaways Foundational skills in marketing and advertising can provide a strong base for a career in the tech industry. Identifying a gap in the market and taking the first step is crucial for starting a successful business. A vertically integrated approach can differentiate a company and provide value to customers. Pivoting to a B2B2C model can lead to scalable revenue growth and partnerships with other businesses. Balancing customer and investor feedback is important for making informed decisions. Baking education into the product can empower customers to make informed decisions and improve their overall experience. Providing advice and access throughout the home buying process can improve the customer experience and save money for customers. Launching a real estate listing site in-house allows for greater control over the customer experience and the ability to provide tailored information to clients. Being open to sharing ideas and collaborating with others in the industry can lead to valuable insights and opportunities for growth. Dealing with hard times as a founder and parent requires a supportive network, engaging in physical activity, and finding joy in personal interests. Building the industry and starting a company requires resilience, thick skin, and a passion for the work being done. Chapters 00:00 Foundational Skills in Marketing 03:21 Genesis of the Idea for HomeWise 06:12 Taking the First Step and Identifying the Gap 10:18 Vertically Integrated Approach 15:23 Capitalizing on the Digital Movement 21:12 Pivoting to a B2B2C Model 26:50 Balancing Customer and Investor Feedback 32:40 Unlocking Competitive Rates 38:20 Baking Education into the Product 43:03 Providing Advice and Access 44:15 Launching a Real Estate Listing Site 49:50 Favorite Books and Excitement for the Future 53:45 Dealing with Hard Times 57:04 Building the Industry and Starting a Company My podcast supporter! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fasken's Emerging Tech and Venture Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada. Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns!