Building a Successful Canadian Startup, Squashing Imposter Syndrome, and the Four Buckets of Fulfillment

5 Key Takeaways:

1. Follow Great People: Rachel encourages young professionals to focus less on specific industries and more on joining forces with successful leaders. She suggests looking for people who’ve won consistently and who you can learn from. 
2. Invest in Accelerated Learning: Embrace uncomfortable learning experiences to level up your skills. Being comfortable with discomfort is key to growth. When Rachel first started her business, she stumbled on a sale but used the experience to improve. She leveled up by putting a development plan in place – calling her friend who’s a pro at sales and finding a mentor who gave her and her team feedback. She accelerated her learning from where she was to where she wanted to be. 
3. Find Your Four Buckets of Fulfillment: For Rachel, fulfillment comes from balancing four key areas: adventure, challenge, impact, and relationships. When all four of these buckets are filled, she feels satisfied and content. Self-awareness is key – figure out what your four buckets are and fill them up as frequently as possible. 
4. Squash Imposter Syndrome: Instead of dwelling on self-doubt and asking yourself, “Do I have the right to be here?” focus on your goals and skill-building. Stay laser focused on what you want to achieve and the skills you need to get there versus getting stuck in your head. 
5. Strategic Partnerships Can Supercharge Growth: Investors in Simple Ventures are more than just financial backers—they can accelerate growth by offering strategic advantages. For example, Sobeys’ partnership with All My Care (a Simple Ventures-backed company focused on postnatal services) provided distribution that helped scale the business faster. It’s about having aligned incentives with corporate partners.  

Show Notes: 

[00:01:00] Rachel explains the venture studio model. A venture studio sits between bootstrapping and venture capital funding. 

[00:02:30] Simple Ventures identifies innovative global concepts that haven’t entered Canada yet. 

[00:03:57] Rachel explains that Simple Ventures attracts two types of investors: founder-operators and corporate investors.

[00:08:18] Canada, particularly Toronto, offers significant advantages as a startup hub. Toronto is a great test market due to its proximity to multinational companies.

[00:12:01] The importance of choosing the right path for your business, whether it’s bootstrapped or venture-backed. 

[00:13:26] Align your actions with your words. Ensure that what you say matches what you deliver, building trust and credibility in any role.

[00:17:08] Rachel shares a personal story of failure early in her entrepreneurial career. 

[00:19:44] Rachel talks about managing work-life integration by focusing on what she calls “interval training.”

[00:24:54] Squash imposter syndrome by focusing on your goals rather than dwelling on feelings of inadequacy. 

[00:25:46] Rachel shares her thoughts on sabbaticals in the corporate world, noting that project-based roles like consulting may have more flexibility for these kinds of breaks.