Startup life isn’t for the faint of heart—especially for women entrepreneurs. Caitlin MacGregor, CEO and co-founder of Plum, pulls back the curtain on what it really takes to build a company, secure funding, and challenge gender bias in venture capital. From navigating the complexities of co-founding a business with her husband to finding the right mentors, Caitlin shares the highs, lows, and lessons from her journey.
In this episode, we look at the fundraising hurdles women face, the unique mindset of Canadian entrepreneurs, the evolving role of venture capital in supporting social impact, and how mentorship and executive coaching shape leadership success.
Key Takeaways
➡️ Plum helps companies match candidates to roles for better productivity and fulfillment.
➡️ Co-founding a business with a spouse brings unique strengths and challenges.
➡️ Mentorship is a game-changer in leadership growth and career success.
➡️ Women face systemic barriers in raising venture capital compared to men.
➡️ Female investors are often more supportive of women-led businesses.
➡️ Caitlin’s executive coach transformed her approach to leadership at 27.
➡️ Work-life balance is a myth—what matters is setting the right boundaries.
➡️ Canadian entrepreneurs approach risk differently than their U.S. counterparts.
➡️ The startup world is shifting toward a greater focus on social impact.
➡️ Engaging men in women’s leadership conversations is crucial for real change.
➡️ Entrepreneurs shouldn’t rely on luck—everyone has the potential to lead.
➡️ The venture capital landscape is slowly evolving, but there’s still work to do.
Guest and Resources
Caitlin MacGregor: https://www.linkedin.com/in/caitlinmacgregor
Learn more about Plum here: https://www.plum.io/about
Connect with us here:
🔗 Connect with William Tincup: https://www.linkedin.com/in/tincup/
🔗 Connect with Ryan Leary: https://www.linkedin.com/in/ryanleary/
Connect with WRKdefined on your favorite social network
🔗 Site: http://www.wrkdefined.com
🎥 TikTok: https://www.tiktok.com/@wrkdefined
💼 LinkedIn: https://www.linkedin.com/company/wrkdefined
📘 Facebook: https://www.facebook.com/WRKdefined/
🐦 Twitter (X): https://twitter.com/WRKdefined
📩 Substack: https://wrkdefined.substack.com
Learn more about your ad choices. Visit megaphone.fm/adchoices
Powered by the WRKdefined Podcast Network.
Related Episodes
The Brutal Truth About Scaling a Tech Company: How Giuliana Corbo Took Nearsure to 22 Countries by 32 Years Old
Giuliana Corbo, the CEO of Nearsure, scaled her company to 22 countries by the age of 32, proving that age is just a number when it comes to leading a global business. She shares her no-BS approach to leadership, project management, and building a company culture that thrives under pressure. Along t...
Mastering Global Hiring: Insights from Nicole Sahin of G-P
Nicole Sahin shares her journey from anthropology to entrepreneurship, leading Globalization Partners to simplify global employment. She discusses the challenges of compliance, the acceleration of remote work due to COVID-19, and the role of intuition in business decisions. Nicole’s insights on buil...
Jon Lowe, Chief People Officer at DailyPay, on Workplace Transformation, Career Growth & Influencing the Future of Work
HR isn’t what it used to be, and neither are career paths. In this episode, we sit down with Jon Lowe, Chief People Officer at DailyPay to explore the evolution of HR, the importance of self-awareness in career choices, and why adaptability is the key to success. From home improvement projects that ...