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Skye Theodorou

Skye Theodorou

CEO & Co-Founder of upcover

Key Topics

  • How funding impacts a startup’s journey and why it is crucial to really consider the context and industry you’re launching into as well as the scope of your product and product to market timeframe when choosing which funding route to take
  • Navigating discrimination and backlash as a female-founder trying to disrupt a traditional, male-dominated industry
  • The catalyst for cultivating a founder mindset and how it’s often not always a ‘lightbulb’ moment but rather being a product of your environment
  • How to manage change when becoming a new mum as well as the importance of implementing a work-life balance and being kind to yourself
  • Skye’s key piece of advice that she would not recommend to those starting out


  • 0:07: Introduction to Sips with Startups & our guest Skye Theodorou, the Co-Founder & CEO of upcover
  • 0:55: Skye introducing herself and how she fits into the startup ecosystem
  • 1:28: Her dream to transformm business insurance herself as opposed to through government or corporate
  • 1:45: Why Skye joined Antler
  • 2:00: Sky tells us what she’s sipping and how it’s secretly an amazing hangover cure
  • 2:36: How Skye is challenging the traditional and male-dominated fintech and insurtech industries and how she’s navigating it as a female
  • 3:10: Skye’s experience in navigating discrimination & backlash and how she manages the risk of being treated differently due to gender
  • 4:00: Skye discussing how she reconnected with her thesis supervisor, Jim, and how her network has responded extremely positively by way of industry introductions
  • 4:44: How Skye’s network rallied behind her when upcover began and the ways in which they shared invaluable skills & knowledge
  • 5:25: ‘There’s never a better time to be a female founder’
  • 5:33: Why your passion and drive matters more than your age, gender or culture
  • 5:57: The importance of having a complimentary co-founder skillset and leveraging your network for your business
  • 6:43: Why women don’t rely on their network enough and the contrast to the frequency that men do
  • 7:16: How the pandemic has impacted people’s ability to support each other
  • 7:41: How funding has impacted Skye’s journey and whether upcover could’ve launched as a bootstrapped business
  • 8:16: Considering the scope and industry you’re launching into as well as your product to market timeframe when choosing which funding route to take
  • 8:38: How receiving Venture Capital funds gave upcover the ‘runway’ they needed to successfully launch
  • 9:20: Skye’s background in law & cybersecurity and what the catalyst was for her to start upcover
  • 9:50: How working in her family’s restaurant as a child instilled a strong work ethic, and witnessing her Dad build multiple businesses allowed her to have a well-rounded perspective of the risks and benefits of being an entreprenuer
  • 10:41: How Skye believes she is a product of her environment, leading her to become a founder
  • 11:14: Why being flexible and pivoting is of the utmost importance to take advantage of available opportunities
  • 11:41: Skye’s key advice to new founders, and what she would not recommend to others
  • 12:10: How being a new mum will change her work-life balance, and how she plans to balance out her time moving forward
  • 13:00 Her opinion of how being pregnant has impacted her experience as a founder

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