Shift & Thrive: CEO Insights on Driving Change

·E114

Why You Shouldn't Sell Fear - Yossi Appleboum - Shift & Thrive - Episode #114

September 16
41 mins

Episode Description

What does it actually take to change how an entire market understands a problem it doesn't yet know it has? In this episode of Shift & Thrive, host Natalie Nathanson talks with Yossi Appleboum, co-founder and CEO of Sepio, about building a cybersecurity company around a category that barely existed when he started it. Yossi shares why he refuses to sell fear, how he can tell when a prospect's thinking has actually shifted, what it costs in time and money to educate a market from the ground up, and how the investor conversation changes entirely once a company moves from early traction into scale. He also opens up about leadership lessons from three decades of company-building, giving his co-founders and team room to grow, and how his family history shapes the way he thinks about bringing value to the world.


Takeaways:

  • Educate before you pitch. In less mature markets, walk buyers through the risk itself rather than assuming they already see the problem.
  • Skip the fear-based pitch. Build trust through dialogue and honest questions instead of worst-case scenarios and pressure.
  • Watch for buyers echoing your language back to you. It's an early signal the idea has landed, well before any deal closes.
  • Match your investor search to your sales cycle. Companies selling to large enterprises need investors willing to accept a longer path to revenue.
  • Give co-founders and senior hires room to lead. Avoid showing up as a unified front to every meeting so others can grow into the space.
  • Simplify your message as you move down-market. What works with sophisticated early buyers won't land with less experienced ones.
  • Keep helping the next generation of founders. Small, consistent mentorship compounds across an industry over time.


Quote of the Show:

  • "You don't sell fear, and you should not sell fear, because then you're losing credibility."


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This show is sponsored by Magnetude Consulting, bringing you the thinking-Power of a Growth Consultancy and the Getting-It-Done Power of a full-service B2B Marketing Agency. Learn more at: https://www.magnetudeconsulting.com 


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