Not Another CEO Podcast

Today we’re bringing you a very special episode of the Not Another CEO Podcast! Joining David this week is Nick Freund, the Founder and Former CEO of Workstream.io, and they discuss his entrepreneurial journey. Five years ago, Nick founded Workstream and successfully raised over seven million dollars before making the difficult decision to shut down the company.

In this episode, Nick shares his experiences, the importance of selecting the right co-founder, and the challenges of pivoting a business. He also talks about the emotional toll of shutting down a company and the subsequent launch of his Substack, 'Failing Forward,' where he aims to educate and support other founders through his lessons learned.
 
Takeaways:
  • Building a Strong Team: As a founder, it’s important to know what you’re good at and be honest about what you’re not. Take your time to find the right person, and don’t skip the reference checks. They can really pay off in the long run.
  • Founder Compatibility: Choosing a co-founder or core team member is a lot like entering a relationship. It’s more than just an employer-employee relationship. You need to think about personality fit and how your working styles mesh.
  • Engaging Customers Early: Start talking to potential customers as early as possible—whether through interviews or feedback sessions. This helps validate your idea and gives you insights into what customers really need. Building early relationships with design partners can also help shape your product development.
  • Mental Readiness and Resilience: Being a founder can be mentally tough. There will be stress, setbacks, and tough days— that’s just part of the journey. Having a clear sense of purpose and a strong support system can help you push through the challenges.
  • Transparency in Failures: Don’t shy away from sharing your failures. Almost every startup faces obstacles, and being open about them can teach valuable lessons to others. Sharing these stories fosters a culture where failure is seen as part of the learning process, not something to hide.
Quote of the Show:
  • “If you're hesitant to pivot, you probably have false positives that you might be pointing to that might be holding you back, but I do think there's another part to it which is the sunk-cost fallacy.” - Nick Freund
Links:
Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #FailingForward

Creators & Guests

Host
David Politis
Producer
Alex Fischer
Guest
Nick Freund

What is Not Another CEO Podcast?

Tune into Not Another CEO Podcast with host David Politis, as he sits down with a new CEO every week to discuss how they got to where they are today. CEOs share their successes, struggles, lessons learned, actionable tactics and the strategies that propelled their growth. This isn't just about the strategies for business success, but also the personal journeys that led CEOs to where they are today.

21 CEOs interviewed and counting.