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June 17, 2025 41 mins

In this episode, I had a great conversation with Annemarie Penny, Founder of Dreamore.

Annemarie shared some fascinating insights from a 14-year study on startup founders and leaders. It really highlighted the different mindsets and personalities needed to thrive in a startup compared to a bigger, more established company. We explored what a healthy startup culture looks like – that "organized chaos" where different ideas, even the seemingly "stupid" ones, are encouraged to spark innovation and avoid everyone just agreeing with each other.

We also dove into the common hiring mistakes that startup founders often make. We emphasized that you need to look beyond just a resume and really assess candidates based on their skills, measurable successes, their personal story, and how well they fit with the company culture. We discussed the idea of "hire slow, fire fast" versus investing in developing employees, and how crucial it is to set realistic expectations during the hiring process.

We also spent some time talking about AI in recruitment. While AI tools can definitely help with things like screening resumes for skills and saving time, Annemarie and I both have concerns about candidates potentially using AI to misrepresent themselves, especially with remote and global teams. However, we agreed that AI can't replace the human element: the authenticity, the personal story, critical thinking, and learned experiences. If a hiring process can be "fooled" by AI, then the process itself needs improvement. We see AI as a tool that should allow recruiters and HR to focus more on connecting with people, understanding the nuances, and assessing things like empathy and experience.

To wrap things up, Annemarie offered some valuable advice for first-time founders building their teams. She stressed the importance of taking care of yourself, being okay with not knowing everything (that vulnerability and fear are normal!), and attracting the right people by being authentic and bringing positive energy. What you put out there really does attract the kind of people you want to work with. And recognizing that you don't have all the answers and building a team that complements your strengths is key to success.

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