The Founder's Financial Compass: Navigating Emotions and Assumptions with Fractional CFO Lauren Pearl
Release Date: 07/24/2025
The Conversation Factory
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Get free chapters of my book, Good Talk, and master the art of conversations big and small: Please support the podcast! 💌 : 💌 : or with : : Check out for the full transcript and video highlights. Money! It can be an emotional topic. But, as my guest on today's podcast, fractional CFO Lauren Pearl says, it's emotional for everyone in different ways! In this episode, Lauren reveals her perspectives on how to approach these difficult conversations. Given how many leaders she’s worked with, we also explore her thinking about effective leadership, intentional...
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Check out https://theconversationfactory.com/podcast/the-founders-financial-compass-navigating-emotions-and-assumptions-with-fractional-cfo-lauren-pearl for the full transcript and video highlights.
Money! It can be an emotional topic. But, as my guest on today's podcast, fractional CFO Lauren Pearl says, it's emotional for everyone in different ways! In this episode, Lauren reveals her perspectives on how to approach these difficult conversations. Given how many leaders she’s worked with, we also explore her thinking about effective leadership, intentional decision-making, and how it’s crucial for founders to be endlessly unafraid to ask why. She makes an excellent point in the opening quote: we often listen to respond. And when we respond from that place we're missing a lot of crucial information. It's hard to do but it's so important to take the risk to slow down, to ask why and to be a little bit more vulnerable with what you don't know - it’s that inner willingness to face your blind spots that separates the best from the rest.
We talk about the life experiences that taught her how to adapt her communication styles for diverse audiences, how she approaches talking with founders about triggering money topics, and we unpack some insights from her course on Business Modelling - how she helps founders turn their core understanding of their business into plain-English business math.
I particularly enjoyed Lauren’s insights around reframing tough decisions not as losses but as opportunities. We unpacked how shutting down a “pet project” can be reframed not as a loss or a mistake but as a day one decision - ie, we made a choice and a decision one day with the information and the knowledge and insights that we had and today with different knowledge, different insights and different information we’re making another decision. We linked this notion back to one of the key ideas in Annie Duke's classic “thinking in bets” - the idea of “resulting”, or judging a decision based on its outcome. A good bet is one that a reasonable person with the amount of information we had would have made at that moment, not necessarily one that works out exactly as you'd hoped. And Lauren urges founders to start admiring business leaders who didn’t just get lucky once…but ones who repeatedly make smart bets - and can explain why they made them.
Strap in! We also unpack some common financial misconceptions, discuss how to be a founder whose advisors can help them, and we unpack some interesting case studies in strategic decision making. Lauren’s on-the-fly explanation of some key financial assumptions was dizzying in the best way possible.
Links
https://www.laurenpearlconsulting.com/
https://www.laurenpearlconsulting.com/newsletter
Thinking in Bets by Annie Duke - A Visual Summary: https://www.youtube.com/watch?v=H49lFODYp7g
Video Highlights
Adapting your communication style on the fly - https://youtu.be/rWtSvkoMkiw
The Founder Finance Gap: Managing Emotions and Unearthing Assumptions - https://youtu.be/Dfc8r9BBtyY
Using Clear Language to define your Critical Business Math - https://youtu.be/l7oosTdqTLo
Admiring Founders who make good bets repeatedly - https://youtu.be/cuwZIjW01TU