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Make Money by Asking Better Questions

Make Money by Asking Better Questions

Update: 2025-12-24
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Description

In this episode, Travis and his producer Eric have fun with icebreaker prompts (“What would you do if you had to double $10,000 in 30 days?”) before diving into how better questions shape better decisions, careers, and relationships. They break down the most powerful questions to ask yourself, to ask mentors, and to ask before you jump into any new opportunity.​


On this episode we talk about:




  • Why Travis likes to ask himself, “This sucks, but what’s the alternative?” and how that reframes hard seasons, workouts, parenting, and business grind without needing fake positivity.​




  • The importance of accepting that every meaningful path has its own kind of “suck,” and why trying to escape all discomfort leads to purposeless, unfulfilling stretches of life.​




  • The key mentor question: “Who do you know that I should know?”—and how that opens doors to new people, books, and resources beyond the mentor’s own answers.​




  • The opportunity filter: asking “What is the absolute worst-case scenario?” and actually writing it out so fear shrinks to its real size instead of staying vague and paralyzing.​




  • Why Travis dislikes questions like “How can I add value to you?” and “What should I be asking you?” when they’re lazy stand-ins for preparation or self-aware strategy.​




Top 3 Takeaways




  1. The quality of your life and results is closely tied to the quality of the questions you ask yourself and others.​




  2. Before saying yes to new opportunities, force yourself to define the true worst-case scenario; most of the time, it’s survivable and not nearly as catastrophic as your fear suggests.​




  3. Great mentors are often most valuable as connectors; asking who they know that you should know can compound your network and knowledge far beyond one conversation.​




Notable Quotes




  • “This sucks, but what’s the alternative?”​




  • “If you’re asking the wrong questions, you’re probably going to end up with the wrong answers.”​




  • “That ‘how can I add value to you?’ question is often a self-serving question disguised as an others-serving question.”​




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Make Money by Asking Better Questions

Make Money by Asking Better Questions

Travis Chappell