Tim Ranzetta interviews NerdWallet writer and personal finance expert Kate Ashford about entrepreneurship, financial education, and lessons from her career in journalism and freelancing. Kate shares early money memories, key insights she's gained from covering a wide range of personal finance topics, and practical advice for young entrepreneurs. From identifying a problem worth solving to funding a startup on a shoestring budget, the discussion explores business planning essentials. They discuss the evolving impact of AI, the importance of curiosity and communication skills, and why early jobs (even tough ones) can teach invaluable lessons. Kate offers guidance on mentorship, business structures, estate planning basics, and cultivating traits like perseverance, adaptability, and the "squeaky wheel" mindset. Packed with practical wisdom for educators and students alike, this conversation highlights what it really takes to build skills, start small, and stay flexible in a changing world.