The Entrepreneur Roller Coaster: Lessons from the Why Not Today? Journey

About this episode

Leslie Kane shares her entrepreneurial journey, highlighting the lessons learned from the ups and downs of building a business.

Have you ever wondered if you're on the right path in your business? What if the twists, turns, and pivots aren't signs you're failing, but signs you're growing? In this episode of the Why Not Today? Podcast, Leslie Kane takes listeners behind the scenes of the Why Not Today? journey. From launching a podcast before feeling ready, to building community events, creating the Why Not Today Connects Luncheon, and ultimately making the difficult decision to let some things go, Leslie shares the lessons she has learned from four years of entrepreneurship. If you've ever felt overwhelmed, uncertain, or frustrated by the ups and downs of building a business, this episode will remind you that progress is rarely a straight line. Highlights • Why most entrepreneurs wait too long to get started • The surprising lesson Leslie learned from launching her podcast • How experimentation and pivots helped shape Why Not Today? • Why letting go of something good can create space for something greater • The importance of mentors, coaches, and community on the entrepreneurial journey • The new direction of Why Not Today? and the focus on helping service-based entrepreneurs grow Ready to Find More…

People in this episode

Host: Leslie Kane

Topics covered

• entrepreneurship
• business growth
• podcasting
• community building
• mentorship
• experimentation

Keywords

• entrepreneur roller coaster
• business lessons
• Why Not Today?
• community events
• mentors
• coaching
• service-based entrepreneurs

More episodes of Why Not Today? with Leslie Kane

• Your One Day Starts Today - The Power of Persistence and Fanatical Consistency · June 5, 2026 · 15 min
• Make People Feel Special: A Business Growth Strategy That Works · May 28, 2026 · 19 min
• The Championship Mindset That Helps You Finish Strong · May 21, 2026 · 20 min
• Building Your Tribe: How to Build Meaningful Relationships with Leslie · May 14, 2026 · 25 min
• Finding Your Tribe: Why Community and Connection Matter with Leslie · May 7, 2026 · 14 min
• The Starfish Effect: How One Action Can Change Everything · April 30, 2026 · 14 min