“Successful Entrepreneurs Fear Things Just a Little Less” — Robin Waite on Breaking the Time-for-Money Trap

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Cut The Tie Podcast with Robin Waite

What if the real reason your business feels heavy has nothing to do with strategy and everything to do with fear? In this episode of Cut The Tie, Thomas Helfrich sits down with Robin Waite, founder of Fearless Business, to unpack why so many entrepreneurs stay stuck trading time for money long after it stops serving them.

Robin shares how productizing services, charging for outcomes instead of hours, and letting go of playing small helped him reclaim time, income, and control. From group coaching models to strategic partnerships, this conversation is a wake-up call for executives and founders who want leverage without burnout.

About Robin Waite

Robin Waite is the founder of Fearless Business, a coaching accelerator that helps coaches, consultants, and freelancers escape the time-for-money trap. With over twenty years of entrepreneurial experience, Robin has helped thousands of business owners simplify pricing, build scalable offers, and create businesses that support the life they want.

He is the author of several books, including Take Your Shot, and is known for his practical, no-nonsense approach to pricing, money mindset, and sustainable growth.

In this episode, Thomas and Robin discuss:

• Why hourly pricing penalizes experience and efficiency
• How to shift from selling time to selling outcomes
• The three pillars of productized services
• Why group models outperform one-to-one coaching
• Cutting the tie to fear, small pricing, and overwork
• Redefining success after a major health wake-up call

Key Takeaways

• Time-for-money is a broken model
  The better you get, the less you earn when you price by the hour.
• Outcomes create leverage
  Clear results, timelines, and pricing reduce friction and scale impact.
• Fear keeps entrepreneurs stuck
  Most people know their value but hesitate to own it.
• Group models unlock freedom
  One-to-many offers deliver better results with less burnout.
• Success comes from fearing less, not knowing more
  Action beats certainty every time.

Connect with Robin Waite

💼 LinkedIn: https://www.linkedin.com/in/robinmwaite/
📺 YouTube: https://www.youtube.com/@RobinMWaite
🌐 Website: https://fearless.biz
📘 Free signed book: https://www.fearless.biz/tys

Connect with Thomas Helfrich

🐦 Twitter: https://twitter.com/thelfrich
📘 Facebook: https://www.facebook.com/groups/cutthetie
💼 LinkedIn: https://www.linkedin.com/in/thomashelfrich
🌐 Website: https://cutthetie.com
📧 Email: [e-mail]
🚀 https://instantlyrelevant.com

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