Setting Sail

Setting Sail

From Remote Pep Talks with Ryan Millar by Ryan Millar

August 27, 2025 · 10 min · Episode 37

About this episode

Ryan Millar explores the lessons sailing offers for launching new ventures.

Remote Pep Talks with Ryan Millar Episode: Setting Sail on New Ventures Episode Summary Ryan once dismissed sailing as an elitist pastime. But after stepping aboard tall ships at SAIL Amsterdam, he discovered something else entirely: sailing is rebellion, discipline, and freedom all at once. In this episode, Ryan unpacks how the craft of sailing offers powerful lessons for launching new ventures — including his own with Dashwell, a company helping people communicate with clarity, presence, and impact. What You’ll Learn in This Episode Why real freedom is built on discipline, competence, and teamwork. How to “put miles beneath the keel” when starting something new. What sailing can teach us about leading, adapting, and showing up fully. Key Quotes “Sailing is the ultimate ‘forget convention’ move — it’s freedom earned through skill.” “Even in calm waters, you’re always working your ship. Progress never happens on autopilot.” “Launching something new means casting off — even if the horizon feels uncertain.” Your Pep Talk Whether you’re sitting on an idea, halfway through a project, or ready for a new chapter, this is your invitation: cast off, adjust your sails, and set your…

People in this episode

Host: Ryan Millar

Topics covered

  • sailing
  • new ventures
  • discipline
  • freedom
  • leadership
  • improvisation

Keywords

  • sailing
  • new ventures
  • Dashwell
  • leadership
  • discipline
  • freedom
  • improvisation

Mentioned in this episode

Organizations: Dashwell

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