Why the Right Decisions Often Scare You First with Kyle Brandon

Fear has a way of feeling real…even when it isn’t.Today Phil sits down with Kyle Brandon, founder of Second Flight Capital, to explore why the right decisions often scare us first, and how that initial fear is usually fooling us.Kyle shares his journey from missionary work to founding a people-first investment firm, including the moment he quit his job (with six kids at home!) and no clear path ahead. What followed was a season of uncertainty that reshaped how he thinks about leadership, trust, and calling.Together, Phil and Kyle discuss why fear shows up before meaningful growth, how legacy is often dismissed as emotional when it’s actually essential, and why mission-driven leadership creates lasting impact in business and life.Key takeaways from this conversation:How to tell the difference between real risk and imagined fearWhy fear often appears right before the right decisionWhat leaders should reflect on before selling their businessHow mission and legacy shape long-term leadershipWhy treating people as whole humans changes culture and retentionHow slowing down creates the clarity needed to move forwardIf you’re facing a big decision and feeling the weight of uncertainty, this conversation will help you slow down, gain clarity, and take the next right step.0:00 Intro1:57 Kyle's Unique Journey from Theology to Capital2:20 The Emotional Weight of Selling a Business9:15 The 200 Conversations That Launched a New Model14:45 Overcoming Limiting Beliefs20:15 Building Businesses that Build People25:57 The Bigger Mission Always Wins32:47 The Three Pillars of Trust and Leadership34:18 How to Build Trust After Acquisition37:33 The Long-Term Vision for Second Flight41:11 Choosing the Right Business to Buy45:06 Slowing Down to Speed UpResources Mentioned:Second Flight Capital: https://secondflightcapital.comCorterra Group: https://corterragroup.comFollow on social @PhilOnPurposehttps://www.instagram.com/philonpurposehttps://www.facebook.com/philonpurpose