Gregg Kaplan & Kirk Dando | For You Leaders Bonus Episode (Full Interview)

#12: Keep Climbing (A Leadership Message I Needed Years Ago)

Leadership isn’t a straight ascent, it’s a long, uneven climb. Some days lift you. Others test you. And most leaders, at some point, wonder whether the weight, the pace, and the responsibility are worth it. This final episode of the season is the message I needed 20 years ago: a reminder that the climb is worth it, especially when you stop trying to climb alone. In this episode, you’ll learn how to:- Stay in the climb when leadership feels heavy or unclear. - Recognize the moments where most leaders quit (and how to push through them). - Build your community of “fellow climbers” who make the journey worth it. - Reframe the leadership journey as something you don’t have to carry solo. Trust the process, the preparation, and the person you’re becoming along the way. This is an honest look at the real journey of leadership: the grind, the gratitude, the doubt, and the deep sense of purpose that makes the mountain worth climbing. Episode Breakdown:00:00 Intro 05:15 Normalizing the Climb 14:14 What’s in Your Control vs. What Isn’t 19:43 The Myth of Doing It Alone: Why Isolation Is Dangerous 25:11 How Great Leaders Build Community, Accountability & Support 37:34 Where Leaders Should Turn When They Went to Give Up 41:33 Staying in the Climb: Rhythm, Reflection & Resilience 52:21 The Gift of Perspective: Humility, Resilience & Gratitude 56:30 What Kirk Wishes He Knew 20 Years Ago 01:06:00 Thank You to the Team & Community 01:10:06 A Surprise Message for Kirk 01:12:27 Final Reflections & Closing the Season 01:13:52 Outro — Keep Climbing Subscribe for bi-weekly episodes and visit https://www.dandoadvisors.com/ for coaching inquiries.Resources & Mentions: * Download Kirk's Business Growth Lifecycle PDF: https://www.dandoadvisors.com/resources/business-growth-lifecycle-normalizing-the-scale-journey * Get Coaching from Kirk: https://www.dandoadvisors.com/services/executive-coaching Follow us on LinkedIn: * https://www.linkedin.com/in/kirkdando/ * https://www.linkedin.com/in/spencertraver/

Mitchell Green & Kirk Dando | For You Leaders Bonus Episode (Full Interview)

Raising and deploying capital can be one of the most defining moments in the life of any company. To explore what really separates the great capital allocators from the rest, I spent over five hours in recorded conversations with five iconic leaders and investors. These aren’t just big industry names — they’re people I’ve had the privilege of working alongside for years. That trust opened the door for candid, behind-the-scenes conversations you won’t hear anywhere else. Each guest was interviewed individually, and those full conversations will be released as bonus episodes. But in this three-part mini-series, we’ve woven those insights together — with Spencer and me in the studio reacting to clips — to reveal the patterns, decisions, and principles that define exceptional capital strategy. In this episode, you’ll hear the full interview with:Mitchell Green [https://www.linkedin.com/in/mitchell-green-56025a1/] — founder and Managing Partner of Lead Edge Capital, the global growth equity firm behind companies like Alibaba, Spotify, Asana, and Toast. Mitchell shares how Lead Edge built its unique investor network, what he looks for in world-class founders, and how great capital partners create value far beyond the check. Lead Edge was recently named the top-ranked growth equity firm by PitchBook. Subscribe to catch the rest of the series and hear from other iconic leaders. Drop your biggest insight from Mitchell's story in the comments below.

Julie Maples & Kirk Dando | For You Leaders Bonus Episode (Full Interview)

Raising and deploying capital can be one of the most defining moments in the life of any company. To explore what really separates the great capital allocators from the rest, I spent over five hours in recorded conversations with five iconic leaders and investors. These aren’t just big industry names — they’re people I’ve had the privilege of working alongside for years. That trust opened the door for candid, behind-the-scenes conversations you won’t hear anywhere else. Each guest was interviewed individually, and those full conversations will be released as bonus episodes. But in this three-part mini-series, we’ve woven those insights together — with Spencer and me in the studio reacting to clips — to reveal the patterns, decisions, and principles that define exceptional capital strategy. In this episode, you’ll hear the full interview with: Julie Maples [https://www.linkedin.com/in/julieallegro/] — founder of FYRFLY Venture Partners and longtime early-stage investor who’s partnered with dozens of founders at the intersection of enterprise software, data, and AI. Julie brings decades of perspective on what it takes to build enduring companies — and the investor-founder relationships that make it possible. Julie also has helped The V Foundation raise over $100M for cancer research as a valued board member. Subscribe to catch the rest of the series and hear from other iconic leaders. Drop your biggest insight from Julie's story in the comments below.

Gregg Kaplan & Kirk Dando | For You Leaders Bonus Episode (Full Interview)

Raising and deploying capital can be one of the most defining moments in the life of any company. To explore what really separates the great capital allocators from the rest, I spent over five hours in recorded conversations with five iconic leaders and investors. These aren’t just big industry names — they’re people I’ve had the privilege of working alongside for years. That trust opened the door for candid, behind-the-scenes conversations you won’t hear anywhere else. Each guest was interviewed individually, and those full conversations will be released as bonus episodes. But in this three-part mini-series, we’ve woven those insights together — with Spencer and me in the studio reacting to clips — to reveal the patterns, decisions, and principles that define exceptional capital strategy. In this episode, you’ll hear the full interview with: Gregg Kaplan [https://www.linkedin.com/in/gregg-kaplan-3a60863/] — founder and former CEO of Redbox, former President/COO of Coinstar, and now CEO at Dentologie, where he's raised over $50M to date. Subscribe to catch the rest of the series and hear from other iconic leaders. Drop your biggest insight from Gregg's story in the comments below.

Dug Song & Kirk Dando | For You Leaders Bonus Episode (Full Interview)

Raising and deploying capital can be one of the most defining moments in the life of any company. To explore what really separates the great capital allocators from the rest, I spent over five hours in recorded conversations with five iconic leaders and investors. These aren’t just big industry names — they’re people I’ve had the privilege of working alongside for years. That trust opened the door for candid, behind-the-scenes conversations you won’t hear anywhere else. Each guest was interviewed individually, and those full conversations will be released as bonus episodes. But in this three-part mini-series, we’ve woven those insights together — with Spencer and me in the studio reacting to clips — to reveal the patterns, decisions, and principles that define exceptional capital strategy. In this episode, you’ll hear the full interview with: Dug Song [https://www.linkedin.com/in/dugsong/] — co-founder and former CEO of Duo Security (acquired by Cisco for $2.35B), investor, and community builder passionate about cultivating the next generation of founders, operators, and civic leaders. Subscribe to catch the rest of the series and hear from other iconic leaders. Drop your biggest insight from Dug's story in the comments below.