S2:E10 - Will & Robert - Business, Setbacks & Perseverance

Will and Robert get real about the challenges, setbacks, and difficult seasons they’ve faced in business—and what it takes to keep moving forward when things don’t go according to plan. From adversity and uncertainty to hard lessons learned along the way, they share what helped them persevere, stay grounded, and remain hopeful.This episode is a reminder that difficult seasons don’t have to define you. Sometimes the hardest roads build the strongest people, sharpen your perspective, and prepare you for what’s ahead.

Will and Robert sit down for a conversation about one of life’s biggest challenges: parenting. They talk about the lessons, responsibilities, and experiences that come with raising kids and trying to help the next generation become strong, confident, and capable adults.Then Will sits down with Matt Emrich, owner of an independent insurance company and former University of Arkansas football player. Matt shares his journey from playing football at the collegiate level to building a business of his own, along with the lessons he’s learned about discipline, leadership, risk, and perseverance along the way.It’s an episode about parenting, personal growth, entrepreneurship, and what it really takes to keep moving forward when the path isn’t always clear.

In this episode of the WillPower Podcast, Will and Rob kick things off with a conversation about their love (and occasional frustration) for the game of golf. From memorable rounds to lessons learned on the course, they share why golf has become more than just a hobby.Then, Will sits down with his golfing buddy, Ryan Weber, for a laid-back conversation about life, business, relationships, and the connections that are built both on and off the fairway.Whether you're a golfer or just enjoy authentic conversations between friends, this episode is packed with laughs, stories, and a few insights along the way.⛳ Tune in and join the conversation!

 Strong businesses are built on strong relationships. In this episode of The Willpower Podcast, Will and Robert have an honest conversation about marriage before Will and Amanda welcome fellow entrepreneurs Jesse and Jolynn Holencik. Together, they explore the unique dynamics of working alongside your spouse, navigating conflict, celebrating wins, and building a business without losing sight of what matters most. Whether you're an entrepreneur, a spouse, or both, you'll walk away with insights and encouragement for the journey. 

On Season 2, Episode 6 of the Willpower Podcast, Will sits down with Chris Gonsalves — multi-business owner, extreme sports enthusiast, and a man relentlessly driven toward excellence.Chris shares the mindset behind building businesses, pushing limits, and refusing to settle for average. From entrepreneurship and leadership to adrenaline-fueled adventures and personal discipline, this conversation dives deep into what it means to live fully committed in every area of life.If you’ve ever wrestled with fear, comfort, complacency, or the pursuit of greatness, this episode will challenge and inspire you to level up.

Will and Robert take a laid-back, story-filled dive into the power of small decisions and life’s biggest transitions. From childhood chaos and cross-state road trips to marriage, money management, and faith-driven pivots, this episode blends humor, nostalgia, and hard-earned wisdom. It’s a reminder that the little choices often shape the biggest outcomes—and that every season has something to teach.

Transition is inevitable—but navigating it well is anything but easy.In this episode of The Willpower Podcast, we sit down with Jimmy Dale to unpack the complexities of stepping into ownership, taking over a company from a previous generation, and the realities of buying and selling businesses.From honoring legacy while embracing change, to the practical and emotional challenges that come with leadership transition, this conversation offers insight for anyone facing a pivotal shift in business or life.Whether you’re preparing to take the reins, pass them on, or position a company for sale, this episode provides real-world perspective on what it takes to move forward with clarity and confidence.

In this honest and often hilarious episode of The Willpower Podcast, Will and Rob dive into a topic every married man understands — “getting in trouble” with their wives. From miscommunication to misplaced priorities, they unpack what’s really happening beneath those tense moments and how growth often hides inside the conflict.Then the conversation gets personal.Will sits down with his wife, Amanda Brown — Office Manager at Brown Boys Roofing — for a candid interview about the real-life transition from stay-at-home mom to full-time leader inside a rapidly growing company. Amanda shares the emotional, logistical, and relational challenges of stepping into the business, redefining identity, navigating marriage while working together, and helping scale a family-run operation.This episode pulls back the curtain on:The tension between home life and business growthWhat it’s like to work alongside your spouseThe unseen weight of operational leadershipIdentity shifts when seasons changeHow communication can make or break both marriage and businessReal talk. Real marriage. Real business.If you’ve ever built something with your spouse — or “gotten in trouble” trying — this one’s for you.

In Episode 2 of Season 2, Will and Robert open with an honest conversation about generational leadership—breaking down the differences between how their father ran the business and how Will leads today. From communication styles to decision-making, they explore what had to evolve as the company and culture changed.Will then sits down with longtime family friend and supply company owner Don Willard, who shares his firsthand experience transitioning the business to his two sons. Don opens up about the challenges of letting go, the importance of trust, and how to lead without stifling the next generation.This episode is a must-listen for business owners, leaders, and families navigating succession, growth, and legacy. If you’re building something meant to outlast you, this conversation will hit home.

Season 2 kicks off with a full-circle moment. Will and Robert open the episode by reminiscing about growing up together—the laughs, the lessons, and the foundation their dad quietly built into their lives. From discipline and work ethic to relationships and character, they reflect on how those early years shaped who they are today.Then, for the first time on The Willpower Podcast, they sit down with the man himself. In an honest and meaningful conversation, their dad shares wisdom on raising a family, leading with integrity, and what it really means to pass the torch of the family business to the next generation.This episode is about legacy—what’s taught, what’s caught, and what lives on.