Too Good to be Drew

Ask a question for the show Not everything needs to be shared. Some dreams grow better in private. No opinions. No noise. No doubt. Truth is—everyone isn’t rooting for you. Some people are only comfortable with the version of you that doesn’t outgrow them. So stop talking. Start moving. In this episode: Why silence is power The risk of sharing too soon Letting results speak louder than words Prote...

Ask a question for the show The best thing you can do for yourself? Bring you into everything you do. Life’s too short to hide, fake it, or try to be someone you’re not. If you’re a great person—be you, fully. If you’re not where you want to be—then do the work to become someone better. Either way, own it. Most of us are already pretty incredible. The problem? We don’t let people see it. We overth...

Ask a question for the show Opportunities don’t always look perfect—and sometimes, we miss them. In The Curious Case of Benjamin Button , one small moment changes everything. A reminder: the little decisions matter more than we think. Missed it? Learn from it. Passed on it? Trust it. What matters is what you do next. No rewinding. No regret. Just forward. Stay ready—because the next opportunity is...

Ask a question for the show Fast Friday energy—but real friendship doesn’t come fast. Making friends later in life takes effort. You’ve got to put yourself out there, take risks, and be willing to be vulnerable. Say what you need. Be real about what you’re looking for. And don’t get it twisted—this isn’t passive. You have to show up. Check in. Be there in the highs and the lows. The bar for friend...

Ask a question for the show Inspired by the timeless words of Dr. Seuss, this episode is a reminder that your greatest strength is simply being yourself. In a world that often pushes comparison, we explore what it means to embrace your individuality, own your values, and understand what you’re truly made of. When you lean into who you are—fully and unapologetically—you create the kind of impact no...

Ask a question for the show Back in the driver’s seat with another real one. This episode of Too Good to Be Drew dives into the everyday world of rideshares—Uber, Lyft, and everything in between. What grinds my gears? The lack of care, energy, and basic customer service that’s somehow become the norm. But on the flip side… what earns a big tip from me? Effort. Presence. Pride in the job. It’s wild...

Ask a question for the show It's good to be back!! This episode is a simple reminder—sometimes it’s just one small adjustment that changes everything. One decision, one shift in your day, one choice about how you move or who you’re around. It’s not about being perfect or stressing over every move… it’s about being a little more intentional and owning whatever comes with it. Win or learn, we keep i...

Ask a question for the show Reading A Promised Land by Barack Obama and one word hit me: SLOG. That slow, steady grind when it’s not fun—but still necessary. In this episode, I break down why the slog is where growth happens and how staying consistent in those moments separates you from everyone else. Because the highlight is earned in the grind. Work with me 1:1 --- Nieces and nephews are encoura...

Ask a question for the show Well… it finally happened. After all the episodes, all the conversations, all the stories… Too Good To Be Drew is coming to an end. No more episodes. No more rants. No more Uncle Drew wisdom in your ears. It’s been an incredible run and I truly appreciate everyone who’s listened, shared, supported, and been part of the journey. … Alright, relax. Just Josh’n. The show is...

Ask a question for the show In Part 2 of the Winning Edge Retreat series, Drew reflects on Saturday morning — the most impactful day of the retreat. Before the group made their way to Joshua Tree, something powerful happened: real connection. When people slow down, share space, and choose to truly engage with one another, it creates something special. That morning served as a reminder that growth,...

Ask a question for the show THE WINNING EDGE - Thomas R. Williams In this episode, Drew reflects on attending The Winning Edge Retreat , created by Thomas R. Williams —a powerful men’s gathering built for growth, accountability, and brotherhood among high-performing men. Leading up to the retreat, the energy was clear: men intentionally stepping away from their routines to sharpen their mindset, l...

Ask a question for the show In this episode of Too Good to Be Drew , I talk about the difference between clean jerseys and dirty jerseys . Some people go through life with a jersey that’s way too clean. No sweat. No grass stains. No evidence they were ever really in the game. They show up, go through the motions, and skate by without ever truly putting themselves on the line. But the people who gr...

Ask a question for the show In this episode of Too Good to Be Drew , I break down a truth many people overlook: luck has nothing to do with it. What people call “luck” is really opportunity meeting preparation . The early mornings. The late nights. The reps nobody sees. The commitment to keep going when it would be easier not to. If you want the results, you have to be willing to apply the pressur...

Ask a question for the show On today’s Monday episode, we’re talking about a simple but powerful truth: if you don’t like the situation you’re in, you have two choices. Change the situation or change your attitude. I reflect on a recent get-together with friends and family where I took a step back and realized something important. I’m wealthy. Not just financially, but relationally. I was surround...

Ask a question for the show Development is personal. Nobody is coming to promote you in your own life. If you want the next level — you have to step up to it. In this episode, we talk about the courage it takes to keep climbing. To stop getting comfortable. To stop shrinking. To stop waiting for permission. Growth requires: Confidence before validation Courage before clarity Commitment before comf...

Ask a question for the show Motivation Monday energy as we slide into the week the right way. No fluff, no shortcuts—just the reminder that growth has a cost, and that cost is usually discomfort. If you’re pursuing what you say you want, the struggle isn’t a sign you’re off track… it’s proof you’re on the path. We talk about leaning into the work, staying disciplined when the hype fades, and choos...

Ask a question for the show Wouldn’t be a Fast Friday without hearing from Uncle Drew. The rain in Los Angeles finally cleared (for now), and that shift sparked a reflection on seasons, solitude, and self-discovery. Drew shares how four years living in Eugene, Oregon pushed him to get comfortable being alone, not waiting on people to make plans, not waiting on someone else to bring the energy, and...

Ask a question for the show In this episode of Too Good To Be Drew , I reflect on the emotional weight of an upcoming movie night featuring The Life of Chuck and Rental Family (both on Hulu) —two stories that remind us how deeply connection shapes the way we experience life. We talk about the quiet toll of disconnection, why growth isn’t meant to be a solo journey, and what it really looks like to...

Ask a question for the show Everybody loves to say they’re “grinding,” but most haven’t even touched the tip of the iceberg. Real work isn’t performative — it’s consistent, quiet, and unglamorous. In this episode, I reflect on a recent stretch of flying and work that had to get done, and why that season of pushing reminded me not to idolize burnout. We talk about working with intention, resting wi...

Ask a question for the show Growth is rarely quiet. It’s awkward. It’s public. And most of the time, it’s uncomfortable. In this episode, I reflect on reading President  Barack Obama's most recent book  and the unexpected inspiration I found in  Kai Cenat stepping away from streaming to pursue his dream of becoming a fashion designer. Two very different worlds. One powerful common thread:  the cou...

Ask a question for the show Celebrity fatigue is a real thing... and I've got a bad case of it. Saturday Special breakdown of this year’s Super Bowl commercials and the growing sense of  celebrity fatigue . With brands spending  $8M+ for 30 seconds  (and some reportedly hitting  $10M ), the ads looked flashy… but did they actually move us? In this episode, I talk about why throwing famous faces at...

Ask a question for the show What happens when you put the phone down, look up, and say hello? 👋 In this episode, Drew dives into the underrated power of presence, human connection, and being bold enough to talk to strangers. From small smiles to meaningful conversations, you’ll hear how simple moments can spark unexpected opportunities. Drew also recaps a recent Super Bowl LIX weekend Trust event...

Ask a question for the show In this episode, Drew sits down with  Angela R. Lewis  to talk about using sport as a tool to teach real-life skills. From keynotes and workshops to basketball-based coaching, Angela breaks down how she helps athletes—especially young women—build confidence, communication, leadership, and resilience that carries far beyond the court. We also tap into her  6V Framework ,...

Ask a question for the show The Super Bowl crowns a new champion, and we’re breaking down what the moment represents beyond the scoreboard. Drew kicks off the week with the  Quote of the Day , delivering the mindset you need to attack Monday with purpose. He also dives into the idea of  “football purgatory”  — that in-between season of life where the game is over, but the next chapter hasn’t fully...

Ask a question for the show It’s Fast Friday and we’re previewing  Super Bowl LX  —  Seattle Seahawks  vs.  New England Patriots . Quick hits on the biggest storylines, key matchups, and my pick for who takes the Lombardi in  Levi’s Stadium  in  Santa Clara . Let’s lock in these predictions. Work with me 1:1 --- Nieces and nephews are encouraged to write in to receive a coaching response to their...