Win The Hour, Win The Day

Two years ago he couldn't take 14 hours off. In two weeks he's going off grid for 14 days. The only thing he's packing is his phone. Dan Bennett is back on the podcast this week, and I want to be clear about something. When we started working together, Dan was not a mess. He was one of the most systems-minded people I've ever worked with. He was still riding what he calls the pendulum. Land some sales, swing over to deliver. Look up, no new sales, swing back to sell. Take a Sunday with the family and pay for it all day Monday. He had the systems. They just weren't simple enough to keep up with him. Here's the line from our conversation I can't stop thinking about: "Build the system for the problem that doesn't exist yet." Because if you don't, you're reacting to the future instead of being ready for it. That's how his hiring went from "ugh, not again" to one quick yes. It's part of how the business has grown about 2.5X year over year. It's why nobody on his team works Sundays. Good systems don't just calm the chaos. They're ready for the growth you've been asking for.

For years, the back half of every sales call was a performance. They'd talk for thirty minutes. I'd listen, take notes, feel quietly proud of myself for not jumping in to fix the thing at minute four. Then some invisible buzzer would go off, it was my turn, and I'd build the pitch on the fly, in front of them, with the clock running. I called that listening. It was closer to waiting. Wesleyne Whittaker came on the show and told me to stop. Split it in two. Meeting one, you only collect. Then you go away, build a very simple slideshow out of their own words and their own problems, and you come back a day later and walk them through it. I pushed back. Hard. A slide deck felt like the most obvious "here comes the sell" move I could possibly make. I was wrong, and my conversion rate is the proof. Here's what nobody tells you about the two-call version. They get to finish their sentences. A five minute story stays a five minute story instead of getting squeezed because I'm watching the clock. And I show up the second time calm, prepared, with their life on the screen in their own language, and they look at me like I wrote a book about them. Wesleyne has a name for the old way. Sales malpractice. Her line: who diagnoses a person without actually touching them, seeing them, feeling them? No doctor prescribes before they've looked at your arm. And no doctor pulls up a generic slide about a fifty year old man's shoulder when you are not a fifty year old man. That's what a one-call pitch is. Someone else's X-rays. The other thing she said that I keep turning over: your prospects don't need to like you, they need to respect you. Liking gets you lunch. Respect gets you the meeting. Which half of your sales call is the performance? This week’s episode of Win The Hour, Win The Day Podcast interviews, Wesleyne Whittaker. Listen in.

I used to think my best stories were too small to post. Then I read someone say she'd sooner jump out a second-story window than sit in a Zoom breakout room. I laughed out loud, because I've felt that way about every "get to know your group" warm-up I ever sat through. I'd kept that to myself for years. Storytelling coach Toby Myles came back on Win The Hour, Win The Day and cleared this up for me. You don't have to squeeze a business lesson out of every moment. The small, relatable ones are what make people feel like they know you, and people hire people they feel they know. She says the number one storytelling skill is noticing and documenting. We all have story-worthy moments every day, we just let them slide by. We also got into her TESS framework (Trigger, Emotion, Shift, Share), why "it's not a documentary" is the best editing advice I've been given, and what AI is doing to everyone's voice, including in job interviews. If you've been staring at a blank post this week, this one's worth your commute. This week’s episode of Win The Hour, Win The Day Podcast interviews, Toby Myles.

I'm at my best in a private conversation. One-on-one, in the comments, on a call, I'm all in. Then it's time to be visible in public, and I shrink. For years I told myself the fix was to pitch harder. Get on a bigger show. Wait for someone with a larger audience to notice me and pull me up. Then Jamie Maglietta got on the podcast. She produced Vice President Kamala Harris at BET and spent 20 years inside MSNBC, Fox and CNN. She said one thing that rearranged how I think about being seen. You don't chase media. You produce it. That sounds like a slogan until she breaks it down. A national hit on CNN feels enormous and often brings in zero clients. She had a legal commentator on her show who'd been on every network, and it never turned into a single paying customer. Meanwhile her people go on one tiny local segment and pick up more followers in a day than any national spot ever gave them. Turns out the chase brings in almost nothing. What pays is being findable, clear, and someone people want to stay connected to. And here's the move I can't stop thinking about. Instead of sending some writer a "loved your article" note and hoping, find an expert you genuinely disagree with, say so publicly, and tag them. Now you're producing a conversation people actually want to watch, and you're in it as an equal. One more line of hers stung a little. You can be smart and really boring. Being the expert isn't enough. People have to want to turn you on. So where do you go quiet when it's time to be seen? This week’s episode of Win The Hour, Win The Day Podcast interviews, Jamie Maglietta. Listen in.

This week’s episode of Win The Hour, Win The Day Podcast interviews, Kris Ward. You're not tired. You're everybody's answer. And nobody has ever named that out loud, so you keep treating it like a discipline problem. Friends, family, clients, the team. Something breaks and the phone rings and it's you, because it is genuinely faster to handle it than to explain it. You have been that person since you were the kid taking somebody else's crisis at eleven at night, and twenty years of practice later you carried the whole habit straight into your business. Here's the thing, that isn't a work ethic, it's a setup. The more you can handle, the more you get handed, and the more you get handed, the more you prove you can handle it. I ran on that for years and called my speed a superpower. It was a symptom, not a strength. So watch the next moment somebody tells you a problem they haven't actually asked you to solve. That gap, between hearing it and fixing it, is where most of your week is going. The work that would move your business forward isn't lost to laziness, it's lost to everything you picked up before anyone asked.