Daily Path with Joe Winters Jr.

Hosted by Joe Winters Jr.

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517

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Aug 2026

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About the show

Welcome to Daily Path Podcast, the #1 podcast for B2B coaches and entrepreneurs turning their expertise into a profitable coaching business. Hosted by Joe Winters Jr., the Podcast Revenue Strategist, this show features in-depth conversations with real B2B coaches who are actively building their businesses and serving clients while staying true to their purpose. Whether you're already fully committed to coaching or you're an entrepreneur thinking about stepping into coaching, this podcast gives you real stories, strategies, and systems behind what actually works.

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60 recent

August 24, 202615 min

The Truth About Growing Past Your Current Deal Size | #517

This year I set my sights on closing seven figure contracts, and I quickly realized that wanting the deal isn't enough. I had to change who I was showing up as first. In this episode I break down the truth about growing past your current deal size: Why you can change without growing, but you can't grow without changing Getting clear on your goals so doubt has less room to creep in Communicating your sacrifices instead of just making them, including how I talk to my daughter about the work I do Separating from the people who oppose you, even when their opposition comes from a good place If you're a B2B coach, consultant, or entrepreneur working toward your next level, whether that's your first 10K client or your first seven figure contract, this episode gives you the framework I'm using to get there. ----- Are you ready to build credibility, generate qualified leads consistently, and close premium deals? Book a discovery call to learn about the Podcast Client System here: https://www.joewintersjr.com/start

August 17, 20268 min

3 Signs You Should Be Coaching and Consulting | #516

I want to share three signs with you today that tell me whether coaching and consulting is actually part of your purpose. This episode is for you if: You've had success in your career, as an athlete, in the corporate world, wherever People keep telling you that you should be coaching or consulting, but you haven't made the move You've already started but you're wondering if you can actually sustain it The three signs I walk through: You genuinely care to see other people win It bothers you when someone won't act on your advice You feel a real return when someone actually implements what you gave them If all three are true for you, the hesitation you feel isn't proof you're on the wrong path. It's proof you haven't built the systems yet to make it sustainable, and that part is fixable. ---- Are you ready to build credibility, generate qualified leads consistently, and close premium deals? Book a discovery call to learn about the Podcast Client System here: https://www.joewintersjr.com/start

August 10, 202639 min

Leaving a 20-Year Career to Become a Coach | 515

After more than two decades in a stable, high-status career, this week's guest walked away at 47 to start over as a coach. He talks through the fear of losing a steady salary, the process of finding his first clients, and the moment he realized coaching had been his gift all along. He also opens up about the hardest part of running his own business: learning to say his price out loud without flinching. From there the conversation moves into his work with MBA students and business leaders, why so many high achievers struggle with confidence in front of a room, and how a chance conversation at the gym turned into a keynote for a major luxury brand. If you are building relationships that eventually turn into clients, or you are still working up the nerve to charge what you are worth, this episode has something for you. BUILD THE PODCAST YOUR VOICE ALREADY EARNED: If you're ready to build a podcast that attracts and converts premium clients while empowering the people you serve. Visit joewintersjr.com/start to book a free discovery call.

August 3, 202610 min

The 5 Things Your Podcast Launch Is Missing | #514

I break down the five things separating coaches who get clients from their podcast from coaches who just get downloads. Most coaches confuse their ideal client avatar with their target audience, and that mix-up quietly kills momentum before they even notice. I get into why your objective, awareness or conversions, has to be decided before launch, why your lead list is doing more work than your content ever will, and why I built my own program only after the market told me what to build, not before. If you're a B2B coach building a podcast, or yours isn't converting yet, this one gives you the fix. BUILD THE PODCAST YOUR VOICE ALREADY EARNED: If you're ready to build a podcast that attracts and converts premium clients while empowering the people you serve. Visit joewintersjr.com/start to book a free discovery call.

July 27, 202610 min

How to Lose $10K Deals in Your Coaching Business | #513

My daughter just started playing tennis, and this week I watched a coach lose a $10K client in one sentence. Not because of price. Not because of skill. Because he said something he didn't actually believe, just to sound indispensable. In this episode, I break down the fastest way coaches lose deals: focusing on selling instead of serving. I share what happened on that court, why prospects can feel it when you're not being truthful with them, and why how you treat someone before they pay you is a preview of how you'll treat them after. If you've ever wondered why a deal that seemed like a lock fell through, this one's for you. BUILD THE PODCAST YOUR VOICE ALREADY EARNED: If you're ready to build a podcast that attracts and converts premium clients while empowering the people you serve. Visit joewintersjr.com/start to book a free discovery call.

July 20, 20266 min

Removing Fear from Your Coaching Business | #512

One of the biggest mistakes I see coaches make is letting fear get in the way of the business they're building. Comparing themselves to coaches on social media, listening to rhetoric built on fear instead of building their own belief in what they can do. In this episode I break down why that's a recipe for disaster. I talk about coaches who never played in a championship game but coached teams that won one, why studying a coach is different from comparing yourself to one, and why fear of judgment, not lack of skill, is the real thing holding most coaches back. BUILD THE PODCAST YOUR VOICE ALREADY EARNED: If you're ready to build a podcast that attracts and converts premium clients while empowering the people you serve. Visit joewintersjr.com/start to book a free discovery call.

July 13, 20268 min

Your Prospects Aren't the Problem, You Are | #511

Do you ever walk into a sales call already convinced the person across from you isn't going to buy? You tell yourself they don't see the value in investing in themselves, or they don't understand why your service matters. In this episode, I break down why that feeling has less to do with your prospect and more to do with a lack of preparation and how projecting your own insecurities onto a call sets you up to fail before it starts. I share two things you can do right now to walk into every sales call prepared instead of anxious: how to properly research and rehearse before a call, and why sending the right content to your prospect beforehand changes the entire dynamic of the conversation. I also leave you with a question worth sitting with: do your prospects really not see the value in what you offer, or do you not see the value in who you are? If you're ready to build a podcast that attracts and converts premium clients while empowering the people you serve, visit joewintersjr.com/start to book a free discovery call.

July 6, 202610 min

The Real Reason Coaches Can't Charge What They're Worth | #510

You're great at what you do. So why can't you charge what you're worth? I see it constantly. Successful entrepreneurs and executives' step into coaching, do incredible work, and still can't get to the income level that lets them take care of their family beyond the basics. If that's you, this episode is for you. I break down why being divided against yourself, pricing from scarcity instead of outcome, and avoiding the marketing that actually attracts premium clients is holding you back and what to do about it. Stop playing small. Stop running from what you should confront head on. Interested in attracting premium clients that buy your programs while empowering the people you serve by building a podcast? Book a discovery call with me here: joewintersjr.com/start

June 29, 20269 min

Know Your Floor: How to Go Full-Time in Coaching | #509

Interested in attracting premium clients and empowering the people you serve by building a podcast? Book a discovery call with me here: joewintersjr.com/start Going full-time in your coaching business is simpler than most coaches make it. It's not easy, but it is simple. In this episode, I break down what it actually takes to become a full-time coach, and why most people never get there. Most coaches stay stuck for one reason: they lie to themselves about where they are. They believe they need hundreds of clients and millions in revenue before they're "allowed" to go pro. They don't. Coaching has a starting point like everything else. Inside this episode: Why your floor matters more than your ceiling, and how to find the real number required to take care of your family The backwards math keeping coaches employed, and why you shouldn't demand more from your own business than you'll accept from a boss The two paths to going full-time: having the time to generate leads and close deals yourself, or having the money to pay someone who will Why niching down means fewer clients, premium fees, and bigger results on the same hours you're already working If you're a coach trying to go full-time and attract premium clients, this one gives you the standard to hold yourself to. ---- Join my podcast newsletter Daily Path Insider here: https://www.joewintersjr.com/insider

June 22, 202654 min

Genuine Relationships Are Your Best Sales System with Debbie Wemyss | #508

Building a purpose-driven coaching business and want to attract premium clients with a podcast? Start at joewintersjr.com/start . ---- Most coaches are out here chasing algorithms, running ads, and burning money on funnels, and completely overlooking the most powerful sales system they already have. Genuine relationships. Debbie Wemyss spent 15 years and worked with 900+ clients building a coaching business with no ad spend, no fancy tech stack, and no venture capital. Just a commitment to showing up for people before she ever needed anything from them. In this episode, Debbie breaks down the exact LinkedIn habits and relationship principles that built her business from the ground up, including how a 20-minute daily routine can generate more pipeline than most coaches get from an entire marketing budget. You will learn: Why most coaches mistake engagement for pipeline and what to do instead The 20-minute LinkedIn habit that keeps relationships warm without being transactional How to position yourself as a resource so clients come to you when they are ready to buy Why your first-person LinkedIn voice is the difference between blending in and standing out How Debbie turned a networking room into a national conference speaking career with no paid placement ---- Join Daily Path Insider here: https://www.joewintersjr.com/insider