They Don’t Care Why It Went Wrong: How to Talk to Clients When Things Go Sideways
Release Date: 11/24/2025
Appointment Only
Not every lead deserves your time, and not every dollar is worth what it costs you. In this episode, we talk honestly about why turning people away is one of the most important skills you can build as a business owner. We break down how to qualify prospects, set non-negotiable minimums, and stop bending over backward for people who aren’t aligned with your goals, values, or process. We share a real email exchange that proves exactly why boundaries matter, how misaligned clients reveal themselves early, and how clear communication actually protects both sides. Tune in to learn how protecting...
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Before we ever ran a high-end business, we picked rocks in farm fields, flipped burgers at the county fair, mowed lawns, landscaped, and parked luxury cars as valets. None of those jobs were glamorous, and most of them weren’t fulfilling, but every single one taught us something we still rely on today. In this episode, we break down the business lessons hidden inside menial work, from understanding value over cost, to pricing projects instead of hours, to learning why not every job is meant to feel inspiring. We also talk about unrealistic expectations around fulfillment, why work ethic...
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Has anyone ever told you to raise your prices and your immediate response was to explain why that won’t work? That reaction alone might be the clearest sign you’re undervaluing your business. In this episode, we break down the most common signs your business is quietly operating from a place of undervaluation. We talk about how these habits train clients to treat your work as less valuable than it actually is, the difference between cost and value, why premium clients don’t want bargains, and how discount-driven businesses train customers to only show up when there’s a deal. Get ready...
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Scope creep. No-shows. “Quick questions.” If any of that just triggered you, press play. In this episode, we’re talking about how to “train” your clients so they actually respect your time and follow your process. We share the real boundaries we’ve built, why we’re obsessed with clarity (and paper trails), and the small, subtle tweaks that make people take you seriously without you having to be a jerk about it. Expect some laughs, a few strong opinions, and a whole lot of “we learned this the hard way” moments, because nothing inspires a better system like getting burned once...
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Feel like you “should” be running ads, but you’re not even sure what’s working… or if you can afford it? In this episode, we share the mistake most small business owners make paying for marketing way too early, and the free (or almost free) marketing moves that actually move the needle for a high-end, service-based business. We’ll walk you through how to set up your Google Business Profile the right way, what your website really needs to convert local clients, how to think about social media without chasing every trend, and how to use earned media (local TV, magazines, radio,...
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Most entrepreneurs worry about getting more clients, not getting burned by the people who are supposed to be “on their side.” In this episode, we share the full story of how our longtime tax preparer secretly stopped paying our payroll taxes, how it spiraled into years of penalties, fear, and cleanup, and what we did to finally get out of it. We walk through the red flags we missed, why “no news” from your tax person is not good news, and the exact steps we took to switch firms, negotiate repayment, and get our business and personal finances back on solid ground. If you’ve ever felt...
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Most entrepreneurs only celebrate when something huge happens, and that isn’t often enough. In this episode, we talk about Thanksgiving, gratitude, and why small and repeatable wins are the things that prevent burnout and keep momentum alive. We share how we set realistic goals, how to reward yourselves when you hit them, and ways you can start celebrating even if cash is tight. Tune in to celebrate more, stress less, and enjoy the business you’ve built. Happy holidays ahead! Highlights 00:00 Holiday sign-offs and the mood before Thanksgiving. 07:30 Why gratitude is hard for...
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Blame might feel satisfying in the moment, but it is quietly torching your reputation, your team culture, and your profit. In this episode, we unpack why the buck really does stop with you as the business owner, and how owning that actually gives you more control, not less. We walk through real stories from our shop and our clients where shipping disasters, customs delays, and vendor mishaps could have turned into finger pointing, and instead became opportunities to reinforce trust and integrity. You will learn how to talk to clients when things go sideways without throwing your team or your...
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Most business objections that sound like “I can’t afford that” are really a priorities problem, and the language we use matters. In this episode, we talk about why saying you can’t afford something hides the real decision, how to reframe tough choices through your priorities lens, and why that clarity makes saying “no” easier and more profitable. We share examples (vacations, trainers, hires, branding) and a few stories from the shop that reveal how thinking in priorities changes decisions, simplifies sales conversations, and helps you run the business you actually want. Get ready...
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We’ve seen a lot over 15 years of running a high-end small business, and some of the things business owners do (including things we used to do) make your brands look way less premium than they actually are. Some of the stuff you think is “nice,” “humble,” or “on trend” is actually making your business look low-end. In this episode, we talk about the business-owner pet peeves that quietly communicate insecurity instead of authority and the signals clients pick up on that communicate whether you’re confident, insecure, or trying too hard. Tune in and see which of these pet peeves...
info_outlineBlame might feel satisfying in the moment, but it is quietly torching your reputation, your team culture, and your profit. In this episode, we unpack why the buck really does stop with you as the business owner, and how owning that actually gives you more control, not less. We walk through real stories from our shop and our clients where shipping disasters, customs delays, and vendor mishaps could have turned into finger pointing, and instead became opportunities to reinforce trust and integrity. You will learn how to talk to clients when things go sideways without throwing your team or your circumstances under the bus, how to design policies that protect you from “unforeseen” issues, and when it is actually helpful to share context or responsibility. We also tackle the classic line “you have to spend money to make money” and show you where that is true, where it is killing your cash flow, and what to stop spending on immediately so you can run a profitable, high end business you are proud of.
Highlights
00:00 Rat boy summer, fat boy fall, and why this episode is really about blame.
04:30 How casual blame creeps into everyday conversations and business stories.
09:15 Why throwing your own team under the bus makes you look insecure and unprofessional.
14:00 Handling mistakes in house without making your client part of the internal drama.
18:45 Blaming circumstances like shipping, weather, and vendors and how that lands on your client.
23:30 Real stories from customs delays, snowstorms, and missing packages that test your policies.
28:15 Building timelines, boundaries, and rush rules that protect you from “unforeseen” issues.
33:00 When it is actually appropriate to share responsibility or context with a client.
37:30 Why the buck stopping with you is the price of freedom in business and how to accept it.
40:45 Breaking down “you have to spend money to make money” for small, high end businesses.
44:00 What new businesses should avoid spending on, including swag and overbuilt branding.
47:30 A simple filter for deciding what to invest in next so you are not blaming your spending later.
Resources + Links
Apply for Luxury Clothier Collective Mastermind HERE
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