Coffee with Kim
Coffee with Kim
Kim Kaupe
How do the Sharks on Shark Tank evaluate deals? What tactic does this NY Times Best Selling author swear by? Who’s behind the social media accounts of today’s hottest celebs? How did this entrepreneur start 3 companies in 1 year and break the million-dollar revenue mark in all three!? Drop into Coffee With Kim – a live-broadcast podcast where host Kim Kaupe brings you along to her coffee meetings with successful CEOs, celebrities & influential individuals. Pull up a chair as you meet these cutting-edge individuals, copy their homework & use it in your everyday life. (Why do the homework when someone else has already done it?!) Want to interact with these impossible-to-access individuals? Join us LIVE on Wednesdays at 1pm EST on LinkedIn. Get involved in the conversation during the live-streamed interviews covering everything from business and entrepreneurship to career and mindset. There’s always a seat at the table waiting for you!
How To Take A Sabbatical With DJ DiDonna
Most of us are stuck in our daily routines. Check emails. Do the work. Sign off and watch a show. If we don’t take the time to look up and make a plan there’s a good chance that’s what years of our life will look like. My conversation with sabbatical researcher and Harvard Business School lecturer DJ DiDonna got really interesting. We talked about what a sabbatical actually is, why it can take six to eight weeks just to start feeling “human” again, and what happens when you finally create enough space to hear your own thoughts. You’ll learn: - Why “functional workaholism” is so hard to spot - How to plan for a sabbatical financially - How and when to ask your boss for extended time off - Real life examples from sabbaticals And here’s the thing: a sabbatical doesn’t have to mean quitting your job, moving to Italy, or coming back with an entirely new career plan. Sometimes the biggest win is simply having enough breathing room to figure out what you actually want. And sometimes? You take the break and realize you really do like the life you already built.
Oct 2
55 min
Building Career Agility in the Age of AI With Jenny Foss
Searching for a job in a world of AI is a new ball game. If you’ve found yourself wondering whether AI is going to change things, what skills you’ll need next, or how you’re supposed to keep up with all of it, grab your coffee. There’s a lot to figure out, but you don’t need to become an AI expert to get started. I sat down with career strategist and recruiter Jenny Foss to talk about building career agility without handing your career over to a chatbot. We get into where AI can actually make your work easier, what should always stay human, and how you can use AI to explore your next career move before making a big leap. You’ll learn: - How to map your day-to-day work and spot the tasks AI can actually help with - When to keep the human in the driver’s seat - How AI can help you uncover transferable skills and explore a career pivot - How to use AI in your job search without ending up with a resume that sounds like…well, everyone else’s - A simple way to start experimenting with AI without adding another overwhelming thing to your to-do list The goal isn’t to let AI take over your career. It’s to use it as a partner, one that can help you save time, ask better questions, explore what’s next, and maybe even see possibilities you hadn’t considered. Your voice, your judgment, and your career direction? Those are still yours.
Sep 25
55 min
How To Price Your Services With Erin Halper
Let’s talk about one of the trickiest parts of running your own business: figuring out what to charge. If you’ve ever stared at a proposal thinking, “Is this too much? Too little? What is everyone else charging?!”, you’re in good company. When I sat down with Erin Halper, founder of The Upside, she had a refreshing take, there may not be a perfect “market rate” for your services. Instead, it’s about understanding the value you bring, the clients you want to work with, and the problem you’re actually solving. Erin and I talked about why hourly pricing can sometimes keep you stuck and unable to scale, and what changes when you start pricing projects, retainers, or engagements around the value of the work. We also got into the four things clients are really paying for: growing revenue, cutting costs, creating access to something, or solving the headache that’s standing between them and their next stage of growth. You’ll learn: - Why there may be no such thing as “market rate” and what to look for instead - The four pillars that help explain the value behind your work - Why taking on something new doesn’t automatically mean you should give a discount - One sneaky sign that you might be undercharging And we definitely get into the uncomfortable stuff, too: when is it okay to work for free, how to take on work you haven’t done before, and what to do when you want to breakup with a client. Erin’s approach is a good reminder that pricing isn’t just about doing the math; it’s also about positioning your expertise and being willing to experiment with what actually works.
Sep 11
58 min
Mini-Workshop: Tips For Job Searching
If your job search has started to feel like a full-time job of its own, tweaking your resume, scrolling LinkedIn, applying for roles, and wondering if anyone is actually reading your application, you are definitely not alone. Between ATS filters, crowded applicant pools, and recruiters searching LinkedIn for candidates, the process looks very different than it used to. I break down how to approach the modern job search, from making sure your resume can actually be read by ATS software to using LinkedIn to show recruiters who you are beyond a list of job titles. I also share why I believe networking should start *before* you need a job and how to use AI as a second set of eyes to help spot gaps, refine your keywords and identify potential questions recruiters might have. You’ll learn: - Why keeping your resume simple works in your favor, and which details are worth highlighting. - How to make your LinkedIn profile clear, searchable, and useful to recruiters. - Why I recommend building relationships with recruiters and industry contacts before you need to ask for something. - How to use AI to compare job descriptions with experience, identify gaps, and save time. - Why staying visible and keeping relationships warm can matter just as much as submitting another application. The job search isn't just about submitting applications and crossing your fingers. Your resume gets you into the conversation, your LinkedIn profile gives people more context, and your network can help open doors you didn't even know were there. Add AI to the mix thoughtfully, and you have a pretty powerful toolkit for your next move.
Sep 4
1 hr 1 min
Coffee Chat: Planning for Q4
If Q4 always seems to arrive in a blur, you’re not imagining it. Between holiday plans, travel, family commitments, year-end deadlines, and everything else competing for your attention, the final three months of the year can get very full, very quickly. The trick isn’t trying to squeeze more into October, November, and December. It’s using September to get ahead. The goal is simple: choose a few priorities, do the thinking before the busy season begins, and create systems that make those priorities easier to stick with. From setting realistic goals to learning new tools before you actually need them, a little preparation now can save you a lot of decision-making later. **You’ll learn:** - Why September is the ideal time to start planning for Q4. - How to choose fewer, more realistic goals and match them to the time they actually require. - Why complex goals, especially learning a new tool, need a research and setup phase. - How pre-deciding meals, books, routines, and priorities can help reduce decision fatigue. You don’t have to do everything before December 31. Some goals are worth completing, while others are better suited for exploring, testing, or setting up for the year ahead. Use September to make those decisions while you have the time and mental space to think clearly. Your future self will thank you.
Aug 31
56 min
Mini-Workshop: Public Speaking
Public speaking can feel intimidating, whether you’re standing on a stage, pitching an idea, leading a meeting, or simply turning on your camera for a Zoom call. Talking too fast, losing your train of thought, or wondering what to do with your hands are all common challenges, and the good news is that they’re skills you can work on. Strong public speaking starts long before you say your first word. From preparing your outfit and technology to slowing down your delivery and focusing on one person at a time, small changes can make a big difference in how confident and comfortable you feel. You’ll learn: - How to prepare before a presentation so you walk in feeling calm and ready - How to focus on one person to make speaking to a room or camera feel more natural - How to review your recordings and get feedback to improve your delivery - What to say when someone interrupts with a question so you can stay on track without shutting them down Whether you’re preparing for a big presentation or simply want to feel more comfortable speaking at work, these tips can help you become a clearer, more confident communicator. You don’t need to become a perfect speaker you just need to keep practicing, paying attention, and finding what works for you.
Aug 21
58 min
LinkedIn Profile Audits: Live
If your LinkedIn profile hasn't been updated in months (or years), you're definitely not alone. But here's the thing: your profile is often the first impression people have of you, whether they're a recruiter, potential client, future collaborator, or someone you just met at an event. In this episode, I'm sharing a simple way to refresh your LinkedIn profile without feeling overwhelmed. From your headline and About section to recommendations, keywords, and those easy-to-miss details, we'll walk through the updates that can help your profile better reflect who you are today and the opportunities you want tomorrow. You'll learn: - How often you should update your LinkedIn profile (and why it matters) - The profile sections that deserve your attention first - Simple ways to showcase your accomplishments with more credibility - Easy updates that can help more of the right people find your profile Your LinkedIn profile isn't something you create once and forget; it's a living part of your personal brand. A few thoughtful updates can make a big difference in how you're discovered, remembered, and connected with new opportunities. So carve out an hour, give your profile a little attention, and let it reflect the work you're already doing.
Jul 17
59 min
Creating AI Systems With Kesha Williams
AI is everywhere, but how do you actually use it in a way that saves time and makes your work easier? When people ask me where to start with AI, my answer is almost always the same: don't try to learn everything. Start with one problem you want to solve. It feels like there's a new tool, update, or headline every day, making it easy to think you need to master it all. But the biggest wins often come from finding a few ways AI can eliminate repetitive tasks so you have more time to focus on the work that matters most. This week, I had the chance to sit down with AI expert and software engineer Kesha Williams to talk about moving beyond simple prompts and using AI to build systems that handle repetitive work. We cover everything from identifying tasks that are perfect for automation to creating guardrails that keep AI helpful, reliable, and human-centered. You'll learn: - Why AI systems are more valuable than one-off prompts - How to identify tasks you can automate today - Why human oversight is still essential when using AI - Examples of AI agents and workflows that save hours each week - The skills that will become even more important as AI continues to evolve Whether you're just getting started with AI or looking to take your workflows to the next level, this conversation is packed with ideas that will help you work more efficiently, without losing the human judgment and creativity that make your work uniquely yours.
Jul 10
48 min
Navigating Emotionally Charged Conversation At Work With Dr. Emily Anhalt
Some of the hardest conversations in life aren't difficult because we don't know what to say, they're difficult because emotions get in the way. Whether it's giving honest feedback, navigating conflict, or speaking up when something feels off, it's easy to avoid the conversation altogether. But what if those moments became opportunities to build stronger relationships instead? This week, I sat down with clinical psychologist and emotional fitness expert Dr. Emily Anhalt to talk about what it really means to build emotional fitness. Just like physical fitness, emotional fitness isn't something you achieve once, it's something you practice over time. Dr. Emily shares simple ways to strengthen your emotional resilience, communicate with more confidence, and create healthier relationships at work and at home. You'll learn: - How to build emotional fitness through small, consistent habits - A simple framework for handling difficult conversations by being clear and kind - What to do when you feel emotions hijacking the conversation - How leaders can model healthy vulnerability while maintaining boundaries - Practical exercises you can start using today to strengthen your emotional resilience The best part? You don't have to be perfect to get better. As Dr. Emily reminds us, emotional fitness is built one conversation, one habit, and one practice at a time. I hope this episode gives you the confidence to tackle that conversation you've been avoiding and reminds you that every small step counts.
Jul 3
52 min
How To Build Resilience With Dr. Judith Joseph
We all have seasons where we're checking the boxes, hitting our goals, and staying busy...but still feeling disconnected from joy. If you've ever wondered why success doesn't always translate to happiness, pull up a chair. I sat down with Dr. Judith Joseph, a board-certified psychiatrist, researcher, and author, to talk about the science of joy, resilience, and a little-known condition called anhedonia, the inability to feel joy. We talked about why so many high achievers struggle to feel fulfilled and what we can do to reconnect with ourselves and slow down. You'll learn: - What anhedonia is and why it often goes unnoticed - The surprising ways burnout and overworking can mask deeper struggles - Why joy isn't a luxury, it's essential to being human - Simple ways to begin rebuilding joy in your everyday life - Why self-awareness is a powerful first step toward healing and growth Dr. Judith shares practical tools, research-backed insights, and an encouraging reminder that joy is not something you have to earn, it's something you deserve. Whether you're feeling overwhelmed, stuck, or simply ready to create more meaning in your life, come sit at our table and remember you’re always welcome to chime in here!
Jun 26
50 min
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