Entrepreneur Encounter

Entrepreneur Encounter
  • 5.0 (7)
  • Entrepreneurship
  • Updated Weekly

Entrepreneur Encounter is a weekly podcast designed to support creative business owners in developing the soft skills that lead to lasting, values-aligned growth.Hosted by Dana Johnson, founder of a boutique Pinterest marketing agency for wedding pros and creatives, and Sara Lowell, a consultant specializing in business management & team leadership along with podcast management, each episode explores the mindset shifts, communication skills, and leadership habits that empower entrepreneurs to grow sustainably—without the burnout.Through real stories, practical frameworks, and transparent conversations, Dana and Sara offer a behind-the-scenes look at what it really takes to run a purpose-driven business in a constantly changing world.Whether you're building your visibility, managing a team, or simply trying to stay grounded while growing, this podcast is your companion in business and in life.

  1. 6d ago

    Your First Client: What No One Tells You About Pricing, Boundaries & Confidence | EP 49

    Send us Fan Mail Landing your first client feels like crossing the finish line, until you realize it's actually the starting line. You celebrate the "yes," hang up the phone, and then the questions hit: What do I do now? Am I charging enough? How much is too much? How do I keep this client happy without giving everything away? In this conversation, we unpack what really happens after you land your first client. It's not a conversation about proposals or onboarding checklists, it's about the mindset shifts that come with getting paid for your work for the first time. Drawing from our own experiences, we explore the habits that many new business owners fall into: overdelivering to prove their value, letting friendly relationships blur professional boundaries, and setting prices that become difficult to outgrow. These early decisions often shape the way you work long after that first project ends. If you've ever struggled to balance great service with healthy boundaries or wondered why raising your rates feels so hard, this episode will help you understand where those patterns begin and how to break them. What you'll hear in this episode: Why overdelivering is often driven by fear, not exceptional customer service.How friendly client relationships can quietly lead to blurred boundaries and scope creep.Why your first pricing decisions can have a lasting impact on your confidence and how to avoid getting stuck there.The mindset shift that matters most when you stop trying to earn permission and start building a sustainable business.Ask yourself:  What did your first client teach you that you're still unlearning today? And if you could go back, what advice would you give yourself? Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

  2. Jul 17

    From Agreeable to Assertive: How to Stop Losing Yourself in Client Relationships | EP 48

    Send us Fan Mail You've said yes when every part of you wanted to say no. You've softened your feedback until it barely meant anything, just to avoid making someone uncomfortable. You've held back your real opinion in a client conversation, a team meeting, a collaboration — not because you didn't have one, but because you were afraid it would cost you the relationship. If any of that sounds familiar, this episode is for you. At its root, people pleasing is more of a survival strategy than a character flaw. And for a lot of you, it's worked. Maybe it kept the peace in a household that needed keeping. Maybe it helped you navigate school or a toxic workplace where your safety depended on being agreeable. Maybe it's the thing that made you good at your job — attuned to what people needed, flexible, easy to work with. In psychology and trauma research, there's actually a name for this pattern: the fawn response, coined by therapist Pete Walker. It's considered the fourth stress response alongside fight, flight, and freeze and what makes it different is that it doesn't look like fear. It looks like helpfulness. It looks like warmth. It looks like being the best team player, which is exactly why it's so hard to recognize and so hard to change. Research on people pleasing in driven, high-achieving women has found that fawning frequently coexists with professional success meaning you can be capable and accomplished at work and still lose access to your own voice the moment a relationship feels even slightly risky.  Want to grow your audience without a big marketing budget? We are so excited to introduce the Spotlight Swap. Here is how it works: we feature you in the Entrepreneur Encounter newsletter and you feature us in yours. No complicated partnerships, no big budget. Just two businesses helping each other get in front of new audiences. If that sounds like something you want to be part of, fill out the form below and we would love to swap spotlights with you. 👉Fill out this form here: https://forms.gle/UMfhMqPQSXDXbU828  What to listen for in this episode: Why people pleasing isn't a character flaw but a nervous-system survival pattern and why understanding it intellectually isn't enough to change itThe hidden costs of chronic accommodation: resentment, lost identity, and burnout that shows up in your energy, creativity, and decision-makingSpecific, practical phrases for replacing over-agreement with honest, assertive communication that actually strengthens client trustIf you've been performing a version of yourself to keep everyone else comfortable, ask yourself: what would it cost you to keep doing that for another year — and what might it cost you to stop? Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

  3. Jul 10

    Why Softening Your Feedback Is Costing You Better Work | EP 47

    Send us Fan Mail You just got work back from the contractor you hired and it's not quite what you asked for but it's close enough, so you quietly fix it yourself. Again. You tell yourself it's faster this way, that you don't want to be "that" client, "that" boss, or the person who makes things awkward. So you say nothing, or you bury the real point under so much cushioning that it never actually lands. Then it happens again next week. In this conversation, we unpack why vague, conflict-avoidant feedback is quietly costing you better work, stronger relationships, and a business you can actually trust to run without micromanaging every deliverable.  You’ll hear the real reason feedback feels so hard; it's not a lack of practice, it's the self-awareness and vulnerability it requires and walk through the specific costs of staying vague: redone work, resentment, and team members who never get the chance to improve. Also you’ll learn a simple framework for giving feedback that's specific, timely, focused on the work, and paired with care. Want to grow your audience without a big marketing budget? We are so excited to introduce the Spotlight Swap. Here is how it works: we feature you in the Entrepreneur Encounter newsletter and you feature us in yours. No complicated partnerships, no big budget. Just two businesses helping each other get in front of new audiences. If that sounds like something you want to be part of, fill out the form below and we would love to swap spotlights with you. 👉Fill out this form here: https://forms.gle/UMfhMqPQSXDXbU828  What to listen for in this episode: Why "no worries, this is great, just one tiny thing" actually buries your point instead of protecting the relationship and what to say insteadThe real, hidden costs of vague feedback: doing the work twice, growing resentment, and a contractor or VA who never gets the chance to actually improveA four-part framework for feedback that lands — specific, tied to the work (not the person), delivered close to the moment, and paired with careIf you've been softening feedback into nothing because it feels safer — what is that silence actually costing you, your business, and the person you hired to help you grow it? Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

  4. Jul 3

    Why Jumping to Fix-It Mode Is the One Habit That's Breaking Your Business Relationships | EP 46

    Send us Fan Mail You're mid-call with a client. They're frustrated, something slipped, something didn't land the way they imagined and before they've even finished their sentence, your brain is already three steps ahead. You're building the solution. You're being efficient. You're doing what you do best. Except they haven't felt heard yet. And that gap - between solving and understanding - is exactly where business relationships start to fall apart without anyone realizing why. In this episode of Entrepreneur Encounter, the conversation gets into empathy as a practical, learnable business skill — not the soft, abstract version, but the kind that directly affects client retention, team communication, and even how you negotiate. You'll hear why fix-it mode isn't the problem (it's actually a strength), but why leading with it before someone feels understood tends to backfire. We cover what empathy actually looks like in day-to-day business situations, where it tends to break down when things get busy, and a handful of small, repeatable shifts you can start using this week. Want to grow your audience without a big marketing budget? We are so excited to introduce the Spotlight Swap. Here is how it works: we feature you in the Entrepreneur Encounter newsletter and you feature us in yours. No complicated partnerships, no big budget. Just two businesses helping each other get in front of new audiences. If that sounds like something you want to be part of, fill out the form below and we would love to swap spotlights with you. 👉Fill out this form here: https://forms.gle/UMfhMqPQSXDXbU828  What to listen for in this episode: 1. Empathy is a shortcut, not a detour. Most entrepreneurs assume that pausing to understand someone costs time. But when someone feels genuinely heard, they stop escalating, stop repeating themselves, and get to "let's solve this" faster. Understanding first isn't in the way of efficiency — it often is the efficiency. 2. Quiet is expensive. If you have even one contractor or team member and they're not bringing you problems, that silence isn't peace — it's a warning sign. Empathy is what creates the psychological safety for people to tell you the truth before a small issue becomes a big one. 3. Empathy in negotiation is a strategy, not a weakness. Understanding what the other party actually needs — not just what they're asking for — is how you find deals that hold. Agreements made without it tend to unravel or end relationships rather than build them. The entrepreneurs who retain the best clients and the best people aren't always the ones who deliver the fastest solutions, they're the ones who make people feel understood first. Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

  5. Jul 3

    Your First Client: What No One Tells You About Pricing, Boundaries & Confidence | EP 49

    Send us Fan Mail Landing your first client feels like crossing the finish line, until you realize it's actually the starting line. You celebrate the "yes," hang up the phone, and then the questions hit: What do I do now? Am I charging enough? How much is too much? How do I keep this client happy without giving everything away? In this conversation, we unpack what really happens after you land your first client. It's not a conversation about proposals or onboarding checklists, it's about the mindset shifts that come with getting paid for your work for the first time. Drawing from our own experiences, we explore the habits that many new business owners fall into: overdelivering to prove their value, letting friendly relationships blur professional boundaries, and setting prices that become difficult to outgrow. These early decisions often shape the way you work long after that first project ends. If you've ever struggled to balance great service with healthy boundaries or wondered why raising your rates feels so hard, this episode will help you understand where those patterns begin and how to break them. What you'll hear in this episode: Why overdelivering is often driven by fear, not exceptional customer service.How friendly client relationships can quietly lead to blurred boundaries and scope creep.Why your first pricing decisions can have a lasting impact on your confidence and how to avoid getting stuck there.The mindset shift that matters most when you stop trying to earn permission and start building a sustainable business.Ask yourself:  What did your first client teach you that you're still unlearning today? And if you could go back, what advice would you give yourself?  Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

  6. Jun 26

    Why Your Client Updates Are Costing You the Relationship | EP 45

    Send us Fan Mail You're two weeks into a client project. Work is moving, you're deep in research, drafting, building exactly what you promised. But there's nothing exciting to report yet, so you stay quiet. You tell yourself you'll send an update once there's something real to show. Meanwhile, your client is staring at an inbox that hasn't moved in over a week, quietly filling that silence with a story you never meant to tell. This episode breaks down what's actually happening on the other side of your "I'll update them later" instinct. You'll learn why client silence almost never reads as "nothing to report",  it reads as something has gone wrong, even when your work is completely on track. You'll hear what's really driving that assumption (it's not about whether your client trusts you specifically, it's about how brains handle missing information), and why the real cost shows up later: hesitant referrals, more micromanaging, quiet doubts about whether you're still the right fit. Then you'll get a simple, low-effort communication cadence you can use on any project so silence never gets the chance to do the damage for you. Want to grow your audience without a big marketing budget? We are so excited to introduce the Spotlight Swap. Here is how it works: we feature you in the Entrepreneur Encounter newsletter and you feature us in yours. No complicated partnerships, no big budget. Just two businesses helping each other get in front of new audiences. If that sounds like something you want to be part of, fill out the form below and we would love to swap spotlights with you. 👉Fill out this form here: https://forms.gle/UMfhMqPQSXDXbU828  What to listen for in this episode: Why client silence almost never reads as "things are fine" and what your client's mind does instead when it has no information to go on.The real cost of going quiet mid-project, it's not just an awkward check-in email, it's the trust and referrals you don't even realize you're losing.A simple four-part update cadence that keeps clients confident without turning you into someone glued to your inbox.If your clients can't see your process, your communication is the only thing they have to go on. What is your silence currently telling them?  Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

  7. Jun 19

    From Taking It Personally to Leading With Clarity: Separate Yourself From Your Business | EP 44

    Send us Fan Mail A lost client. A bad review sitting underneath ten good ones. A slow month that suddenly feels like proof you should never have started. You tell yourself it's "just business," but somewhere underneath that, a quieter voice is asking a much harder question: what's wrong with me? If you've ever found yourself there, you're not imagining it, and you're definitely not alone; this is one of the most common, least talked-about experiences in entrepreneurship. This episode breaks down identity overlap, the moment when the line between who you are and how your business is performing disappears. You'll hear an honest, personal story about letting go of three clients without contracts in place, the part-time job that followed, and the slow realization that stepping back wasn't a failure but a setup for something stronger. Along the way, you'll learn why this overlap quietly sabotages your decision-making, and walk away with four practical tools to start separating your self-worth from your business outcomes, without losing the passion that got you here in the first place. Want to grow your audience without a big marketing budget? We are so excited to introduce the Spotlight Swap. Here is how it works: we feature you in the Entrepreneur Encounter newsletter and you feature us in yours. No complicated partnerships, no big budget. Just two businesses helping each other get in front of new audiences. If that sounds like something you want to be part of, fill out the form below and we would love to swap spotlights with you. 👉Fill out this form here: https://forms.gle/UMfhMqPQSXDXbU828  What to Listen for in This Episode Why identity overlap happens almost automatically. When you build something from scratch and put your name, time, and values into it, feeling personally tied to its outcomes doesn't mean you’re failing, it's a predictable result of how deeply entrepreneurs invest in their work. How to spot the difference between a fact and a story. "I lost a client" is a fact. "I lost a client because I'm not good enough" is a story your brain is telling you in the moment and learning to separate the two changes everything about how you respond. Four practical tools for building distance, including a routine that replaces shame spirals with structured questions, and why anchoring your identity in your values instead of your metrics protects you during the inevitable slow months. Your business is something you do. It is not something you are. The next time a setback shows up, the real question isn't whether you're good enough,  it's what the data is actually telling you. Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

  8. Jun 12

    Why Letting AI Do Everything Is Quietly Costing You Your Best Clients | EP 43

    Send us Fan Mail You spent hours learning a new AI tool. You optimized your prompts, automated your workflows, and maybe even let it draft your client proposals. And it was good, maybe really good. But then a client chose someone else. Someone who charged more, moved slower, and seemed to have a less polished process. And yet, they won. Not because of their tech stack. Because of how they made that client feel. That moment (the one that stings a little)is exactly what this episode is about. AI is changing everything, and we are not here to tell you to avoid it. We use it too. But there is something happening underneath all of this that not enough entrepreneurs are actually talking about. The more AI handles, the more your human skills become the thing that wins the business, keeps the client, and builds the reputation. In this episode, we get into what AI actually can and cannot do, why that gap matters more than most people realize, and what it means practically for how you show up in your business every single day. Want to grow your audience without a big marketing budget? We are so excited to introduce the Spotlight Swap. Here is how it works: we feature you in the Entrepreneur Encounter newsletter and you feature us in yours. No complicated partnerships, no big budget. Just two businesses helping each other get in front of new audiences. If that sounds like something you want to be part of, fill out the form below and we would love to swap spotlights with you. 👉Fill out this form here: https://forms.gle/UMfhMqPQSXDXbU828  What to Listen for in This Episode 1. The three soft skills rising to the top in an AI-saturated market Everyone has access to the same tools. What sets you apart is trust-based communication, emotional regulation under pressure, and the kind of judgment and discernment that only comes from knowing your client deeply. These are the things AI cannot replicate and the things clients are willing to pay a premium for. 2. How to stop asking the wrong question Most entrepreneurs are asking, "How do I keep up with AI?" The more powerful question is: "Where am I the most irreplaceable human in my business?" Those are the places worth protecting, your discovery calls, your check-ins, the hard conversations, the moments where showing up fully is what builds long-term loyalty. 3. How to decide what to automate and what to keep human Being intentional about what you automate versus what you keep human is not about using AI less, it's about using it smarter. Use it to handle the transactional and repetitive tasks so your time and energy are freed up to be fully present where it matters most: with your clients. AI is not your competition. The version of you who hides behind automation instead of leading with connection…..that's the competition. Your soft skills were never soft. They were always at work. And right now, they are the most strategic investment you can make in your business. Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

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5
out of 5
7 Ratings

About

Entrepreneur Encounter is a weekly podcast designed to support creative business owners in developing the soft skills that lead to lasting, values-aligned growth.Hosted by Dana Johnson, founder of a boutique Pinterest marketing agency for wedding pros and creatives, and Sara Lowell, a consultant specializing in business management & team leadership along with podcast management, each episode explores the mindset shifts, communication skills, and leadership habits that empower entrepreneurs to grow sustainably—without the burnout.Through real stories, practical frameworks, and transparent conversations, Dana and Sara offer a behind-the-scenes look at what it really takes to run a purpose-driven business in a constantly changing world.Whether you're building your visibility, managing a team, or simply trying to stay grounded while growing, this podcast is your companion in business and in life.

Information

  • Creator
    Entrepreneur Encounter
  • Years Active
    2023 - 2026
  • Episodes
    163
  • Rating
    Clean
  • Copyright
    © 2026 Entrepreneur Encounter
  • Show Website
    Entrepreneur Encounter