The Art Of Entrepreneurship

There’s a lot of talk lately about hustle culture—glorifying long hours and non-stop work as the only path to success. That kind of mindset just doesn’t fly with me (or my team).In this episode of The Art of Entrepreneurship, I’m sharing how we approach growth, motivation, and momentum without burning people out. I talk about how we’ve built a values-driven team at Accelity, from quarterly conversations that go beyond performance reviews to the ways we recognize wins, share praise, and make learning part of the culture.If you’re trying to grow your team without grinding them down, this episode is for you. There’s a better way to build, and it starts with how you lead.If you like this episode, here are some others you'll enjoy.Podcast: Bad leadership habitsPodcast: Above vs. below the linePodcast: Prioritizing, delegating & asking for help: answering your questions💡 Submit your topics for the podcast: https://www.jackiehermes.com/connect👋 Learn more about the podcast: ​​www.jackiehermes.com/podcast⭐️ Love the podcast? Please consider leaving a 5-star rating on Apple Podcasts!💛 Production support is provided by Accelity, a full-service marketing agency for bold people growing bold companies.✉️ Hit me up!LinkedInInstagramTikTokWebsite

This episode of The Art of Entrepreneurship is for anyone who’s navigating the ups and downs of building a startup during unpredictable market conditions.My guest today is Kyle York, co-founder, CEO, and managing partner of York IE VC firm that focuses on investing in pre-seed and seed-stage companies. Kyle and I talk about the mistakes companies are making right now, what to do if you're looking to raise money and the ways that your company might be bleeding cash that you don’t even know about. Make sure you tune in for actionable tips on how founders can stay steady through uncertainty, avoid overcorrecting, and make smart financial decisions that support long-term growth.About Kyle YorkKyle York is the co-founder, CEO, and managing partner at York IE, an advisory and venture capital firm focused on helping technology companies scale. With a team of over 200, he partners with entrepreneurs, operators, and investors to build impactful, lasting companies in B2B SaaS. Throughout his career, Kyle has championed growth in product, go-to-market, and finance strategies, prioritizing strong teams, customer satisfaction, and enterprise value.WebsiteLinkedIn - KyleLinkedIn - York IEIf you like this episode, here are some others you'll enjoy.Podcast: Optimizing cash flow with Ryan Calton, CEO of RC MKEPodcast: Getting in front of investors + funding underrepresented founders w/ Alex Chompff, angel investor and serial entrepreneurPodcast: How did I go from $0 to 7-figures without funding?💡 Submit your topics for the podcast: https://www.jackiehermes.com/connect👋 Learn more about the podcast: ​​www.jackiehermes.com/podcast⭐️ Love the podcast? Please consider leaving a 5-star rating on Apple Podcasts!💛 Production support is provided by Accelity, a full-service marketing agency for bold people growing bold companies.✉️ Hit me up!LinkedInInstagramTikTokWebsite

Too many companies pour money into marketing but stop short of making the bold moves that truly set them apart.In this episode of The Art of Entrepreneurship, I’m diving into why playing it safe won’t get you real results—and why calculated risks are key to real growth.I share some behind-the-scenes insights from my own brand work, including a story about a client who came to us for a simple messaging refresh... but what they really needed was a full rebrand. I talk about why we’re often so resistant to change, the dangers of blending in, and how shifting your perspective can lead to bigger, better opportunities.Tune in to hear why standing out matters, how to know when it’s time for a change, and six questions I use to challenge my own thinking (and my clients’) when hesitation creeps in.If you’ve been playing it safe—at work or in life—ask yourself: what’s really holding you back?If you like this episode, here are some others you'll enjoy.Podcast: How to change the change-resistant w/ Bob Gaydos, CEO of PendellaPodcast: Embracing intellectual humility w/ Dave Hersh, Founder & CEO of In TandemPodcast: Taking calculated risks💡 Submit your topics for the podcast: https://www.jackiehermes.com/connect👋 Learn more about the podcast: ​​www.jackiehermes.com/podcast⭐️ Love the podcast? Please consider leaving a 5-star rating on Apple Podcasts!💛 Production support is provided by Accelity, a full-service marketing agency for bold people growing bold companies.✉️ Hit me up!LinkedInInstagramTikTokWebsite

In part two of our rebranding journey, we’re continuing the conversation with Michelle Breen and Abby Bruckner as they walk us through the details of the rebrand process. Abby and Michelle share how we approached the creative aspects, from gathering team feedback with surveys to developing mood boards and selecting the final direction for our brand.Make sure you tune in to hear how we navigated the rebrand, why we chose a vibrant and bold mood, and how we customized every detail to ensure the final product truly reflects our company's identity. Plus, we share key questions to ask yourself before rebranding, and how to decide whether a full overhaul or a simple refinement is the right choice.About Abby BrucknerAbby is a designer at Accelity, creating digital content that brings brands to life. She uses visual storytelling to make marketing more engaging, clear, and memorable.About Michelle BreenMichelle is a Strategic Copy Manager at Accelity, helping companies craft clear, compelling messaging. She specializes in turning complex ideas into stories that connect with the right audience.WebsiteLinkedIn – AbbyLinkedIn – MichelleIf you like this episode, here are some others you'll enjoy.Podcast: Why (and when) to rebrand your business w/ Abby Bruckner & Michelle Breen, lead creatives at Accelity (Pt.1)Podcast: Bold brand, big moves: Why we relaunched our business w/ Jenny Weeden, President of AccelityPodcast: Marketing & sales strategies to fill your pipeline in Q1💡 Submit your topics for the podcast: https://www.jackiehermes.com/connect👋 Learn more about the podcast: ​​www.jackiehermes.com/podcast⭐️ Love the podcast? Please consider leaving a 5-star rating on Apple Podcasts!💛 Production support is provided by Accelity, a full-service marketing agency for bold people growing bold companies.✉️ Hit me up!LinkedInInstagramTikTokWebsite

Rebranding is a big decision—but how do you know when it’s the right time?My guests today are Abby Bruckner, Art Director, and Michelle Breen, Strategic Copy Manager at Accelity, who led our company’s recent rebrand. Abby and Michelle share which signals tell you it’s time for a rebrand, how to decide between a full rebrand or a simple refresh, and why branding trends are shifting toward more personality-driven design.Make sure you tune in for key considerations before rebranding, why brand consistency matters, and how to ensure your brand truly represents your business.About Abby BrucknerAbby is a designer at Accelity, creating digital content that brings brands to life. She uses visual storytelling to make marketing more engaging, clear, and memorable.About Michelle BreenMichelle is a Strategic Copy Manager at Accelity, helping companies craft clear, compelling messaging. She specializes in turning complex ideas into stories that connect with the right audience.WebsiteLinkedIn – AbbyLinkedIn – MichelleIf you like this episode, here are some others you'll enjoy.Podcast: Bold brand, big moves: Why we relaunched our business w/ Jenny Weeden, President of AccelityPodcast: Stop chasing your ideal customers: make them come to you w/ SHFT Founder & Senior Strategist Jason VanaPodcast: Positioning yourself for career advancement and building a people-first brand w/ Megan Bowen, CEO of Refine LabsSubmit your topics for the podcast: https://www.jackiehermes.com/connectLearn more about the podcast: ​​www.jackiehermes.com/podcastLove the podcast? Please consider leaving a 5-star rating on Apple Podcasts!Production support is provided by Accelity, a full-service marketing agency for bold people growing bold companies.More about the show: ​​www.jackiehermes.com/podcastHit me up!LinkedInInstagramTikTokWebsite

In this episode of The Art of Entrepreneurship, we’re talking about stress. Because let’s be real, it never fully goes away: especially when you’re running a business. It’s how you handle it that makes all the difference.I’ll share the hard truths about stress management, why saying “no" is sometimes the best move, and what I’ve ultimately learned about getting back to even when stress starts taking over.Make sure you tune in for an honest conversation about mental health, boundaries, and how taking care of yourself is the most important business decision you’ll ever make.If you like this episode, here are some others you'll enjoy.Podcast: Do you take care of yourself? No, really?Podcast: Take your PTO! What I learned from time away from my businessPodcast: Breaking the cycle of stress w/ Rachel Sanders, Founder & CEO of Rootine💡 Submit your topics for the podcast: https://www.jackiehermes.com/connect👋 Learn more about the podcast: ​​www.jackiehermes.com/podcast⭐️ Love the podcast? Please consider leaving a 5-star rating on Apple Podcasts!💛 Production support is provided by Accelity, a full-service marketing agency for bold people growing bold companies.✉️ Hit me up!LinkedInInstagramTikTokWebsite

This episode of The Art of Entrepreneurship is for anyone considering a major business transformation and wondering how to make bold changes without losing what made them great in the first place. My (very special) guest today is Jenny Weeden, President and Partner at our marketing agency, Accelity. Jenny and I discuss our recent relaunch of Accelity, what led to the decision to shake things up, and how the team approached rebranding while staying true to our roots. We talk about the tough calls, the mindset shifts, and why embracing change—no matter how uncomfortable—can be the key to long-term success.Tune in for our conversation on how Accelity embraced fearless moves to reinvent the brand and why sometimes, you have to blow things up to build something even better.✨ Check out the new website! accelitymarketing.comAbout Jenny WeedenJenny Weeden is President and Partner at Accelity, a marketing agency focused on growing scaling businesses. She understands startups and scaling companies, having been a first-time small business entrepreneur as a co-founder of Women’s Entrepreneurship Week, a week dedicated to connecting, supporting and empowering women professionals in the Milwaukee area.In her free time, Jenny loves volunteering at Kinship Community Food Center and, as a proud UW-Madison alumni, cheering on the Wisconsin Badgers.WebsiteLinkedInIf you like this episode, here are some others you'll enjoy.Podcast: How to make lasting personal and cultural change in business w/ Jenny Weeden, President of Accelity Podcast: Evaluating new business ideas, making the leap & handling change w/ Marcus Murphy, co-founder and CEO of The Five PercentPodcast: Big swings & betting on yourself with solopreneur Justin Welsh 💡 Submit your topics for the podcast: https://www.jackiehermes.com/connect👋 Learn more about the podcast: ​​www.jackiehermes.com/podcast⭐️ Love the podcast? Please consider leaving a 5-star rating on Apple Podcasts!💛 Production support is provided by Accelity, a full-service marketing agency for bold people growing bold companies.✉️ Hit me up!LinkedInInstagramTikTokWebsite

This episode of The Art of Entrepreneurship is for anyone curious about diving into the world of AI. It can feel like an extreme topic—some fear it, while others are all in, ready to capitalize on it.My guest today is AI consultant and coach Jonathan Mast, who has trained thousands of professionals in AI and built a community of over 400,000 enthusiasts. Jonathan and I discuss why AI isn’t just for entrepreneurs and business leaders, how it can simplify routines, and which AI tools—beyond ChatGPT—are worth exploring.Make sure you tune in for a deeper look at how AI can enhance everyday life, creating smoother and more efficient experiences.About Jonathan MastSince 1995, Jonathan Mast has been at the forefront of digital innovation, seamlessly blending marketing expertise with cutting-edge technology. Over the past two years, he has emerged as a leading authority on AI prompting mastery, helping businesses and entrepreneurs save time, increase profits, and deliver exceptional value through actionable AI strategies with his consulting firm, White Beard Strategies.WebsiteLinkedInYouTubeInstagramIf you like this episode, check out these resources.Podcast: Choosing a billion-dollar mindset w/ Suneera Madhani, Founder & CEO of Worth AIPodcast: Admiring your success w/ technology exec Zuhairah Scott Washington       Podcast: Do what you love & you'll never work a day" w/ mindset coach William DeckSubmit your topics for the podcast: https://www.jackiehermes.com/connectLearn more about the podcast: ​​www.jackiehermes.com/podcastLove the podcast? Please consider leaving a 5-star rating on Apple Podcasts!Production support is provided by Accelity, a full-service marketing agency for bold people growing bold companies.More about the show: ​​www.jackiehermes.com/podcastHit me up!LinkedInInstagramTikTokWebsite

In this episode of The Art of Entrepreneurship, we’re prioritizing discernment. As you grow in your career, it’s not about spotting every problem, it’s about knowing which ones truly matter.I’ll share how I’ve learned to filter what’s urgent versus what’s important, let go of the need for control, and focus on the bigger picture (not just my personal preferences).Tune in to hear how sharpening your discernment skills can make you a stronger leader and help you center on what truly moves the needle.🔗 Here’s the TikTok I mentioned in the episode (via Grace McCarrick) https://www.tiktok.com/@graceforpersonalityhires/video/7433091337286585642?lang=en If you like this episode, check out these resources.Podcast: The best work is not done at your deskPodcast: How to be a leader when you don’t want to be a managerPodcast: How to turn letdowns into opportunitiesSubmit your topics for the podcast: https://www.jackiehermes.com/connectLearn more about the podcast: ​​www.jackiehermes.com/podcastLove the podcast? Please consider leaving a 5-star rating on Apple Podcasts!Production support is provided by Accelity, a full-service marketing agency for bold people growing bold companies.More about the show: ​​www.jackiehermes.com/podcastHit me up!LinkedInInstagramTikTokWebsite

In this episode of The Art of Entrepreneurship, we’re exploring a simple yet powerful way to reframe your mindset: choosing a victor mentality over a victim attitude. Embracing accountability in business, relationships, and daily life can lead to greater success and fulfillment.I’ll share how I’ve seen this play out with clients, in my own experiences, and in pivotal moments that reshaped how I handle both wins and setbacks. Tune in to hear why adopting a victor mentality (even when it’s tough) puts you in control—and how small mindset shifts can create big change.If you like this episode, check out these resources.Podcast: It’s always partially your faultPodcast: It never hurts to be the bigger person Podcast: Apologize only when you need to—the why & howSubmit your topics for the podcast: https://www.jackiehermes.com/connectLearn more about the podcast: ​​www.jackiehermes.com/podcastLove the podcast? Please consider leaving a 5-star rating on Apple Podcasts!Production support is provided by Accelity, the full-service marketing agency featuring bold people growing bold companies. More about the show: ​​www.jackiehermes.com/podcastHit me up!LinkedInInstagramTikTokWebsite