The Art Of Entrepreneurship

Jackie Hermes
  • 4.9 (161)
  • Entrepreneurship
  • Updated Weekly

Let's be honest: building a company from nothing is freaking hard. It has been for me. I grew my company Accelity from 0 to 7 figures with no partners and no funding. I'm also a startup mentor, a speaker, and a dedicated mother of three. Welcome to The Art of Entrepreneurship podcast—I’m your host, Jackie Hermes. Listen in as I share all the mistakes I’ve made and, more importantly, what I’ve learned from them, with no fluff, and no rose-colored glasses. The Art of Entrepreneurship is a show where we cut through the BS and dig into what it actually takes to start and grow a business. I’ll be giving unfiltered advice 1 episode per week, up to 20 minute per episode. I want you to walk away from this podcast with the mindset and tools you need to be successful. This podcast is for entrepreneurs, side hustlers, and busy professionals with a short attention span (like me)—you’ll get quick-hitting, actionable information in every single episode. If you give me your time, I promise it won't be wasted. Now let's get to work!

  1. 6d ago

    Will AI replace marketing? Here's where the line actually is. (My stance on AI)

    This episode of The Art of Entrepreneurship is for agency owners who've been told AI is coming for their business next. AI changes everything for agencies, full stop. But it doesn't do the work clients actually hire an agency for. Tune in if you're ready to find the line where AI's usefulness ends and your judgment becomes the entire product. ✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies. If you're ready to level up your B2B marketing, check us out. → accelitymarketing.com  🎧 Catch up on past episodes, submit topic ideas, and learn more jackiehermes.com/podcast ⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show. 📲 Let’s connect! LinkedIn: linkedin.com/in/thejackiehermes/ Instagram: @thejackiehermes TikTok: @jackie.hermes Website: jackiehermes.com

  2. Jul 21

    How to make change at the speed of trust w/ David McFarland, CEO of Coterie

    This episode of The Art of Entrepreneurship is for founders building inside industries that move slowly, even when everyone agrees they need to change. My guest is David McFarland, founder and CEO of Coterie Insurance, who has spent seven years modernizing insurance from the inside instead of building around it. Coterie has scaled to over $200 million in premium, more than 100,000 small business policies and a recent equity investment from Allianz. David shares what it took to self-fund Coterie's early days after an investor backed out the night before he moved his family to start it. We talk about delusional optimism and why David believes tenacity, not talent, separates founders who make it. He gets honest about fundraising, including a less than 1% investor success rate and why he'd rather have the right investors than the highest valuation. We also discuss why individual accountability, not committee consensus, lets a company move fast in a slow-moving industry. Tune in if you're ready to stop waiting for permission and start building the tenacity to change your industry from the inside. About David McFarlandDavid McFarland is the Founder and CEO of Coterie Insurance, a P&C insurance MGA focused on bringing speed, simplicity, and service to the small business insurance market. A Fellow in the Casualty Actuarial Society, he works across the org to drive profitable growth, strengthen loss performance, expand product offerings, and build durable carrier and reinsurance partnerships, all while aggressively leveraging AI and automation to create a highly expense-efficient operating model. David lives in Wisconsin with his wife and six children. Follow David on LinkedIn: https://www.linkedin.com/in/davidmcfarland23/ About Coterie InsuranceCoterie Insurance (Coterie) is a tech-enabled, data-powered managing general agent (MGA) providing commercial property and casualty (P&C) coverages for small business (SMB) owners in all 50 states. Coterie’s technology enables a rapid, transparent, accurate, quote-to-bind process that results in opportunities for agents and the right coverage for small businesses, on-demand. Check out Coterie: https://coterieinsurance.com/ If you like this episode, here are some others you'll enjoy.Episode 219. Bob Gaydos, CEO of Pendella — winning over change-resistant industries with AI-driven insurance underwriting: https://www.jackiehermes.com/podcast/bob-gaydosEpisode 235. Alex Chompff — how founders (especially underrepresented ones) get in front of angel investors: https://www.jackiehermes.com/podcast/alex-chompffEpisode 311. Dilip Rao, CEO of Sharebite — leading through crisis with responsibility over ego: https://www.jackiehermes.com/podcast/dilip-rao ✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies. If you're ready to level up your B2B marketing, check us out. → accelitymarketing.com  🎧 Catch up on past episodes, submit topic ideas, and learn more jackiehermes.com/podcast ⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show. 📲 Let’s connect! LinkedIn: linkedin.com/in/thejackiehermes/ Instagram: @thejackiehermes TikTok: @jackie.hermes Website: jackiehermes.com

  3. Jul 14

    How to win the end of the year (hint: it starts now)

    This episode of The Art of Entrepreneurship is for founders who assume August is a throwaway month because everyone's out of office. Today we're talking about the difference between resting on purpose and coasting by accident, and why the two get confused every summer. This isn't a hustle-culture take; it's the opposite, and it’s a distinction I've come back to all year. I share the story of a dead Q4 we had a few years back and how tracing it back showed the real problem started in July, not October, because the pipeline that feeds Q4 always begins two to three months earlier. I get into why service businesses need to manage for even capacity across months and not just total revenue, and why the quiet months are exactly when the biggest pipeline pushes should happen instead of the loudest ones. I also share why I've started counter-scheduling my own time off, taking my breaks when everyone else is working and working when everyone else is out. (Side note, it's one of the most practical ways I've found to stress-test whether a business actually runs without you.) Tune in if you're ready to stop treating August like a dead month and start treating it like a head start. If you like this episode, here are some others you'll enjoy.Episode 248. It's not time to slow down: generating business at the end of the year – https://www.jackiehermes.com/podcast/generating-business-at-the-end-of-the-yearEpisode 287. Are you taking a break, or running away? 6 tips for building a life you love – https://www.jackiehermes.com/podcast/taking-a-break-vs-running-awayEpisode 218. Marketing & sales strategies to fill your pipeline in Q1 – https://www.jackiehermes.com/podcast/marketing-sales-strategies-for-q1 ✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies. If you're ready to level up your B2B marketing, check us out. → accelitymarketing.com  🎧 Catch up on past episodes, submit topic ideas, and learn more jackiehermes.com/podcast ⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show. 📲 Let’s connect! LinkedIn: linkedin.com/in/thejackiehermes/ Instagram: @thejackiehermes TikTok: @jackie.hermes Website: jackiehermes.com

  4. Jul 7

    Pivoting isn't failure, it's iteration w/ Tom Szaky, Founder and CEO of TerraCycle

    This episode of The Art of Entrepreneurship is for founders who are trying to evolve the business without losing the reason they started it. My guest is Tom Szaky, Founder and CEO of TerraCycle, a company built around one core mission: eliminating the idea of waste. Tom and I talk about how TerraCycle has evolved over 25 years while keeping that mission at the center. He shares how the company started by selling worm compost fertilizer in used soda bottles, why that model eventually had to change and how the team realized the bigger opportunity was solving the problem itself, not just the product they were selling. We also get into why pivoting has such a negative reputation, and how founders can think about it differently. Tom explains how treating failure as “tuition” helps his team turn ideas that don’t work into learning instead of wasted effort. One of the biggest takeaways from this conversation: the only thing that should be sacred is the mission. Products, systems and models have to stay open to change, because the thing that got you here may not be the thing that gets you to the next stage. Tune in if you’re building through change and want to get better at knowing what to hold onto and what to let evolve. About Tom SzakyTom Szaky is the Founder and CEO of TerraCycle, an international leader in innovative sustainability solutions that creates and operates first-of-their-kind platforms in recycling, recycled materials and reuse. Across 18 countries, TerraCycle is on a mission to rethink waste and develop practical solutions for today’s complex waste challenges. The company engages an expansive multi-stakeholder community through a wide range of accessible programs, from Fortune 500 companies to schools and individuals. Website: https://www.terracycle.com/en-US/ LinkedIn – Tom Szaky: https://www.linkedin.com/in/tomszaky/ LinkedIn – TerraCycle: https://www.linkedin.com/company/terracycle/ Instagram: https://www.instagram.com/TerraCycle Facebook: https://www.facebook.com/TerraCycle/ If you like this episode, here are some others you'll enjoy.Episode 200. Learning what’s on the other side of failure w/ serial entrepreneur Chris Harder — Turning failure into learning: https://www.jackiehermes.com/podcast/chris-harderEpisode 171. Evaluating new business ideas, making the leap & handling change w/ Marcus Murphy, co-founder and CEO of The Five Percent — Knowing when to make the next move: https://www.jackiehermes.com/podcast/marcus-murphyEpisode 57. The importance of process—Building processes that evolve with the business: — Simpler growth, smarter execution: https://www.jackiehermes.com/podcast/the-importance-of-process ✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies. If you're ready to level up your B2B marketing, check us out. → accelitymarketing.com  🎧 Catch up on past episodes, submit topic ideas, and learn more jackiehermes.com/podcast ⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show. 📲 Let’s connect! LinkedIn: linkedin.com/in/thejackiehermes/ Instagram: @thejackiehermes TikTok: @jackie.hermes Website: jackiehermes.com

  5. Jun 30

    Your old role has expired

    This episode of The Art of Entrepreneurship is for founders realizing reinvention means becoming the version of themselves their business needs next. A few episodes ago, I talked about the long middle of entrepreneurship and how staying in that phase is about more than endurance. It’s about figuring out how to keep growing inside the company you already created. This episode is the other half of that conversation. Because as your business grows, your role has to change with it. I talk about the difference between proactively reinventing your role and being forced into it because the company has already outgrown how you operate. I also get into what reinvention is and what it isn’t, including why stepping back too fast can create just as many problems as holding on too long. Reinvention doesn’t mean checking out of the business. It means becoming more intentional about where you’re involved, where your team is ready to own more and where your involvement creates the most leverage. The biggest shift is learning to tell the difference between being needed and being comfortable. If you’re still in every problem, every decision and every client conversation because that’s what feels familiar, your role may already be expired. The goal isn’t to become uninvolved. It’s to become correctly involved. Tune in if you’re ready to redesign your role so you and your company can keep growing. If you like this episode, here are some others you'll enjoy.Episode 318. The long middle of entrepreneurship — Growing inside the company you built: https://www.jackiehermes.com/podcast/the-long-middle-of-entrepreneurshipEpisode 308. Who you need to be at each stage of building a business — Leadership evolves as your company grows: https://www.jackiehermes.com/podcast/who-you-need-to-be-at-each-stage-of-building-a-businessEpisode 320. Behind on everything (but not panicking) — Leading through seasons of change: https://www.jackiehermes.com/podcast/behind-on-everything-but-not-panicking ✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies. If you're ready to level up your B2B marketing, check us out. → accelitymarketing.com  🎧 Catch up on past episodes, submit topic ideas, and learn more jackiehermes.com/podcast ⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show. 📲 Let’s connect! LinkedIn: linkedin.com/in/thejackiehermes/ Instagram: @thejackiehermes TikTok: @jackie.hermes Website: jackiehermes.com

  6. Jun 23

    The CEO your kids are watching w/ Timothy Rexius, Founder and CEO of Omaha Protein Popcorn

    This episode of The Art of Entrepreneurship is for founders who are building ambitious companies while thinking about what their kids are learning from the way they work. My guest is Timothy Rexius, entrepreneur, speaker and business owner who is building multiple companies while raising six kids. Timothy and I talk about the overlap between entrepreneurship and parenting, and why those identities are not as separate as we sometimes pretend they are. He shares how his kids and family have become part of the businesses over time, what it looks like to build with legacy in mind and why he and his wife keep their kids involved in conversations about the companies, money and the bigger picture behind the work. We also get into the difference between leading at work and leading at home. Timothy talks about the sense of urgency that can work in business, why that same approach does not always translate to family and how he thinks about giving his kids context around ambition, success, pressure and the grind they see modeled every day. One of the biggest takeaways from this conversation: your kids do not just inherit what you build, they inherit how they watched you build it. Timothy’s perspective is a reminder that if your family sees the work, they also need to understand the purpose, the tradeoffs and the values behind it. Tune in if you’re building something ambitious and want to be more intentional about the example your kids are watching. About Timothy RexiusTim Rexius is a personality that checks all of the above: entrepreneur, speaker, business owner, husband and dad in a family of eight. Alongside his beautiful, determined wife, Tim is the CEO and President of Rexius Nutrition, Co-Owner of Iron Heaven Gyms Inc., and President and Founder of VHI Nutraceuticals and the OPP Omaha Protein Popcorn Company. His work spans fitness, nutrition, consumer products, business coaching and keynote speaking, with family deeply woven into the way he builds. And if you think it stops there, it doesn’t. There is still so much more in the works. Website – Iron Heaven Gyms Inc.: https://ironheavenomaha.com/ Website – Rexius Nutrition: https://www.rexiusnutrition.com/ Website – Omaha Protein Popcorn: https://www.omahaproteinpopcorn.com/ LinkedIn – Timothy Rexius: https://www.linkedin.com/in/timothy-rexius-2968422b/ LinkedIn – Omaha Protein Popcorn: https://www.linkedin.com/company/omaha-protein-popcorn/ YouTube: https://www.youtube.com/user/marcman55 If you like this episode, here are some others you'll enjoy.Episode 187. Q&A: questions we get as a two-entrepreneur household starring my husband, Ryan Calton — Building a business when work and family overlap: https://www.jackiehermes.com/podcast/two-entrepreneur-householdEpisode 31. Some mother you are — Parenting while chasing your own dreams: https://www.jackiehermes.com/podcast/some-mother-you-areEpisode 210. Create the professional and personal life you want now w/ Nat Berman, Co-Founder of Brand Built — Build the life you actually want: https://www.jackiehermes.com/podcast/nat-berman ✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies. If you're ready to level up your B2B marketing, check us out. → accelitymarketing.com  🎧 Catch up on past episodes, submit topic ideas, and learn more jackiehermes.com/podcast ⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show. 📲 Let’s connect! LinkedIn: linkedin.com/in/thejackiehermes/ Instagram: @thejackiehermes TikTok: @jackie.hermes Website: jackiehermes.com

  7. Jun 16

    Setting the table for hard conversations

    This episode of The Art of Entrepreneurship is for founders and leaders who want to stop waiting for hard conversations to become unavoidable—and start building a culture where they never have to be. Most leadership advice focuses on how to have the hard conversation. This episode is about everything that comes before it. Inspired by a LinkedIn comment that I couldn't stop thinking about, I walk through four practices we've institutionalized at Accelity that make hard conversations easier long before they ever happen: accountability loops, our Growth Hero upskilling program, intent versus perception, and MRI (Most Respectful Interpretation). Each one builds something different: direct communication habits, shared skills, a framework for when things go sideways, and a default assumption of good intent. None of these are scripts or meeting formats, they're cultural expectations that every business needs in place; standards you adopt, repeat and reinforce until they're just how your company operates. Jenny and I didn’t always get this right. A lot of what I'm sharing here, we learned by doing it badly first. And if your team doesn't have any of this in place yet, don’t worry about it—you're not behind. You just haven't started yet. Tune in if you're ready to stop treating hard conversations like emergencies and start building an environment where clarity is just part of how you operate. If you like this episode, here are some others you'll enjoy.Episode 322. Can you actually build a great company by prioritizing people w/ Andy Gallion, Co-founder of InCheck — Hard conversations and people-first leadership: https://www.jackiehermes.com/podcast/andy-gallionEpisode 203. Giving the benefit of the doubt: Most Respectful Interpretation — The full episode on MRI: https://www.jackiehermes.com/podcast/giving-the-benefit-of-the-doubtEpisode 293. On being a manager, not a therapist — Leading with empathy without absorbing everyone's problems: https://www.jackiehermes.com/podcast/on-being-a-manager-not-a-therapist ✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies. If you're ready to level up your B2B marketing, check us out. → accelitymarketing.com  🎧 Catch up on past episodes, submit topic ideas, and learn more jackiehermes.com/podcast ⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show. 📲 Let’s connect! LinkedIn: linkedin.com/in/thejackiehermes/ Instagram: @thejackiehermes TikTok: @jackie.hermes Website: jackiehermes.com

  8. Jun 9

    Headcount is not a status symbol w/ Amos Bar-Joseph, Co-founder and CEO of Swan AI

    This episode of The Art of Entrepreneurship is for founders who are realizing growth in the age of AI might have less to do with hiring more people and more to do with creating more leverage. My guest is Amos Bar-Joseph, Co-founder and Chief Executive Officer of Swan AI, a company building around the idea that businesses can scale through intelligence instead of headcount. Amos and I talk about why the old growth playbook of raising money, hiring quickly and treating headcount like a status symbol is breaking down. He shares how previous startup experience led him to question the assumption that bigger teams automatically create better companies, and why Swan is building toward $10 million ARR per employee as a measure of leverage instead of valuation inflation. We also get into what Amos calls “cog culture,” where companies add people to scale the business instead of using systems, processes and AI to scale their people. He explains how AI-native companies can push employees closer to their zone of genius, why managers still need to understand processes and best practices, and how managing AI agents requires context, coaching and clear direction. One of the biggest takeaways from this conversation: becoming an AI-native company doesn’t require deep technical expertise. Amos explains that the starting point is looking inward, identifying one repetitive process, finding the bottleneck and using AI to improve it one step at a time. Tune in if you’re ready to stop treating headcount like the proof of growth and start building a company designed for leverage. About Amos Bar-JosephAmos Bar-Joseph is the Co-founder and Chief Executive Officer of Swan AI, a technology company exploring new ways for modern businesses to go to market in the era of AI. Swan’s flagship product, the AI GTM Engineer, helps companies design and deploy go-to-market workflows in real time, using AI agents to assist with qualification, routing, pipeline orchestration and other GTM tasks. Amos is building Swan around the idea of collaborative autonomy, where AI amplifies human capability and helps lean teams create more leverage without relying on traditional headcount-heavy growth. Website: https://www.getswan.com/ LinkedIn – Amos Bar-Joseph: https://www.linkedin.com/in/amos-bar-joseph/ LinkedIn – Swan AI: https://www.linkedin.com/company/swan-ai-gtm/ If you like this episode, here are some others you'll enjoy.Episode 309. The post-2025 entrepreneur: speed, ideas and AI w/ Dr. Alex Mehr — AI changes how founders build: https://www.jackiehermes.com/podcast/alex-mehrEpisode 319. Building with instinct while scaling with best practices w/ Yoni Tserruya, Co-founder and CEO of Lusha — Scaling beyond default playbooks: https://www.jackiehermes.com/podcast/yoni-tserruyaEpisode 301. Selling your product from day one w/ Safeer Qureshi, angel investor and CEO at SPG Media — Simpler growth, smarter execution: https://www.jackiehermes.com/podcast/safeer-qureshi ✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies. If you're ready to level up your B2B marketing, check us out. → accelitymarketing.com  🎧 Catch up on past episodes, submit topic ideas, and learn more jackiehermes.com/podcast ⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show. 📲 Let’s connect! LinkedIn: linkedin.com/in/thejackiehermes/ Instagram: @thejackiehermes TikTok: @jackie.hermes Website: jackiehermes.com

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4.9
out of 5
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About

Let's be honest: building a company from nothing is freaking hard. It has been for me. I grew my company Accelity from 0 to 7 figures with no partners and no funding. I'm also a startup mentor, a speaker, and a dedicated mother of three. Welcome to The Art of Entrepreneurship podcast—I’m your host, Jackie Hermes. Listen in as I share all the mistakes I’ve made and, more importantly, what I’ve learned from them, with no fluff, and no rose-colored glasses. The Art of Entrepreneurship is a show where we cut through the BS and dig into what it actually takes to start and grow a business. I’ll be giving unfiltered advice 1 episode per week, up to 20 minute per episode. I want you to walk away from this podcast with the mindset and tools you need to be successful. This podcast is for entrepreneurs, side hustlers, and busy professionals with a short attention span (like me)—you’ll get quick-hitting, actionable information in every single episode. If you give me your time, I promise it won't be wasted. Now let's get to work!

Information

  • Creator
    Jackie Hermes
  • Years Active
    2021 - 2026
  • Episodes
    332
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Jackie Hermes
  • Show Website
    The Art Of Entrepreneurship

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