Andrew Oliver has built a creative empire from persistence and passion. As the founder of 4th Write Records and producer of the Amazon Prime film Paperweight, he proves that success in business and art comes from testing limits, trusting instincts, and creating work that feels alive. He opens up about how a simple mindset shift helped his team scale twenty times faster, why decision-making beats hesitation, and how joy became his most reliable business strategy. Whether you run a studio, a startup, or anything in between, these lessons will remind you that growth is not about luck. It is about persistence, perspective, and purpose. Here are three takeaways every founder can put into action right now.

When chaos hits close to home, it changes how you lead. Tara Rolstad never planned to become a speaker, author, or mental health advocate. But after her family’s journey through trauma, parenting, and survival, she found purpose in helping others tell the truth about their struggles. From Toastmasters to the National Speakers Association, Tara built a business around vulnerability and turned her story into a message that saves lives. In this conversation, she and Jennifer Sutton talk about what it really takes to run a business with heart. They explore burnout, focus, and the power of community. Tara’s story is raw, hopeful, and full of lessons for any founder trying to make impact without losing themselves along the way. Here are three takeaways every entrepreneur can use right now

Some founders build brands. Cynthia Johnson builds truth. After years in the agency grind, she walked away to start Bell & Ivy and flipped the script on what branding really means. Forget the glossy image. Cynthia shows how real growth starts when founders stop chasing perception and start leading with perspective. She’s been through acquisitions, chaos, burnout, and rebirth, and she’s learned what every entrepreneur eventually figures out. Authenticity isn’t a strategy. It’s survival. Here are three takeaways every founder will relate to:

Some founders chase growth. Others chase meaning. Sri Kaza chases both. After years in the corporate world, he walked away from the security of McKinsey to build something real and something his own. Along the way he learned what most entrepreneurs figure out the hard way. Plans burn fast, purpose lasts longer, and small businesses win when they lean into what makes them different. From surviving the chaos of the PPP rollout to defining his Three Ps for small business success, positioning, proximity, and purpose, Sri’s story is proof that resilience is built, not bought. Here are three takeaways every founder will relate to:

Finding your purpose is one thing. Turning it into something real is another. For Monique Elliott, CEO of S.A.V.Y., entrepreneurship started with faith and evolved into a mission to help others build success on their own terms. What began as a calling became a journey of conviction, courage, and clarity. Monique’s story hits at the heart of what it means to be a founder. The fear, the resilience, the faith to keep showing up when no one else would. She reminds us that building a business is not just about growth but about grounding yourself in purpose and protecting the energy that fuels it. Here are three takeaways every founder will relate to:

Leaving a stable corporate career to start over is bold. Doing it while raising two kids, navigating divorce, and building a clean-ingredient cookie brand from scratch is next-level courageous. Lindsay Hancock, founder of My Better Batch and former Kind Snacks executive, shares what really happens when you trade the comfort of corporate life for the chaos of entrepreneurship. She opens up about rebuilding confidence, facing bias as a female founder, and finding purpose again through her better-for-you food brand. From scaling startups to mastering imbalance, this conversation is packed with honest insights for entrepreneurs and founders who are ready to take risks, embrace reinvention, and redefine what success truly looks like.

Building a business is equal parts chaos and clarity. Yesenia Garcia and Stephanie Kronen share founder stories that cut past the polish and get real about what it means to bootstrap a startup, figure out cofounder dynamics, and stumble into the startup lessons no one warns you about. From shaping a startup go to market strategy to crafting a product differentiation strategy that actually sticks, you will hear how founders are turning scrappy into smart. Authentic branding for founders and founder led marketing are not just buzzwords, they are survival skills. And for women founders, showing up with your own story becomes the edge that no competitor can copy.

Fractional support gives founders access to specialized expertise without the overhead. In this Hello Chaos bonus episode, Jennifer Sutton and attorney Doug Lineberry share how small business growth depends on smarter choices in legal support and marketing strategies. They explore brand therapy, reveal how to spot predatory marketing agencies, and emphasize why ROI should guide every decision. Entrepreneurs will walk away with a clear view of how strategic marketing and fractional services help overcome business challenges while strengthening business leadership.

From family therapist to founder, Ruban Roberts has lived the messy reality of entrepreneurship. Steady paychecks traded for uncertain contracts, big promises that never materialize, and the grind of building from scratch. As CEO of RER Consulting and founder of Amplify Community Resources, Ruban opens up about the business challenges of scaling, the importance of team dynamics, and why leadership means letting go of control. He also shares how mental health practices fuel personal growth, why community support is a game changer, and how technology’s impact is reshaping both opportunity and risk for today’s founders.

Former Georgetown soccer player turned founder, Marina Paul, is rewriting the playbook for entrepreneurship in athletic apparel. Through her company Superhera, Marina is tackling one of the overlooked business challenges in women in sports, ill-fitting uniforms that undermine confidence and performance. Her startup journey is as much about innovation as it is about personal growth, feedback, and self-trust. Marina shares how she evolved from scrappy prototypes to a tech platform empowering female athletes, why female founders need to embrace both grit and fun, and how building with users at the center creates lasting impact.

Entrepreneurship is never a straight line. It’s chaos, deals that almost blow up, and the wins that make it all worth it. In this episode of Hello Chaos, JJ sits down with George Otel, CEO of U.S. Business Funding, to talk about the real side of financing for founders. From equipment loans to commercial real estate and SBA programs for buying businesses, George shares the strategies that fuel business growth even in unpredictable markets. He opens up about the challenges of scaling, the power of delegation, and why networking and focus are non-negotiables for success. Whether you’re looking to fund expansion, acquire your next company, or simply navigate uncertainty, this conversation delivers unfiltered insights every entrepreneur can use.

What happens when a banker turned entrepreneur pioneers crowdfunding, disrupts financial services, and then sets his sights on rebuilding the hemp industry? For Steve Cinelli, it’s all part of the chaos. In this episode, JJ and Steve dive into technology, sustainability, and business strategy as they explore creating new demand for plant-based innovation and rethinking the future of farming. This one’s for founders chasing big change and bold ideas where entrepreneurship meets creative thinking and vision drives lasting impact.

Entrepreneurship lives at the intersection of vision and grit. Geoff Weber, founder of Heirloom Cloud, reveals the spark that launched his company, the emotion behind safeguarding family legacies, and the reality of finding fuel to scale. Expect lessons on leading through turbulence, navigating international growth, and building a team that reflects the world it serves. Curiosity drives innovation. Diversity strengthens outcomes. Networks open doors. If you are growing something meaningful, Geoff offers a playbook for courage, connection, and next moves.

She’s faced hyperinflation, shelf life disasters, lost facilities, and market shake ups. Ana Rodriguez’s path from launching a backpack company in Venezuela to co-founding Inbite, a thriving gluten free brand in Florida, is proof that grit and adaptability can turn chaos into opportunity. In this episode of Hello Chaos, Ana opens up about the messy reality of building a food manufacturing business, from costly packaging mistakes to the surprise growth that came through co-manufacturing. She shares how constant learning, clear focus, and the courage to pivot have shaped her 30 year entrepreneurial journey. For founders navigating uncertainty and high stakes, Ana’s story is a reminder that every challenge can feed your growth if you are willing to keep moving forward.

She kept it hidden for 25 years. Jane Pilger’s struggle with binge eating didn’t stop her from building a successful career. It pushed her toward something deeper. In this episode of Hello Chaos, Jane opens up about her business journey from high-achieving real estate pro to founder, coach, and guide for others navigating the messy intersection of entrepreneurship and mental health. She shares how nervous system regulation, shifting self-talk, and personal growth became the foundation for her coaching practice. From overcoming shame to building community support, Jane gets real about the emotional well-being required to lead a business while doing the inner work. For entrepreneurs who know the journey is personal and the stakes are high, this one is a powerful reminder to show up fully and embrace the chaos.

Cybersecurity is not just a tech issue. It is a business risk and a leadership challenge hiding in plain sight. Jeff Lyon, founder of TheCyberWild, shares what every entrepreneur should know about protecting their business from costly blind spots and false confidence in IT support. After leaving corporate life, Jeff found himself rebuilding more than just a business. He talks about the mindset shift, the small business struggles, and how humor helps him stay grounded while standing out. A candid look at what it takes to stay secure, stay focused, and keep moving forward as a founder.

They told her it would take $15 million. Mallory Vaughan Patton built Saint Spritz with grit, Google, and a clear vision. In this episode of Hello Chaos, Mallory sits down with Jennifer Sutton to unpack the raw and unfiltered reality of launching a healthy drink brand in the competitive beverage industry. From testing flavors in her kitchen to landing shelf space in Target, Walmart, and Whole Foods, Mallory shares how she navigated the chaos of startup life, one bold decision at a time. This story is rooted in family business, driven by women founders, and powered by a belief in doing things differently. The team behind St. Spritz moved fast, trusted their instincts, and figured out every piece of the process on their own. They balanced product launches, retail distribution, and regulatory hurdles with relentless determination. For any founder building something from scratch, this is a masterclass in making it happen. No shortcuts. No fluff. Just real talk on entrepreneurship and the daily grind of turning an idea into a movement.

Demi Knight Clark builds movements, not moments. Founder, builder, and culture-shifter, Demi sits down with Jennifer “JJ” Sutton to talk about disrupting industries, scaling with purpose, and rewriting what leadership looks like. From the launch of She Built This City to the bold vision behind Reimagining Rosies, she’s leading from the front with welders, with astronauts, and with next-gen talent. This episode is a call to action for founders who are ready to think bigger, act bolder, and stop waiting for permission. Here’s what every founder should take away from this one:

Cat Dunn didn’t just start a business. She claimed her power. Jennifer Sutton sits down with Cat to explore how entrepreneurship became her way out of a coercive relationship and into a life built on purpose, control, and impact. She built a coaching and online business management company from the ground up while navigating mental health recovery, housing instability, and the emotional weight of starting over. Her story covers the real business challenges most entrepreneurs face but rarely talk about. Cat also opens up about owning her identity, her deep connection to the horror community, and how authenticity fuels every decision she makes. This conversation speaks directly to founders who are building with heart and leading with truth.

Kevin Smith knows the chaos. He spent years in commercial marketing before launching For Goodness Sakes, a mission-driven agency built for nonprofits, public health, and social impact. In this episode, Kevin joins Jennifer Sutton to talk founder mindset, business leadership, and what it takes to turn strategy into outcomes that actually matter. He breaks down how behavioral science makes messaging work, why nonprofits need sharper tools, and what founders can learn from the frontlines of community engagement. This one’s for the builders who want to lead with purpose and still win.