This year was not defined by the wins alone. It was shaped by the work underneath them. In this Hello Chaos year in review, Jennifer Sutton reflects on 2025 as a season of shedding, refinement, and more disciplined growth across Bright Marketing, OrangeWIP, and her own leadership journey. The same truth surfaced again and again in both business and life. Growth did not come from adding more noise or chasing more tools. It came from letting go of what no longer fit and choosing forward motion anyway. The shedding created space. The momentum followed.

Some founder stories rise because they are polished. These rose because they were honest. The Best of Hello Chaos 2025 brings together ten conversations founders listened to, shared, and sent to friends who needed to hear them. From legacy driven tech and practical AI to hospitality, accessibility, product design, mental health, and brand building, these founders showed what it actually looks like to build in the messy middle. Across industries and backgrounds, one truth stayed consistent. Chaos is not something to escape. It is something to work through. These stories mattered because they met founders where they are and reminded them why they keep building.

Losing his job became the moment Geoff Thatcher stepped into his real work. That setback pushed him to build Creative Principles, a family run creative studio rooted in creative leadership, storytelling and the kind of speed most experience design agencies cannot match. Geoff shows how getting fired can reveal your true value, clear out the noise and give founders the push they need to build something on their own terms. From avoiding minority equity traps to embracing fast cycles and serving the work instead of ego, Geoff offers a grounded playbook for entrepreneurs who want ownership, momentum and clarity. Here are the takeaways every founder can carry into their own messy middle.

Kris Rice turned a personal search for calm into ChillPod, a cold plunge product that's changing how founders think about wellness and building hardware. Her journey is all about self-funded manufacturing, figuring out how to create a physical product with zero experience, and the grit it takes for a woman to break into the cold plunge industry. It's an honest look at what entrepreneurs go through when they can't shake an idea. Kris talks about the reality of manufacturing challenges, moving production overseas, and learning to trust herself while dealing with the mental toll of being a founder. Her story is a guide for anyone building a hardware startup, getting into cold plunge wellness, or stuck in the messy middle of their own thing. It's packed with takeaways that any business owner can actually use.

What do you get when you mix Nigerian American roots, neurodivergent brilliance, and an obsession with beauty? You get Kelly Dowd, founder of FIDA Design. He's built something rare: a practice that weaves together interior design and fashion branding with a deeply human approach. His story is shaped by strategic empathy for entrepreneurs, British influence, and an unshakable eye for what works. And as a neurodivergent founder, he's proof that ADHD, dyslexia, and intuition aren't obstacles. They're design tools. Kelly embodies the kind of empathetic leadership for founders that most people talk about but few actually live. This conversation covers everything from his approach to interior design and fashion personal brand blueprint to the realities of entrepreneurial burnout and recovery. He gets honest about founder mental health and energy, and shares the uncomfortable truth that your so-called chaos might actually be your superpower. If you've ever felt misunderstood, underestimated, or just too much, this Hello Chaos podcast episode is for you. Kelly's story will make you rethink what it means to build something extraordinary.

Elena Ciccotelli built her EV podcast and EVs for Everyone brand by doing what most people in the electric vehicle industry would never attempt. She took a technical, fast moving space and turned it into a human centered platform filled with humor, insight, and real electric vehicle thought leadership. Her path from Lyft and automotive partnerships to creating a niche EV media brand shows how clarity, consistency, and a smart content strategy for founders can open unexpected doors. She shares what it looks like to navigate EV industry trends, push back on stale B2B marketing in automotive, and trust your voice even when the market gets loud. Entrepreneurs will recognize the grit in her story, but the spotlight stays fully on Elena and the way she built something original in a crowded industry.

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.