There’s a time and a place for following the rules—but ask any successful entrepreneur, and they’ll tell you that the early days of building a business usually aren’t it. The founders who make it happen aren’t afraid to challenge convention, test limits, and trust their instincts over playbooks. Their secret? Knowing when to break the “right” rules to carve out something original, necessary, and lasting.
In this feature, visionary leaders from the Dreamers & Doers community reveal the bold moves and rule-bending decisions that helped them defy expectations, grow thriving businesses, and create ripple effects across their industries.
Lakeya Cherry
CEO & Founder of Lakeya Cherry LLC, a dynamic executive coaching and consulting business that empowers leaders and organizations to maximize their potential.
When I left my role as CEO of a national nonprofit to start my own coaching and consulting practice, I broke every rule about stability, timing, and predictability. Many thought it was too risky, especially as a woman of color leading an already successful organization. However, I knew I was being called to build something that reflected my deepest values, a business that helped leaders grow without losing themselves in the process. That leap birthed a body of work that now empowers hundreds of leaders and teams across sectors to lead with heart, dismantle barriers, and thrive without burning out.
My bold advice: Don’t wait for perfect timing or external validation! Clarity comes in the doing. Start where you are, move with intention, and let each step reveal the next.
Ciara Siegel
Brand and Marketing Strategist & Founder of CJC, bringing the strategy behind billion-dollar brands to small businesses.
In a world where everyone wants quick marketing wins, I made the unconventional choice to only offer marketing strategy after I’d helped a client get clear on their brand. Most people want to skip straight to content or lead generation, but without strong brand foundations, marketing becomes guesswork. Standing by that conviction has led to better results for my clients and a reputation for clarity people can actually use.
My bold advice: Use your brand mission and values as filters. If a move aligns with what you stand for and the kind of business you’re building, it’s probably a step toward integrity more than it is a risk. Unconventional ideas can feel uncomfortable, but discomfort doesn’t mean it’s the wrong path.
Kodi Kitchen Berg
Founder & CEO of equipt, fusing functionality with design to create fitness equipment for homes, studios, and hotels.
As a new mom and former soap opera actress, I had little sleep and little business acumen. What I did have was an interest in moving my body because I knew I felt better the minute I started doing so. I strapped a baby to my chest and went to steel yards in Burbank to find out how things were made. From there, I took the spirit of little details that made me feel good—red lipstick, a good dress—and applied it to fitness equipment.
My bold advice: Silence the noise and don’t be afraid to look foolish. I can’t count the number of times I’ve heard that gold weights are dumb. Now the narrative has shifted. If you want something to exist, make it.
Chef LaToya Larkin
Founder & Tamale Disruptor of Black Girl Tamales, a gourmet fusion tamale brand that reimagines tradition by blending Southern comfort flavors with classic masa.
When I told my son I was going to put leftover collard greens inside tamales, he laughed and said nobody would buy them. But I trusted my gut and went for it anyway. That “crazy” idea became the foundation of Black Girl Tamales: proof that innovation often looks unconventional before it becomes undeniable. Breaking the rules opened doors for cultural fusion, creativity, a new wave of culinary storytelling, and tamale disruption.
My bold advice: Bet on yourself every single time and double down extra heavy. The very thing that feels unconventional or risky is often the exact thing that will set you apart.
Rozella White
CEO of The Waymaker Agency, a collaborative of coaches and consultants united by a shared mission: to help organizations and leaders undo the knots that hold them back.
I broke the unspoken rule that says stability should come before purpose. After 15 years of rising through leadership roles in faith-based communities, I walked away from a seemingly secure path to follow a deeper call to entrepreneurship. I knew my impact could be more expansive beyond institutional walls, creating spaces that center love, justice, and transformation. That leap led to building brands and companies that reflect who I am, not just the titles I once held.
My bold advice: Trust that your vision is worthy, even when the world hasn’t made room for it yet. Every leap I’ve taken has required courage before clarity—and the clarity always came. Remember: your work isn’t meant to replicate old systems; it’s meant to build new ones.
Kellie Chen
Co-Founder of 8Rue Branding, a boutique branding agency with big-brand expertise and startup hustle.
When I started 8Rue, I didn’t want to chase billion-dollar beauty accounts—I wanted to build for the founders still mixing formulas in their kitchens. After years in the Fortune 500 world, I saw how smaller, mission-driven brands were often dismissed as “too early” or “too small” to matter. But those were the ones with the heart, innovation, and story that big brands couldn’t replicate—allowing me to build an agency that’s actually meaningful.
My bold advice: Every founder is told to follow their gut—and they should, but do it after you’ve done the homework. Great vision will get you noticed, but preparation will keep you alive.
Megumi Calver
Founder & Sommelier of Merobebe, a media and events platform using wine as a starting point for community, confidence, and candid conversation among ambitious women.
Earlier this year, I made the decision to cancel a wine tasting event in Los Angeles just days before it was set to take place despite months of planning, ticket sales, and confirmed partners. Canceling felt like breaking all the rules of professionalism: risking trust from those who purchased tickets, losing money, and disappointing my partners. But the event was scheduled in Beverly Hills just as protests were erupting across the city, and promoting a luxury wine gathering during that moment didn’t feel right, especially when my brand is rooted in community—and that community responded with deep understanding.
My bold advice: Let your mission and the value you’re offering—whether it’s community, creativity, or care—be your focus and the energy that gives you courage.
Fatima Teos
Co-Founder of NJK Partners & Founder of Vita Nova Media, a family of ventures built on the shared mission of helping families, businesses, and communities grow with purpose, creativity, and sustainability.
I broke the rules by slowing down when everything around me said to speed up. After years in finance, I stepped away from chasing metrics to build a business rooted in meaning—one that values purpose over pressure. I chose to prioritize clarity, creativity, and community instead of rapid growth, and the result has been a deeply aligned ecosystem of ventures that create lasting impact across media, finance, and education.
My bold advice: Trust your pace. Growth that’s intentional compounds more powerfully than growth that’s rushed. If your vision feels different from everyone else’s, it probably means you’re building something worth waiting for.
Kylee McGrane-Zarnoch
Founder & Executive Director of A Moment of Magic, a national nonprofit harnessing the power of play to spark joy, foster connection, and support the mental health and emotional healing of medically vulnerable children.
As a 20-year-old college sophomore, I started with a $300 crowd-funded costume and a belief that joy should be part of every healthcare plan. Ten years later, that unconventional beginning has grown into a national organization creating community-based pediatric mental and emotional health solutions—proof that heart-led ideas and credibility aren’t opposites, but partners. I’ve learned to trust what feels right, even when it doesn’t fit the mold.
My bold advice: Don’t wait for permission. Start with what you have, where you are, and who you are. When you let your why light the way, everything else has a way of falling into place.
Catalina Parker
Co-Founder & CEO of Relatable Nonprofit, helping nonprofit leaders build profitable, sustainable consulting businesses aligned with their values.
I broke the biggest rule of my career when I walked away from my dream job at a $500M foundation with no clear plan, just a text to a friend that said, “Want to start a business?” As a mom and the primary breadwinner for my family, everyone told me it was reckless to leave security for uncertainty. But that decision became the catalyst for building a business that reflects my values and the kind of life I actually want to live. Choosing authenticity over approval changed everything about how I define success.
My bold advice: The leap might look risky, but it’s often the most responsible thing you can do for your soul. Clarity always lives on the other side of courage.
Rocio Leon
Co-founder & CEO of Tozi Azteca Superfoods, a Mexican women-owned food company rooted in heritage and health.
After losing my last grandparent, I walked away from a successful corporate career and turned heartbreak into purpose. I founded Tozi to honor my family’s six-generation ranch legacy in Jalisco, proving that Mexican food can be both authentically delicious and clean. Tozi breaks the rules of how modern food is “supposed” to be made, honoring the ancestral wisdom deeply rooted in my heritage.
My bold advice: Do the scary thing; that’s where the magic happens. Every bold move I’ve made for Tozi and in life started with fear, but growth always lives on the other side of it.
Hila Lauterbach
Co-Founder of 10XGTM, building the go-to-market roadmap that drives strategy, execution, and traction.
I broke the rules by redefining go-to-market as an umbrella discipline that sits above marketing, sales, and product, aligning them around a shared system of buyer truth, product design, and revenue growth. I built a continuous customer-interview playbook to validate and refine that truth at every stage, from concept to scale.
My bold advice: Trust the signal, not the noise. If your idea challenges the norm yet feels true to the problem you’re solving, that tension is usually where the breakthrough lives.
Ulrika Gustafson
Global Executive Coach & Advisor of Ulrika Gustafson Advisory, working with Fortune 500 leaders and executive teams to recalibrate leadership tone, rebuild trust, and sustain credibility when the pressure is high and the politics are real.
When I left a thriving law career in Sweden to become one of Scandinavia’s youngest female City Managers, everyone told me I was throwing my legal future away. But I trusted the undercurrents that the system needed a reset, and ended up turning around entire municipal systems. Years later, I broke the rules again by walking away from everything I had built in Sweden to start over in the U.S. I rebuilt from the ground up, turning the experience of being underestimated into the foundation of my global advisory practice today.
My bold advice: Stop waiting for certainty. You won’t get it. What you will get is data; clarity through movement, not overthinking. The safest thing you can do as a founder is to stay in motion and recalibrate faster than everyone else.
Sam Yarborough
Co-Founder of Arcadia, a leadership community and event series for GTM business leaders who care as much about how they lead as what they achieve.
When I left my executive SaaS role to build Arcadia, every logical rule said not to. I walked away from stability, a title, and a steady paycheck to build something that didn’t exist yet. But I knew the kind of leadership I wanted to see in the world wasn’t being built inside the old systems. Because I followed that instinct, my husband and I have co-founded and built a community of leaders who are redefining success not just by metrics and titles, but by who they become along the way.
My bold advice: High-achievers are conditioned to believe we need a perfect plan before we move, so we spend so much time trying to figure it out on paper that we never get to figure it out in real life. Clarity comes from movement. The first step leads to the next, and even the best plans will shift as you go.
Lori Sussle Bonanni
Fractional Communications & Communications Consultant at elssus, a strategic communications partner helping tech and healthcare companies build awareness, strengthen reputation, and deliver results.
After college, when everyone was landing their first jobs, I moved to London with a loose plan and a lot of curiosity. Years later, I quit a perfectly good job at NBC to explore more of South America after falling in love with Argentina on a previous trip. Those choices taught me that the best decisions often come from curiosity instead of convention
My bold advice: Do it. If it scares you a little and excites you a lot, that’s usually the right direction.
All individuals featured in this article are members of Dreamers & Doers, a highly curated community and PR Hype Machine™ amplifying extraordinary women entrepreneurs and leaders through authentic connections, credibility-boosting visibility, and opportunities that accelerate big dreams. (Learn more about membership here.)
