Montreal Magic: What Happens When Women Entrepreneurs Ask “What If?
Sometimes the best business insights come from the most unexpected places. Last month, I found myself in Montreal for the 2025 EO Women Summit, and what started as a speaking engagement turned into something much more transformative.
The theme of the summit kept echoing in my mind: “What if?” Three simple words that somehow managed to challenge everything. What if people genuinely care? What if the agency model transforms? What would it look like? What if you could genuinely connect with everyone here?
I wasn’t just there as an attendee as I’d originally intended. I’d been invited to present a session called “What if you had every Friday off?” A topic that’s become close to my heart as I’ve watched so many talented women (& humans in general) burn themselves out trying to prove they can do it all. The session was part of the summit’s broader focus on serving personal life, work life, home life, and community, but it quickly became clear that we were touching on something much deeper.
From the outset, the summit promised to “shatter every convention of what a business gathering can be” – and it delivered. One of the first surprises was a 7 AM “pajama party” meditation session led by Marsha Ralls, founder of a healing retreat center. Dozens of entrepreneurs showed up in their PJs for a HeartMath-guided meditation on coherence and resilience . This cozy, intimate start set a tone of vulnerability and openness that lasted throughout the event.
The Power of Bold Questions
Walking into the summit venue, I could feel the energy immediately. There’s something electric about being in a room full of women who’ve taken the leap into entrepreneurship, women who are married to entrepreneurs, and the children of these women. (with a few men too) Most of these were women who’d already built companies, navigated challenges, and were now ready to push even further.
The summit’s central questions weren’t just conversation starters, they were genuine challenges:
What if we led with even more clarity and courage? What if we redefined success on our own terms? What if the next breakthrough came from one bold conversation?
During my session on AI and how it can give you your life back, I watched as faces around the room shift from skepticism to curiosity to genuine excitement. We weren’t just talking about taking Fridays off. We were discussing what it means to build a business that serves your life, rather than the other way around. And it just so happens that AI can help you get there faster than ever.
Entrepreneur Lauren Reed presents “What If Wealth Was a Mindset?” on stage, exploring how financial success starts with one’s mentality. One by one, speakers tackled some of the most talked-about topics in today’s business landscape. Lauren Reed, a financial educator, asked “What if wealth was a mindset?”, guiding the audience to explore unconventional approaches to building and sustaining wealth beyond just spreadsheets and markets. Her session on financial psychology showed that building wealth starts internally, with beliefs and confidence, rather than external factors .
On the theme of scaling companies, a powerhouse trio – Renee Russo, Anthony Rice, and Carrie Kerpen – led a panel on “What if you could build an exitable business?”. Russo (an exit planning advisor) broke down how to engineer a company that can thrive without you, highlighting pillars like intentional profit, strong teams, global talent and scalable systems . Anthony Rice brought in a people engineering perspective, showing how a well constructed, global team can be “force multiplier” for entrepreneurs when used thoughtfully. Complementing them, Carrie Kerpen (who famously built and sold a social media agency) shared hard-won wisdom on visibility and leadership. She challenged women to stop shrinking and start showing up, encouraging us to claim our seats at the table and speak up about our achievements . Kerpen’s energetic talk on personal leadership had the room cheering as she insisted that women leaders must stop underestimating themselves (a message that clearly resonated).
Personal growth and wellness were also front-and-center. Dr. Mireille “Mimi” Vega, a chemist and skincare entrepreneur, asked “What if clean living could transform your life?” and drew a fascinating connection between eliminating toxins and improving one’s energy, resilience, and leadership capacity . She even hosted a hands-on skincare workshop, reminding everyone that how we treat ourselves (skin included!) ripples into how we show up in the world . Along similar lines, Dr. Lucia Aronica, a Stanford University epigenetics expert, delivered one of the summit’s most eye-opening sessions on longevity and health. In “What if your fork was a pencil?” (an intriguingly titled talk), she illustrated how our daily food choices literally rewrite our genetic expression and can extend not only our lifespan but our “health-span”, the years we can lead and innovate at peak performance. Attendees were amazed to learn how “food isn’t just food – it’s information for your genes”. Aronica’s cutting-edge research reinforced a big theme of the summit: sustainable success is built from the inside out, blending business acumen with personal well-being.
The agenda also touched on emotional and interpersonal growth. Stephanie Camarillo led an introspective session on forgiveness and letting go of past baggage (titled “What if you could forgive?”), setting the stage for attendees to step into who they truly want to be . Melissa Davis, an Enneagram expert, explored “What if you saw yourself clearly?”, using the Enneagram personality framework as a mirror for self-discovery and leadership growth . Even the summit’s MC, Jenny Feterovich, became part of the inspiration: a serial entrepreneur and award-winning film producer (and former world-touring DJ!), Jenny (from the Eastern Block;) shared her personal story of breaking barriers in the electronic music industry showed what’s possible when you dare to say “what if?” in a non-traditional field . Her high-energy emceeing – and the fact that she’s performed alongside the likes of David Guetta and Akon – injected extra flair, earning her a shoutout in the closing session for “elevating the entire Summit” .
Through these speakers and topics, a few clear themes emerged: Embrace technology and innovation, but stay true to your story. Build businesses that can thrive without you, but also invest in your personal growth and health. Challenge your limiting assumptions, but lean on your community for support. In every talk, that “What if…?” question pushed attendees to imagine new possibilities – from what if I sold my company?, to what if I completely reinvented my brand at age 50?, to what if taking better care of myself could 10x my business? The range of topics was broad, but all funneled toward one idea: empowering women entrepreneurs to lead boldly and live fully.
The Friday Experiment
Instead of just talking theory, we decided to get practical. I challenged everyone in the session to experiment with their own version of “What if you had every Friday off?”
For some, that meant literally blocking Fridays from their calendar. For others, it meant identifying one recurring commitment they could eliminate or delegate. The key wasn’t the specific day, it was the mindset shift.
“What would have to change in your business for you to take every Friday off?” I asked. “What systems would you need? What help would you require? What would you have to stop doing?”
The room got quiet as people actually thought through the logistics. Then the conversations started. Women began problem-solving together, sharing strategies they’d used to streamline operations, delegate effectively, and set boundaries with clients.
Beyond the Summit: Building Community
What struck me most about Montreal wasn’t just the formal sessions. It was the conversations that happened over coffee breaks, during dinner, and even in the hotel lobby late at night. There’s something about bringing together entrepreneurs from different industries and backgrounds, they see solutions you might miss when you’re too close to your own business.
I left with contact information for women in over 60 cities in 30 different countries. More importantly, I left with a network of people who understood the unique challenges of building something from scratch while trying to maintain some semblance of balance.
The summit’s emphasis on “real connection, in business and in life” wasn’t just marketing speak. These women were genuinely interested in supporting each other’s success, not just during the event, but long afterward. I’ve enjoyed so many follow-up conversations since the event.
I know I have a supportive community cheering me on from around the world. We chat on what’s app, have zooms, and will continue to support each other for years. A handful of the women I’ve known for over 18 years already. I’m lucky to have connected with more genuinely good humans.
Atmosphere of Camaraderie and “Sisterhood”
Perhaps the most remarkable outcome of the Montreal summit was the intangible atmosphere of trust and camaraderie that developed. Attendees repeatedly described the environment as “electric,” “transformative,” and deeply supportive. The event’s design – mixing serious learning with fun, bonding experiences – created a space where women felt comfortable being authentic. It’s not every day you see CEOs in yoga pants doing morning meditations together, or dancing in a circle at a gala after discussing exit strategies and AI! By deliberately breaking the mold of stiff corporate conferences, the summit allowed genuine friendships to form. “For years, I have worn loneliness like a second skin… but this summit reminded me of the power of sisterhood,” one founder shared emotionally . That sentiment of “you are not alone” was echoed countless times.
Redefining Growth on Own Terms: A key takeaway was that growth can (and should) be redefined beyond traditional metrics. Whether it’s growing through strategic partnerships instead of constant hustle. Or reshaping a company so it can be successfully exited. Women entrepreneurs are looking at growth more strategically. The summit conversations showed a trend toward intentional growth. Making bold moves like restructuring businesses for scalability , seeking acquisitions or exits, and leveraging networks to grow smarter, not just faster.
Holistic Leadership and Well-Being: There was a strong emphasis on viewing health, mindset, and personal development as integral to leadership success. It’s clear that the next wave of women leaders values mental and physical well-being as competitive advantages. From meditation techniques to epigenetics, the summit highlighted cutting-edge ideas on longevity and stress management for entrepreneurs. Don’t be surprised if you see more founders talking about their “health-span” or integrating wellness retreats into their annual business plans. The influence of sessions like Dr. Vega’s and Dr. Aronica’s is real.
Authenticity and Personal Brand: A recurring theme was authentic storytelling and brand building. From Martha Stewart to emerging founders, the advice was consistent: infuse who you are into what you do. The trend here is a move away from the polished “perfect” image and toward a more genuine, even vulnerable style of leadership. Many attendees felt validated to share their true stories, failures, quirks and all, as a result of hearing speakers emphasize authenticity. “Personal branding isn’t curation, it’s conviction,” one attendee summarized, recalling Martha’s counsel that authenticity is key
Women Supporting Women: Perhaps the most heartening trend was the intentional creation of women-centric support networks. The summit itself marked a milestone: it was the first time the EO Women Summit was held as an official global event (having evolved from a grassroots “MyEO” initiative over the past nine years) . This reflects a larger movement to carve out spaces where women leaders worldwide can connect, share, and lift each other up. As summit chair Marina Byezhanova learned, “women supporting women is our competitive advantage.” The outcomes of the summit, new mentorships formed, deals sparked among attendees, a buzzing WhatsApp group that’s still active, all suggest that this community will continue to pay dividends. In the words of one participant, “the connections made here are going to last us a lifetime.”
Embracing Tech & AI Fearlessly: Rather than shying away from technology, attendees were urged to embrace AI and other innovations to amplify their impact. The dialogue shifted from fear of AI to “How can I use AI to reclaim my creativity and time?” (as speaker I framed it). This reflects a broader trend of women entrepreneurs becoming early adopters of tech tools, not just to automate tasks, but to free themselves for higher-level creative and strategic work. The summit reinforced that staying tech-savvy is part of staying competitive, and that women can lead in this arena.
Questions Worth Asking
The summit reminded me why I love working with women (and female friendly) entrepreneurs. There’s a willingness to examine not just what we’re building, but why we’re building it. The “What if?” framework gives us permission to question assumptions we might not even realize we’re making.
What if success doesn’t require sacrificing your health? What if you can build a profitable business without working every weekend? What if asking for help is actually a sign of strength, not weakness?
These aren’t rhetorical questions. They’re genuine invitations to experiment with different approaches.
“Own your story before others narrate it.” – Martha Stewart, urging entrepreneurs to embrace authenticity in personal branding.
“Food isn’t just food, it’s information for your genes.” – Dr. Lucia Aronica on how our daily choices shape our long-term health and capacity to lead.
“Stop shrinking, start showing up.” – Carrie Kerpen encouraging women to claim their space and voice in leadership.
Make Your Own Montreal Moment
You don’t need to attend a summit in Montreal to start asking better questions. The magic wasn’t in the location or the formal presentations, it was in the willingness to challenge the status quo and connect with others who were doing the same.
Start with your own “What if?” What if you approached your biggest business challenge from a completely different angle? What if you gave yourself permission to prioritize differently? What if you stopped comparing your behind-the-scenes to everyone else’s highlight reel? What if you let AI do your work for you?
The women I met in Montreal reminded me that entrepreneurship doesn’t have to be a solo journey working in an echo chamber. Sometimes the breakthrough you need comes from one connecting conversation, with yourself or with others who understand what you’re trying to build. If you come with a beginners mind to the conversations, the ideas can bubble up.
I personally had a breakthrough in a business problem I’ve been thinking about for months in a moment when I felt resistance because I’d heard this stuff many times before. In that moment, I went though the exercise with a beginners mindset and finally saw what I was looking for!
At the final event, the Red Dress Gala, 100+ women entrepreneurs, all clad in bold red, gathered to celebrate the summit’s close, embodying the event’s spirit of unity and empowerment. The “Red Dress Party” made for an unforgettable group photo and a fitting celebration of four days of growth. As music played and glasses clinked, the hall was filled with laughter, embraces, and a palpable sense of accomplishment. Many remarked that the summit felt “like nothing else, zero fluff and all the stuff that helps you grow,” to quote one participant’s social post. It was clear that EO Women’s Summit 2025 wasn’t just about learning business tactics, it was about creating an experience and community that would linger long after everyone returned home.
What attendees said about my session:
“This was an engaging session which has me rethinking how to further leverage AI in my business. Loved the tech shares at the closing!” -Anonymous Entrepreneur
“Super accessible and actionable.” -Andrea Herrera
“Incredible overview of how ai can make business life easier”
-Anonymous Entrepreneur
“This is more hands on, practical AI advice for business owners versus broad, futuristic AI “dreams”. Thanks for sharing!”
-Jennifer Jurgens
