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Skyler Healy

@skyhealy27

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🚀Chief Builder @joinunchartedcommunity
📚Founding Partner @reading_rhythms
Appreciate the Journey, Admire Your Strength

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Henry David Thoreau (1817 to 1862) was an American writer, naturalist, and philosopher, born in Concord, Massachusetts, and one of the central voices of Transcendentalism alongside his mentor Ralph Waldo Emerson.In 1845 he left town life behind and built a small cabin on the shore of Walden Pond, where he lived mostly alone for just over two years. The goal was simple and radical: to strip life down to its essentials and see what remained. *Walden*, published in 1854, is the book that came out of that experiment. It was one man finding out his relation to the simplicity of nature, and of life. Part nature journal, part philosophy, part quiet argument for living deliberately and owning less, it has outlasted nearly everything written around it.Thoreau watched the pond freeze and thaw, kept careful note of the seasons, and asked what a person actually needs to live well. His answer, less than most of us think, still lands a century and a half later. by @skyhealy27

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a month ago

The storyline here is that to speed up, I’ve had to learn how to slow down.De-acceleration doesn’t come naturally to me. My brain likes movement, momentum, intensity. Stillness can feel unfamiliar. But that’s the growth opportunity - learning that peace and ambition don’t have to exist in opposition.Duality. Trees and wind. Open space. Adventure, yet calm. Friendship, making space for love, and creating room for a life that isn’t only focused on output.When you’re building the operating system of a company, you wear a thousand different hats and often risk burnout. I used to think leadership meant holding everything together myself. Sometimes I had no choice. I’ve been learning that real leverage is architected through trust, systems, and empowering other people to fully own their role. Force multiplying. Empathy. That process comes with friction (lots of recent learnings). Letting go of control is uncomfortable. Sitting still long enough to actually think is uncomfortable too. Clarity usually doesn’t come from force - but from creating space for it.That’s why nature is so important to me. I’m still in the fast lane. Just learning how to stay there sustainably.Thanks for the epic mountain biking rides and dope photos 📸@paul.borash @calvin.fagley @sophie.fagley. States covered:- Montana - Wyoming- IdahoNational Parks:- Yellowstone - Grand Teton Can’t wait for biking across Chile / Argentina January 2027. by @skyhealy27

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2 months ago

“May you have the courage to recognize the voice of desire that disturbs you when you have settled for something safe… May you have the wisdom to enter generously into your own , to discover the new direction your longing wants you to take“ - John O’Donohue (Irish Poet, Author, Priest, and Philosopher).Today’s dump is about appreciating (many) of those closest to me, acknowledging growth and recent milestones, but also about entering a new season where the path and mentality to get here may not be fully aligned for the next chapter. Safety is an ambiguous term, and it does not mean stillness. But closer to what’s familiar… by @skyhealy27

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3 months ago

Spent the last several months in deep operator and architect mode. This past week’s biggest decision was pool, hot tub, or ocean. Grateful to be with close friends. Recharging the batteries. The next six months are going to be special. The Great Lock In 🚀 by @skyhealy27

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5 months ago

Becoming more of myself.Letting myself be seen.Same values.More range.Still building.Still learning.Still me.Grateful to be alive and doing work that feels purposeful. Thank you @glaciernyc for the shoot.#becoming#entrepreneurship#operatorexcellence #coherence#growth by @skyhealy27

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6 months ago

In 2025, I chased big goals and accidentally learned how to rest and build joy. I have often been running toward the next thing, the next accomplishment, the next challenge, the next milestone. There’s always more. I don’t want to slow down. I’m chasing something bigger, something deeper, something that requires real hard work and patience to be the best. But I’ve been more intentional about doing it sustainably, making sure I save time for joy along the way and giving myself permission to rest (I’ve learned that sleep + operating systems are critical). I want to enjoy the process. I have learned to embrace duality. I’ve traveled some dark and lonely roads and accumulated some deep battle scars. I haven’t always had joy - I’ve had to build it. To look for and cultivate it. Most often, joy for me comes from the quality of my relationships, most importantly with myself. Making time for health and fitness, for new experiences, and for those that are closest to me. Joy comes from gratitude. I’ve been relentless to not let my professional success outpace my personal growth. That’s a game I refuse to play, and takes a lot of patience and humility. I work really hard to give to others and spread joy through value created. Through outcomes achieved. I work really hard to give respect to those who came before me and appreciation for all the wisdom and mentorship shared. I work really hard to remain hungry, humble, and human. I work really hard to make mistakes. I work really hard to show, not tell. I’ve fallen in love with the challenge and the chase toward something deeper and more meaningful. Finding joy in the process means weaving my identity into my work, yet my ambition exists to serve a purpose bigger than myself, and not just the business I’m building either. The real opportunity is when I can succeed at and integrate both and demonstrate that with coherence. As this year closes, I’m proud of the way I showed up.Thank you for reading and to my friend @jelabela of @the_confetti_project for the incredible experience and photos, and if you haven’t checked out her community - please do. Cheers to 2026 🚀 by @skyhealy27

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7 months ago

Happy Holidays from your local upstairs neighbors. Life doesn’t need to be fancy and all things influence. All you need is quality friends like @larenzo__ to drag you to @jcpenney for a photoshoot. Call it multi-faceted 🎁@avibenmayor by @skyhealy27

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7 months ago

Huge congrats to my friend @kameronmonet on the launch of @socialdocket 🚀, an AI-powered platform designed to provide modern legal and business tools for the creator economy. If you don’t know Kameron, you will — as she is relentless and an authentic force whom I have the pleasure of knowing, supporting, and learning from 🚀. Thanks for the dope pics 👏🏾 it’s indeed now a tradition. 📸: @itsmariamaaa 📍: @citizens.of by @skyhealy27

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7 months ago

On November 13th, 2025, I did something I once thought was decades away.It was a true honor to lead a conversation with an incredible friend, mentor, adventurer, and role model, Joe Gagnon (@thehighperformancelife). For those who don’t know Joe, he’s a 6x CEO and ultra endurance athlete, most notably famous for running 6 marathons on 6 continents in 6 days, plus 6 Ironman triathlons and 90 marathon distance races.Joe and I spent months workshopping this talk, and throughout that time, I kept feeling fear, imposter syndrome, and doubt. Am I ready for this? Can I truly contribute to a conversation with someone so accomplished? What if I don’t know what to say?Joe is one of those people who makes it easy. Over the last several months, we spent hours discussing how Living Intentionally applies not just to those who have “arrived” but also to those still “becoming”, and that starts with defining your why and choosing your hard, as his book explores.I pride myself on living an integrated and holistic life, intentionally working on my inner world and alignment as much as my external world and output, with the goal of stronger integration into coherence as I elevate. I have the unique privilege of building the infrastructure and operating system of Uncharted, and I’m constantly reminded and humbled by the incredible wisdom in the rooms we create, and I’m eager to continue expanding our impact far and wide. Uncharted will continue to accelerate and uplift the entrepreneurial ecosystem, creating incredible experiences that create real relationships that accelerate business outcomes. My why is still becoming communicated externally, but it’s safe to say Joe and I have much in common in the way we lead and live. In the process of “becoming,” I’ve found it enormously important to be intentional about who your inner core is, what values and integrity you uphold, and to continue pushing yourself toward fear and humility.Grateful for this opportunity, and for all those who attended and supported. Many more amazing @joinunchartedcommunity opportunities nationwide coming soon. by @skyhealy27

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8 months ago

May 2024: Backstory - what started as a text from @calvin.fagley @paul.borash and Todd Fagley turned into one of the most challenging and rewarding experiences of my life - bikepacking across Iceland. Inspired by the great @jesseitzler, we called this our yearly Misogi. August 2025: Trip #2. Bikepacking across Slovenia - dipping into Austria, Italy, and Croatia - 260 miles, 75% unpaved road, and 29,367 ft of total ascent (yes higher than Mt. Everest) in under 10 days. Between the injuries, 2 flat tires, a broken derailleur and chain, and an emergency van rental, we learned what grit really means. More than that, it’s about the quality time with people I love, the countless strangers who helped us along the way, and the raw beauty of these countries and communities at ground level.Iceland 2024 ✓ More videos dropping soon (yes I procrastinated)Slovenia 2025 ✓2026 Destination TBD.I love this stuff🚴‍♂️ ⛰️🏕️grateful to keep going. #bikepacking #adventure #brotherhood #slovenia #lakebled #grit #nature #misogi #camping #mountainbiking #italy #croatia #austria #family #cousins by @skyhealy27

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9 months ago

2025 UNCHARTED SUMMIT 🚀600+ world class founders, funders, and industry leaders came together for a day of real conversations, curated connections, and a celebration of entrepreneurship and community. As Head of Community and Operations at @joinunchartedcommunity, I’ve spent the last two years helping build this vision, designing every detail and system to help people move faster and farther, together.I’m so proud of what we built, and so grateful to every person who helped make it happen. From world class speakers like @thefbinegotiator, @thesharkdaymond, @stevemadden @wendystarland who helped shape the conversation, to incredible founders of Unicorn companies like Martin Eberhard (Co-Founder of Tesla), @brian_halligan (Co-Founder of Hubspot), Shuo Wang (Co-Founder of Deel) and @ryantakesoff (Co-Founder of Bolt) and more, you set the bar for what’s possible. To the greatest team, wonderful interns, and incredible partners like @nyse @fidelityinvestments @whistlerpartners, @sentientjet @pga @ubs and more, you made it look effortless, even when it wasn’t. And to the community - thank you for showing up with trust, generosity, and intention. We’ve come a long way. And this is just the beginning.@noahsfriedman @tarynelisabethh @mikeyedelman @benlaker23 @shannpagnepapi @ecgalasso @mollyforrester @bradiannone @katieloebishere @therealmichaelloeb @heyfeifer @justinbarth_ #UnchartedSummit #CommunityBuilding #OperationalExcellence #StartupEcosystem #TrustFirst #DreamBigger #Empathy #systemsthinking #leadership #venturecapital by @skyhealy27

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a year ago

A couple weeks ago, I was invited to a very unique and informative dinner gathering the operators behind NYC’s top private member clubs.Those in attendance included @sohohouse @chief.network @casaciprianinyc @flyfishclub @theathletichq @continuumclub @remedyplace @springplace @thenednomad @thecoreclub @maxwellsocial and more.Conversation ebbed and flowed and much insight was shared, but some discussion points included:1) Belonging Beats Access:Members stay for connection, not perks. Rituals and micro communities build loyalty. 2) Differentiation Wins:Most members choose clubs based on clear values and identity - social, professional, or cultural - not overlap. 3) Monetize With Care: Growth is healthy when it enhances the experience, not commodifies it. 4) Curated > Massive:The future is intentional and deeply human. Members want utility, intimacy, and identity - all in one. Thank you to the incredible Anna Cogswell of Hampton and Nadine Choe of the Stanza for facilating and @davidlitwak of @maxwellsocial for hosting. Very honored and grateful to be there and learn from some of the best 🙏 by @skyhealy27

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a year ago