Andres Camilo lost everything and picked up a paintbrush.

The home. The studio. The marriage. The identity he'd spent decades building.

All of it. Gone.

This episode is about what happens after that. Not the motivational poster version. The real one. The one where you're sitting in the wreckage and you don't know who you are anymore… and you have to figure out whether that's the end of the story or the beginning of a different one.

Andres chose different.

In this conversation with Ken, he talks about what collapse actually feels like from the inside — not the cinematic version, the 3am version…

How travel became part of his recovery. Not as escape. As excavation. Going to places that had no memory of the person he used to be… so he could figure out who was left.

We talk about making art when you have nothing left to prove…

Being a gay veteran in spaces that were never designed for people like him…

The intersection of military service, queerness, and creativity — three things the world keeps telling you don't go together…

And the moment he realized the truth he'd been searching for in every new city, every new country, every new canvas… was never somewhere else.

It was inside him the whole time.

This is for anyone who's ever had their life fall apart and wondered whether starting over at this age is even possible.

Andres didn't wonder. He did it.

And what he built from the wreckage is more beautiful than what was there before.

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Should I go?

Not "can I afford it." Not "do I have the PTO."

Should I go… there. As myself. Visibly.

TJ Chernick has spent years thinking about this question. And their answer isn't simple — which is exactly why this conversation matters.

In this episode, TJ gets into what it actually means to travel as a political act.

Not in the abstract, inspirational-poster sense.

In the real sense. The one where you're standing in a country that hasn't decided whether it wants you… and your presence — your visible, unapologetic, queer presence — is itself a form of resistance.

We talk about LGBTQ+ safety in travel. The real version. Not the sanitized "check this government website" version.

How to assess genuine risk versus perceived risk — because they're not always the same thing, and confusing them can cost you in both directions…

What it means to be a visible queer traveler in destinations that are still working out where they stand…

And the uncomfortable truth that showing up matters most precisely when it's uncomfortable.

TJ also covers the practical side. How to prepare for trips to less welcoming places. How to connect with local queer communities safely — without putting anyone at risk. What queer travelers owe each other when we move through the world.

This isn't about being reckless. It's about being intentional.

And understanding that sometimes, the most radical thing you can do is just… be there.

And then there's the version that actually works long-term.

Jeremy Tran has been living the second one. And in this episode, he gets into what sustainable nomadism in Asia really looks like — not the Instagram version, not the "quit your job and figure it out" version, but the one where you've actually built systems that let you live this way for years without burning out or going broke.

We talk about the cities that work for queer digital nomads — and the ones that look good on paper but fall apart in practice…

The visa situations that are more manageable than you think (and the ones that aren't)…

The community infrastructure that makes long-term nomadism actually livable versus just survivable…

And Southeast Asia's complicated relationship with queerness — more nuanced than the travel blogs suggest, in both directions.

Jeremy also gets into the moment this stopped being a phase and became a life.

That shift. When you realize you're not on an extended vacation. You're not running from something. You've just… built the thing. The location-independent, self-directed, genuinely free thing.

And it's not perfect. But it's yours.

If you've been researching Asia as a base… or just wondering whether this whole nomad thing is sustainable past your 30s… Jeremy's proof that it is. With receipts.

Hotels and restaurants throw away an almost obscene amount of food. Every day. Everywhere you travel.

And you're paying full price for the stuff that doesn't get thrown away.

Ben Liegey looked at that equation and built BetterTable — a platform that connects travelers with surplus food from restaurants and hotels at a fraction of the retail price.

Which means you eat well. Spend less. And stop contributing to one of the most under-discussed environmental problems in the travel industry.

In this episode, Ben walks through how BetterTable actually works…

Why food waste in travel is a bigger deal than almost anyone is willing to talk about…

What it looks like to eat your way through a city while doing less damage and keeping more money in your pocket…

And what it takes to build a sustainable business in an industry that's historically allergic to sustainability.

We also get into what travelers can do beyond downloading an app — the choices that actually move the needle — and why the intersection of food, travel, and environmental responsibility is one of the most interesting spaces in the industry right now.

This isn't a guilt trip. It's a better trip. Literally.

In every queer expat Facebook group. In every "where should I move?" conversation. In every daydream you're having at your desk right now.

Shasta Townsend actually did it. Moved there. Built a life. And in this episode, she gives you the version the Instagram accounts won't.

The real one.

Not the "paradise found" version. Not the "don't come, it's terrible" version either.

The honest one. With actual numbers.

We talk about the Romantic Zone — what it is, what it isn't, and what it's becoming as the city grows faster than its infrastructure can handle…

The real cost of living (Shasta gives you figures, not vibes)…

The bureaucracy of actually moving to Mexico — it's real, it's annoying, and it's survivable if you know what to expect…

Healthcare. Safety. The social scene. How you find your people when you land.

And the thing most PV cheerleaders won't say: the city is changing. Fast. What worked five years ago doesn't always work now. The vibe is shifting. Some of it is great. Some of it requires trade-offs you should know about before you sign a lease.

Shasta doesn't sell you on Puerto Vallarta.

She gives you enough truth to figure out whether it's actually right for you — or whether you should be looking somewhere else.

Either way, you'll leave this episode with the clearest picture of queer expat life in Mexico that anyone's put together. No fantasies. No horror stories. Just the real thing.

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Not the money math. The other math.

The one where you're standing in a hotel lobby with your kids, scanning the room, calculating how visible you are. Whether the front desk person clocked your family structure. Whether this is going to be one of the easy places or one of the hard ones.

Kari Payne and Scott Bishop Falcone know that math by heart.

In this episode, two of the most thoughtful voices in LGBTQ+ family travel get into what it actually looks like to navigate the world with kids when your family doesn't match the one in the brochure.

Not the sanitized version. The real one.

The destinations that genuinely welcome queer families — not just tolerate them with a tight smile…

The ones that sound welcoming until you arrive and realize the welcome was for a different kind of family…

How to have age-appropriate conversations with your kids about safety and identity while traveling — without scaring them or lying to them…

And the moments — because there will be moments — when the world reminds you that your family is still considered political in some places. Even at a beach resort. Even on a Tuesday.

We also get into the practical stuff. How to research destinations as a queer family. What questions to ask before you book. What to do when something goes wrong.

Kari and Scott bring warmth, humor, and the kind of hard-won wisdom you only get from actually doing this — not theorizing about it.

Whether you're a queer parent, planning to be, or traveling with chosen family… this conversation doesn't get nearly enough airtime.

And your family deserves better than a brochure that wasn't made for you.

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Francesco Mevoli builds trips about feeling things.

Gay Up Travel started with a radical premise: that travel — real travel, not the checklist-and-selfie kind — is one of the most powerful tools for queer liberation and connection that exists.

And he built it in Italy. Which is both the most obvious and the most complicated choice he could have made.

Because Italy is not the postcard.

It's more welcoming than a lot of queer travelers expect… and more complicated than the tourism board wants to admit. Francesco knows both versions. He lives in the tension between them.

In this episode, he takes us inside the world of Italian queer travel — the food, the culture, the very specific joy of sitting at a long table with your people in one of the most beautiful places on earth…

Having the kind of conversation that only happens when you're far from home and completely yourself.

We talk about what it means to design travel that goes beyond sightseeing…

Why food is the most underrated connection point in queer travel…

What happens when you stop moving through a place and start belonging to it, even temporarily…

And what Francesco has learned about the difference between a trip that moves you around… and one that fills you up.

If you've ever come home from a vacation and felt emptier than when you left… this is the episode that explains why. And what the alternative looks like.

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When's the last time you saw a queer person in an outdoor adventure ad?

Not a Pride Month Instagram post from a gear company. An actual ad. For an actual trip. With an actual queer person doing the thing.

Yeah. Chris Smith noticed that too.

So he built Pride Adventure Travel — and spent years proving something the outdoor industry apparently needed proof of: that queer people belong on mountains, on trails, in the water, and everywhere else the adventure world used to pretend we didn't exist.

In this episode, Chris gets into the outdoor industry's complicated (and honestly, pretty embarrassing) relationship with diversity…

What it actually feels like to show up at a trailhead as a visibly queer person…

And why group adventure travel does something for queer people that solo trips can't — it builds a community that holds you while you push yourself.

We also cover the practical stuff. How to find queer-friendly outdoor adventures. What to look for in a guide or operator. Red flags. Green flags.

And the thing Chris keeps coming back to: the best trips of your life will probably be the ones that scare you a little first.

If you've ever stood at the edge of something — a mountain, a decision, a new chapter — and wondered whether you were allowed to go…

Chris Smith's answer is yes.

Full stop. Always yes.

Does spending more money make you safer as a queer traveler?

Duncan Greenfield-Turk has been sitting with that question for years. And his answer is more complicated — and more useful — than you'd expect.

As one of the leading voices in LGBTQ+ luxury travel, Duncan lives at the intersection of high-end experiences and the very real safety math that queer travelers run every single time they book a trip.

You know the math. The one you do silently. Can I hold my partner's hand here? What happens if someone clocks us at dinner? Is this resort actually welcoming, or did they just update their website for Pride Month?

In this episode, Duncan gets into what luxury travel actually buys you when you're queer. (Hint: it's not thread count. It's control over your environment.)

He talks about how to tell the difference between a destination that's genuinely welcoming versus one that's performatively rainbow-flagged…

The emotional labor of traveling while queer — a real cost that nobody's pricing into the trip…

The destinations that are actually leading on inclusion… and the ones that are all marketing and no substance…

And what happens when some of the most beautiful places on earth are also some of the most dangerous for people like us.

Duncan doesn't sugarcoat it. Some expensive resorts will still make you invisible. Some cheap guesthouses will make you feel like family.

He knows which is which.

We also talk about the moment he knew he wanted to specialize in LGBTQ+ luxury travel… what clients ask him that they won't ask anyone else… and what one perfect trip changed for him personally.

This is for anyone who's ever looked at a gorgeous photo on Instagram and suspected it wasn't telling the whole story.

You were right. Duncan tells the rest.

Cute cafés. Brownstones. Maybe a rainbow crosswalk.

And then there's the version Michael Venturiello knows.

The one with blood on the sidewalks. The one where people died — of violence, of neglect, of a plague the government pretended wasn't happening. The one where a community built itself out of nothing, in the face of everything, on streets you can still walk today.

Michael founded Christopher Street Tours because those stories were disappearing.

Not accidentally. Deliberately.

Gentrification paves over them. Assimilation smooths them out. And historical amnesia does the rest.

In this episode, Michael takes us through the real West Village — the Stonewall era as it actually happened inside the neighborhood, the AIDS crisis and how it reshaped every block, and the ongoing fight to make sure LGBTQ+ history gets treated as history… not a footnote someone can skip.

We talk about what it means to run a queer business on the exact streets where queer history was made…

Why place matters so much to identity — especially queer identity…

The threat of erasure that's happening right now, not in some abstract future…

And what Michael hopes people carry with them after the tour ends.

This isn't a charming walking tour episode.

It's about the radical act of refusing to let our stories be forgotten. Every name Michael says out loud is a name someone tried to erase.

And every tour he gives is an argument that our lives are worth remembering.

But according to Queer Tours France, it has also always been a lot more queer than your history books admitted.

In this episode of Pride Nomad Unleashed, Ken sits down with the fabulous trio behind Queer Tours France: Charlotte, Alex, and Doina—three licensed guides who decided they were done letting queer people be treated like footnotes in French history.

Together, they created a series of LGBTQ+ history tours across Paris and Versailles that reveal the stories hiding in plain sight: royal gardens used as cruising spots, sapphic rumors around Marie Antoinette, queer traces inside the Louvre, the hidden LGBTQ+ history of Le Marais, and the uncomfortable truth that many of the “classic” Paris stories were straight-washed for centuries.

This is not your boring museum tour.

Charlotte brings activism, music, deep research, and filthy jokes. Alex brings storytelling, history, Instagram brilliance, and the kind of guide energy that could apparently start a new religion. Doina brings wit, website wizardry, queer historical arguments, and the ability to turn a classic Paris tour into something far more alive.

The conversation covers how Queer Tours France came together, why LGBTQ+ travelers need spaces where they can relax into their own community, and how queer tours change the emotional experience of travel. As Doina explains, a queer tour feels different because the guide and guests are not just sharing facts—they are sharing community.

Ken and the trio also talk about the business of queer tourism, why platforms like GetYourGuide and Viator can be useful but problematic, and why booking directly with local guides is often better for both travelers and the people creating the experience.

And yes, things get deliciously naughty.

You’ll learn why the Tuileries Garden has been associated with cruising since the 1600s, why some parts of Paris still shift energy dramatically after dark, and why Charlotte’s “bushes open 24/7” line may deserve its own plaque.

But underneath the laughter is something serious: queer history matters.

It matters because it reminds us we were always there. In the museums. In the gardens. In the palaces. In the cafés. In the art. In the scandals. In the revolutions. In the love stories they tried to erase.

Whether you’re planning your first trip to Paris, returning for the tenth time, or dreaming of a more meaningful LGBTQ+ travel experience, this episode will make you see the city differently.

Paris was never just the City of Light.

It was also the city of hidden rainbows.

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In this episode of Pride Nomad Unleashed, Ken sits down with Tom and Mike of Take Time To Travel, a Canadian couple who did exactly that. In the middle of COVID, they made a decision most people only fantasize about: they got rid of nearly all their possessions and began traveling full-time.

Almost five years later, they’re still going.

This conversation is refreshingly real. It’s not the glossy influencer version of travel where everything is sunsets, cocktails, and suspiciously perfect linen shirts. Tom and Mike talk about the actual mechanics of living on the road as a couple: money, healthcare, Airbnb research, travel insurance, family obligations, packing, visa limits, relationship dynamics, airport stress, and the occasional cold shower in Colombia.

They share how they transitioned from careers in finance, real estate, and trading into a location-independent life supported by pensions, smart budgeting, YouTube, sponsorships, and choosing destinations where the cost of living actually works.

Ken, Tom, and Mike dig into what it means to be “slowmads”—staying in places for months at a time instead of racing through countries like a checklist. They talk about Mexico City, Spain, Thailand, Lisbon, Athens, Colombia, Paris, Singapore, Kuala Lumpur, Taipei, and the constant question that follows every great destination:

Could we live here?

The episode also gets into something many travel shows skip: what it’s really like to travel full-time as a couple. Tom and Mike talk about navigating travel-day stress, spending almost every waking hour together, maintaining connection with family and friends back home, and why compatibility matters more than age.

For anyone who has ever wondered whether full-time travel is possible after 50, whether it’s too late to start, or whether selling everything is brave or insane, this episode is both practical and inspiring.

Tom’s advice is simple:

If you have your health, go now.

Because at some point, health, insurance, family obligations, or life itself may make the decision for you.

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Apparently… David Reddish.

In this episode of Pride Nomad Unleashed, Ken sits down with David Reddish—journalist, novelist, political commentator, creative force, and one of the sharp voices behind the Occupy Democrats YouTube channel—for a conversation that goes far beyond the headlines.

David has lived several lives already: child actor, classical vocalist, entertainment journalist, novelist, political activist, fashion designer, former go-go dancer, and now daily political commentator. But underneath the wild résumé is something more urgent: a man trying to help people stay awake, stay brave, and stay human in a moment when democracy feels frighteningly fragile.

The conversation starts with how David found his way into political commentary after years in entertainment journalism, then moves into the emotional cost of reporting on political chaos every day. As David says, he did not fully realize what it would mean psychologically to live in “all Trump, all American carnage, all the time”—but he also found something powerful in it: a voice. Not just his voice, but a way to help others channel their frustration, fear, and rage.

From there, Ken and David dig into persuasion, political division, queer visibility, and why being nice may be one of the most underrated tools in the fight for democracy. They talk about Pete Buttigieg’s ability to walk into hostile media spaces and stay calm, prepared, and human. They explore why coming out has been one of the most powerful civil rights strategies in American history, because it forces people to realize: you’re not talking about an abstract issue—you’re talking about me.

And because this is Pride Nomad Unleashed, the conversation also turns toward travel, perspective, and why Americans need to get out of their bubbles. For Ken, travel is not just escape. It is a way of building bridges, softening fear, and showing the world that queer people are not the enemy—we’re usually better dressed, more fun, and throwing the best parties.

David also brings a fascinating lens as a cultural critic, connecting political moments to the stories we tell through film, superheroes, and art. He argues that art is where we record the human experience, wrestle with morality, and learn empathy—whether through Mr. Smith Goes to Washington, It’s a Wonderful Life, Philadelphia, The Lord of the Rings, Spider-Man, or The Dark Knight.

But the episode does not stay in the darkness.

Ken asks the question we all need answered: How do you relax when you are carrying this much intensity?

David’s answer is refreshingly human: yoga, friends, trivia, wine, creativity, making things with his hands, and radical gratitude. He talks about the need for creative people to create—because when creative energy has nowhere to go, it can become destructive.

By the end, this becomes one of the most unexpectedly hopeful conversations in the Pride Nomad Unleashed archive. Yes, the world is chaotic. Yes, democracy is under pressure. Yes, the news can feel like poison. But there are still flowers blooming, friends laughing, books being written, art being made, and people brave enough to keep speaking.

And sometimes, that is where the fight begins.

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In this episode of Pride Nomad Unleashed, Ken sits down with David and John, the Debt Free Guys and hosts of the Queer Money Podcast, for a brutally honest, funny, and deeply necessary conversation about money, shame, status, debt, and the very queer pressure to look fabulous even when your finances are falling apart.

David and John know this story personally. Before becoming financial educators, they were two financial professionals sitting in a gloomy basement apartment with $51,000 in credit card debt, dreaming about a vacation home they absolutely could not afford. That wake-up call became the beginning of their transformation—and eventually, the foundation for helping LGBTQ+ people build real financial freedom.

This conversation goes way beyond budgeting apps and boring spreadsheets.

We talk about why money is different for LGBTQ+ people, how self-worth gets tangled up in spending, why so many of us chase approval through clothes, trips, cocktails, bags, and “A-list gay” performance, and how to stop living like your Instagram feed is more important than your future.

You’ll also hear about their Debt Lasso Method, why it may beat the traditional snowball and avalanche debt payoff strategies, and how they paid off $51,000 in credit card debt in under three years by attacking interest, automating payments, and treating debt payoff like a real bill.

And because this is Pride Nomad Unleashed, we also get into the travel side: how living abroad or becoming location-independent can dramatically reduce your cost of living, why you don’t need a luxury hotel to have a rich life, and how to build a lifestyle that actually gives you freedom instead of just looking good from the outside.

This is one of those episodes every queer person should hear—especially if you’ve ever thought:

“I can’t afford that life.”

“Everyone else seems to be doing better than me.”

“I’m too old to fix my finances.”

“I want to travel, but I’m broke.”

Or…

“I know my BMI, but not my credit score.”

Honey, this one’s for you.

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In this episode of Pride Nomad Unleashed, Ken sits down with Greg Hamman, the force behind Undersea Expeditions, a global LGBTQ+ dive travel company that’s been quietly building something far more powerful than vacations: community, safety, and belonging—underwater.

This isn’t just about scuba.

It’s about:

• 🌈 Why LGBTQ+ travelers still need safe spaces—even today
• 🦈 The truth about diving (and why sharks aren’t the scary part)
• 🌍 Traveling to places that don’t fully accept you—and why it still matters
• 🤝 How “found family” forms when you put people in extraordinary environments
• 💥 The evolution from rejection (“we don’t want your group”) to demand (“please bring your group”)
• 🌊 How the ocean becomes a level playing field—where identity fades and connection deepens

You’ll also get a real behind-the-scenes look at how these trips work—from beginner divers to hardcore liveaboard experiences (yes, 4 dives a day), and how even total newbies can safely enter the world of scuba.

And if you’ve ever thought:

“I want adventure… but I want to feel safe doing it.”

This episode is for you.

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You get Jungle Gayborhood—a soul-charged retreat center in the Costa Rican jungle where queer people come not just to relax, but to reconnect.

In this episode of Pride Nomad Unleashed, Ken goes deep with Shelby Clark, the Silicon Valley disruptor turned spiritual entrepreneur. Once the brains behind Turo (the “Airbnb for cars”), Shelby now builds spaces that heal, awaken, and empower queer folks through sacred plant medicine, sex-positive experiences, and jungle-born adventures.

This is not your average gaycation. It’s a full-body, heart-forward revolution.

We dive into:

• Why he left Turo after building a billion-dollar startup
• The truth behind his psychedelic awakening in Bali
• How Jungle Gayborhood became a queer sanctuary (and yes, a little “gay womb”)
• Sacred retreats like Jungle Fag, embodied adventures, and plant medicine journeys
• The wild power of living in flow—and why success without alignment is just empty

✨ Plus: Get $100 off any retreat using our Pride Nomad community code (link in show notes)!

This isn’t just an episode—it’s a permission slip to rethink success.

Meet Nick Read, founder of Pride Expeditions—a rare breed of adventure guide who’s smashing stereotypes while scaling summits.

Whether it’s the snow-capped Andes, the deserts of Morocco, or a tea-house trek in Nepal, Nick’s trips aren’t just about adrenaline—they’re about creating inclusive, empowering experiences for queer adventurers around the globe.

In this high-altitude episode of Pride Nomad Unleashed, Ken and Nick hit the trail with:

• 🏕️ Behind-the-scenes stories of running a queer expedition company across 5 continents
• 🇹🇿 How climbing Kilimanjaro became a literal Pride March in a country where being gay is illegal
• 🏞️ The truth about Everest Base Camp, why Gosaikunda might be better, and how yak traffic is a real thing
• 🚁 Wild rescue missions in the UK mountains and what not to do when your knee gives out
• 💡 The secret to building lifelong friendships (and confidence) through shared adventure
• 📍 A full list of LGBTQ+ trekking destinations from Patagonia to Peru, Iceland to India, plus what’s coming next
• 
  

🎒 Whether you’re a first-time camper or a rugged explorer, Nick’s trips are designed to be challenging but achievable. You’ll never carry your gear, you’ll always be supported—and you’ll come home with one hell of a story.

🌍 TRIPS & LOCATIONS DISCUSSED:

• 🏔️ Kilimanjaro (Tanzania) – A literal Pride trek in a not-so-LGBTQ-friendly zone
• 🇳🇵 Nepal – Gosaikunda Lakes trek + Trishuli River rafting
• 🇵🇪 Inca Trail to Machu Picchu (Peru) – With 3-course tent meals and sunrise views
• 🇲🇦 Mount Toubkal (Morocco) – A four-day intro to high-altitude trekking with Berber hospitality
• 🇮🇸 Iceland – The Laugavegur Trail: lava fields, steam vents, and glacier valleys
• 🇦🇷 Patagonia (Argentina) – Vertical granite spires, fewer crowds, epic solitude
• 🇪🇨 Ecuador & Galápagos – Coming soon
• 🇬🇧 Wales Adventures – Rock climbing, coasteering, and mini expeditions
• 
  

🎒 FOR FIRST-TIMERS:

Never done an adventure trip?

Start with Morocco or Iceland. Both offer a perfect blend of challenge, culture, and comfort—with no altitude worries and plenty of fun.

You don’t need to be super-fit. You do need:

• Stamina (think 6–8 hours of walking)
• A sense of humor
• A spirit of adventure
• Zero diva drama (this isn’t Atlantis, darling)
• 
  

🎁 EXCLUSIVE FOR PRIDE NOMADS:

Mention “Pride Nomad” when booking and receive:

• A private consultation with Nick to match you with the perfect trek
• A free gear checklist & training plan tailored to your trip

And a mystery gift you’ll receive on your expedition 🏳️‍🌈

That’s Dr. Andrew Lear—Harvard professor turned museum renegade and the mastermind behind Oscar Wilde Tours the first travel company to boldly say:

“Forget tourist traps. Let’s take queer people to where their history actually happened.”

From ancient Greek love stories to Renaissance scandals, from Call Me By Your Name landscapes to secret drag scenes across Asia, Andrew’s leading LGBTQ+ travelers on journeys that are smart, sexy, and spiritually satisfying.

In this wildly entertaining episode of Pride Nomad Unleashed, Ken and Andrew go deep on:

• Why most queer history has been scrubbed from museums—and how he’s putting it back
• The truth about same-sex love in Ancient Rome (spoiler: it wasn’t all togas and orgies)
• His upcoming TV series with Stephen Fry and Tan France (yes, really)
• The power of “slow travel” and how to get adopted by an Italian café
• Queer birds of paradise, rogue princes, and how 3 million hijras are rewriting gender norms in India
• PLUS: A sneak peek at upcoming LGBTQ+ history tours from Japan to the Nordic countries
• 
  

🎁 Mention “Pride Nomad” when booking for a special discount on Oscar Wilde Tours—whether it’s the Death in Venice itinerary or the one where you follow Michelangelo’s gay little footprints across Italy.

For our viewers: 

Get $100 off any tour of Europe and Asia on top of the discounts already offered! Call or email us and we can make a discount code for you. 

Contact Andrew:

• ☎️ (646) 560-3205
• Email 
• Facebook

You get Jonathan Geen, founder of Purple Light Vacations, one of the most seasoned, passionate, and fabulously informed LGBTQ+ travel advisors in the business.

In this episode of Pride Nomad Unleashed, Jonathan joins Ken for a lively, globe-hopping convo about:

• His pivot from litigation to luxury LGBTQ+ travel (trial by cruise, literally)
• How Purple Light helps queer travelers explore the world safely, joyfully, and often for less than you’d pay solo
• The real scoop on all-gay vs. gay-friendly cruises (hint: there’s a LOT more than just Atlantis)
• Insider perks, destination secrets, and why custom-curated experiences > cookie-cutter trips
• How travel is about belonging, not just checking off countries
• Plus: Why you should never trust a travel advisor who doesn’t pronounce “Antarctica” correctly
• 
  

🚢 Whether you’re a digital nomad, vacation queen, or finally ready to plan your gay safari, Jonathan’s got tips, insights, and possibly some dramamine for the Drake Passage.

🌍 Mention “Pride Nomad” for a special bonus when you book with Jonathan! Details in the show notes.

Contact Jonathan:

• Email
• Website

Guest Bio:

Jonathan is the President of Purple Light Vacations, one of the country's few LGBT owned and operated travel agencies that concentrates on LGBT and LGBT-friendly travel. He is an ASTA (American Association of Travel Advisors) verified travel advisor and holds the highest certification of Elite Cruise Counselor ("ECC") from the Cruise Lines International Association. He has traveled and cruised around the world and credits his love of travel to attending the United Nations International School in Manhattan. Purple Light Vacations has been in business for over 12 years and provides clients nationwide with added value at no additional cost. It books everything from LGBT charter cruises and land vacations to custom trips and vacation rentals.

Contact Jameson:

• ☎️ +33 (0)9 75 18 57 80
• Email 
• Instagram
• Substack

Most of them were built for a very specific person. And if you didn't fit that mold — if you were older, or queer but not a gay man, or just someone who didn't want a floating circuit party — you were kind of out of luck.

Brian Miller looked at that and said: we can do better.

So he built VACAYA.

Not a gay cruise with a few inclusive touches bolted on.

A travel company designed from scratch — from the entertainment to the excursions to the damn deck chairs — for the full spectrum of the LGBTQ+ community.

In this episode, Brian gets into what "truly inclusive" actually means when you're filling a ship with a thousand people…

Why the "daddy" demographic — and frankly, anyone over 40 — has been criminally underserved by queer travel…

What happens when your entire business model is built around joy… and the world tries to cancel joy…

And the specific moment he realized VACAYA wasn't just a cruise line. It was the thing people had been waiting for without knowing how to ask for it.

This is for anyone who's ever "tolerated" a vacation. Who showed up, looked around, and thought: this is nice, but it's not for me.

Brian built the one that is.

Or your mortgage payment…

Or just the walls of your apartment…

And think: "What if I just… didn't?"

Daniel Milks actually did it.

He figured out how to live and work from anywhere — legally, affordably, and without the kind of logistical nightmare that keeps most people stuck.

In this episode, Daniel walks through the surprisingly un-scary mechanics of full-time nomadism.

Including the South Dakota domicile trick that seasoned nomads swear by. (Yes, it's real. Yes, it's legal. No, you don't have to like South Dakota.)

He gets into how to maintain health insurance when you don't have a "home state"…

How to stay connected to people when your zip code changes every few weeks…

And what LGBTQ+ travelers specifically need to think about before cutting the cord — because the freedom calculus is different when certain states and countries are actively hostile to your existence.

Here's what Daniel won't do: romanticize it.

Full-time travel has trade-offs. Some days are lonely. Some logistics are annoying.

But the version of freedom on the other side?

Way more accessible than you think. And way more worth it than you've let yourself believe.

If you've been staring at a map whispering "what if" — Daniel has the answers. The real ones.

You already knew that.

What you might NOT know is that a gay venture capitalist has been quietly rewiring the system from the inside… and making a killing doing it.

Ben Stokes founded Gaingels — one of the most powerful LGBTQ+ investor networks on the planet.

And the thesis is deceptively simple: when queer people have access to capital, and when queer founders get funded, everybody makes more money.

Not "eventually." Not "in theory."

Right now. Measurably.

In this episode, Ben breaks down how he turned inclusion into an investment strategy…

What it actually takes to build wealth as a queer entrepreneur when the traditional funding world wasn't designed for you…

Why boardroom representation isn't a PR play — it's a competitive advantage…

And what happens when you build a global investment network and accidentally become one of the most well-traveled people in the room.

We also talk about the uncomfortable truth that money IS power… and what it means when our community starts wielding it intentionally.

If you've ever felt like the financial world was a club you weren't invited to… Ben didn't wait for an invitation. He built his own club. And it's outperforming.

Most of it wasn't built for queer women.

Vivian Perez noticed. And instead of waiting for someone else to fix it… she built Ladies Touch Events & Travel from scratch.

What started with a feather boa moment — literally — turned into a company that's taken thousands of LGBTQ+ women around the world.

Not "women-friendly" trips tacked onto someone else's itinerary.

Trips designed from the ground up for queer women who want to travel surrounded by their people… without having to explain themselves, shrink themselves, or settle for being an afterthought.

In this episode, Vivian gets into what it actually takes to build a travel business as a queer Latina entrepreneur…

How she curates spaces that feel genuinely safe — not just "inclusive" in the brochure sense…

Why group travel does something for queer women that solo travel simply can't…

And the moment she realized she wasn't just booking flights. She was building a community that didn't exist before her.

If you've ever scrolled through trip options and thought "this wasn't made for me"… Vivian built the thing you were looking for.

Corner offices. Global teams. The whole machine.

Then he walked away from it.

Not because he failed. Because he finally got honest about what success was actually costing him.

In this conversation, Jim gets into the stuff most executives would never say out loud.

Like how "authentic leadership" is mostly a buzzword… until you've actually had to fire someone while pretending you're fine.

How being "too American" in a global role isn't confidence — it's a liability.

How AI isn't coming for experienced people… it's coming for rigid ones.

We also talk about planning a queer wedding while semi-nomadic…

Managing dogs across multiple time zones…

And why the hardest part of leaving corporate wasn't the money.

It was the identity.

Jim doesn't give you a TED Talk. He gives you the version he'd tell you over a drink — the messy, funny, uncomfortably real version of what it looks like to burn down a "successful" life and build one that actually fits.

Fair warning: this episode has been known to cause sudden urges to quit your job, adopt a rescue, and stop performing competence for people who don't deserve it.