How This Travel Influencer Grew a 4,000+ Person Travel Community Practically Overnight | Ep 140

What happens when you throw a completely unhinged idea onto TikTok… and then 40 strangers actually show up? Maddy Garrett knows a thing or two about turning travel content into an actual travel community.After moving to Lake Tahoe and realizing she knew approximately… nobody, Maddy posted a TikTok asking, “What if we got a bunch of single people together and went camping?”The internet said YES.Within a week, her Facebook group had 4,000+ people. Two weeks later, 40 strangers from across the U.S. showed up for a camping trip in the Nevada desert. And just like that, Outsiders Together was born.In this episode, we’re talking about what it REALLY takes to turn a following into a community — and how travel influencers and travel content creators can use group travel and retreat travel to create experiences people actually want to pay for.We’re getting into:✈️ How Maddy turned one TikTok into a 4,000+ person travel community⛺ Why starting with FREE meetups can be the smartest way to build community🌎 How to sell group travel when you don't have a huge audience💰 How travel content monetization can work through group trips🔥 Why FOMO was one of Maddy’s biggest marketing strategies📱 The simple content strategy she used to make people feel like they were missing out🗓️ How she would launch a group trip TODAY in just two weeks👯‍♀️ Why people often aren't buying the trip — they're buying the chance to hang out with YOU💻 How travel influencers can turn their audience into an actual travel community🥂 And why you need to stop overthinking it and JUST DO THE THINGMaddy also shares what she learned from hosting international trips through Trova, including trips to Peru, Iceland, Alaska and Costa Rica, and what the financial side of group travel can actually look like.If you’ve been thinking about creating a travel community, hosting group trips, or adding retreat travel to your business… this is your sign to stop waiting for everything to be perfect.CONNECT WITH MADDY:Find Maddy at @maddyoutdoors.coachListen to her podcast: Paid to Travel Sign up for my newsletter, the Content Compass, the weekly newsletter for travel creators who are already landing brand deals and are ready to build the business behind their content.Get five shifts that will take you from travel creator to business owner with actionable next steps included. AND two private podcast episodes. Get the Creator to CEO Playbook for $5Say hi on InstagramJoin Us 👉 The Travel Creator Business Plan Community!The only business-building community designed specifically for travel creators.  You’ll get:  ✔ monthly business systems  ✔ coworking + Q&A calls  ✔ a private community of creators building real businesses  ✔ guidance to help you move from “content machine” to “CEO energy”Sign Up HERE

💌 Want your newsletter to feel as easy as texting your bestie? Join my next workshop From Overthinking to Outbox Your newsletter does NOT need to be complicated. If you’re a travel content creator trying to grow your audience, get more eyes on your offers, or turn your followers into actual business leads, email marketing needs to be part of your strategy.In this episode, I’m answering some of the questions I get asked ALL the time about newsletters — from how often you should send them to what actually belongs inside your emails.We’re talking:✈️ How often you should send your newsletter (and why consistency matters more than frequency)💌 Why a simple email template can make newsletter growth SO much easier👀 What your email open rate is actually telling you✍️ How much educational content you should include👋 How to weave your personal story into your emails without making every email about you👀 Why I LOVE a good PS📝 Why a TLDR can be especially useful for travel creators💰 How to balance value and selling in your emailsPlus, I’m sharing my actual approach to email marketing for travel influencers so you can stop overthinking your newsletter and start sending emails people actually want to open.And if you want to learn how to make sending an email feel as easy as sending a text message, I’m hosting a training where I’ll walk you through exactly how to create strong educational email content, choose a sustainable sending cadence, and actually get people opening your emails.👉 Sign up for my next email marketing workshop here on how to send a newsletter as easy as sending a text. This is usually invite-only, but I’m opening it up to my podcast fam. 💌Happy creating, happy emailing, and I’ll see you on the internet!Sign up for my newsletter, the Content Compass, the weekly newsletter for travel creators who are already landing brand deals and are ready to build the business behind their content.Get five shifts that will take you from travel creator to business owner with actionable next steps included. AND two private podcast episodes. Get the Creator to CEO Playbook for $5Say hi on InstagramJoin Us 👉 The Travel Creator Business Plan Community!The only business-building community designed specifically for travel creators.  You’ll get:  ✔ monthly business systems  ✔ coworking + Q&A calls  ✔ a private community of creators building real businesses  ✔ guidance to help you move from “content machine” to “CEO energy”Sign Up HERE

Today’s episode is a little different because I’m actually stealing an episode from my friend and podcast producer  Marie’s podcast, Your Girl, where we sat down with Andrea to talk through our biggest business lessons from July.And honestly? There are A LOT.We’re talking about delayed gratification, client rejection, self-trust, networking, burnout, CEO time, making more money by doing less, and why sometimes the best thing you can do for your business is… go outside.In this episode, we’re talking about:Why the clients you sign today might have been watching you for monthsThe reminder that business is basically one giant lesson in delayed gratificationWhy you should never celebrate until the money is in the bankHow to stop taking client rejection personallyThe difference between someone rejecting your offer and rejecting youWhy people can say yes on a sales call and change their mind afterwardHow setting boundaries can completely change the way you show up in businessWhy your network is probably much closer than you thinkHow “one degree away” relationships can lead to clients, referrals, friendships, and opportunitiesWhy you should stop forcing yourself into a productivity schedule that doesn't actually work for youThe weird realization that sometimes the less I work, the more money I makeWhy successful business owners can become addicted to being busyThe importance of creating actual CEO hours instead of spending every second doing client workWhy you need to work on your business, not just in itGiving yourself permission to have hobbies, travel, go to the beach, and have a personality outside of your businessWhat it looks like to let your business grow up a little so it doesn't need you 24/7Why self-trust becomes absolutely essential when you're making big life and business movesWant to check out more from Marie?🎧 Listen to her podcast about scaling your business: Your Girl 👉 Follow her on Instagram: @yourgirlmedia Sign up for my newsletter, the Content Compass, the weekly newsletter for travel creators who are already landing brand deals and are ready to build the business behind their content.Get five shifts that will take you from travel creator to business owner with actionable next steps included. AND two private podcast episodes. Get the Creator to CEO Playbook for $5Say hi on InstagramJoin Us 👉 The Travel Creator Business Plan Community!The only business-building community designed specifically for travel creators.  You’ll get:  ✔ monthly business systems  ✔ coworking + Q&A calls  ✔ a private community of creators building real businesses  ✔ guidance to help you move from “content machine” to “CEO energy”Sign Up HERE

If the word “website” makes you want to crawl under your desk and never come out, this episode is for you.Because apparently, you do not need a giant, expensive, perfectly designed website to start building your business online. You just need somewhere on the internet that you actually own.In this episode, I’m chatting with my friend Andrea, owner and lead designer of Merveille Creative Studios, about websites, SEO, branding, and what creators actually need when they’re building a business.And honestly? We are making websites feel way less overwhelming.If you’re a travel content creator, UGC creator, influencer, or creator who wants to work with brands, tourism boards, and businesses, this episode is packed with practical advice for building an online presence that makes you look legit — without spending your entire life trying to figure out your website.In this episode, we talk about:Why you should stop relying entirely on Instagram and social media to house your businessWhy a simple landing page is better than nothingWhy you should have your own domain instead of relying on platforms like Linktree or hosted landing pagesWhat your website actually needs if you're just getting startedWhen it's time to graduate from a landing page to a full websiteThe essential pages every creator website should haveWhy your UGC portfolio should NOT live on CanvaHow your website can help you get discovered through SEOWhy having a website can help creators look more legitimate to brands and tourism boardsWebsite platforms including Squarespace, Wix, Showit, and WordPressWhy Andrea personally prefers WordPress for SEO and customizationThe difference between easy-to-use website platforms and platforms that give you more flexibilityWhy website speed matters for SEOHow to check your website speed with Google PageSpeed InsightsThe biggest website mistake creators make in their hero sectionWhy you need to tell people who you are and what you do immediatelyHow to use analytics to understand who's actually visiting your websiteWhy you should have an email opt-in on your websiteWhat platform you should use if you're selling digital products vs. physical productsHow your website can become a home base for your travel content creation business🎧 Want to listen to my producer's podcast all about scaling your business to the next level? Check our her podcast, Your Girl Connect with Andrea:Follow her on Instagram: @merveillecsCheck out her websiteWant a FREE website audit? Click HERE Want to Book a VIP Day? Click HERESign up for my newsletter, the Content Compass, the weekly newsletter for travel creators who are already landing brand deals and are ready to build the business behind their content.Get five shifts that will take you from travel creator to business owner with actionable next steps included. AND two private podcast episodes. Get the Creator to CEO Playbook for $5Say hi on InstagramJoin Us 👉 The Travel Creator Business Plan Community!The only business-building community designed specifically for travel creators.  You’ll get:  ✔ monthly business systems  ✔ coworking + Q&A calls  ✔ a private community of creators building real businesses  ✔ guidance to help you move from “content machine” to “CEO energy”Sign Up HERE

 ✈️ Sign up HERE  for access to my FREE workshop: From Overthinking to OutboxWhat would happen to your business if Instagram disappeared tomorrow?For travel creators, social media can feel like the entire business — the content, the audience, the brand deals, the money. But there’s one major problem: you don’t actually own your Instagram audience.In this episode, we’re talking about why email marketing might be one of the most overlooked tools in a travel creator’s business — and why building an email list can completely change the way you grow, connect with your audience, and make money.Because being a successful travel creator isn’t just about creating beautiful content. It’s about building a business you actually own.In this episode, we’re diving into:Why your Instagram followers aren’t actually your audienceThe difference between rented audiences and owned audiencesWhy travel content is especially well-suited for email marketingHow your audience is already using your travel content to plan tripsWhy hotel recommendations, packing lists, visa tips, and destination guides can become the foundation of your newsletterWhy email can be more valuable to brands than your Instagram followingHow a newsletter can support your brand deal strategyWhat makes a travel newsletter actually worth openingWhy consistency matters more than sending emails every weekHow to create short, conversational emails that don’t take hours to writeWhy your newsletter needs a clear purpose beyond “here’s what I’ve been up to”How to stop overthinking your emails and actually hit sendSign up for my newsletter, the Content Compass, the weekly newsletter for travel creators who are already landing brand deals and are ready to build the business behind their content.Get five shifts that will take you from travel creator to business owner with actionable next steps included. AND two private podcast episodes. Get the Creator to CEO Playbook for $5Say hi on InstagramJoin Us 👉 The Travel Creator Business Plan Community!The only business-building community designed specifically for travel creators.  You’ll get:  ✔ monthly business systems  ✔ coworking + Q&A calls  ✔ a private community of creators building real businesses  ✔ guidance to help you move from “content machine” to “CEO energy”Sign Up HERE

👉 Sign up HERE  for access to my FREE workshop: From Overthinking to OutboxA free 25-min workshop on building a newsletter that feels as easy as texting — structure, consistency, and how to turn readers into clients.For creators who know they need a newsletter and just need it to feel doable.Today I’m sharing the apps and tools I think you are absolutely sleeping on if you want to grow your business, save time, and stop doing everything manually.I’m a big believer that the right tools can make running your business so much easier and there are a few that I use constantly that I think more travel creators need to know about.In this episode, I’m breaking down my favorite creator tools, business systems, AI tools, and apps for everything from project management and pitching to email marketing, time tracking, content creation, and staying organized.We’re talking about:Why Asana is one of my non-negotiable business systems and how I use the desktop app to quickly capture tasksWhy I use Instagram on desktop instead of my phone to avoid the doom-scroll trapHow I use LinkedIn as a more intentional engagement activityThe dictation tool I’m OBSESSED with and why WhisperFlow is a game changer for writing emails and YouTube scripts. 👉 USE MY WHISPERFLOW LINK TO GET STARTEDHow I use Airtable as a lead tracker for my more complicated pitching systemThe simple Google Chrome tab organization trick that makes my life way easierWhy I’m moving from Fathom to Granola for meeting notesHow I’m experimenting with Claude to clean up my desktop and take some of those annoying manual tasks off my plateWhy the humble Notes app is one of my favorite business toolsThe new Kit MCP feature and why I’m excited about connecting AI directly to my email marketingHow Subscriber Signals can help you identify potential collaborators and opportunities hiding inside your email listNew design features, landing pages, and forms inside KitWhy I think you should be using Google Sheets and Google Forms instead of constantly adding another paid platform and another login to your lifeHow I’m using Toggl to track exactly where my time is goingWhy I’m doing a time audit to figure out what I should be automating, delegating, or using AI to help withSign up for my newsletter, the Content Compass, the weekly newsletter for travel creators who are already landing brand deals and are ready to build the business behind their content.Get five shifts that will take you from travel creator to business owner with actionable next steps included. AND two private podcast episodes. Get the Creator to CEO Playbook for $5Say hi on InstagramJoin Us 👉 The Travel Creator Business Plan Community!The only business-building community designed specifically for travel creators.  You’ll get:  ✔ monthly business systems  ✔ coworking + Q&A calls  ✔ a private community of creators building real businesses  ✔ guidance to help you move from “content machine” to “CEO energy”Sign Up HERE

What if your newsletter could do more than just sit in someone’s inbox every week?In this episode, I’m taking you behind the scenes of two recent email marketing projects I’ve been working on and breaking down the exact strategies we’re using to turn subscribers into warm leads, create FOMO, and ultimately convert people into paying customers.Because your email list should not be an afterthought.I’m walking you through how I’m building a waitlist strategy for Cocktails & Clothes, including the welcome sequence, weekly newsletter, segmentation, speed networking events, early-access offers, and the systems that keep the waitlist warm.I’m also sharing how I took a business strategist from basically zero to a fully automated newsletter system in just three weeks — including why I chose GoHighLevel over Substack, how we’re using different signup forms and welcome sequences based on where someone came from, and why having a content strategy behind your newsletter matters SO much.And honestly? This is the unglamorous backend stuff that actually works.In this episode, I’m breaking down:How to build an email marketing strategy that turns followers into paying customersThe influencer strategies and creator tips you can use to create FOMO around your offerHow to create a waitlist that actually stays warm and convertsThe email sequence I’m using to nurture people from waitlist signup to purchaseWhy segmentation from day one is non-negotiableHow to use a weekly newsletter to consistently showcase wins, testimonials, events, and social proofWhy your newsletter should have a goal beyond simply “sending content”How to create different welcome sequences based on where your subscribers came fromWhy you may need multiple signup forms for your email listHow to build a newsletter content bank so you’re never starting from scratchWhy I chose GoHighLevel instead of jumping on the Substack trainHow to build automated email marketing systems without adding another million tools to your businessThe importance of documenting your backend systems so you actually know how everything worksHow I took a newsletter system from kickoff to launch in just three weeksWant to see behind the scenes of my client Marie's waitlist email strategy for Cocktails & Close? 👉 Sign up HEREInfluencer strategies, creator tips, email marketing, newsletter strategy, email marketing strategy, newsletter automation, email list growth, creator business, content strategy, waitlist strategy, email sequence, lead nurturing, digital marketing for creators.Sign up for my newsletter, the Content Compass, the weekly newsletter for travel creators who are already landing brand deals and are ready to build the business behind their content.Get five shifts that will take you from travel creator to business owner with actionable next steps included. AND two private podcast episodes. Get the Creator to CEO Playbook for $5Say hi on InstagramJoin Us 👉 The Travel Creator Business Plan Community!The only business-building community designed specifically for travel creators.  You’ll get:  ✔ monthly business systems  ✔ coworking + Q&A calls  ✔ a private community of creators building real businesses  ✔ guidance to help you move from “content machine” to “CEO energy”Sign Up HERE

👉 Join the Travel Creator Business Plan Community and get the systems, support, and strategy to grow your creator business. Sign up here! ✈️ creators spend years figuring out how to make more money... but almost nobody teaches us what to do once the money actually starts showing up.In this episode, I'm sitting down with my friend Jillian Todd from The Money Confident Podcast to talk about the financial side of running a creator business that nobody prepared us for. If you've ever looked at your bank account, shrugged, and thought, "I think I'm doing okay?"—this episode is for you.We're talking about the numbers every creator needs to know, how to stop running your business on vibes, why recurring revenue is one of the most underrated ways to reduce stress, and how to actually build wealth without giving up the things you love.Because here's the truth...Knowing how to create content and knowing how to run a profitable business are two completely different skills.And it's time we started treating our creator businesses like actual businesses.In This Episode We Cover:Why so many successful creators still feel anxious about moneyThe four financial numbers every creator should knowRevenue vs. expenses vs. profit (without the confusing finance jargon)How to stop running your business "on vibes"Creating a monthly income minimum that gives you peace of mindFinancial systems that actually work (even if you hate spreadsheets)QuickBooks vs. Google Sheets vs. Monarch MoneyWhy recurring revenue creates financial freedomSmart tax planning for creators and freelancersInvesting your money instead of letting it sitHow to build wealth while running a creative businessWhy pricing—not working more hours—is often the key to scalingSetting realistic income goals that your brain can actually believeHow to reward yourself while still building wealthBecoming your own "sugar daddy" (yes... we went there.)💸 Join Jillian's FREE live class on August 17:$50K Goal in 12 Months: The 3 Steps to DONELearn the exact framework she teaches creatives to hit big financial goals without burning themselves out.👉 https://jilliantoddcoaching.com/50k📈 Grab Jillian's FREE Cash Flow Planning WorksheetFinally get a clear picture of what's coming in, what's going out, and plan your income months ahead.👉 https://getmoneyconfident.myflodesk.com/supercreative🎙️ Binge The Money Confident PodcastIf you loved this conversation, you'll love Jillian's podcast packed with practical money advice for creative entrepreneurs.👉 https://podcasts.apple.com/us/podcast/real-breadwinner-success-stories-retirement-cash-flow/id1518160629?i=1000776168731✨ Want hands-on support?Check out Breadwinner, Jillian's signature group coaching program designed to help creative entrepreneurs build wealth, hit big financial goals, and create a business that actually supports the life they want.👉 https://jilliantoddcoaching.com/breadwinnerSign up for my newsletter, the Content Compass, the weekly newsletter for travel creators who are already landing brand deals and are ready to build the business behind their content.Get five shifts that will take you from travel creator to business owner with actionable next steps included. AND two private podcast episodes. Get the Creator to CEO Playbook for $5Say hi on InstagramJoin Us 👉 The Travel Creator Business Plan Community!The only business-building community designed specifically for travel creators.  You’ll get:  ✔ monthly business systems  ✔ coworking + Q&A calls  ✔ a private community of creators building real businesses  ✔ guidance to help you move from “content machine” to “CEO energy”Sign Up HERE

 👉 Get the Creator to CEO Playbook for $5You don't need another content strategy.You don't need another trending Reel.And you definitely don't need 47 open tabs, six Notes app lists, and random ideas living in your Instagram DMs.If you're a travel content creator who feels busy all the time but still wonders why your business isn't growing, this episode is your wake-up call.Because chances are... you don't have a content problem.You have a business systems problem.In this episode, I'm breaking down exactly how to build an Operations Hub—the boring backend system that actually helps you make more money, stay organized, and finally start running your creator business like a CEO instead of constantly putting out fires.Yes, it's boring.Yes, it works.In this episode, you'll learn:Why most travel influencers don't actually have a content problem—they have an infrastructure problem.What an Operations Hub is (and why every creator needs one).How to organize your business using Asana, Notion, Google Sheets, or whatever works best for your brain.The three things every Operations Hub should track.How to stop recreating content from scratch every week.The simple weekly operating rhythm that actually moves revenue.How to organize leads so you stop letting opportunities go cold.Why building boring business systems is one of the biggest business hacks successful creators use.The mindset shift from creator to CEO that changes everything.Resources MentionedAsana ( myfavorite free project management tool)Notion (great alternative if it fits your workflow better)Google SheetsNotes AppAirtableSign up for my newsletter, the Content Compass, the weekly newsletter for travel creators who are already landing brand deals and are ready to build the business behind their content.Get five shifts that will take you from travel creator to business owner with actionable next steps included. AND two private podcast episodes. Get the Creator to CEO Playbook for $5Say hi on InstagramJoin Us 👉 The Travel Creator Business Plan Community!The only business-building community designed specifically for travel creators.  You’ll get:  ✔ monthly business systems  ✔ coworking + Q&A calls  ✔ a private community of creators building real businesses  ✔ guidance to help you move from “content machine” to “CEO energy”Sign Up HERE

👉 Join the Travel Creator Business Plan Community and get the systems, support, and strategy to grow your creator business. Sign up here! ✈️Some days you're the smartest, most beautiful person to ever grace the earth. Other days you want to crawl into the back of a dumpster and hope somebody sets it on fire. This is an episode for the second kind of day.Okay so. Real talk: running your own travel creator business does not come with a "smartest and most beautiful person alive" setting every single day. Sometimes it comes with a "maybe I should just go polish up my resume and see if I could even get hired as a barista" setting. And if you've never had a barista day, congratulations, I don't believe you.In this episode I'm walking you through exactly what I do when I hit one of those days — when the highs are high, the lows are LOW, and I genuinely consider giving it all up for a full-fledged coffee bar situation instead. This is not a "hustle harder" pep talk. This is the actual toolkit I use to get myself off the floor and back to running my travel influencer business like the boss I am 80% of the time.We're talking:Why baristas get up at 4 AM and what that has to do with anything (spoiler: it's about structure, not caffeine)Letting yourself actually feel the barista feelings instead of toxic-positivity-ing your way past themWhy your best ideas never happen while you're sitting at your computer — get the fuck outThe Parkinson's Law trick I use to get killer work done before 3 PM so I can have my whole evening backMy feel-good folder — the one piece of proof that you've won before and you'll win againScheduling movement, changing your environment, and giving yourself something (anything) to look forward toWhy phoning a friend in the business-building world might be the most underrated business hack nobody's talking aboutLetting yourself do the "unnecessary" fun work — yes, even the mean-girl-style carousels — because it gets you excited to come backThis episode is basically permission to have a bad day, followed by an actual plan to get out of it. Because knowing how to create good content and knowing how to run a content creation business are two completely different skills — and nobody's talking about the second one. Except me.Sign up for my newsletter, the Content Compass, the weekly newsletter for travel creators who are already landing brand deals and are ready to build the business behind their content.Get five shifts that will take you from travel creator to business owner with actionable next steps included. AND two private podcast episodes. Get the Creator to CEO Playbook for $5Say hi on InstagramJoin Us 👉 The Travel Creator Business Plan Community!The only business-building community designed specifically for travel creators.  You’ll get:  ✔ monthly business systems  ✔ coworking + Q&A calls  ✔ a private community of creators building real businesses  ✔ guidance to help you move from “content machine” to “CEO energy”Sign Up HERE