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Working ON vs IN your Business with Brianna Glenn

By Travel Advisor - May 18, 2026

Working ON vs. IN Your Business

Bliss to Abundance Podcast | Cindy Williams & Brianna Glenn


Guest Introduction

Brianna Glenn — Founder of Milk and Honey Travel, co-leader at Masters in Travel. Came into the travel industry and went straight independent. Now a multi-year million-dollar travel advisor and frequent business strategy speaker, including at Wanderlust Campus's Wander Beyond Virtual Retreat.


Part 1: Working ON vs. IN Your Business

The Core Mistake Most New Advisors Make

  • New advisors jump straight into finding clients before building systems
  • Result: overwhelm hits fast, and the business becomes impossible to scale
  • Brianna's advice to her earlier self: start with the vision, build the systems and workflows, then invite clients in

What Overwhelm Actually Signals

  • You finally have clients but no repeatable process to serve them
  • Every day starts in triage mode instead of from a place of calm and control
  • Can't say yes to more business even though you want the revenue
  • The fix isn't more clients — it's building the infrastructure first

Why Systems Matter Before Scale

  • Bringing someone into chaos to help you just creates more chaos
  • A clear system makes it easy to delegate and bring on support
  • Serving 1–2 clients well is easy; serving 20–30 without systems is where things break down
  • Referrals come naturally when you do good work early — but without systems, that growth becomes a "giant mess of spaghetti"

The Wanderlust Campus Approach

  • New students often ask: when do I learn to be a travel agent?
  • Answer: foundational systems and business architecture come first (Modules 1–5)
  • Client invitation, sales conversations, and closing come later (Modules 6–7)
  • By then the mechanics are already in place — everything clicks

Working Reactively vs. Proactively

  • Without intention, you accept whatever walks in the door — wrong niches, wrong clients, wrong trips
  • With systems and a clear vision, you attract the clients and trips you actually want
  • The two work hand in hand: systems + intentional marketing = a business that flows

Serving Clients Well Requires Staying in Your Lane

  • Hopping into unfamiliar niches to chase revenue is a disservice to the client
  • Build your book of business around who you want to serve and where they're going
  • When that alignment exists, everything snaps together — it feels like kismet

Part 2: Marketing Strategy

Why Every Business Needs to Market

  • No business — regardless of size — can skip marketing
  • Effective marketing = attracting the right person to the value you specifically provide
  • Without marketing, alignment between you and your ideal client is nearly impossible

Positioning vs. Marketing

  • Most advisors don't have a marketing problem — they have a positioning problem
  • If you're attracting tire kickers, your messaging is off
  • Good marketing attracts the right clients and almost offends the wrong ones
  • Be direct: "Am I the cheapest? No. Will I get you results? Yes. Decide."

Where to Market — It's More Than Social Media

  • Social media is top of funnel only — necessary for social proof, but not sufficient alone
  • Email list/newsletter: people who opt in are actively asking for your expertise; highly effective
  • In-person networking: especially important for new advisors who don't yet have a full client book; if you're not booking trips, you should be out talking to people
  • Content marketing: blogs, video, behind-the-scenes — all serve different stages of the client journey

Two Different Types of Content

  • Brand awareness post: "I just need people to know I exist"
  • Problem-aware post: "I need someone ready to call and book tomorrow"
  • Understanding where your audience is in the journey changes what you create

Architecture vs. Activation

  • Building the architecture (social pages, Google profile, SEO, website) and putting it to work are two completely different functions
  • Too many advisors put up a Facebook page and wonder why inquiries aren't pouring in
  • The house is built — but you haven't invited anyone to the party yet

Part 3: Paid Advertising

When Organic Isn't Enough

  • Organic reach is down across platforms; algorithm is unpredictable
  • Organic will always bring some traffic with strong positioning — but not at scale
  • For 30–50% growth, the bottleneck is almost always leads
  • Paid advertising solves the leads-on-demand problem — but only with strategy behind it

How to Approach Paid Ads

  • Start small: $5–$10/day to test
  • Without strategy, paid ads are just money out the window
  • Every ad needs a clear purpose: what do you want people to do after they see it?
  • Content that doesn't attract or repel — vanilla, neutral — gets ignored entirely
  • To stop the scroll, your message needs an edge; someone should either say "that's me" or move on

Cindy's Real Numbers on Ad Testing

  • Currently has $50,000 actively testing in the marketplace across multiple campaigns
  • Assessed the last 24 months: ~$300,000 in "wasted" spend — intentionally, to find what works
  • Current monthly ad testing budget: $15,000–$20,000 across businesses
  • One campaign is performing 4x better than a month ago after a strategy change
  • Results get shared in real time with Wanderlust Campus students and agency owners

The Importance of Knowing Your Numbers

  • You can only confidently scale ad spend when you know your ROI
  • Many travel advisors are creative by nature and resist the data side — but it's non-negotiable
  • Brianna reviews ad performance every Monday morning: coffee, no meetings, just numbers
  • Wanderlust Campus includes a KPI dashboard so students can track key metrics from the start
  • "You will waste money and time if you don't know your numbers."

Part 4: Video Marketing

Why Video Wins

  • Video allows people to be in the moment with you — a connection static images can't create
  • Travel advising is a personal business; video lets your personality come through before a client ever calls
  • Even audio-only video builds more connection than text or photos

You Don't Have to Be an Influencer

  • Goal: get the attention of the right people, not millions of views
  • Case study: a 10–15 minute video about a cruise ship (not even a new ship) generated 57,000 views and over $100,000 in bookings — all organic, zero ad spend
  • Commission per booking on that video type: $500–$1,000 per booking
  • You don't need the YouTube creator fund — you need a few of the right people to book

Don't Create Content — Be the Content

  • What are you already working on today? Put it on camera
  • Show the behind-the-scenes of a complex FIT itinerary
  • Show the transformation, not the day-by-day breakdown
  • People are fascinated by what travel advisors actually do — use that

Getting Comfortable on Camera

  • It will feel awkward at first — that's normal and necessary
  • Wanderlust Campus embeds a video boot camp into the certification: Day 1 is just hitting record and saying hello; ums and nerves are encouraged
  • Every 100 videos = 100% improvement
  • Cindy has clocked thousands of videos across YouTube and campus content; hitting record isn't hard anymore
  • First year is about learning your voice — you won't find it until you make your first few hundred videos

Staying Consistent

  • Don't chase TikTok trends — build a smarter strategy instead
  • Test hooks and messaging; a "flop" is just feedback on what to adjust
  • Pair strong organic video with paid promotion once you know what resonates

Key Takeaways

  • Build systems before you need them — it's far easier than retrofitting under pressure
  • Market with strategy, not just activity — a checklist without a strategy is wasted effort
  • Position clearly — attract the right clients and repel the wrong ones
  • Know your numbers — data is how you make confident decisions and stop wasting money
  • Go slow with paid ads — test small, learn fast, then scale what works
  • Video is non-negotiable — start ugly, get better, and let your passion carry you

Where to Find Brianna Glenn

  • Personal: @BriannaGlenn (social media)
  • Podcast: @MastersInTravel
  • Agency: Milk and Honey Travel

Wanderlust Campus

  • Free account + resources: TravelSchool.com
  • Certified Travel Professional designation (registered mark, patented program)
  • Hitting 10-year anniversary
  • Cindy speaking at ASTA Conference: sessions "Lights, Camera, Bookings" and "Cut, Edit, Publish"
Read more...

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