Learning Everything About The Travelers We Don’t Have

Schonbrunn Palace gardens

Let me paint you a picture. 🖼

I’ve spent the last seven years building and breaking through marketing challenges for other startups. It’s fun!

Whether it was with a local veterinary clinic needing to find a path towards profitable client acquisition, or direct-to-consumer products needing a clear digital acquisition plan to breakthrough stagnant growth, I’ve managed to help solve these marketing problems that run the gamut.

But when it comes to my own business, why is it so much harder?

Ever since I started my life in “entrepreneurship” I’ve always been obsessed with the customer experience.

I remember back when I had my first business, a t-shirt brand for pilots, I would do anything and everything for each and every customer. Even if it meant hand delivering local packages.

It was never strategic, it was just logical… your success is predicated on having customers. Why wouldn’t you care about them the most?

So when I sat down to try and really get a grip on how we are going to get consistent customers for Life Nomading, I knew I needed to put this at the very forefront of priorities every single day.

How could I blend digital with a personal touch?

No one wants to go on a group trip and feel like they’re left in the dark during their decision making. Duh!

Our travelers are about to drop $1,000 to $3,000 on a trip of a lifetime with us. The least we can do is be their lifeline into an adventure.

It’s no secret tourism is competitive. My hypothesis right now is that I believe in my crowded marketplace of group trips, customer service is definitely one of the things I can control and be the best at.

Sure our trips are truly different than those on the market, but quite honestly that is proving to be the most challenging thing to educate right away for new traveler communication. So I think we need to try and get travelers into our brand first, educate over-time.

I also have a small business mover advantage, ie. I have plenty of supply and very little demand at the moment. I can take the time to get to know every email subscriber and every Instagram follower we get. (more on that later)

Okay, so I’m going to care about each and every prospect more than anyone in the industry, logical.

But how am I going to get in front of them in the first place?

Initial Marketing Strategy

Be a ninja on digital. It’s what I know best and quite honestly it’s the best bang for my dollar. We’ve tried hosting happy hours, meetup groups, handing out flyers in person, networking at tradeshows, etc… but those all take a ton of time and quite honestly isn’t all that targeted.

So for now, I want to be everywhere I can be online before going broke.


Build out a 60-second story that hits home our why, our who, and our what. It has worked for other brands I’ve worked with, so I don’t intend to re-invent the wheel, to begin with.


Build out all the nitty-gritty digital marketing assets:

    • Facebook Ads – to get in front of our traveler persona in their ~20’s & 30’s with the video above [performing pretty well at the moment, all the interactions are from people that clearly travel]
    • Google Ads – to capture those already searching for trips to Iceland, Bulgaria, or Portugal [we did get a booking from this last month, but I’m continually cautious that this only really be profitable when the timing is perfect for our related trip dates]
    • Retargeting digital campaigns for all different stages of our website traffic. [so cheap to keep people coming back, a must I believe]
    • Build out email sequences to educate subscribers with Klaviyo for anyone that joins our newsletter, visits our Itinerary pages, etc… [ultimately this is where I end up owning “the rest of the customer story”.]


Don’t let a single opportunity pass with these ads.

I’ve done the math and at the moment, if I generated two bookings a month from our paid strategy, I break even. In November 2019, we got one from these efforts and I was beyond elated. I was also cautious because as this month closes in we have yet to close one for December.

Unlike being a product company where, in my past, we were managing sometimes thousands of transactions per day, this is much different. Getting a few email subscribers a day on our newsletter or followers on Instagram is early encouragement.

So much so, the moment they join our list or follow us I can’t help but send them a personalized message:

I do this same thing on Instagram whether someone follows us or just likes our video ad. I do this in audio memo form in their DMs and this is being received SUPER well. It takes a ton of time to be quite honest, but I’d say I have been getting probably about 40-50% response rate from my audio messages.

I even had a group of two friends pretty much verbally commit to Bulgaria through this outreach. But any good salesperson knows it doesn’t count until the transaction is made.


Learn from the insight I’m getting from every response. Before doing manual outreach it was much harder to understand why the hell people aren’t booking trips with us.

Just in the past couple of months of doing this strategy, I have learned so much from all those interactions.

For the most part, people actually take the time to read our itinerary pages and respond with crazy positive praises and a desire to go on a trip with us.

The issue? They either have a hard time getting off work/school for our few dates available throughout the year (a huge conundrum I’m trying to tackle as a small operator), or they are looking at other destinations for 2020 and will keep us in mind for 2021. UGH!

The nice part is people love our brand and our trips. The frustrating part is how many variables go into having the perfect departure date for the right traveler, and cross paths at the perfect time when they want to book.

Step 5

And finally, to round out my digital strategy, we try our best to keep Instagram and LinkedIn organic posting consistent. Chopping up hours and hours of travel footage into bite-size 15-second clips that will live on those channels for our hard-earned audiences to continue seeing our brand daily.


Instagram is our wanderlust angle, to show the beauty of travel for those who resonate best with that vibe.

LinkedIn to get those same people when they are behind their desk perhaps a bit frustrated with the slog. And quite honestly, if you’ve read this far you are part of the strategy too 🤷‍♂️

We know for a fact that our trips can be beneficial to those that are too busy to plan a trip, but still want to take advantage of the time off they have from their busy careers.

And that’s why I am sharing my progress with you! I hope you can see behind a company that someday you may decide to support by joining on one of our trips.

My Current Objectives (KPIs)

Right now I am hyper-focused on a few things:

A. Qualified traffic to our website – I say qualified because we generate a healthy amount of traffic from pages that have nothing to do with trips or travel even. My goal is to ensure that all our ads hit the right people because I care more about retargeting them after they’ve first been exposed to us as a brand.

B. Adventure Call Bookings – I completely changed our checkout process recently. It now requires you to book a 15-minute call with us to get approved. My goal this month and next is increasing our call bookings from well, one.

C. Trip Bookings – obvious, we need to book our trips. The even more challenging part is booking out the trips we have that are still 8-9 months away.

That’s where I’ll leave you this week. I could go on for hours but welcome to why you are now seeing more ads and posts from us. 😀

What do you think I could be doing better? Where are the gaps I’m missing? What would you like to hear about more? Share and send me a message or comment on the social post to help a fellow founder out!