This question caused a minor instance of PTSD. “You don’t know what you don’t know” suddenly made sense. I was a traveler, an adventurer at heart. I had a grip on most of what was needed, but setting up SaharaTrek took me off the map, and there were indeed monsters there (in business casual attire).
4. What were the biggest obstacles you faced when starting out?
Here’s the thing about jumping off cliffs: you don’t know what you don’t know until you’re already falling.
The question “What were the biggest obstacles?” is like asking “Which grain of sand in the Sahara?”
Short answer? Nearly everything.
Long answer? Strap in.
My years in Tallahassee rebuilding Main Street communities had taught me the dark arts of bureaucracy. Corporate structures? Check. EIN numbers from the Feds? Please. Business filings? I could do that in my sleep. The paperwork that makes most entrepreneurs weep into their keyboards? That was my warm-up lap.
I thought I was ready.
I was adorably naive.
Florida, land of sunshine and inexplicable regulations, drops this bomb: You need a license to sell travel.
Okay, fine. I’ll get a license.
But first you need a bond.
A bond. As in, post money guaranteeing you won’t abscond to Morocco with people’s deposits. Which, given that I was literally sending people to Morocco, seemed like a valid concern.
But wait—there’s more!
Someone from California books a tour? You need a California seller of travel license too. Different state, different bond, different paperwork, different bureaucratic nightmare. It’s like discovering that every state is its own country with its own customs and border guards who really care about forms in triplicate.
I went from navigating the souks of Marrakech to navigating the labyrinth of multi-state licensing. Honestly? The souks were easier.
Then came the fun part: international banking.
Imagine trying to explain to a Florida bank in 2000 why you need to regularly wire large sums of money to Morocco—a country most Americans couldn’t find on a map, much less trust with their vacation deposits.
“So you’re sending money… to Africa… for tours… you’re running… from Florida… but you live in… wait, where do you live?”
The banks looked at me like I was either a criminal or insane. Possibly both.
Wire transfers that should take days took weeks. Fees that should be reasonable were highway robbery. Every transaction felt like negotiating a hostage exchange. And God forbid something went wrong—try calling Moroccan banks from Florida on 2000-era international phone rates.
The Sahara was less hostile.
But those were just the opening acts. The real adventure? Learning to speak the emerging language of the internet.
How do I make a website?
Not just any website—a website that doesn’t look like it was built by someone’s nephew in 1997. A website that loads in less than five minutes on dial-up. A website that actually convinces people to trust a stranger with their vacation money.
HTML. CSS. FTP servers. Domain registrars. Hosting companies that went out of business every other month. I became a reluctant web designer, teaching myself code at midnight, breaking things, fixing things, breaking them again.
How do I accept credit cards?
Merchant accounts. Payment gateways. PCI compliance (before most people knew what PCI compliance was). SSL certificates. Shopping carts that actually worked. Every transaction that didn’t fail felt like a minor miracle.
And how do I market with this new Google thingy?
SEO before anyone called it SEO. AdWords when it was still called AdWords and cost pennies instead of dollars. Meta tags. Keywords. Page rank. Learning to speak robot so Google would tell humans we existed.
I’d gone from dodging faux guides in M’hamid to dodging digital landmines in the wild west of early e-commerce.
Every obstacle was a lesson I didn’t know I needed. Every failure was a map to success I couldn’t have drawn in advance.
The paperwork maze taught me compliance. The banking nightmares taught me resilience. The technology struggles taught me to adapt or die.
Because here’s what nobody tells you about starting a business: the obstacles aren’t bugs in the system.
They’re the system.
And if you can navigate multi-state travel licensing, international wire transfers, and the fever dream that was the early internet?
Well, a few faux guides in a square in M’hamid don’t seem quite so scary anymore.
