Over the past 15 years, I’ve logged over 11 million miles—not for vacation, but to build businesses, speak at events, meet clients, and train teams.
Here’s how I travel in a way that’s efficient, affordable, and lets me get work done wherever I am.
1. Always Include Buffer Time
Travel rarely goes exactly as planned. That’s why I build in margin on every trip.
- In Costa Rica, my rental car broke down a full day from any major city. Because I had buffer time, I didn’t miss any meetings.
- The unplanned time led to strategy sessions over tacos with founders.
I plan for flexibility, not just efficiency.
2. Use the Right Travel Programs Together
These are the programs I rely on:
- TSA PreCheck for domestic travel.
- CLEAR to skip security lines.
- Global Entry + NEXUS to speed up international re-entry.
- TripIt to track flights (over 11 million miles logged).
If you travel more than twice a year, these programs save hours.
3. Never Check a Bag
Once, an airline lost my bag and I had to show up to a client meeting in gym shorts. That only happens once.
Here’s what I pack:
- 22” TravelPro roller (same brand flight attendants use).
- Backpack with chargers and a change of clothes.
- Two dress shirts, two pairs of pants, a few t-shirts, running shoes.
- Spare clothes in case I’m forced to gate-check.
4. Airline Loyalty + Credit Card Strategy
Southwest is my go-to for domestic flights:
- Companion Pass: Bring someone with me for free.
- Book-and-cancel: Lock in low fares and cancel if plans change.
- Priority Pass lounges: Quiet space to work and eat.
5. Lower Flight Costs with Smart Tactics
I booked two round-trip business class tickets to London for under $2,000. Here’s what I used:
- Choose smaller airports when possible (Burbank instead of LAX).
- Points when cash fares spike.
- Hidden city tickets (only if you’re not checking bags).
- Back-to-back round trips to reduce overall fare.
- Use SkipLagged for search, then book direct.
6. Stay Productive in Transit
Downtime is still work time:
- I filmed a training in the Atlanta lounge that reached 8,000+ views.
- I preload videos via YouTube Premium so I can review them without Wi-Fi.
- My backpack always has batteries, adapters, and backups.
- Jack Wendt and I often shoot quick clips between flights, upload them to Google Photos, and pass them to our VAs for the Content Factory process.
“When Dennis is at the airport, he’s on his laptop answering emails.” — Jack Wendt.
7. Pack What Helps You Work
If it’s in my bag, it earns its keep:
- TravelPro roller board and backpack.
- Chargers, adapters, power bank.
- Goggles for hotel pools, frisbee for light exercise.
- Ring lights to reward people who record videos.
- Gift cards for flight attendants.
8. Choose Functional Hotels
I avoid hotels that drain my energy. Here’s what I look for:
- 24-hour gym.
- Reliable Wi-Fi.
- Quiet rooms with a work desk.
That’s where I review video edits, run team calls, and catch up on campaigns.
9. Use Other Flight Programs Too
I don’t just fly Southwest. Here’s how I’ve saved more:
- Frontier GoWild Pass: $299/year for unlimited direct flights.
- When I worked at American Airlines, I flew first class for $21.
- I once got international first class with caviar service for under $100.
The key is tracking your routes and finding what fits.
10. Go Where Others Don’t
One of the most memorable trips I’ve taken was to Svalbard—close to the North Pole.
- Flew in from Oslo and stayed near the 78th parallel.
- Filmed content there with Logan Young.
- That footage still powers agency training years later.
Make Your Own System
I follow this checklist every week because it works.
Test it. Refine it. Find what works best for how you travel and get work done.
If you’re trying one of these, let me know what result you get.
