Travel Like a Pro in 2025: Secrets from My Personal Stack


Founder Mode - Travel Stack

First, a quick note: Sorry about the delay this week. I upgraded Kit to paid and fixed some of my DNS settings—DMARC, DKIM, and SPF for the email nerds. Now, we have a verified sender domain. Kit then restricted my account for a few days, but we sorted that out, so we're back.

I got great feedback from folks who replied to the welcome email—many different ideas and topics to work on. I want to spend the first ~15 emails going through various "stacks." Things I use and things I do, and in turn, hope that spurs conversations. Feel free to reply and make requests. Please tell me if you like it, you hate it, or if you have a suggestion of what I should write about next.

On Tuesday, I'm going to discuss vendor negotiation. Several people I have worked with have suggested that I do so. I love negotiating, particularly with vendors. :)

Steve Jobs, Warren Buffett, and Paul Graham won by "getting on the plane." Jobs flew to Corning's CEO to revive Gorilla Glass. It was a pivotal moment in the iPhone's history. Buffett insists on meeting people in person to assess their character. He believes face-to-face interactions are essential for building trust. Paul Graham urged founders to immerse themselves in Silicon Valley. He believed that being close to the action speeds up learning and growth. The lesson? In-person interactions build trust and spark innovation. They often achieve results that virtual meetings can't. Traveling to new places accelerates your perspective. Get out in the world and see new places, things, and people.

Hence, we're kicking off today's email with my "Travel Stack." I travel a lot, and these essentials help me stay organized, healthy, and stress-free while on the go.

  • TripIt: A comprehensive app for organizing travel itineraries. Imports details via email or PDFs.
  • Flighty: A real-time flight-tracking app with a clean interface and faster-than-airline updates. Pulls the trip data from TripIt.
  • PackPoint: A packing app. It pulls weather and trip duration. You pick activities. Optionally pulls next destination from TripIt.
  • TimeShifter: Optimizes sleep schedules to adjust to new time zones. Game changer.
  • Ozlo: Noise-canceling earbuds pair with an app to block out travel or hotel noise. Try them for $22/mo.
  • WAOAW Sleep Mask: My favorite sleep mask blocks out the light on flights or at hotels.
  • Mozi: A social app designed for close friends and in-real-life meetups.
  • United: Airline app but for me based in SFO & LAS it's non-stop to most places.
  • Marriott: Good range of hotel and reliable benefits during stays as you get status.
  • ExpressVPN: Solves airplane & hotel WiFi access by bypassing restrictions. It's also safer way to use semi-public networks.
  • US Mobile: It's easy to share data plans. A ton of options for international travel. With iPhone, just add a 2nd eSim, so you can now have BOTH Verizon + AT&T/T-Mobile on the same device. Much better coverage where one carrier may have a dead zone.
  • Uber: Rides when and where you need it.
  • Turo: Rental cars brought to you. Great for small airports or when you need a specific car or flexibility.
  • Global Entry + TSA Pre + APEC Card: Simplifies TSA, Intl travel and customs in the U.S. + Asia. They have an iOS app many folks don't know about.
  • CLEAR: Pass security for faster processing at some of the busy U.S. airports.
  • Whoop: Tracks sleep, activity, and recovery metrics to optimize health.
  • Oura: It tracks sleep, activity, and recovery. It provides insights on workout readiness and travel impact.
  • Athena: Highly trained remote executive partner to manage travel plans, calendars, and workflows. Also allows you to keep your life and business running when you are on the go.
  • Audible: Audiobook leader. Long flights, train rides, or road trips. It's the perfect way to catch up on the latest books.
  • Spotify: My goto for podcast and music.

Typical travel starts with TripIt. It consolidates all my itineraries in one place. Flighty syncs for real-time flight updates. The night before, I used PackPoint to check my packing list. It ensures I have everything I need for the weather and activities at my destination. TimeShifter helps me optimize my sleep if I go to new time zones. Ozlo and the sleep mask ensure uninterrupted rest on a plane and at a hotel.

CLEAR and TSA PreCheck speed up security. For international flights, use Global Entry to clear customs at the airport. I use ExpressVPN for reliable access to airplane WiFi to finish work or catch up on emails. Upon landing, I use on Uber or Turo to get where I need to go. Mozi helps alert me for IRL connections if I'm meeting friends or colleagues.

Whoop and Oura track my activity and recovery. I use both with an Apple Watch, but I will discuss that in the health stack. They help me watch my health, especially after a long flight or busy schedule. My Athena assistant keeps my calendar and travel plans synced. She flags any conflicts or delays before I notice them. If I have slack time, Audible or Spotify are the perfect escape.

The travel stack is more than convenience. It's my system for staying focused, productive, and healthy while on the move. From when I pack to when I return home, these tools make travel less stressful. If you want to get the most from your trip, try adding a few of these to your routine. Their impact might surprise you.

Do you use any other travel gadgets or apps? Hit reply and let me know.

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Catch up on past emails here -> https://foundermode.kit.com/

-kevin

2810 N Church St #87205, Wilmington, DE 19802
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Founder Mode

Founder Mode is a weekly newsletter for builders—whether it’s startups, systems, or personal growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh perspectives to help you think like a founder and build what matters most.

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