How to Maximize Your Travel Experiences | Entrepreneur Aligned
Entrepreneur Aligned Wealth Digest 05 26 23 Entrepreneur Aligned Wealth Digest 05 26 23

Entrepreneur’s Wealth Digest

How to Maximize Your Travel Experiences

One of the frequent questions asked by our entrepreneur families is, “What are the best trips that other clients are taking?” Because we get to hear about some truly amazing adventures from our clients, we here at Entrepreneur Aligned are effectively trip advisors as well as financial advisors. Most of our families love to travel and want to take multiple excursions each year, so I am taking this opportunity to talk about travel platforms instead of specific destinations.

Over the past few years, we have heard most of our clients talk about using four primary platforms:

  1. Self-booking or using a travel agent

  2. Airbnb

  3. Inspirato

  4. Wander

Entrepreneur families look for ways to maximize the time they spend away from their businesses and want to make the most of family travel time. They also love to be in control, which is why self-booking is the number one platform used by our client families. Airbnb could be considered a tool for self-booking. Even so, I am including it in the list as its own category, because it offers a variety that is not present when booking through an app like Marriott Bonvoy.

Here are some general differences between our three platforms: Inspirato, Wander and Airbnb.

Inspirato is a luxury travel platform that focuses on providing exclusive, high-end vacation experiences. With a subscription-based model, Inspirato offers a variety of benefits, as follows:

  • Premium properties - Inspirato carefully curates a selection of luxury homes, villas and hotel rooms to ensure quality and consistency.

  • Personalized service - Inspirato assigns a dedicated trip planner to assist you with all aspects of your vacation from booking to onsite concierge services.

  • Exclusive access - Members enjoy special rates, perks and access to private events and experiences that are often unavailable to the general public.

  • Flexibility - Members can book vacations without blackout dates, giving them more freedom to travel during peak seasons.

Wander is a newer entrant to the luxury travel space, offering a mix of high-end homes with a consistent set of amenities on their properties. Their main benefits include the following:

  • Curated properties - Wander carefully selects luxury properties that meet their high standards for design, amenities and location.

  • Support - Guests can text message their concierges for any needs during their stay.

  • Cost - Membership is currently free, and guests only pay for the properties that they use.

Airbnb connects travelers with a wide range of accommodation options from budget friendly to luxurious. Some benefits of booking directly through Airbnb include the following:

  • Variety of options - Airbnb allows you to choose accommodations that suit your preferences and budget.

  • Flexibility - Booking through Airbnb allows you to choose from a vast number of locations and property types without any membership fees or commitments.

  • Direct communication - Airbnb allows you to communicate directly with property owners or managers to ask questions, negotiate prices or request special arrangements.

  • Reviews and ratings - Airbnb's review system helps ensure that you have a clear understanding of a property's quality and expectations.

When digging a little deeper into Inspirato, travelers will discover three membership options: Inspirato Club, Inspirato Pass and Inspirato Select. Each offers access to over 1,000 properties in the Inspirato portfolio, as follows:

  • Inspirato Club: This membership has an initiation fee of $650 followed by a monthly membership fee of $650 and provides access to the Inspirato portfolio. As an Inspirato Club member, you have access to the full portfolio of luxury homes, villas and hotel rooms. You also have access to personalized trip planning, onsite concierge services and exclusive member rates. You also enjoy priority booking windows, members-only events and partner benefits with luxury travel providers.

  • Inspirato Pass: This membership has an initiation fee of $2,550 followed by a monthly membership fee of $2,550. With Inspirato Pass, you can book unlimited trips from a rotating selection of homes, hotels and experiences with no nightly rates, taxes or fees. It also includes membership in the Inspirato Club.

  • Inspirato Select: $2,000 enrollment fee and $24,000 per year. Inspirato Select includes three trips per year which can be used by the member family or gifted to others. It also includes membership in the Inspirato Club.

Wander's membership structure is simpler and registration is free. As a Wander member, travelers have access to a curated collection of luxury homes and a text-based concierge. Wander focuses on guests who want premium homes with consistent amenities such as multiple workspaces dedicated to video conferencing, in-home fitness areas and a Tesla for use in the garage. There are currently only about 15 homes in the Wander portfolio, but after completing recent fundraising for $100 Million, that portfolio should expand quickly.

In summary, Inspirato and Wander cater to different preferences within the luxury travel market. Airbnb serves a wider variety of travelers with properties across the price spectrum from budget to luxury. Inspirato offers a comprehensive and personalized experience with a higher membership cost, while Wander provides a more budget-friendly alternative with a focus on unique experiences and consistency of amenities. Whichever platform you choose, make sure to set aside time away from your business and have some travel adventures with your family! If you have a question or simply want to talk through your financial planning, we are here to help.

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Wealth Digest





DISCLOSURE: Jarrod Musick is an officer of Destiny Capital and Entrepreneur Aligned, a DBA of Destiny Capital. This article is for informational purposes only and should not be relied upon as a basis for your investment, business, or personal financial decisions. We recommend consulting with your wealth advisor, CPA/tax advisor and/or attorney, as applicable to your situation, prior to implementing any new tax, legal, or investment strategy.


Jarrod was born into financial planning and solving financial problems. With his financial advisor father Steve telling stories about finance around the dinner table from an early age, the idea that everyone has a different financial situation was always there. After an early professional career spent in nonprofit and government, Jarrod came back to his roots helping people plan and invest in 2011. Since then, he has worked with individual clients, led internal teams and ultimately became partner and the CEO of Destiny Capital in 2017. With a passion for helping entrepreneurs change the world, Jarrod ultimately oversaw the creation of Entrepreneur Aligned in 2020. With both Destiny Capital and Entrepreneur Aligned, Jarrod leads teams that help people live lives of abundance where money is simply a tool to let everyone be a positive force for the world around them. When he isn’t working with the talented teams for EA and DC you can find him chasing his twins, wily trout or a podium spot at an OCR race.

Jarrod Musick


Posted: 05/26/2023

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