Team Spotlight: Travel Later

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Rob Holland has a thirst for travel. However, he struggled to maintain the budget that would allow him and his family to go on vacation every year.

Vacations sometimes feel like an undeserved luxury when you’re busy with work and putting money towards groceries. However, vacations are necessary if you want enough energy to do your best work. After going three years without a vacation, Rob’s own budgeting struggles and his belief that everyone deserves to go on vacation lead to the creation of Travel Later.

Travel Later is a payment solution to help consumers budget, plan and pay for vacation in a fun and interactive way. Read on to hear from Rob, the CEO and founder of Travel Later, about his experiences as an entrepreneur.


What attracted you to the FlashStarts accelerator?

I discovered Flashstarts with a simple Google search for summer accelerators and was impressed by their first graduating class. I initially decided to apply to Flashstarts because, unlike most other accelerators, they didn’t automatically disqualify you for being a single founder. I met with Charles and Jennifer and was immediately sold. They were sincerely engaged with my business idea and even gave some advice in our first meeting that potentially saved the company thousands of dollars.

Tell us about your company

As a consumer, I wanted a tool that makes sure I can take a vacation every year and that was part of my thinking when starting this business. 

Travel Later’s goal is to help consumers budget, plan and pay for vacation while linking their financial & social accounts online, helping consumers achieve their vacation savings goals. Travel Later wants to make saving and budgeting for vacation a fun and interactive experience.

What has been the biggest challenge?

In an accelerator, you have very limited time to present an idea that originated in your head and I want version 1.0 of Travel Later to have all the functionality that will be developed and implemented in later versions. So the biggest challenge has been to stay patient with version roll outs and not trying to cram everything into the first version.

Tell us about working and living in Cleveland

I’m from Chicago and I relocated to Cleveland to work with Flashstarts. Although, most of my time is at the office I have been able to explore a little bit of Cleveland. Downtown can be a little too quiet but overall this is a great city with good down to earth people.

How do you like working with interns?

Working with the interns has been great. I heard somewhere that being an entrepreneur often can be one of the loneliest professions because the buck starts and stops with you. Having interns in our corner, willing to help out with projects, was very helpful and appreciated.

What is some advice for future interns?

I would advise anyone who is still in school and considering being an entrepreneur one day to intern with Flashstarts. It gives you the realistic picture of all the hard work it takes to launch a business.

What surprised you about your experience at Flashstarts?

I was surprised at how fast the time went by.

What are some things you’ve learned this summer, so far?

I’ve learned a lot this summer. I learned a lot from our invited Food for Thought guests, but if I had to pick the most valuable things I’ve learned throughout this experience, it would be learning how to raise funds, putting together an investor pitch and launching a scalable business.

Interested in learning more about Travel Later? Visit Travel Later online and on Twitter at @travellater to engage in conversations and stay updated on progress.

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