Rising StarRising Stars: Co-Founders of TripGrid Want to Make Travel Planning Fun

It’s winter in Portland, you need some sun, and you have a few vacation days to use. With gusto, you post to Facebook to ask your friends for advice on their favorite coastal destinations. You start a Pinterest board. You research plane fares to various beach towns. You look for Groupon deals. You email a few online travel articles to a friend. By the end of the day, you have 25 tabs open on your browser and your gusto is officially depleted.

This is an all-too-familiar scenario for intrepid travelers Jake Hoskins and Joe Stevens, who believe that travel planning should be fun and inspirational, not a huge headache. That’s why they founded TripGrid. Jake and Joe tell us more:

What was the spark that inspired the birth of your concept?

We began developing a product based around travel inspiration in 2014 called Travelstash. The first concept was born from an idea Jake had while traveling between his work in Africa and his apartment in Medellin, Columbia. For Jake, planning was a true personal pain point realized from years of traveling. Travelstash would provide travel inspiration and collection, a ‘Pinterest’ for travel, heavily focused on content. After a year of team building and discovery, with help from our new co-founder, Jake Horn, we pivoted the idea to what is now TripGrid, a truly intuitive travel planning and collaboration platform.

What problem does it solve?

Travel planning is broken. For each task that needs to be done, you have to visit a different website, and  you end up with a mess of tabs to click through. Communicating with other travelers around logistics starts happening across Facebook, text, WhatsApp, Skype or email. If you are simply looking for new ideas, you have to copy and paste URLs into an email to share with your travel buddies. When it comes time to pull the trigger, you have to book across multiple platforms and then somehow split costs. TripGrid allows travelers to store, plan, communicate, organize and book in one place. It ends so many logistical headaches, we can’t even fit them into a one-page description.

How did you come up with the name?

As is typical in the startup world, we had several rounds of creative naming sessions with our team. We wanted something that would clearly describe the product and that was easy to pronounce.  In a crazy turn of events the .com for TripGrid was already owned but Jake Hoskins discovered that the owner was connected to someone he knew on Facebook. So he contacted the owner and appealed to his love of traveling. An offer was made and accepted and the name purchased.  We’ve since trademarked the name and started both Facebook and Pinterest pages.

How are you better than your competition?

Simplicity. The few sites that have tried to tackle this problem as a whole have done so from a feature-first stand point. Interfaces are confusing and complex, and the user continually gets lost within the platforms. We have built design-first from the beginning.  Our co-founder, Jake Horn, is a highly experienced designer specializing in user experience and interface. The key is to make it so user friendly that planning travel actually becomes fun again.

How do you make money?

TripGrid will be free for users.  We will provide booking capability through affiliates like Expedia and Kayak for transportation, accommodation, adventure and activities.  We also plan on developing affiliate partnerships with larger unique travel companies and businesses that show up in our map feature.

What’s the best thing about being an entrepreneur?

There are two that come to mind. The first is freedom to follow your passion and make it a reality.  Though neither of us has kids, we have compared the experience to having a child. This is our baby.  We’ve sacrificed time with friends and family over the last 20 months, and have confronted several opportunities to walk away or quit, but the passion for the concept, and the passion from our extended team have kept us going.  The second best thing about being an entrepreneur is the opportunity to build a winning team.

What has been the biggest surprise in your entrepreneurial experience to date?

Honestly, there have been no real surprises, just what we would call ‘serendipitous’ events that have affirmed our path, like meeting the team members that we did, when we did, and being introduced to other people who would eventually help us on our path.

Your biggest success?

There have been many small successes, but the largest was recently winning the OEN PubTalk PitchFest at Lucky Lab.  We spent a week straight nailing the one-minute pitch and Jake spent several days memorizing it.  It was one of the biggest highs we’ve had on this journey, and there have been quite a few.

Do you have a failure story to share? What did you learn from this failure?

We spent nearly eight months working on our previous concept, Travelstash. We hired two remote developers who, while qualified, were not engaged with us or our passion.  They were not full-time and were eventually let go.  We would caution against this for anyone working to develop a web platform. Try to bring on dedicated full-time staff in the form of a co-founder or contractors who can relate to you and/or your vision.

As an entrepreneur, what keeps you up at night?

I think the most common answer to this would be money, and we’re no exception.  As we’ve said, we made mistakes in the beginning that we’re chalking up to education. We are now on a tight budget for working on our launch and raising our seed.

What is the best entrepreneurial advice you have received?

The first advisor we brought on, Paul Burkett (co-founder of Safetec.net) really drove home the idea that we could push our idea forward and not quit.  Paul is an experienced developer and entrepreneur himself and was an enthusiastic fan.  He was instrumental in getting us past our initial pivot stage.

What is your #1 piece of advice for a budding entrepreneur?

Know what you are getting into, or team up with somebody who does. We have learned so much during the last 18 months, making mistakes and spending money unnecessarily.  If we knew then what we knew now, we would have focused on the product first and getting our product in front of potential users.

What is the #1 book you would recommend for a budding entrepreneur?

I think the one that for us has been the most useful as a guide in this later stage is What Every Angel Investor Wants You to Know by Brian S. Cohen and John Kador. Brian is a prominent NY Angel Investor, Chairmen of the NY Angels, and was one of the lead early investors for Pinterest.

Imagine your venture becomes wildly successful. What does that look like?

As for the product, we’d like to see a change in the online travel planning paradigm, a platform that brings travelers worldwide together to collaborate around travel itineraries and passions.  If we can make traveling the world easier and more accessible to millions of people then we feel we have in fact changed the world for the better. To be successful at developing our passion into a business that helps millions of people become their better self….. we can’t imagine being more fulfilled. We’ve both traveled the world extensively and for others who have had the opportunity, you understand how small the world becomes. There is an thrill to travel that everyone should feel in their lifetime. It changes you.

What’s your favorite local business?

Vacasa. They are scrappy and savvy. They trusted so much in what they were doing and never gave up. They saw a problem and they trusted in their abilities to fix it. As they grew, they never took funding and continued to stay on the course they knew was right. In the process, they have affected hundreds of small business now worldwide for the better. They get to do what they love and enjoy the fact that they are doing the right things in business.

Do you think Oregon is a good place to start a business?

The startup scene here is more accepting of budding entrepreneurship then other cities.  People were immediately open, and making connections was simple after we knew where to go. There is no startup ‘guide’ for Portland though so you need to be willing to find those meetup groups or events and avenues for connection like the startup board on Switchboard.hq and organizations like OEN and TIE.

Any other tidbits or fun facts to share?

You can find us on Facebook at www.facebook.com/tripgrid. If you’re interested in helping with beta testing, go to our landing page at www.tripgrid.com and sign up!