David Chait – Co-founder and CEO of Travefy

[quote style=”boxed”]User stories! Nothing brings an idea to life like writing out a narrative of how and why someone would use your tool. Wireframes and technical specs are important parts of the “building” process, but user stories make it real and functional.[/quote]

David Donner Chait is the co-founder and CEO of Travefy, a group travel planner that solves the coordination headaches of travel. He is also a regular contributor to Young Entrepreneur.

Chait previously served as the Senior Policy Advisor to the Administrator at the U.S. Small Business Administration (SBA). At the SBA David focused on key policy issues including the small business economic and credit environment and international trade among other topics. Prior to joining the SBA, he worked as a consultant for McKinsey & Company in its New York City office helping Fortune 500 companies, governments, and non-profits to define strategies and improve operations.

Chait graduated magna cum laude from Columbia College with a B.A. in economics-political science and earned his MBA with Dean’s Honors from Columbia Business School.

What are you working on right now?

I’m currently working on Travefy, which is a tool that solves all of the headaches of group travel! Travefy helps groups determine their best trip, collaborate on details, book travel, and manage expenses. You can check out our exciting beta at www.travefy.com.

Where did the idea for Travefy come from?

The idea for Travefy came from my own personal group travel experiences. Last year I was involved in planning a bachelor party for one of my best friends. The group was over 75 emails into a scattered planning discussion without any real sense when worked for everyone and what people actually wanted to do. One guy tried to be helpful and booked a hotel room for the date that he thought most people wanted. He was right that the date worked for most of the group – just not our friend getting married!

I sought out tools to help us vote for dates and locations, find hotels and collect payments and realized that no comprehensive group travel planner existed. At that point Travefy was born.

How do you make money?

Travefy earns revenue from three key sources. First, Travefy earns a commission on any travel booked through the site from our partnerships with online travel agents like Expedia. Second, we earn a cash management fee for any expenses settled through our ground breaking expense management tool. Lastly, Travefy also offers a B2B white-label version of our software to travel agents and management companies for a monthly license fee.

What does your typical day look like?

Up at 6:30am. Feed Sadie (the cat), kiss Amanda (the fiancé) goodbye and jump on my bicycle to get into the office by 7:30am. Beyond that every day is its own unique blend of challenges, meetings, and deliverables.

The most important thing is I love what we’re building and enjoy every moment of it.

How do you bring ideas to life?

User stories! Nothing brings an idea to life like writing out a narrative of how and why someone would use your tool. Wireframes and technical specs are important parts of the “building” process, but user stories make it real and functional.

What’s one trend that really excites you?

One trend that I love is the rise of “continuity across devices”. As someone always on the go or travelling I have no idea whether at any given moment my device of choice is my phone, tablet, or computer.

With the rise of the cloud programs and apps are adapting to this new paradigm and creating an amazing continuity across devices. Whether it’s storing documents in Dropbox or finishing a movie on Netflix, I love this trend and can’t wait for more of it.

What was the worst job you ever had and what did you learn from it?

In high school I worked a summer in maintenance at the local swim club. The job entailed typical maintenance work with daily tasks like taking out the trash, mowing the lawn, moving chlorine jugs, etc. In retrospect it was a good job with very fair pay, but at the time I was pretty down on it.

My attitude had nothing to do with the work itself, but the fact that I wanted to be doing something else. I desperately wanted to be a lifeguard, but I was too young that summer. The maintenance job was not only the only real work available to me, but was also my foot in the door to get the lifeguard job the next summer.

In the end, I worked hard that summer and earned a good reputation. When lifeguard hiring came the next summer, I easily got the job. From that experience I learned valuable lessons on the importance (and expectation) of paying your dues and to think big picture and keep your eye on the prize.

If you were to start again, what would you do differently?

I truly believe that life is a journey and every experience (no matter how good or bad) is formative in developing who we are and informing what we do and how we do. With that in mind, and despite personal and professional highs and lows like everyone, I wouldn’t change a thing.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Question everything and never stop iterating!

No matter how much you believe in your product or vision, you should constantly question everything and feel comfortable throwing things away and rebuilding. Pride of ownership and a resistance to change can be dangerous.

The best way to learn and refine your product is to bring in new people “blind” to your product and talk to them. You’ll be shocked by the interesting and informative things you’ll learn.

What is one failure you had as an entrepreneur, and how did you overcome it?

I’ve had a lot of failures as an entrepreneur (which is normal and a good thing). The most important thing is to take your failures and learn from them to inform changes to your product or service. In that respect, failures are actually valuable parts of the development process.

For me, one failure at Travefy was our interpretation of how Facebook users would use our tool. When we first created Travefy our Facebook integration was built to allow users to invite Facebook friends to any trip. The technical way of doing this was by creating an “event”.

We wrongly assumed that once that event was created all users would click the provided link to come to Travefy. We were dead wrong and users stayed on the events page for discussion. That led us to lose many potential customers.

In the end this “failure” was an invaluable lesson on the need to better integrate the Facebook events into Travefy. This valuable change not only preserves existing users but creates a value proposition for new ones.

What is one business idea that you’re willing to give away to our readers?

One idea worth sharing is graduation cap and gown rentals (similar to Rent the Runway). Having just graduated from business school, a graduation cap and gown are very expensive items that are worn for a few hours and then useless.

Research would have to be conducted to see how many different colors Universities actually use (too many SKUs would be infeasible), but assuming big blocks of specific colors exist, such a business could be worthwhile.

If you could change one thing in the world, what would it be and how would you go about it?

If I could change one thing in the world I would ensure that everyone regardless of geography or economic background has access to a solid education. Education truly equals opportunity.

How I would go about creating this change is a much larger question and I wish there were a simple panacea. On a micro-level, I would examine alternatives to property-tax based education funding schemes in the U.S. which often have the unintended consequence of preserving economic disparity.

Tell us something about you that very few people know?

I love to cook. I never really have the time to do so, but whenever I get the chance, I love it.

What are your three favorite online tools or resources and what do you love about them?

Sqwiggle – Sqwiggle is a great collaboration tool that is a must have for any team not sitting together. Sqwiggle puts everyone into a browser or app based room with chat and one click video for conferencing. It also takes a static photo every few minutes of everyone in the room so you have the feeling of sitting together.

Trello – At Travefy we’ve used quite a few tools for project management and have found Trello to be the best by far. Its rapid board is very light and user friendly, allowing us to easily map out and assign deliverables.

Notable – It used to be extremely difficult for multiple people to comment on a single design sketch. We’d either have to pass it around one by one or assign one person to be the “owner” and collect comments. Notable is an awesome tool that allows you to upload any sketch and collect team comments in the cloud.

What is the one book that you recommend our community should read and why?

Great question and there are so many great books worth reading. In general, I love to read non-fiction and think there is so much to learn from past experiences. I recently finished John Meacham’s Thomas Jefferson: The Art of Power and think it’s an extremely useful biography for any entrepreneur.

The book dives into the problem solving process of Jefferson at various stages of his career, which are fascinating case studies for any entrepreneur. Human thought is timeless and his methods of analyzing issues are still extremely relevant today (only the circumstances of the inputs have changed).

Three people we should follow on Twitter and why?

@skift – If you love travel then you must follow Skift. They are not only a one-stop shop for all travel news, but they’re also data geeks (like me) and share awesome insights and tools.

@AndrewRusseth – Andrew is a good friend from college and an art expert. His insights found on twitter, The Observer, and elsewhere are not only fascinating, but accessible to anyone regardless of your knowledge base.

@FredWilson – You probably already follow Unions Square Ventures’ Fred Wilson on twitter, but if not, start now. His insights and regular features like MBA Mondays are a must follow.

When was the last time you laughed out loud? What caused it?

Today actually – When I read this tweet from an old fraternity brother:

“I used to procastinate in MS Word in highschool, by replacing a word with a synonym over and over until left with its antonym.”

Who is your hero, and why?

I have two – my parents. They’ve literally given everything to their kids and I’d be nowhere without them.

What about Travefy excites you the most?

For me the most exciting aspect of Travefy is by far our groundbreaking expense management tool, which will be released in September 2013.

Group expenses can be a pain! It’s tough to keep track of who spent what and used what. Even if you do manage to track everything and figure out who owes or is owed money, collecting payments can be painful and still require distributing money again to those owed.

Travefy’s expense tool solves all of this. It’s a simple platform that allows trip participants to track expenses (e.g., we went to dinner and I paid $125.00 for me, Chris, and Jim). At the end of the trip anyone who owes money is emailed simple payment link and funds are automatically distributed to everyone owed money.

You love to travel. Where’s your next trip?

My next trip will be in October to Palm Beach, Florida for my wedding, which is extremely exciting. After that Amanda and I are off to Thailand for our honeymoon, which will be the trip of a lifetime!


Travefy on Twitter: @travefy
David Donner Chait on Twitter: @donnerchait
Travefy on Facebook: