Jim Thomas – Founder and CEO of Itemize.com

[quote style=”boxed”]Ask iconoclastic questions. Assemble talented and diverse teams of smart and motivated people. Challenge them to combine their expertise to solve new obstacles. Make people explain it in English. Draw a lot on the walls. Roll up my own sleeves to communicate the vision, demonstrate commitment and be ready to adapt..[/quote]

Prior to founding Itemize, Jim Thomas was Managing Partner for Information Asset Strategy Group LLC, a payments innovation advisory firm. Prior to working for Info ASG, Jim was Global Practice Leader & Senior Vice President for MasterCard Advisors, a division of MasterCard Inc. Jim has over 20 years of experience, including positions at First Manhattan Consulting Group, Booz-Allen Hamilton, and Morgan Stanley.

Jim has authored numerous articles and been cited in several industry publications including American Banker, CNN, Reuters, Dow Jones, and the ABA’s Bank Marketing magazine. Jim holds a BA from Franklin and Marshall College, a Masters of International Affairs from Columbia University and an MBA from Columbia Business School. In his spare time, Jim enjoys playing piano and spending time with two very active Portuguese Water Dogs. Jim is also certified in both German and Swedish.

What are you working on right now?

I just launched the first digital Personal Shopping Agent, Itemize.com. Itemize is an intelligent app that learns what brands, stores and products you love the most. Based on your unique profile – your Shopping DNA, it scans hundreds of sites to find you the most relevant deals and offers. Itemize lets you focus on the fun parts of shopping. Plus, it helps you stay organized by keeping all of your itemized receipts in one place.

What does your typical day look like?

I get into the office pretty early and have some alone time to organize for the day. I have a few regular standing team calls to check progress on technical developments and marketing strategy. I’ve got my hand into most parts of the business so I’m frequently jumping into different projects with my team to help them be their best and execute on our vision. Throw in a few meetings here and there and the day is over. I try to get out for at least two business dinners a week, but it’s not easy while trying to launch a start up.

Three trends that excite you?

1. Putting Big Data and Algorithms to Work for Consumers: Large organizations started dialing up data mining and information intelligence over ten years ago. Now it’s coming to consumers in a big way – individual consumers, not just groups of them. What’s more, it’s happening on mobile devices and by extension all around us. There is so much data, barely scratched, that will change nearly every aspect of our daily lives.

2. Mobile and mobile payments – two in one – We saw the internet kill book stores, travel agents, and record stores. Mobile is going to accelerate that. For example, consumers won’t need bank accounts
like they used to, so there are going to be a whole lot fewer banks branches in America in the coming years. And that will have ripple effects we haven’t even considered.

3. Curation: The web is becoming more curated. While algorithms can return some amazing things, you still need a human’s touch to make judgment calls and filter the good from the great. But it will occur
with great focus and efficiency. Pretty cool.

How do you bring ideas to life?

Ask iconoclastic questions. Assemble talented and diverse teams of smart and motivated people. Challenge them to combine their expertise to solve new obstacles. Make people explain it in English. Draw a lot on the walls. Roll up my own sleeves to communicate the vision, demonstrate commitment and be ready to adapt.

What inspires you?

I want to do things that are interesting and distinctive. I want to solve problems that both gnaw at me and that I know other people face. And I want to always be learning. I grew up in a family that put great stock in education. And since I’m still just an oversized child, I get a real thrill out of working with talented people to learn new ideas and then figure out how to put that knowledge to work solving a practical challenge, whether in technology, information analytics, or puttering around the garage trying to fix some broken gadget.

What is one mistake you’ve made, and what did you learn from it?

The adage that I have relived several times is “ you can lead a horse to water but you can’t make it drink.” I have been guilty of that more than once, both with people and organizations. I’ve learned the hard way not to confuse my motivation with that of others who don’t share it. No judgment, it just is what it is. So I try to start by filtering for high energy, smart people, because they are usually the motivated ones.

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

Assume that the things you’re building are going to take longer than you think, especially if you work in technology. New challenges pop up all the time so you need to be ready to adapt and adjust. The old rule holds – twice as long and twice as expensive. Oh, and of course, “ time kills deals,” which can be a bummer when you realize development is going to take twice as long as you think.

What do you read every day, and why?

I’ve always been a voracious news junkie. The web has just been an amazing enabler of that. I scan 20-30 news sites every day from around the world. You never know what you will turn up if you quickly look under a lot of rocks. In tech, I hit TechCrunch.com first because it keeps me on top of what’s happening. Its layout and content work for audiences like me.

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

“ ReWork” by Jason Fried and David Heinemeier Hansson. It’s a must-read if you’re running or working for a startup and shows how much “ conventional” wisdom is really fear or laziness in disguise. It’s pretty breezy. You don’t have to implement everything they advise, but even taking just a few things will improve your product.

What is your favorite gadget, app or piece of software that helps you every day?

My iPhone 4. I put off buying one to replace my BlackBerry for the longest time. Now it’s become a far more integral part of my life than my discarded Crackberry ever was. And I love the design. Yeah, I still can’t type very fast, but that has its benefits, too.

Three people we should follow on Twitter, and why?

@garyvee Gary Vaynerchuk: Gary’s enthusiasm and zest for life is infectious.

@CNN CNN: In case anything important happens in the world.

@steverubel Steve Rubel: Steve’s insight on social media is second to none.

Who would you love to see interviewed on IdeaMensch?

Dead? Abe Lincoln: I’m sure he’d have a lot to say, though I also suspect he’d be really modest about it.

Alive? Richard Branson: He’s one of the most interesting businessmen of our time. I’d love to hear his answers to the same questions I’ve answered.

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

Every day – I have my two Portuguese Water Dogs in the office with us, and they never fail to give everyone a laugh. I think they’re in on the jokes, but they play along like good sports anyway. They also remind me to enjoy the simple things in life and never forget that life isn’t all about work.

What was the best job you had as a young person and how did it prepare you for your current role? What sorts of qualities do you look for in hiring others?

I had a lot of jobs as a kid. I think that is actually part of the answer. I cut lawns, worked in a couple of bike shops, several restaurants, and a long string of burger joints. I think the one that was most important was three summers at a supermarket in Ocean City NJ. It was a great experience – dealing with people, handling a lot of money, stocking soda during the graveyard shift one summer, stocking the ice cream another. Nice customers, and some not so nice. And a diverse set of employees on various career tracks, from college kids like me stocking shelves up to the coveted position of produce department manager.

What’s a personal passion of yours most people don’t know about?

I’ve played the piano since third grade, and couldn’t imagine a life without it. Really. It’s what helps me be creative while also developing and maintaining real technical skills. It keeps me sane. A couple of years ago I picked up the most amazing hundred year old Steinway, and my idea of a fun weekend is to put it through its paces for a couple of hours.

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