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In certain situations gift giving can be an absolute nightmare. How am I supposed to know what to get for the silver anniversary of my girlfriend’s boss? A clock? A goldfish? Why am I even involved in this gift giving situation? It always turns out the same: you find yourself in the Walgreens parking lot feverishly wrapping a Chili’s gift card inside of a shoebox, ashamed at your lack of creativity.

Chicago startup The Gift Insider is aiming to eliminate the ambivalence of gift cards forever with a platform that helps people find the perfect gift for all kinds of scenarios. Using the gift giving service you can discover a whole variety of unique gifts to inject your caffeine-fried brain with a little creativity. With gift ideas for moms, girlfriends, coworkers and much more, you’ll be hard pressed to find a better resource next time that special (or dreaded) day rolls around.

I sat down with The Gift Insider founder Lindsay Roberts, who told me that the only gift to give a struggling entrepreneur is a solid 30 second hug.

What is the story behind The Gift Insider?

I started it as a small hobby blog. I used to work in the magazine industry for Good Hosuekeeping and Esquire. Part of my job was looking through all of our competitors’ magazines and I started trying to make a blog of cool products I found, cool gift ideas, and kind of framed it in that way.

I’ve always been very creative-minded with gift ideas and trying to find new things or personalized things. It was really just a hobby blog and I never really saw it going much further than that.

Then I started doing some local TV where I’d do little table talk segments. I started getting a lot of exposure and traffic on the site. It seemed like people needed a thing like this, where there’s someone out there helping them and a curated list of cool gift ideas. When it started getting bigger I decided to turn it into a full-fledged website.



Could you take us through the process of how you decide which gift is right for the giftee?

We are very, very curated in our gifts. That’s one of the things that we think has really allowed us to succeed in this and have credibility. We really only pick the coolest ideas. We started out by reaching out to a lot of companies that we thought were awesome.

We work with a lot of independent, smaller Etsy-type companies who are really cool but don’t have the capability to get their product out to a wide audience. We started out by telling cool companies what we’re about and see if they’re interested in working with us, but now luckily we’ve gotten to the point where a lot of companies are coming to us and pitching us their products.

We curate from there. We try to do a range of gifts -- a lot of personalized gifts, a lot of startups will try to get exposure with us and we’ll try to feature a lot of newer companies, companies on Kickstarter and subscription boxes.

What has been your biggest challenge?

My biggest challenge has definitely been the business side of everything. I never went to business school. I never in a million years thought I would start my own company. I’m much more creative-minded. I have a lot of ideas, but there’s so much that goes into running your own business; it’s constant. You always have to be learning, which I enjoy.



It’s pretty much me who works on the site. I have two people who work part-time. I’m dealing with the PR, sales, design, accounting, and bookkeeping. Teaching myself all those things all while running this businesses and traveling for TV segments and trying to find the coolest gifts has been very difficult.

What are some fun things you do as a team in or outside of the office?

One of our interns works remotely from Madison so we mostly do things online with her. We do a lot of brainstorming sessions. We’re always pulling things out from magazines and brainstorming on the latest gifts this year and the ways we can expand The Gift Insider brand.

We’ve been talking about doing a gift concierge service where we more directly help men find gift ideas and also a similar service for weddings. Trying to help users more directly one on one is something that we’ve been really wanting to do, like wedding gift bags, bridesmaid gifts, what to get if you get in a fight with your girlfriend. We’re really trying to brainstorm more of the one on one angles of helping people find gifts.

What advice would you give to any beginning entrepreneurs out there?

I would say to really try and get a team in place. I started this on my own and if I would have started over I think I would’ve tried to find a partner right from the beginning, someone who I knew and trusted. It’s really hard to find someone along the way. I think starting out with a team where you guys are on the same page the whole time is definitely something I wish I’d done from the beginning.

What’s next for The Gift Insider?

We want to grow, we want to have more girls on staff that can help recommend creative gifts. We want to start a service where we can do a little chat and we’ll help you find a perfect gift for your girlfriend, or wedding gift ideas, which I think will be huge for us this season. Just a lot of the things that people wish they had time to do and might need a little help.

Men have really been one of our most needed users. They really are the ones who are always saying they need a site like this. There’s a lot of etiquette and things people don’t know, like what gift to get a girl you just started dating for Christmas and things like that. We want to start working with them a little more personally and make it a more personal experience.



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