Innovators: Co-Founder and CEO of Stray Boots, Avi Millman

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Innovators. They come in many forms. They dream big but they aren’t just dreamers. They form raw ideas into cool products with disruptive business models. They shatter entire industries and leave established leviathans running scared with their tails between their legs. The Innovators interview series connects you with the most driven people on the planet. What makes them tick? What advice do they have for tech founders? What tools do they use to get the job done? Read on to find out.

Avi Millman, Co-founder & CEO of Stray Boots, has spent his professional career rapidly growing businesses. After graduating cum laude from Princeton with a BA in History, he joined national apparel retailer Steve and Barry’s, working for the COO in its internal consulting group. Rising to Director of Logistics, he grew the company’s supply chain systems from handling 60 stores to over 200 in two years, supporting annual sales of over $500 Million. He then went on to join beverage startup Q Tonic, now Q Drinks, as the fourth employee, where he grew top line sales by 500% in one year, adding prominent clients such as the Four Seasons, Waldorf Astoria, and Fairway Market. An avid traveler and life-long game enthusiast, Avi started Stray Boots after a trip to Rome, where he realized the guidebook experience was far too passive for the digital era.

What do you enjoy most about your work and why?

Though it’s corny, what I most enjoy is seeing smiles on customers faces and knowing that we’re creating incredibly happy, memorable moments in people’s lives. We’re not just creating a new feature or a way to make money; rather, we’re giving people a way to have fun together and actually do something in the real world that adds value to their lives. I regularly look at our customer photo feed and that makes me appreciate why we started doing this and continue to pour ourselves into the work. Reading customer emails about how much they learned doing our tours and what an amazing time they had really makes the hard work worthwhile on a day in and day out basis. For instance, one mom emailed us about when she and her daughter returned home from one of our games, she had no idea how much her daughter had leaned until her kid started relaying all of the facts to her husband.

Where does your passion come from? What drives you, inspires you, excites you?

I’ve always enjoyed traveling and have played games my whole life, so Stray Boots combines two of my strongest passions. As a history major in college, I spent my days learning about different people, cities, and cultures, and being able to work on something that builds on my interest in that regard is great. And before I started the company, I would spend my weekends just walking around random neighborhoods in New York. So starting a company that relates to those things I love doing felt completely natural. I also have played all sorts of games since I was a little kid, but particularly ones where you have to solve things to win. Whether it was playing Scrabble with my grandma, doing a crossword puzzle with my mom, or trivial pursuit with the whole family, I’ve always been a competitive trivia-file to make up a word. I consider myself extremely fortunate to be building a business that relates to multiple of my life-long interests.

Someone reading this wants to start a tech company. What’s your best advice for them?

My biggest piece of advice would be to stop strategizing and go do something. Until you put a product to market, try a marketing strategy and it flops, or pitch investors and get rejected, you’re just dreaming about starting a business. I spent a good 3-6 months writing a business plan and strategizing how Stray Boots would work before I did anything really meaningful. In retrospect, it was all a big waste of time. Not until I had the personal financial pressure to start selling something, did I actually start building a product that would ultimately be refined into what the company is today (at the time that was holding public paper scavenger hunts in different parts of NYC). And the truth of it is I could have done it on day 1, as opposed to day 181, and I would have been six months ahead on learning about my customers, the marketplace, what technology to use, and so on. The first paper hunt I did was worth 1000 times as much as all the financial modeling I’d done in Excel up to that point, even though it’s nothing like what we offer today. So build a prototype and put it in front of customers. Don’t worry about the company name or the colors of your logo or anything else like that. Just start building and selling, and the rest can be adjusted and will ultimately fall into place.

What are a few tech startups that you’re really excited about right now and why?

PublicStuff, one of the ERA companies that preceded us, is doing one of the most meaningful, smartest things in the tech industry today. Their platform gives municipalities a portal through which everyday citizens can report things around the city that need fixing (a traffic light that’s gone out, a sign that’s fallen, fire hydrant that’s running water, flooding on a highway, etc). I think they’re fundamentally changing the way that cities respond to the needs of their citizens, empowering citizens by creating a super-easy way to improve everyone lives, and improving efficiency a ton in the process.

I think Smartling is fantastic. The ability to translate content dynamically is huge for globalization. Obviously we see direct relevance to what we’re doing as a travel brand, but the way they apply both advanced technology and a practical human touch to solving translation problems is terrific.

I really love SmartAsset and Grovo for trying to help educate people about solving real-world, complex problems. SmartAsset helps people navigate complex financial decisions while Grovo helps educate the layperson on new web tools and technologies. To me both are incredibly practical and valuable for staying informed in a rapidly changing environment. Given the questionable reliability of answers you get when you Google “how to do XYZ” or the outdatedness of results for “how to use this website,” these central informational repositories for up-to-date and expert information should be extremely valuable

What tech tools (websites, apps, gadgets, etc.) do you rely on both for work and in your down time?

I use Dropbox like a fiend. We use it in the office as our way of sharing and syncing files, and I even use it with my grandmother for sharing photos. Their mobile apps are great.

Venmo is another tool that’s just brilliant. We use it around the office all the time when someone buys lunch or coffee for the group, and in terms of splitting a bill with friends or roommates, it can’t be beat. Best part about apps like Venmo and Dropbox is that they pride themselves on utility and simplicity above all the bells and whistles. They don’t worry about changing UI just because they’ve become bored with it. It remains consistently easy to use and of immense value.

Wikihood is one of my favorite apps. It geolocates wikipedia information to places around you, so for a history nut like myself it’s a really phenomenal tool.

When it comes to staying up to speed on things, I love Flipboard. It allows me to browse news on my iPad in a fraction of the time, and from a diverse range of sources. Only complaint is the repeat-content you end up getting when one story is picked up by multiple sources.

Speaking of news, one of my non-tech friends tipped me off to this website called The Browser, when we were talking about what we read (I’m generally an NYTimes guy). The Browser’s great, their motto is “Writing that’s worth reading” because they have human beings curating the most interesting articles from around the web. They’re approach to curation for news articles what we’re trying to accomplish with our tours, which is to hand-select the best places to go based on folks who have great taste rather than rely on user-generated or crowd-sourced selections of just the most popular stuff. The site makes for a wonderful read.

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