No Approval Needed

This is where the walking tour came from

I’ve been pretty active writing and talking about Free Chicago Walking Tours in the last couple of weeks. I mentioned it in the last blog post, I have been posting a bit on Facebook and I emailed just about everyone I could think of about our Friends and Family day in April – which will be the first time we get a chance to show off our tours. So all that being said I am not going to say too much about Free Chicago Walking Tours, but just write about how the heck we left the country last January and returned with a tour business.

Spicy Chile

I have to hand it to Lindsay on this one. She came across the first of many free walking tours in Santiago, Chile. We absolutely loved it. Wish we would have known about it earlier in our trip. We liked it so much in fact that we took another one while in Santiago and wrote an entire blog post about them. We didn’t know back then that less than a year later we’d be working on launching our version over 5,000 miles away.

We took advantage of walking tours – both free and paid – for the remainder of our trip. La Paz, Cusco, Lima, Quito, Cartagena, Bogota, Miami, Bangkok, Chicago, Washington D.C., Charleston, New York, Siem Reap, Puno — we did walking tours everywhere, genuinely all over the world.

Free Chicago Walking Tours is born..kind of

Lindsay and I took a walking tour around Quito in June and fell in love with the guide and the city. The gal giving the tour had 42 people show up, I couldn’t believe it. I assumed that it was going to be a disaster. But she killed it. Did she lose a few people along the way – absolutely, but we still must have finished with close to 35. I gave a generous tip and started picking her brain on how the whole business model worked. How does she make money, how does the company make money, how do they find guests, how ofter she does it, are there other guides, is she licensed, is this her only job, etc etc etc – if you have been on a tour when I am “feeling it” then you know I can really lay it on thick with the line of questioning. And she just kept answering and answering and answering. Later that night I went back to our apartment, searched for URLs that had to do with free Chicago walking tours and no more than 30 minutes later I had purchased plus another 20 or so URLs for other cities in America. In total it was roughly a $300 investment. A week before we had spent $500 on a lunch in Lima – so this seemed like a great deal.

The next night – which in hindsight was way too soon – I posted a job on the website elance (they have since changed their name to Upwork). This is a site where little Joe Schmo’s like myself can find freelance workers. Looking back I realize I had zero clue what I was doing. I didn’t have my requirements, I didn’t really have a design in mind, I wasn’t sure how the functionality of the site would work – I had nothing. I had excitement and a few hours later I had my job posted. I was familiar wit elance because back in the beginning of our trip I was testing the waters of the site by looking for freelancers to help me with me SEO (search engine optimization) for No Approval Needed’s website. Lindsay put the kabash on that pretty fast with saying something along the lines of “I don’t care if strangers never come to our site, it’s for our family and friends. And shave that beard you look gross.”

My post was “Website design and creation”. I just re-read my job description and cringed. I ask for an experienced designer to “bounce ideas off” and that I will have a “two-phase” launch – nothing that would have helped someone prepare for what they were getting into. And all for under $500. I had 15 proposals. Another unexpected bump in the road. Do I interview these people? Skype? Some had world-class proposals and were suggesting what I wanted (even though I didn’t really say what I wanted) was going to cost somewhere between $1,500-$2,500. Some didn’t have a good grasp of the English language. And some just seemed to be promising everything for $498. One guy stood out. TTG Design. These guys have been great. I’ve continued to work with them to this day. For less than $500 they built the site, designed a logo and handed me the keys.  Now my total investment is up to $800.

What I really wanted to do..

At some point between Quito and our brief stint in the USA I had an idea to bring on homeless people as the guides for the tour. I believed that this would be an excellent way for individuals to make money and they would be able to share their incredible stories with the guests. Win-win. I went as far to contact a couple of companies that offer public speaking courses to see if they were interested in donating their courses as part of the program. I spoke to a a couple people that work with non-profits helping find employment for homeless people as well. In the end I just couldn’t pull it all together. One day maybe.

There were two main reasons I didn’t pursue this route. The first was I wasn’t confident that I could develop a training program and implement in time for a spring 2016 launch. I had no experience with something like that. The second was that 90% of people that I told this was my plan (20-30 people total) all gave me a look of confusion. Many thought it came off as exploiting the guides awful living condition, especially if I was going to market it that way. Change of plans.

Each day we get closer

I have no previous experience doing this sort of stuff. Neither does Lindsay. Her dad owns his own business and my dad used to and so did my brother. But we really were never involved in any of the operations. What I have found out – whether this is right or wrong – is that so long as we just keep on trucking we make progress. It can be boring some days and break neck pace the next. It’s all over the board. We’re learning, we’re having some fun and I’m really happy with where we’re at.

As of today there are 7 guides signed up to be a part of Free Chicago Walking Tours. I am an officially licensed City of Chicago home-based business. We’re registered as a business on Google, Trip Advisor and Yelp (no reviews, yet). I’ve had two marketing pieces designed and printed (postcard and a mini brochure).  Our Facebook, Instagram and Twitter accounts are starting to come out of hibernation little by little. Our reservation software system is live and running. I’ve begun to build an email list through Mailchimp (thanks Mom for signing up). I’m really happy with the content that is on our Free Chicago Walking Tours blog and I have sourced more content through Upwork at what I think is a great price. And if anyone wants to write an article and have it published on blog – let me know, we can figure it out.

I have no idea what is going to happen next. We could just as easily have an unbelievable day on April 10th as we could have terrible weather or no one show up. We shall see. I’m as excited as I ever have been about this. I’ve learned a ton and will continue to do so. Feel free to send me any comments or questions through this blog or directly to me at


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