My first attempt at validating a startup idea (month 1, business 1 - part 1)

Lindsay Saewitz
10 min readMay 10, 2018

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Back in February I embarked on a journey to try and validate one startup idea a month in 2018. So far, it’s been fun, exciting, stressful, and overwhelming…..to say the least!

Here’s the story of Month #1.

Some Background

As I mentioned in my previous post, I’ve always loved planning social events and activities because I love bringing people together and creating memorable experiences. (I’m also hyper-detail-oriented and love being in control 😬).

My penchant for activity planning dates back to my time as a camp counselor where I’d plan elaborate ice cream raids for my 10-year old campers, into college where I planned nightly activities for the sorority pledges, up through my young professional life in Chicago where I served as the Programming Chair for my local alumni board (not to mention being the unofficial official event coordinator of my group of friends).

In 2010, when the “group buying” concept started taking off, I made sure I was at my desk before the morning Groupon arrived, snagging tickets for me and my friends to Cubs rooftops, wine festivals, and every event in between.

While attending Groupon events, I noticed that very little socializing took place between groups of attendees. After all, the only thing binding us together was our love for discounts. A Michigan alumni event was different — you paid nearly any price (within reason) to hang out and network with your fellow Wolverines.

I thought, why can’t you do both — socialize AND get discounts? Social clubs have existed for ages but don’t seem to capitalize on their group buying power.

And so I launched CitySwarm — part group buying platform, part social club, and a way to experience Chicago in the easiest, most-hassle free way.

Essentially I’d come up with fun event ideas like Kayak & Kick It — a guided kayak tour on the Chicago River followed by a patio party with food and drinks — or the Pumpkin Crawl — a trolley crawl encompassing all things pumpkin — pumpkin pizza, pumpkin patches, pumpkin carving, and of course, pumpkin beer. I’d then negotiate steep discounts with vendors in exchange for the marketing exposure and incremental revenue I was providing, then I’d package it all together, plan the logistics of the experience down to the tiniest detail, and sell the package to customers via email.

Kayak & Kick It, a popular CitySwarm event

There were many problems with this business model. The events were labor intensive (run by me and part-time staff I contracted), the group sizes generally needed to be small, and the margins on event tickets were low. In order for it to work, I really needed to scale the volume of events which meant dramatically scaling the customer database (from scratch, on a budget of $0). I never sought outside capital (I didn’t even know what that meant back then, to be honest🤪).

The bulk of my revenue came from a sponsorship agreement with MillerCoors, and having all of your eggs in one basket is never good. CitySwarm eventually reached nearly 10,000 local subscribers, but it was a slow burn and I was exhausted. In 2014 (four years later) I was ready for a change and sold CitySwarm to another Chicago event company.

The problem that emerged

I started CitySwarm to try and fill a dual need: more ways to socialize at cost-effective prices. I think we adequately addressed this problem.

But at the end, a third problem emerged and seemed to trump the initial challenges I was interested in tackling.

Yes, there were some people that attended CitySwarm events to expand their networks socially, but at least half the attendees (or more) were couples, groups of friends and even coworkers using the experience as a small team outing. The group discount certainly didn’t hurt, and the opportunity to meet new people was a bonus.

But most people attended due to ease.

It was SO EASY to attend.

Every part of the experience was planned from A to Z — from food to transportation, price to dates and times. All you needed to do was buy a ticket, show up, and have fun — without spending any time on discovery or planning.

So, in #bizamo Month 1, I wanted to revisit this need for easy “things to do” but try to tackle the problem in a more scalable way.

How could I provide a fun, unique, local experience with the same level of ease as CitySwarm, but without actually having to lead people in person or be constrained by dates, times, and group sizes?

I decided I wanted to test out the idea of local experience itineraries.

I’d curate an experience just like before, figure out all of the tiny logistical details, and document it all for customers to access. All they had do is grab & GO!

Week 1

Competitive Analysis

With my validation framework in tow, I went to work.

The initial problem statement I started with is it’s cumbersome and time-consuming to find and plan fun things to do.

There are two elements of the problem that impact time: 1) discovering things to do that meet your requirements, and 2) actually planning the logistics — transportation, cost, dates, nearby activities or meals that pair nicely, etc.

To kick things off I did a quick competitive analysis.

When it comes to discovery, there are SO many sites, newsletters, and tools out there covering “things to do”. In Chicago, we’ve got the Chicago Reader, Time Out, Thrillist, Do312, Facebook….the list goes on and on. Tack these on to newsletters you already receive from the individual bars/venues/activity providers, and sifting through all of it to find the right option can take hours on its own.

There’s also an inherent problem with “curated” lists of things to do. They are generally incomplete, as by definition we are only presented with options chosen by the editor (who may or may not have similar preferences), and they usually include things happening on a specific date/in a specific neighborhood — so your criteria must match in order for the suggestion to be beneficial.

I wanted to provide more “evergreen” options with the ability to narrow down itineraries by preference or neighborhood.

The second part of the problem is around coordinating the logistics. Let’s say you’ve decided that you want to go to the Logan Square Farmer’s Market on Sunday.

Yay, let’s go!

Hold up. At times, for some people, winging it works.

What if you have two screaming kids, or a boyfriend that gets super hangry if he doesn’t eat by 1:00 PM, or a grandmother visiting who can’t walk very far? You might want a few more questions answered before heading out. Like, what’s the best way to get there? Is there a place to park? Where can we eat lunch after that’s within a couple blocks and won’t have an hour-long wait?

This second, often overlooked part of the equation — researching and coordinating logistics — can be incredibly time consuming, and the devil is in the details.

With my competitive analysis in mind, I crafted Version 1 of my elevator pitch: [Super Cool Name TBD] will make it faster and easier to find and plan fun, unique things to do around Chicago.

Early Feedback Group

The next part of Week 1 was creating an early feedback group, and my goal was 50 busy young professionals between 25–39 who enjoy maximizing their limited free time. This was the easiest part of the week for me as I have plenty of these folks in my network.

I created a simple email template that outlined my initial value proposition and ended with a question — are you willing to participate in the feedback group?

The initial email I sent to early feedback group prospects

Then I made a list of 48 people to email, including friends, acquaintances, and former colleagues that I thought might be interested in providing feedback. I knew that not everyone would respond or be interested, and my conversion rate was 64% (31 people responded saying they were in). Next, I emailed those people back, thanked them, and asked if they knew one other person who’d be interested in participating. From that effort, I got an additional 4 people on board.

Next I wanted to engage with relevant online communities. I posted on all of my social media personal accounts, then posted in specific Facebook and Slack groups of which I was a member with a pared down version of the email:

Hi friends! I’m thinking of starting a new digital event guide business that makes it easier and faster to find unique activities and itineraries around Chicago (without having to spend hours scouring multiple websites). Looking for people to be in my early feedback group. Anyone interested?? (This is part of a little entrepreneurial experiment I’m running called #Bizamo. More info here > http://bit.ly/bizamoproject_1 )

Through the online communities, I was able to get an additional 11 participants, bringing the total group to 46. I felt like this was good enough to get started.

Surveying the Feedback Group

The last task of Week 1 was creating my feedback survey (feel free to take it!).

I started broadly by asking people about their habits when it comes to planning things to do and then asked about their biggest frustrations.

From there, I solicited ideas for a “perfect solution” and how it might fit into their lives, how much they’d pay for it if it existed, etc. Finally, I introduced the specific idea of itineraries and asked for feedback on if/how it addressed the frustrations.

Snapshot of the early feedback group survey

I emailed the survey to a few people individually and then sent a mass campaign using Vocus.io (similar to MixMax). Overall, 41 people submitted survey responses and Week 1 was complete!

Week 2

Analyzing the Data

Now that the data was collected, it was time to analyze. I’m no analytics expert, but I tried my best to isolate recurring words, themes, and patterns referenced in the responses.

If I noticed something particularly interesting, or noticed that someone seemed extra-engaged in solving this problem, I reached out to ask follow-up questions. In total, I got 23 “extra” responses (about half of the group).

This was my summary of the data:

Some of the results I expected. People are frustrated by the time it takes to coordinate logistics and overwhelmed by the amount of sources out there, wishing that there was just *one source*.

But a few patterns surfaced that I hadn’t initially considered or weighted as heavily.

The ability to sort or find things by personal preference was SUPER high on the list. Also, in addition to discovery and logistics, a third element of the overall problem emerged: getting group consensus. People were frustrated dealing with the group dynamics — deciding on dates, times, places, etc — when more than one decision maker was involved.

Time to Choose

This was the point in Week 2 where I was supposed to hone in on my product and my value proposition, and here’s where things got a little rocky.

Overall, the feedback group reacted positively to the idea of itineraries, but there could have been some biases at play (they were friends trying to please me, I had already introduced the idea, etc.). I was unsure of whether I pulled enough insight from the data, or whether I should spend more time analyzing. I was also unsure of how the findings impacted my initial solution — did the data support my idea, or point towards a different solution to the problem? What was I supposed to do with all this info?

Another area where I felt hesitant was my target market. Many respondents mentioned challenges specific to the people they were planning for, such as families with small children, significant others, and out-of-town visitors.

Startup/Entrepreneurship 101 says to narrow in on the smallest possible target market you can, and deep down I knew I should do this. But like many before me, I didn’t want to choose! Knowing the risks, I still moved forward trying to be everything to everyone.

And so, moving into Week 3, I stuck with the value proposition of a product that helps Chicagoans save time on planning fun outings with friends.

You might be saying to yourself…..but what is it? And that’d be a fair question.

At this point, while I wanted to move forward with my itinerary idea, I was still questioning the data and unsure if this was a solution to the problem. I was also resisting “picking a side” — both in concept and target market — and purposely kept the elevator pitch vague.

How did this turn out? You’ll have to wait until the next post which is hopefully not too far behind.

For now, I’d love your thoughts!

Did you go through a similar process to validate your own idea, or did you just launch it?

Is there a key part of the process I overlooked? Did I pay too much attention to the data, or not enough?

How would you have changed the value prop after seeing this data?

Comment below or feel free to send me an email anytime at lindsay@bizamo.co.

Other ways to connect:

  • Subscribe to the #Bizamo email and stay updated on the latest happenings / get involved in providing early feedback
  • Click Follow above to follow me on Medium and get notified instantly of new posts
  • Check out bizamo.co for updates as new businesses get launched!

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Lindsay Saewitz

Entrepreneur, startup/small biz enthusiast, wannabe creative, lover of the hunt. Recovering self-critic. Karaoke singer with affinity towards all 90’s jams.