Ethan Denney

8 Reasons Why We Chose to Move ConvertFlow to Chicago

As founders of a SaaS startup, we recently were faced with a big decision. A decision that would have a major impact on our lives, and on the success of our new company.

Like many startups, we started in our hometown (Miami), but knew we needed to relocate to a city with access to mentors, partners, and investors in our industry to have better chances of growing quickly.

In summer of 2016, we were fortunate enough to get accepted into Techstars, and participated in their Chicago program.

While we liked being in Chicago during the Techstars program, my co-founder and I had previously decided to move to NY after the program was over. That had been our plan for more than a year.

But then, reality hit. Coming out of the program, we saw that competition in our market began heating up quickly. We realized that if we wanted to stay ahead, we would need to hunker down and hit the ground running. So, we began asking ourselves… is moving to NYC right now really what’s best for our company?

We started getting real about what our values and goals are. After considering how to best make use of the resources we have at our disposal, and after researching the pros & cons of moving to New York City, San Francisco, Chicago and other startup hubs around the country, it quickly became apparent to us — that Chicago was the best city to move ConvertFlow to.

So why would we pack up and move from sunny Miami to Chicago?

Here are 8 reasons why we chose to move our company to Chi-Town…

1. Alignment is key to a startup’s growth

My co-founder and I had already built and run a few businesses. Some were in alignment with our skills, values, the needs of our customers, and what was right for the industry at that time, while others weren’t. Needless to say, the ones that weren’t aligned correctly, failed or just faded away.

However, each business that was in alignment with the forces that create the right conditions for building a successful company, got traction fast. And while the “aligned ones” still required a lot of work, it didn’t feel like we were swimming upstream.

For each fast-growing business we built, it felt like the wind was at our back, and we fully believed in what we were doing. I think every experienced entrepreneur would agree that you always want the wind at your back, when you’re building a company. If you feel like despite your best efforts you can’t get some momentum compounding, then get ready to pivot your company into a version that does.

Looking back, we realized that our startups that weren’t properly aligned with those market forces just didn’t hit it off. Any sort of growth took extreme amounts of work. And behind most of our actions and decisions, there always seemed to be this underlying feeling that we weren’t doing the right thing.

So, when building a new business, always be on the lookout for that underlying feeling of misalignment. Sometimes this unspoken truth is very apparent when making big decisions about your product and / or company.

In other words, if your gut is speaking, listen to it. In many cases, you’ll find that it’s best to follow it.

Fortunately with our latest venture, ConvertFlow, there’s great alignment between our team’s skills, values, what our customers need, and what the industry is ready for. Yes, timing is a big part of alignment. That’s why it’s always a big part of success.

The ConvertFlow brothers with Infusionsoft CEO, Clate Mask

For my co-founder and I, the results from this kind of alignment have been great. The wind has been at our back.

For example, 4 days after starting our paid beta last Spring, ConvertFlow was selected as Battle of the Apps Champion by Infusionsoft.

They gave us the award and endorsed ConvertFlow to their community at their annual user conference.

Going into summer time, we started developing relationships with top experts and CEOs in our industry, and were accepted into Techstars. Since August, we’ve started marketing heavily, and our revenue and customer base has been growing quickly.

And while all of that was happening over the summer, 2 developers on our small team essentially rebuilt our entire product, so it would be ready for our next stage of growth.

While all of this was going on, we asked ourselves this question. If we’ve already reached this level of momentum and alignment, why in the world would we shake things up, and potentially screw up what’s working, by leaving the city that was nurturing our company, and fostering our rapid growth?

For reasons that I’ll explain below, it was obvious to us that Chicago and ConvertFlow were well aligned, and building out of Chicago offered us an opportunity to grow much faster.

2. Startups need support, and so far Chicago has had our back

Let’s be honest, startups need all the support they can get, especially when they want to create the best conditions for success.

From what we’ve seen so far, Chicago has a really supportive startup community.

While, it isn’t as big as the coastal cities like SF and NYC, Chicago’s growing community is still small enough that there is a “pay-it-forward” mentality, and everyone seems to want to play a role in helping the startup ecosystem succeed.

We can attest to this. While much of the mentorship we’ve experienced came as a result of being selected for Techstars Chicago, simply being inside 1871, attending events, working at local coffee shops, and living in River North, has connected us with top-notch mentors and other talented people working in the technology and marketing industry.

These kind of collisions didn’t happen very often while we were living in South Florida. And after living in NYC, and visiting the Valley, we’ve noticed that people here in Chicago, genuinely want to help you out more.

Entrepreneurs are collaborating to host great events for everyone to attend. VC firms and angel groups are working together to support the community.

Co-working spaces like 1871, and companies like Designation and General Assembly are providing the space and workshops needed to cultivate a growing startup community.

Plus, we have Technori, Chicago Tribune and Built In sharing the latest in local startup news.

Based on who we’ve met so far, the founders and people involved in Chicago’s business community, in and outside of Techstars, have been helpful, humble, and have gone out of their way to connect us with people they thought could help us be more successful.

Hey, maybe it’s just Midwestern hospitality, or maybe Chicago is actively looking to create more success stories that will attract more startups to the Midwest. Either way, we like it.

3. We’re optimizing for building a meaningful, successful company, and NOT for unicorn culture

In case you didn’t know, Chicago is home to many startups that have built great businesses. This is something my co-founder and I value greatly.

Basecamp, Sprout Social, Active Campaign, Groupon, GrubHub, BrainTree, Trunk Club, Sure Payroll and Belly are just a few of the many companies that were founded here. Many have downtown offices within blocks of each other.

Unlike Silicon Valley’s focus on breeding billion dollar unicorns and the pressure it creates for many startups to prematurely raise too much venture capital, Chicago’s focus appears to be different, and far more pragmatic.

What we find refreshing about Chicago’s startup scene is that it reflects Chicago foregoing to build an economy around trends popularized by the media, and instead, people here are more practical, and focused on building companies that are going to be around for the long term.

4. Chicago offers a pool of tech talent for early-stage startups to draw from

Our team is currently working out of 1871, Chicago’s most popular incubator and co-working space. It’s really cool when you see designers, developers, sales reps in Tech running around everywhere.

After doing research on Chicago’s talent pool, and comparing hiring talent here, versus other tech hubs, we’ve concluded that there’s a lot of opportunity to recruit talented team members early on, before they get swayed to move out to the coasts.

In a recent article in the Huffington Post, Kevin Willer, President and CEO of Chicagoland Entrepreneurial Center (CEC), said “we have two of the top five business schools, five renowned design schools, and access to several universities with leading computer science programs. It’s not that the talent isn’t here, it’s that we are tasked with keeping them here.”

For early-stage startups like ConvertFlow, hiring great talent without breaking the bank, and not having to compete with mammoth-sized companies like Google, Apple, Facebook and Tesla for talent, is ideal.

Or put another way, Chicago’s current environment offers optimal conditions for building an early team, and growing our company fast.

5. Growth, branding, fundraising, mentors, investors: Chicago’s got it on all levels

During Mentor Month at Techstars, we got to experience a month of accelerated networking with some of Chicago’s top entrepreneurs and investors. And I have to say, the expertise is here.

Whatever we could need help with at our current stage, and the next few stages of our company, there are experts accessible here that have more than enough experience to help us get to the next level.

Growth, sales, design, branding, culture, marketing, fundraising — We met plenty of experts in all of these areas during Mentor Month, and we know that’s just scratching the surface when it comes to the kind of expertise available from within Chicago’s startup community.

6. Higher margins create greater paths to growth. Chicago’s startup ecosystem makes them possible

Considering the nature of most startups, resources are tight enough as they are. So, anything a young company can do to create higher margins will help generate the funds needed to experiment and reinvest in growth. Obviously, this creates better conditions for success.

By relocating to Chicago, we’re able to conserve cash and keep our operating costs lower than they would be in San Francisco or New York. And we can still benefit from the momentum that comes with hiring from a strong talent pool and having our team work together in person.

As an added bonus, rental costs for office space in Chicago are much lower than in many other startup hubs located in the United States.

Due to the lower cost of living, hiring early team members is a lot more affordable for us in Chicago, than if we were hiring in SF & NYC.

We did some research, and numerous studies show that while Chicago’s average salary for developers is significantly lower than in coastal cities, salaries go a lot further because of the lower cost of living. Hiring the same type of developer in New York or San Francisco, might cost us $20,000-$50,000 more a year.

Paying that kind of premium for salaries would come at the cost of valuable customer acquisition budget, incentives for our team members, runway, or anything else that may contribute to growth.

7. Chicago built the best place for tech collisions in the Midwest — 1871

Anybody who’s been there would agree that 1871 is simply an amazing co-working space. It currently houses over 400 startups, and is bustling with high-energy designers, developers and entrepreneurs.

1871 was founded by Chicagoland Entrepreneurial Center (CEC), and led by CEO, Howard Tullman.

1871 is at the epicenter of most of Chicago’s tech and startup scene. It hosts everything from Techstars Chicago to Fireside chats with industry leaders, events, meetups, and incubators for almost everyone in Tech. It also attracts lots of tech talent from the nearby universities.

Within a few feet from our desks, ConvertFlow’s team has easy access to experts in almost any area of growing a startup, as well as quick access to VC firms and angel groups.

Needless to say, it’s a really convenient place for us to work from, and offers great conditions for attracting early team members, while getting initial traction.

8. Chicago is a great city for us to land and expand from

The ConvertFlow brothers

When considering all these great reasons, it’s easy to see that Chicago is a great city for ConvertFlow and other startups to build from at an early-stage, and as they grow.

Like many companies, as we grow, we may find it necessary to open more offices, so we can develop a presence in the coastal cities.

But for a tree to reach such heights, it needs to grow in the most fertile soil. And that’s why we’re so excited to call Chicago our homebase, and be a part of its growing community.

Oh, and we almost forgot to highlight this very special reason for choosing Chicago.


1. We get to work alongside some of our amazing local batchmates in our cohort; Bright, Logic Gate, EatPakd, Jio, PartySlate. And I’m sure our non-local batchmates, Fitbot (now True Coach), BrightWork, CompleteSet and Arena, will come to visit.

2. This city is home of the World Series Champions, the amazing Chicago Cubs

Source: The Onion

Guess what?

The Cubs won the World Series the same day my co-founder, Jonathan, and I arrived from our cross-country move from Miami.

Coincidence? 😉

By the way, if you’d like to connect, feel free to contact us at

About the author
Ethan Denney
Co-Founder & CEO, ConvertFlow
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Ethan is the Co-Founder & CEO of ConvertFlow. He loves reading about and sharing anything that helps marketers convert more website visitors.