Dan DiGangi - Software Engineering Manager, Tech Instructor/Mentor
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Leaving Behind $60k, Corporate Stability, and a Big Data Startup


If you don't happen to follow me across social media (yet), I've recently made an announcement that I decided to leave my job behind at ClearStory Data as a UI software engineer. It was a great 7 months with the team but it is time for me to move on. The bigger story here is that this is the 2nd job I've left in the past year. I first left my position as the lead web developer for Apartments.com in order to pursue a career with ClearStory Data.


I worked for Apartments for about two years. It was another valuable experience in my career that I cherish. I spent a multitude of time practicing my craft and also helped push forward their front end technology. I led projects including a site wide responsive redesign and rebuilding their DoubleClick advertising platform that presented millions of impressions to consumers daily.

Towards the end of Q1 2014, an impending buyout by CoStar Realty Group had finally closed for about 600 million dollars. Crazy, right? It was in the top 5 largest buyouts in Chicago that year.

If you've never been part of a buyout process, as an employee, there are two eventual outcomes you can look forward too:

  1. You'll receive a new contract under the purchaser and continue to have a job
  2. It's time to start hunting for something new

Per the leadership of then CEO, Dick Burke, nearly every Apartment's employee retained their job. I wasn't too worried at the time as I was the star front end developer for the company. Thanks to my efforts early on that year, I had already received nearly 10k+ additional compensation on my salary along with several bonuses.

During the final weeks of the buyout, each employee was sat down in a conference room where we were to discuss our new contract. Frank, CoStar's CIO, began to read through the contract I was being offered.

I was first told that my salary would be jumping over 25k.

This pushed me just over a light 6-figure salary. Not bad for a 24 year old I'd say. But... he continued. I was going to be offered 10k in stock incentive w/ a 4 year vest. At this point, I was beginning to sit on the edge of my seat in excitement. He continued. Lastly, upon my completion of one year's time with CoStar Group, I would be receiving a 50k retention bonus.

Excuse me? What did you just say? Fifty thousand dollars as a bonus?

I'll never forget what I did next. A giggle came out of nowhere. Both chief technology officers smirked. It was amazing and I accepted graciously while still in the room. Who wouldn't?

About 4 months later, one of the few recruiters who I actually like contacted me about a new developer role for a startup. I was hesitant to schedule the call but being one who seeks opportunity, something about it felt right. A few days later, I scurried to a quiet place on lunch in order to discuss the role with the chief UX architect. It was a great conversation and without knowing much about their software, I got excited.

I decided to take the chance by interviewing in person to see where I landed. Things continued to move forward positively and I was offered a position. Exciting as it was, I had a big decision to make. It had only been about 3 months since I received my CoStar offer. I had enjoyed the increased salary but the other perks were a long ways off.

The Decision

Truthfully, I had thought the decision would be more tough. I hadn't had issues with Apartments generally minus some normal gripes with corporate bureaucracy. I did however begin to feel as though I was not learning and code felt hacky. Hearing about the technologies the startup was using and quality of their developers, my instincts said it was what I needed to do. This meant giving up my amazing office, great friends, corporate stability, and most abundantly of all, the amazing offer I had received not so long ago. Looming on the horizon, CoStar Group has also planned a massive rebuild of the Apartments website that I would play a key role in.

I had thought those things were what would weigh heaviest on me but it ended up being something entirely different. The drivers behind my decision were two fold. First, I wanted to learn. I wanted to be surrounded by star developers in order to push my learning experience. The second, the more important of the two, is my want to build my own products. Startups are core of what it means for someone to have an idea, build it, and take it to market. It is something I've wanted to do for years but never got quite there. I had done plenty of work under the guise of my company Adexa Media but nothing felt substantial. And, with that, I left behind Apartments.com.

Saying Goodbye to a Growing Startup

I spent the better part of 7 months working with the ClearStory product. They are a fast growing startup on track to be a top tier company in big data analysis. The team houses some of the smartest people I've ever met. It was bitter sweet making the decision to leave but it's what needed to happen. It was a mutual decision between both sides.

I knew going into ClearStory that I needed to improve my programming skills. If you have ever worked in a startup that bootstraps or procured funding, you know that every minute and every dollar matters. While my skills improved significantly prior to and throughout my journey, my ability to produce was slower than I and them would have preferred. And, with that, I left behind ClearStory Data.

Hello, Miami!

I had no qualms about finding a new job but figuring out what I really wanted to do was a mystery. I decided to buy a one way ticket down to Miami to visit a close friend. I had no intention of returning. After a fun week of partying during Miami Music Week, my friend and I began to discuss moving into together for a fresh start. I've been living in Chicago since I was born so a new place excited me. We began moving forward quickly.

Derailed Plans

A few days earlier, a previous associate contacted me about an introduction to someone who was looking for a UI/UX designer with skills in programming. I jumped on the opportunity.

We met at 1871 aka the Merchandise Mart. Our conversation revolved around a new business idea. My original intention was to take on a contract role to help launch the MVP. Our conversations quickly turned into something more along the lines of taking on a co-founder role that focused on developing the product's technology stack. I had hoped for the potential of a telecommute role but collaboration during a stage in which we are developing a brand new product would be only setting us up for failure. This quite possibly was about to derail my plans to move to Miami.

It wouldn't be easy to dismiss the idea of moving to there so I spent time with some of my closest for advice. I researched the business, economic patterns, and reread the business plan at least 10 times. The creative side of my mind began to take off with ideas. The potential for the business was very clear. And, with that, so long Miami.


When I began writing this long winded story, I wasn't sure exactly of what my intention was for you as the reader. As I sit here preparing the final statements, I know exactly what I want to say you.

The past couple years have pushed me into some of the hardest decisions of my life. My brain fought hard to continue the habit of staying safe. But, no more. Nothing great ever came from sitting idly by on the sidelines. I want to live a life of calculated risk, not regret.

If you have the vision to look past short term reward at what could be, you'll become empowered. If you have the confidence to jump in the deep without knowing how far you might just sink, you'll be inclined to swim harder. If you are like me, you want more. You crave it. You need it.

Don't let your brain's survival instinct deter you from taking risks. Let yourself fail but let yourself learn. In the end, I can't see a situation where you don't come out on top.

- DD