SimpleForms Is My Startup of Choice

25 June 2016
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SimpleForms was not the first startup that I have had the opportunity to engage. Over the course of my career, I have had the privilege of speaking with many startup companies about potential work roles. Every time I entertained one of these conversations it ended in hesitation and a lack of earnest motivation for that company. It’s not that all of these companies were unfavorable or had unrealistic business models, but something didn’t fit for me personally. In most cases, I knew one of the core founders of these potential startups from my time at Loyola Marymount University, but the personal relationship was more valuable to me than trying to add a business relationship into the mix. At the end of the day there was not enough critical momentum to overtake the motivation I felt for my existing role combined with forecasted opportunity from the startup.

Regardless of not finding the right fit in my ongoing search for a potential startup job, my interest in the startup community never wavered. Continuing to learn about new companies and watching more mature startups take leaps into full fledged corporate status continued to capture my attention. While I reached a point of relative comfort in my role as a technology consultant, the more I considered the risks of giving up that comfort…the more I realized that my experiences had prepared me for the unknowns of startup life. I met Emily Rotolo, CEO of SimpleForms, through an introduction from one of my Loyola Marymount fraternity brothers. I was having lunch with him one day and had mentioned my recent feelings of wanting more out of my career. He said, “Hey my cousin has got this project she just started and I consider her one of the smartest people I know. She went to a Jesuit school just like us, Georgetown, and I would be happy to connect you, but I’m not sure it’s anything you would be interested in.” I told him I was interested.

My attitude forever has been that I will always entertain an initial conversation with just about anyone and any company if there is interest in learning more about them. My justification has been that you can never really find out if opportunity is beckoning unless you are willing to meet people, learn what they are working on, and ask questions. So in November of 2015 I met Emily in Venice beach and got to learn all about her vision for SimpleForms. I’ll be honest, during that first conversation I was not entirely clear on how this idea would become a business but Emily’s passion was unwavering. The point that was initially clear to me was the addressable market (all working individuals in the United States) and my belief that any company coming close to providing this functionality offered it at a much higher barrier to entry as part of an all encompassing application platform for HR. Aside from Emily’s passion, she proved to me that she knew how to network with people and that she was extremely well connected to resources in every category of necessity for a startup company (e.g. investors, advisors, developers, salespeople, experienced startup founders, bankers, marketers, designers).

That first conversation stretched from one restaurant that closed, through a long walk to another coffee shop and lasted much longer than either of us expected. I took this as a great sign. We were able to communicate effectively and get on the same page about SimpleForms. After that first conversation, I agreed to think about what value I could bring to Emily and take more time to fully internalize the business model. A large part of my early thought process involved what I would have to do to balance two jobs effectively. Emily set big expectations for what she was doing in the meantime. She had a developer already working on a first run of the web application. She was in talks with another developer to take over and get an MVP ready by March 2016. She had experienced advisors already reviewing her business plan and providing guidance for fundraising. I was impressed to say the least. Emily was not someone that was going to sit still. She was going to do what she could every day to bring her vision to life, and it was this trait that sold me on working with her above all else. To abandon career comfort for the many twists, turns, ups and downs of trying to create and run a company…the ability to push forward at all costs is an absolute. True Grit.

Initially, I thought that I would have no problem balancing my “day job” with the early needs of SimpleForms. I quickly learned that because I was more interested in working on SimpleForms, I had to consciously ensure my “day job” responsibilities did not go by the wayside. It took a few months to truly balance out because I’ve never done such a thing before. Not to mention, I figured out how to make multiple trips to San Diego from Los Angeles to meet with Emily and the growing team. We went to New Orleans to present at Collision conference…that was a fun trip to figure out while still taking personal vacation in the same month. You begin to realize very quickly that your time is everything, and learning to manage it effectively is paramount to accomplishing the crazy number of tasks facing you every day.

It amazes me to look back to November last year and realize all the things we have already achieved together. At the beginning, it felt like one foot was in technology consulting and one foot was in SimpleForms. Now it feels like everything is leaning into SimpleForms and I’m planning my move to full time. I will be trading comfort for risk, but it won’t be my first time going down an unknown road with no directions and a changing destination. I can’t wait!

Feel free to email us or message us if you have any other compliance tips or questions!

Written By: Emily Rotolo Founder & CEO

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Simple Forms Employee Onboarding Software

Streamlining completion, compliance and storage W-4 forms, i-9s and W-9s. We build in a custom forms portal and keep you fully compliant against audits.

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