Mar 01 2013

My Start-up Journey

  • Posted by: admin

Hi Everyone!  This week marks my six month anniversary at Dashfire and next week, we’ll launch a new Dashfire competition that I’m spearheading.   The competition is focused on digital startups, Chicago collaboration, venture capital, and business school – all components of my journey from Wall Street to River North (I don’t think “digital prairie” is very flattering) over the past 3 years.  As such, I wanted to share some my experiences with you:


I wanted out of finance in 2009.  Partly because we were amidst the financial crisis and partly because I was no longer feeling challenged.   I could handle the hours (and don’t get me wrong, the pay was awesome), but the value we created for our clients was not tangible – especially as an analyst.  I wasn’t ready to take the leap into my own venture (I hadn’t found a problem I passionately wanted to solve, I can’t code), so I chose to attend business school at Kellogg as a reformed financial professional.

I know many people question the merits of business school if you want to pursue entrepreneurship.  Why take loans, you’ll end up back in banking, etc., but I believe that business school can be a breeding ground for founders – if you are committed (i.e., don’t work at McKinsey your first summer).  I took the following approach:

It’s no different than recruiting for a banking or consulting job.  You connect with the influential professors and alumni.  You attend all the industry events and you craft a course load that prepares you for your future.   For me this consisted of working closely with people like Mike Marasco and Carter Cast, joining the e-club and Wildcat Angels, and enrolling in an entrepreneurship heavy schedule.   All other time was spent with classmates ideating on new startups (and enjoying the fine establishments Evanston has to offer).   At the beginning of 2011, I was connected with a CS professor who had developed a promising technology, acquired interested customers, had access to angel funding and a team of developers.  Importantly, the technology’s initial application was in the soccer industry, a sport I had played my whole life and followed religiously.  It was the perfect coupling of a startup and one of my passions.  I convinced the professor to let me help him run the company and I spent the summer between my first and second year working full time on the business.

I enjoyed the ride over the summer.  I worked out of a co-working space, attended TechWeek, and managed a team of interns.  I also worked my ass off. I researched the market and competitive landscape exhaustively, established strategic partnerships, managed product development, and leveraged the Kellogg network to meet with professional soccer management teams.

By the end of the summer, after countless late nights, piles of research, hundreds of conversations with potential partners, and highly informative powerpoint presentations, we did not have a single new paying customer.  I reiterate, not one.  The summer wasn’t a complete failure. We knew the market better, grew our brand awareness to a small degree and added features to the technology to please our existing customers, but overall, our progress was not where I wanted it to be.

At the time, I thought I had done everything right and believed our lack of success was a consequence of the product.  I realize now that I was wrong.  The product – given the maturity of our company – was acceptable.  I just failed to sell it. More specifically, I failed to do the following:

  • Create a Brand Identity: Because our product was still in beta and open to changes, I focused on selling an idea and not a brand. We didn’t have a “voice” or cohesion among all of our external communications and people were confused about what we offered and how we were different.
  • Enterprise Sales: I had never been involved in an enterprise sales process and didn’t understand the lifecycle, approach, measurement, and importantly, closing.  I learned how to over the course of the summer but even as a technology driven company, sales was the backbone of the business.
  • Manage Messaging: I thought by hiring interns with relevant backgrounds that they would be a cheap way to manage our entire digital marketing. I didn’t realize that they needed direction on choosing the right outlets to target, how to increase engagement and more. Interns should be used for implementing strategies not creating an entire campaign. Writing a blog post doesn’t add any value if no one reads it.
  • Integrate Strategy & Technology: I spent hours with the development team brainstorming new product features. Just because a feature sounds cool does not mean it should be built. It’s essential to understand the importance of balancing the desire for new features with the strategy and testing behind each incremental feature release.

Like many others, my startup journey has been a road filled with success and failure. There is no perfect way to operate a startup – there are a number of right ways most of which are born out of failure or realized retrospectively.   At Dashfire, we work with ambitious and passionate entrepreneurs who are building their own path.   We are excited to continue to extend our platform in Chicago.  Stay tuned for our new program next week!

  • Piyush K Desai

    Great blog and great journey!!


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