Meet Elevate EIR Cy Megnin

Elevate EIR Cy Megnin: “I have had my highest highs and my lowest lows as an entrepreneur…


Cy Megnin has been an entrepreneur, founder and advisor for the past two decades. Past companies include Intel Capital portfolio company PrepFlash, an AI company that uses NLP to automatically create flashcards from any content, and CloudCoreo, a configuration management company that garnered investment from Microsoft and ultimately sold to VMware. Cy was in the 2014 class of “Forty Under 40” for Professional Remodeler Magazine at the helm of the long-running real estate investment firm OCPS and was twice-featured on TLC’s hit TV show “Flip That House”.  He is currently back in his hometown of Bloomington, IN with his wife Andrea and son Jack working for Elevate Ventures as an Entrepreneur-in-Residence serving the Velocities region in south central Indiana. He has a degree in Economics from Indiana University and an MBA from Baylor University, where he is an executive judge for their annual MBA Ethics competition. 

In your role as an EIR, what are key areas you consistently work on with entrepreneurs?

If we are talking on a practical level, then I would say I work with entrepreneurs mostly on fundraising, product-market fit, and/or building an effective pitch deck. Those, however, are simply tools or processes that we can work through as entrepreneurs to get the desired result.

What myself and other EIRs bring to the table is the experience from our own successes and failures, which enables us to look at an entrepreneurs business/situation through a different lens. We are able to ask questions about their approach, get a feel for their mindset and way of thinking, and really get to the core of their solution. Our experience helps us think through the situation in a different way, which usually results in a desired outcome.

Tell me about your experience as an entrepreneur.

I think it’s easy to talk about all of the highlights in an entrepreneur’s journey. I dreamed about being an entrepreneur the same way a kid dreams about being a firefighter. Way before I was able to legally work, I was selling stuff door to door, mowing lawns, buying candy for a quarter and selling it at school for a dollar – anything I could do to make a buck. I was driven by the fact that my actions could change any situation for the better. We are all protagonists of our own story, and I was determined to make mine an interesting one. At the time there was no such thing as tech news, and people typically thought ‘entrepreneur’ just meant you were unemployed. There were very few role models to look up to as examples of how to run a high-growth high potential company. There were a lot of learning lessons along the way, some more painful than others.Now when you read tech news, it typically talks about the highpoints of being an entrepreneur: successfully raising money, big wins, and about the exits. What is less talked about is how hard it is to be an entrepreneur and the tremendous amount of pressure we put on ourselves to succeed. I feel like I can empathize with the entrepreneurs I work with today because of the struggles that I went through during my own journey. The successes, such as raising millions, participating in Microsoft and Intel accelerators, and going through multiple exits, give me credibility but the struggles give me authenticity and empathy.[nectar_single_testimonial testimonial_style=”small_modern” text_color=”#ff6b00″ color=”Accent-Color” quote=”Working with entrepreneurs through Elevate and the Velocities region is a dream job for me. I get to help entrepreneurs avoid pitfalls and talk them up when they need encouragement.”]I feel like my job working with entrepreneurs through Elevate and the Velocities region is a dream job for me. I get to help entrepreneurs avoid pitfalls and talk them up when they need encouragement. There is not one right way to do entrepreneurship and there is ALWAYS a learning curve. I have had my highest highs and my lowest lows as an entrepreneur (and frankly those can be in the same day).

You’ve lived all over the country – including Austin, Seattle, and the Bay Area. How has that experience helped you as an EIR?

All the places we have lived have very vibrant entrepreneurial ecosystems and are all successful, but they accomplish that work in very different ways. Living in all of those areas has taught me that there is more than one ‘right answer’ when it comes to entrepreneurship and ecosystem building. It is really a matter of trying as many things as you can before you find what works for your state, region, town, and company.

What ultimately lead you back to Indiana?

We were living in Austin and I was serving as an advisor, board member and mentor to several startups. I found I really enjoyed working with companies at the early stages of growth. So, when a friend and mentor called and told me about the EIR role I knew I had to apply. I honestly didn’t think a job like what I do now was even possible; it just sounded like a dream job to me. To sweeten the pot even more it was in my hometown and is where my parents still live. We had been gone for about 20 years and it felt right to come back and raise our son in the same community I grew up in.

From your experience, is there anything you would have done differently?

I think as an entrepreneur there is a whole lot I would have done differently. It’s pretty easy to look back and think that. The reality is there are so many resources available to aspiring entrepreneurs and I wish I would have sought those out and asked for advice and mentorship earlier. That said though, as an EIR if everything had gone perfectly, I am not sure I would be able to add as much value now. There is a lot of long-term value in learning from mistakes and if I hadn’t made them, I wouldn’t be able to coach others into not making them. I certainly don’t regret those times, but I’m sure life would have been easier and less complicated with
a team around me.

What’s the most rewarding part of working in your region?

The diversity of people, companies and stakeholders, and that despite all of those differences, they have all come together to help increase entrepreneurship and innovation in south central Indiana. You can’t help but have an awesome day when you are around people working towards a common and worthwhile mission.[nectar_single_testimonial testimonial_style=”small_modern” text_color=”#ff6b00″ color=”Accent-Color” quote=”You can’t help but have an awesome day when you are around people working towards a common and worthwhile mission.”]

If you could give just one piece of advice to aspiring entrepreneurs, what would it be?

Concentrate way more on the problem you are trying to solve than the solution you are providing. If you adequately explain how much of a pain point it is, the solution will seem obvious.

Do you have any books or podcasts that you recommend for entrepreneurs?

Some books that are for the most part not business books, but ones I have been able to learn “life lessons” from:

  • Being OK with uncertainty = The Biggest Bluff by Maria Konnikova
  • Making tough decisions = The Hard Thing About Hard Things by Ben Horowitz
  • Testing ideas and product-market fit = The 4-Hour Workweek by Timothy Ferriss
  • Living a good story = A Million Miles in a Thousand Years by Donald Miller
  • Podcast = ‘Like a Glove’ is a podcast about product-market fit from Pat East
Which 1-2 resources in your region (or Indiana) do you consistently direct entrepreneurs to take advantage of and why?

The Dimension Mill is the co-working space I work out of on the Bloomington side and is filled with creatives, startups, entrepreneurs, and dreamers. It is an excellent place to find your people and level your business up.

I also direct a lot of high-growth, high-potential startups to SCORE out of Columbus. It’s a phenomenal resource and a place where you can tap into the mind of someone who has been there and done that several times – not something you can find just anywhere.