Six Questions with Entrepreneur-in-Residence Ron Stubblefield

Earlier this month, Leaders from the Economic Community Development Institute (ECDI), the Hispanic Business Center, The Presidents’ Council, The Urban League of Greater Cleveland and JumpStart announced Ron Stubblefield as the group’s first shared Entrepreneur-in-Residence (EIR).

A nationally recognized lawyer, scholar, economic development professional and entrepreneurial advisor, Stubblefield acts as a collaborative resource between all four organizations as they work to advance Black and Brown tech and tech-enabled entrepreneurship in Northeast Ohio. He comes to Cleveland from Baltimore, where he was Assistant Director for Emerging Technology Centers, a venture of the Baltimore Development Corporation focused on the incubation and acceleration for early-stage technology-based startups.

Recently, we connected with Ron for a conversation about his background and his goals for this new position.


what attracted you to this position, and to Cleveland?

For me, this was a perfect combination of passion and purpose. I’m very excited about the opportunity to not only build up tech entrepreneurship in this region while focusing on those who are too often left behind.

My family is also from Cleveland and the city invested so much in them that was then reinvested in me. Cleveland helped make my success possible, so to be able to return and help make success possible for others is something special for me. This is noble and powerful work that can make a difference for a lot of people.


You’ve had a very eclectic career thus far. How have your previous experiences shaped your approach to this new role?

I think my past work has given me three important frames of reference.

First, in this work, you are always a community organizer at some level. That means you need to be passionate, heartfelt, diplomatic and empathetic. You must be able to listen first, then act. This is so important when you are navigating a space where there is historically justified levels of distrust and frustration.

Second, my time in public policy and management has shown the importance of being precise about defining the problem you are trying to solve, then developing clear proposed solutions and measuring your progress to be sure you are making the right level of impact.

Finally, as an attorney and someone who has been through graduate school multiple times, you learn what “work ethic” really means. You need that because all the easy jobs are already taken. This work is hard, because you’re dealing with real structural inequalities in society. You need to be ready to roll up your sleeves if you hope to get things done.


This is a unique role because you are an entrepreneur-in-residence working with four organizations at the same time. How do you navigate this collaboration?

Well we all work for entrepreneurs, specifically Black and Brown entrepreneurs who are trying the navigate the tech space. So, I start there. I think it’s a real opportunity to be innovative and cross-leverage resources, because each of these organizations has great expertise and knowledge to bring to the table.

JumpStart has great programming and resources, but you also have great mentoring and business advising coming out of the Presidents Council, and the Urban League who can be so helpful to businesses in terms of the hard skills, whether it’s learning Quickbooks or understanding how to navigate the world of government contracts. Then you have the Hispanic Business Center, who are experts at helping businesses tap into SBA-related resources. Further, you have ECDI who is providing great technical and financial assistance to help launch business ventures.

Finally, you have a collective of organizations working together to advocate for more robust programs and funding support to advance innovation led Black and Brown entrepreneurs. Together, we can build more pathways and platforms to help Black and Brown entrepreneurs succeed. And that’s’ the end goal. Whatever we do, entrepreneurs need to succeed as a result.


People have a general concept about what it means to run a “tech-business,” but your role specifically mentions the term “tech-enabled.” How are these terms different?

When we talk about a tech-oriented business, we mean a business that is selling a technology. A tech enabled business might not be selling technology, but they are leveraging technology to power their business and provide either more efficient or new solutions for consumers.

Often when people think of “tech” or “innovation” they are only thinking of tech-oriented businesses, but we want tech-enabled businesses to know there are resources in our ecosystem to help them grow as well.

And right now, we’re working with the Ohio Third Frontier and the ESP program as a whole to help us broaden this scope. Because if a support service is good for a tech-oriented startup, it’s usually good for a tech-enabled business too. So we need to expand our mindset to be more inclusive and meet entrepreneurs where they are. And we are very excited to see what this journey will look like in the coming months.


COVID-19 has hit Black and Brown businesses especially hard. Do these circumstances change the way you think about your work in the coming months?

It changes some of the tactics for certain. For example, a lot of in-person gatherings are not going to be happening this summer. So, people are relying on digital outreach, but there is a major digital divide in our city. Part of my role is to ask the questions of the community, collaborators and the ESP program as a whole to push the system to be more inclusive of those most impacted by this divide.

Some of these questions focus on ensuring we’re optimizing this outreach for people who rely only on mobile phones to connect to the internet or understanding that a native Spanish speaker may have literacy challenges in both English and Spanish. So what are we providing to make sure they have what we need to make sure we do not take for granted that certain traditional business terminology is not the way business owners talk about these issues. We have to think about how we bridge these gaps.

We can also learn some things from the way Black and Brown communities are innovating during COVID-19 when it comes to gathering together as a community. Just seeing what churches have done. These are pillars of the Black community and they are now leveraging Zoom to engage with their congregations. If we also stop to take some lessons from the communities we’re trying to reach, I think we’ll be stronger for it.  Black and Brown communities are the original innovators in America. As an ESP program and a consortium of organizations, we need to make sure we’re focused on more than us teaching these communities; it must also start with learning from them.


What are some of your other near-term plans for this new role?

I can tell you we are going to be very aggressive with community engagement and outreach, especially in the first year of this partnership. The results of this engagement and outreach will impact long term programs we develop and enhance for the community. We know the entrepreneurs are out here, it’s just a matter of meeting them where they are, properly supporting them, and navigating through unforeseen challenges like COVID to make sure people aren’t being left even farther behind in the future.