in Business District, News by


Denzel Washington is quoted as saying, “The two most important days in your life are, the day you’re born and the day you find out WHY.”

A successful small business CEO can thrive once they discover their purpose and pour into their passion to unlock their potential. Yet we cannot overlook the need for skill, education, and the ability to plan and problem solve.

Brian Smith and Jackie Cuscuna, co-founders of Ample Hills Creamery, started with an ice cream push cart before opening their first Ample Hills shop in Brooklyn, New York, in 2011. At its height, Ample Hills was valued at $40 million, with 13 shops and an online store that shipped ice cream nationwide. Eight years in, missteps led to business and personal bankruptcy, closed shops and selling off the business for $1 million, according to CNBC reporting.

While their journey does include an incredible rebound to scale up again, it is an example of the risk associated with scaling a business and the fleeting experience of what outsiders deem to be success.

In her book, Scale or Fail, bestselling author Allison Maslan identifies five components that are central in scaling a company.

S: Strategic Vision

C: Cash Flow

A: Alliance of the Team

L: Leadership

E: Execution


Identifying the destination is essential to determine the pathway and stay on course during a journey of unknow challenges.  Building a revenue-driven business that creates daily cash is paramount to invest in the strategic vision.  Every CEO needs an executive leadership team that has the expertise and capacity to align around the vision and rally on the collective effort.  As well every CEO needs to be grow personally and be well grounded with strong emotional, physical and intellectual reserves required to lead the team. Lastly, committing to action that generates higher profits and impact is ability to move forward in spite of the miscalculations, mistakes and course corrections that are always required along the way.

Scaling up is risky to some but the payoff for great execution is reward, progress, and sustainability of the company. Maslan’s five components are prerequisites, along with the book in its entirety. Evaluating each of the five components independently will help determine what areas to solidify before pouncing on the opportunity to leapfrog to the next level.

Most businesses fail to scale because they are ill prepared to face the real challenges involved in scaling.  With that hard truth on the table, the question “how do you prepare?” is top of mind.


On October 14, 2023 the South East Chicago Commission will host its 5th year of the Southside Connection Symposium to convene small business owners, economic development professionals, and civic leaders.  The Symposium focuses on empowering entrepreneurs, fortifying startups, ensuring long-term sustainability, and equipping businesses for scalable growth in the Southeast Chicago region.

NBC5 Chicago News Anchor & Reporter, Evrod Cassimy will moderate this year’s candid keynote conversation, Pathways to a Multi-Million Dollar Business, with Kimberly Lewis, CEO and Co-Founder of CurlMix, and Marc Brooks, President and CEO of Hyde Park Hospitality.

Lewis started with a small product portfolio that she eventually scaled her company to full manufacturing and distribution after generating more than $6 million in investment capital. Brooks started with one employee in Chicago and made excellent acquisitions and partnerships to expand his portfolio company that has scaled into 16 states with more than 600 employees.

Following the keynote, the executive leadership panel moderated by Kenya Merritt, Deputy Mayor, City of Chicago will present “Fundamentals Needed to Scale Your Business,” focused on access to capital and essential resources for small businesses to succeed. This engaging panel offers insights from Daryl Newell, SVP, Community Development Banking Market Manager, PNC Bank, Terrand Smith, Founder and CEO, 37 Oaks and Dr. C. Adam Callery, Managing Director, Sagesse Lumier.

The 2023 SECC Southside Connection Symposium is sponsored by The Allstate Foundation, Comcast NBC Universal, Charity & Associates, CEI Media Group, Cleveland Avenue, The Study Hotel, ComEd, Self-Help Federal Credit Union, and The Sophy Hotel.

The Symposium will be held in Chicago at The DuSable Museum of African American History and Education Center.  Online registration is required to secure a complimentary seat.



Jared L. Kelly

CEI Media Group

Chicago, IL