Side Hustle Pro

488: The Power in the Pivot: How Keewa Nurullah Is Rebuilding After Closing Her Dream Business

November 12, 2025

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  • Entrepreneurs must be willing to recognize and heed the signs when economic shifts or customer behavior changes necessitate a pivot, rather than holding onto a failing business out of identity or belief. 
  • Consumer support for small businesses is primarily driven by actual dollars spent, not just social media engagement or emotional pleas, highlighting the disconnect between online awareness and necessary conversion. 
  • Success in entrepreneurship can be defined in multiple ways beyond traditional scaling (like VC funding or franchising); it should align with the founder's personal values, community focus, and desired lifestyle, as exemplified by the 'Circulate' initiative. 

Segments

Entrepreneurial Debt and Identity
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(00:01:02)
  • Key Takeaway: Avoiding further debt and personal sacrifice is crucial when an idea is failing, even if it means walking away from a deeply held belief about a single concept.
  • Summary: Entrepreneurs often cling to failing ideas, leading to debt, divorce, and personal decline, believing one last push will lead to success. Keewa Nurullah consciously chose not to follow this path, prioritizing self-preservation over extending a failing business lease. This decision underscores the importance of recognizing when to stop investing in an idea that is no longer viable.
Guest Introduction and Backstory
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(00:01:44)
  • Key Takeaway: Keewa Nurullah founded Kido, a children’s boutique, after identifying marketplace gaps, growing it from online to a physical store (2018-2024) and receiving national recognition.
  • Summary: Keewa Nurullah is an artist, entrepreneur, and strategist, a fourth-generation entrepreneur descended from the Greenwood District era. She founded Kido, a Chicago children’s boutique focused on color, culture, and community, which operated for six years. Her initial success was amplified during the pandemic due to her established online presence and shipping infrastructure.
Noticing the Retail Shift
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(00:05:11)
  • Key Takeaway: Shifts in customer spending behavior, supply chain issues, and geopolitical events (post-October 7th) signaled the need to pivot away from the brick-and-mortar model.
  • Summary: The peak of inclusivity-focused retail success during the pandemic began to wane due to external factors like supply chain issues and changes in consumer spending habits in 2023 and 2024. Keewa recognized that if she benefited from following positive timing, she must also respect the signs indicating a downturn. She observed peers going into debt trying to force survival, a path she was determined to avoid.
Advice on Closing a Business
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(00:11:08)
  • Key Takeaway: If a business’s decline is evident in the numbers and there is no secure plan to reverse the trend without relying on a miracle, it is time to walk away to protect generational wealth.
  • Summary: If a business’s wave is going down and the recovery plan depends on external factors like a sudden influx of cash, the decision to close should be made. Tying one’s worth and future to external customer behavior, especially in physical goods retail, is risky because many factors are outside the owner’s control. Believing in oneself is vital, knowing that if one venture fails, another chance will emerge.
Social Media vs. Real Conversion
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(00:17:04)
  • Key Takeaway: Social media support (sharing, liking) does not replace the critical need for actual monetary conversion, especially for brick-and-mortar businesses.
  • Summary: The consumer education around supporting small businesses often confuses awareness with actual spending; sharing content is not equivalent to making a purchase. Keewa noted that even after successful partnerships (like with the White Sox), the online enthusiasm did not translate into necessary sales conversion. Education programs are insufficient without tangible capital investment flowing into the businesses.
Brand Trust and Vulnerability
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(00:19:40)
  • Key Takeaway: Successful, ‘bright and shiny’ brands face a paradox where their perceived stability discourages the community support needed during tough times, as asking for help can undermine retail psychology.
  • Summary: Black-owned businesses often walk a fine line regarding brand trust: appearing too successful discourages support, while appearing too vulnerable can cause customers to stop supporting them, believing they cannot stand on their own. Retail psychology suggests customers are less likely to support a business perceived as unable to survive independently.
Closing the Store and Recovery
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(00:22:22)
  • Key Takeaway: The emotional toll of closing a beloved business requires a dedicated recovery period focused on mental and physical health before planning the next venture.
  • Summary: Keewa did not have a concrete plan immediately after closing Kido, as the two months leading up to the closure were emotionally draining from absorbing customer reactions. She needed several months to recover equilibrium, acknowledging the end of that era before figuring out what was next. Recovery of mental and physical health must precede strategic planning for a new chapter.
Obama Foundation Collaboration
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(00:25:01)
  • Key Takeaway: Keewa leveraged her design skills to create merchandise for the Obama Foundation’s toy giveaway, establishing a secondary revenue stream beyond product sales.
  • Summary: The collaboration with the Obama Foundation involved providing toys for a surprise giveaway at a South Side school. This relationship allowed Keewa to utilize her design expertise to create mission-forward merchandise for nonprofits, diversifying Kido’s revenue streams beyond retail inventory.
Launching Circulate Initiative
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(00:26:47)
  • Key Takeaway: Circulate is a monthly event designed to ’love-bomb’ a local shop by directing Keewa’s community network to boost their revenue just before rent and utility payments are due.
  • Summary: Circulate functions as a monthly ‘rent party’ for a small retail storefront, providing a significant revenue boost before major expenses are due. This initiative leverages Keewa’s built network to introduce customers who intentionally shop small to other local businesses. The impact is seen in tripled or quadrupled revenue for participating shops and a consumer realization of where their spending truly impacts the community.
Defining Success Beyond Scaling
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(00:28:43)
  • Key Takeaway: Growth and success should be defined by the entrepreneur’s desired lifestyle and community connection, not by external metrics like franchising or meeting others’ definitions of ‘cool.’
  • Summary: Citing Angel Gregorio of Spice Suite, Keewa emphasizes that not every entrepreneur desires massive scaling or franchising; manageable growth supporting the community is a valid success metric. Scaling should not lead to isolation or burnout, especially for entrepreneurs whose brand is rooted in being present and connected to the collective.
VC Funding vs. Self-Funded Paths
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(00:33:29)
  • Key Takeaway: Chasing VC funding solely based on popularity or perceived coolness can lead entrepreneurs into situations where they lose freedom and alignment with investors focused only on financial flips.
  • Summary: There is pressure to pursue VC funding, but this route often means becoming beholden to external parties whose values do not align with the community or the founder’s mission. Alignment is crucial, as investors focused purely on a 10x return may not share the entrepreneur’s foundational values.
Coaching and Reciprocity
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(00:37:18)
  • Key Takeaway: Coaching others is fulfilling because it fills the mentorship gap Keewa experienced as a mother who lacked time for traditional networking and conferences while building Kido.
  • Summary: Keewa felt isolated during Kido’s growth because motherhood limited her ability to attend evening networking events or travel for conferences. She finds fulfillment in sharing expertise with entrepreneurs currently ‘in the weeds,’ believing that serving this role may eventually open doors for her to receive mentorship when she pursues her next venture.
New Chapter and Renaissance Women
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(00:43:16)
  • Key Takeaway: The next chapter of success involves combining Keewa’s artistic self (writing, expression) with her business knowledge, acknowledging that all parts of the self can be integrated, just not simultaneously.
  • Summary: Keewa views her life in chapters: performing artist, then mother/entrepreneur. Her next goal is to merge her creative, expressive self with her business acumen learned through consulting. This demonstrates that entrepreneurs can fulfill all aspects of their identity throughout their life, even if they require sole focus in different seasons.
Self-Acknowledgement and Resilience
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(00:44:59)
  • Key Takeaway: It is essential for entrepreneurs to actively give themselves credit for major accomplishments, like building a brick-and-mortar store, rather than constantly rushing to the next goal.
  • Summary: Keewa learned the importance of pausing to acknowledge accomplishments, such as building Kido without a guide or external support, instead of immediately focusing on the next challenge. Furthermore, she advises against self-blame for failures in areas one has never navigated before, like running a specific type of business.
Lightning Round: Current Resources
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(00:47:36)
  • Key Takeaway: LinkedIn is an underestimated resource for entrepreneurs, effective for initiating relationships with larger companies through direct, offline-focused DMs.
  • Summary: Keewa successfully secured partnerships, like the one with the White Sox, by using LinkedIn DMs to identify synergy with larger organizations. Entrepreneurs should use the platform less for broadcasting and more for targeted outreach to connect their business to relevant, larger entities.
Lightning Round: Fueling Creativity
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(00:48:58)
  • Key Takeaway: Atomic Habits provides a valuable framework for structuring a productive, holistic post-pivot routine by utilizing habit stacking and connecting new behaviors to existing ones.
  • Summary: Keewa found the audiobook format of ‘Atomic Habits’ helpful for structuring her open schedule after closing the shop. The book offers a framework for stacking habits and integrating new routines into daily life to achieve holistic productivity.
Lightning Round: Black Woman Entrepreneur
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(00:50:13)
  • Key Takeaway: Tracy Ellis Ross embodies an intentional lifestyle and business approach (Pattern) that reflects her authentic self, making her an aspirational figure to learn from.
  • Summary: Tracy Ellis Ross is admired for building a business, Pattern, that reflects her personal style and intention, making her a ‘movement.’ Her ability to maintain a lifestyle true to herself while running a successful venture is highly valued.
Lightning Round: Key Personal Trait
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(00:51:03)
  • Key Takeaway: Early and extensive rejection faced as a performing artist provided Keewa with a high tolerance for ’no’ in business, preventing personal devaluation from setbacks.
  • Summary: Keewa’s background in performing arts, which involved thousands of rejections during auditions, built resilience against hearing ’no’ in entrepreneurship. This experience allows her to separate business outcomes from her intrinsic value, viewing pitches as transactional rather than personal failures.
Parting Advice for Pivoting Entrepreneurs
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(00:52:35)
  • Key Takeaway: Entrepreneurs with existing jobs should keep them to stack resources (especially health insurance) until the side hustle demands full transition, while those without jobs should follow their gut instinct to launch an idea now.
  • Summary: The current economic climate requires hedging: if a side hustle is stable but not overwhelming, maintain the primary job for essential resources like health insurance. Conversely, for those facing job insecurity or sitting on an idea, now is the time to follow that instinct and launch the venture.