39 Dexter Avenue, Suite 201, Montgomery, Alabama 36104

March Small Business Mixer: Legacy Edition

Date: March 18, 2025

In celebration of Women’s History Month, this edition featured a candid and strategic conversation centered on entrepreneurship, community building, and legacy. Moderated by Dr. Nichole Thompson, SBOSS Project Director and Principal Consultant at Gaitway Solutions LLC, the discussion featured Monica Whiting, attorney, entrepreneur, and founder of Baristas & Barristers—a unique hybrid concept blending a law office, coffee shop, and community space.

Through transparent storytelling and real-world insights, Monica shared her journey of building a multi-layered business rooted in purpose, adaptability, and community impact.

Key TakeAways

Community as the Foundation

A central theme throughout the conversation was the role of community in entrepreneurship. Monica emphasized that her “why” has always been rooted in community—creating spaces that bring people together, foster conversation, and ultimately lead to collaboration. Her business model reflects this philosophy: intentionally designing an environment where people from different backgrounds can connect, share ideas, and build relationships.

Building Through Evolution, Not Perfection

Monica’s journey reinforced that businesses are not built in a straight line. Baristas & Barristers was not a pre-planned concept, but rather something that evolved out of necessity and opportunity.

From transitioning out of a corporate role to creating her own law practice, to identifying unused space and developing a secondary revenue stream, her story highlighted the importance of adaptability and continuous refinement.

Entrepreneurship Requires Problem Solving

Entrepreneurship was framed as an ongoing process of identifying gaps and creating solutions. Monica described herself as a “community builder” and “problem solver,” emphasizing that successful businesses are rooted in recognizing needs and responding to them intentionally.

This mindset extends beyond individual business success and contributes to broader economic and community development.

Understanding Systems & Processes Early

A key learning moment shared was navigating the complexities of starting a physical business, including permitting, licensing, and regulatory requirements.

Monica noted that a lack of early knowledge around these processes delayed her opening, reinforcing the importance of:

Understanding city requirements
Leveraging available resources
Seeking guidance early

This highlighted the value of organizations like SBOSS in supporting entrepreneurs through these critical steps.

Pricing, Value & Experience

The conversation revisited a recurring theme across SBOSS programming: pricing based on value, not perception.

Monica shared a pivotal lesson where she initially adjusted her pricing based on customer feedback, only to later recognize that customers were not just paying for a product—but for:

Experience, Environment, Safety, and Community

Entrepreneurs were encouraged to price with confidence and fully account for the value they provide.

Creating Space That Drives Opportunity

One of the most impactful outcomes shared was how physical space can influence business success. Monica noted that customers have closed deals and built relationships within her space, reinforcing that intentional environments can create economic opportunity.

This aligns with SBOSS’s broader focus on place-based entrepreneurship—using physical spaces to drive collaboration and community growth.

Collaboration Over Competition

The mixer reinforced a consistent SBOSS philosophy: collaboration drives growth.

Participants were encouraged to:

Share resources
Support fellow small businesses
Explore bartering opportunities
Build partnerships within the local ecosystem

As emphasized during the discussion, there is significant opportunity within Montgomery, and collaboration is key to unlocking it.

Time, Systems & Scalability

A recurring challenge discussed was time management and scalability. Entrepreneurs must be intentional about:

Creating time for strategic word
Building systems and processes
Delegating where possible

Without structure, growth becomes difficult to sustain.

Mindset, Support & Longevity

The conversation closed with a powerful reflection on mindset and support systems. Monica emphasized the importance of

Clearly defining your “why”
Building a personal “board of directors”
Surrounding yourself with people who provide accountability and perspective

Entrepreneurship was described as challenging but ultimately worthwhile when grounded in purpose and supported by community.

The Small Business Mixer: Legacy Edition delivered a powerful reminder that entrepreneurship is not just about building a business—it is about building community.

Through honest conversation, practical insights, and shared experiences, attendees gained a deeper understanding of what it takes to create sustainable, impactful businesses in Montgomery.

As the city continues to evolve, entrepreneurs remain at the center of shaping its future. SBOSS remains committed to providing the space, resources, and support needed to help business owners assess, adapt, and advance.

We look forward to continuing this work at future mixers and programming as we collectively build a stronger small business ecosystem.