DETAILED AGENDA
This year’s Cultivate Summit theme, Innovating to Meet the Moment, reflects the evolving realities and opportunities facing today’s entrepreneurs. As the business landscape continues to shift, the Summit is designed to equip founders with the insights, tools, and resources needed to adapt, lead, and grow with intention and resilience. Through forward-thinking conversations, practical workshops, and hands-on support, the Cultivate Summit empowers entrepreneurs to move beyond day-to-day operations and into innovative, strategic decision-making that meets the demands of the moment. Explore the programming below to learn more.
Friday, March 27, 2026 | 8:30 AM - 5:00 PM
Convene (600 14th street NW, Washington, DC 20005)
9:30 AM | Opening Plenary
The Cultivate Summit will kick off with a warm welcome from the WACIF teams, setting the tone for a day rooted in innovation, collaboration, and impact. During this opening plenary, attendees will receive important housekeeping information, an overview of the day’s programming, and guidance on how to make the most of their Summit experience. The session will also energize the room and officially launch the day—plus, attendees can look forward to multiple giveaways throughout the opening session.
Shannan Herbert
Chief Executive Officer, WACIF
Marisela Rodela
Program Director, OWI, WACIF
Janet Lopez
Senior Vice President, Pinnacle Financial Partners
FEATURED PANEL DISCUSSION
State of the Ecosystem
The State of the Ecosystem Expert Panel will feature a 40-minute Fireside Chat with experts from the national and DMV business ecosystem who support entrepreneurs exploring current trends, gaps, and opportunities shaping the small business and entrepreneurial landscape.
WACIF’s CEO, Shannan Herbert, will moderate this panel, centered on practical insights on policies, funding and resources, partnerships, strategy, and implications of the political and business environment on our local business ecosystem.
Shannan Herbert
Moderator, Chief Executive Officer, WACIF
Jonathan Fantini-Porter
Senior Vice President, Mastercard Social Impact
John Holdsclaw
President & CEO, Rochdale Capital
Rosemary Suggs-Evans
Director, DC Department of Small and Local Business Development
11:00 AM | Concurrent Breakout Tracks
Choose from one of the three breakout sessions to attend, each offering an intimate workshop opportunity with one of our featured speakers.
Pre-Registration is not required to attend!
Track 1: Resources to Support Small Business Expansion
Leveraging Entrepreneurship Centers to Grow Your Business
A large variety of Entrepreneurship Centers (ECs) support small businesses in the local and national business ecosystem. What are the differences and strengths of the various EC accelerator and incubator programs? Learn more about the Accelerator and Incubator Entrepreneurship Centers in the DC Metro Region and beyond, and how they can help you grow your business. Identify the benefits of participating in ECs. Learn strategies to leverage your participation in ECs and how they can help expand your business.
Track 2: Tech Innovation
AI Is Bigger Than the Internet — And Business Leaders Can’t Afford to Ignore
Seema Alexander, CEO & Founder, Host of The AI CEO Podcast, and Keynote Speaker
In this workshop, Seema breaks down what this shift actually means for builders and operators. Drawing from two decades of scaling businesses to $100M collectively, corporate leadership experience, and hands-on work designing AI-powered operating models, Seema moves the conversation beyond tools and hype.
You’ll explore:
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Why AI is bigger than the internet as a structural business shift
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The widening gap between incremental adoption and intelligence-led companies
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How modern teams are redesigning workflows and decisions around AI
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What AI fluency really means for non-technical leaders
You’ll leave with clearer mental models, strategic language, and a practical roadmap to lead confidently as intelligence becomes the advantage.
In partnership with
Track 3: Pivot Project - Fed to Founder
Exploring the Path from Public Service to Entrepreneurship, Bootcamp Part 1: Exploring the Entrepreneurial Path
Connie Russell, CEO, C L Russell Group
Are you a federal or government professional curious about what comes next? FED2Founder is a practical and empowering workshop designed to help you explore entrepreneurship as your next chapter. Whether you’re nearing retirement, considering a side business, or simply craving more freedom and impact, this two-part session introduces the mindset, models, and first steps of becoming your own boss. Learn how to transform your public service experience into a business idea, evaluate your readiness, and discover key tools to guide your transition—from federal employee to fearless founder.
In partnership with
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11:00 AM - 1:50 PM | Technical Assistance Expert Hours
Experts will be available to meet one-on-one to provide support and technical assistance on a variety of topics such as accounting, legal matters, Certified Business Enterprise (CBE) certification, Women Business Enterprise (WBE) and Women Owned Small Business (WOSB) certification, Capital readiness and business financing, and credit building. Pre-registration for these meetings are encouraged as day-of registration will be limited.
12:00 PM | Networking Luncheon
The Networking Luncheon marks the official kickoff of the Innovation Marketplace, bringing attendees together over lunch for connection, conversation, and collaboration. During this interactive midday experience, guests are invited to network with fellow entrepreneurs while exploring the Innovation Marketplace, featuring a curated group of partners, vendors, and small businesses showcasing innovative products, services, and resources. This luncheon offers a relaxed, engaging environment to build meaningful connections, discover new opportunities, and engage directly with organizations supporting entrepreneurial growth.
1:00 PM | Concurrent Breakout Tracks
Choose from one of the three breakout sessions to attend, each offering an intimate workshop opportunity with one of our featured speakers.
Pre-Registration is not required to attend!
Track 1: Resources to Support Small Business Expansion
Certified Up: Demystifying and Leveraging Business Certifications
Explore how your business can tap into contracting opportunities across the DC Metro area. This session will feature representatives from state, local, and corporate agencies who will elaborate on the various certifications and eligibility, break down the contracting process, highlight available opportunities, and clarify how small business certifications—such as WBEC, SWaM, MBE, CBE, and others —can position your business for success. Attendees will gain practical insights into becoming certification-ready and building credibility within the procurement ecosystem. This session is part of the PIVOT initiative, focused on empowering local founders with the tools, structure, and confidence to build sustainable and scalable businesses.
Track 2: Tech Innovation
Vibe Coding in Practice: Turning AI Ideas into Real Products
Adalbert De La Cruz, Founder, RapidLabz
AI can generate ideas, but shipping a real product takes clarity, structure, and strong product thinking. In this session, Adalbert De La Cruz shares how leaders in the Vibe Coding movement turn AI capabilities into intuitive, reliable, and human-centered products. Drawing from real builds, shipped prototypes, and lessons from teaching over 1,500 builders, this talk breaks down practical frameworks for moving from concept to execution without burnout. Attendees will leave with a clearer mental model for building with AI and the confidence to ship their ideas.
In partnership with
Track 3: Pivot Project - Fed to Founder
Exploring the Path from Public Service to Entrepreneurship, Bootcamp Part 2: Exploring the Entrepreneurial Path
Connie Russell, CEO, C L Russell Group
Are you a federal or government professional curious about what comes next? FED2Founder is a practical and empowering workshop designed to help you explore entrepreneurship as your next chapter. Whether you’re nearing retirement, considering a side business, or simply craving more freedom and impact, this two-part session introduces the mindset, models, and first steps of becoming your own boss.Learn how to transform your public service experience into a business idea, evaluate your readiness, and discover key tools to guide your transition—from federal employee to fearless founder.
In partnership with
2:00 PM | Afternoon Plenary
The Afternoon Plenary will focus on WACIF’s work and partnerships in the Tech Innovation space. The plenary will include remarks from WACIF and Summit partners, reflecting on our collaborative work to support access to emerging technologies for entrepreneurs in the region. These remarks will highlight key takeaways from the day, celebrate the entrepreneurial community, and set the stage for continued connection beyond the Summit.
Following these remarks, attendees will transition into the Keynote Fireside Conversation featuring Madia Brown, Founder of Brandire Agency and Hellobrand. Moderated by Kimberlye Gayle, Chief Programs Officer at WACIF, this engaging conversation will explore Madia’s entrepreneurial journey, the growth and innovation behind her brands including her new AI-driven branding tool, and insights designed to inspire and empower small business owners as they look ahead.
Marisela Rodela
Program Director, OWI, WACIF
Jessica Randolph
Associate Creative Director, Anacostia Arts Center, WACIF
Darius Clair
Director of Programs and Community, DC Startup & Tech Week
Kimberly D. Gayles
Chief Programs Officer, WACIF
FEATURED KEYNOTE SPEAKER
Madia Brown, Founder, Brandire Agency and Hellobrand
The Keynote Fireside Conversation will feature an engaging, 40-minute moderated discussion offering an inside look into the entrepreneurial journey behind two innovative brands. In this relaxed, one-on-one conversation, Madia Brown, Founder of Brandire Agency and Hellobrand, will share her path to entrepreneurship, the evolution and growth of her businesses, and her vision for the future.
Moderated by Kimberlye Gayle, Chief Programs Officer at WACIF, the conversation will explore lessons learned, innovative strategies, and practical insights designed to resonate with small business owners at every stage of their journey.
This fireside chat offers attendees a candid and inspiring perspective on building, scaling, and leading with intention—closing the Summit with both reflection and forward-looking inspiration.
The day will conclude with the Pivot Project Networking Reception, a high-energy closing experience designed to celebrate connection, community, and continued momentum beyond the Summit. Attendees are invited to enjoy light refreshments and snacks while networking with fellow entrepreneurs, speakers, and resource partners in a relaxed and social setting.
The reception will feature DJ Ty Alexander's curated soundtrack to keep the energy flowing, along with a special raffle for Professional Service Scholarships.
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3:00 PM | The Pivot Project Networking Reception
Featuring DJ Ty Alexander