Small Business Day
Revisit the conversations and expert insights from Small Business Day 2026.
Your guide to smarter business strategies
Small Business Day 2026 brought together business leaders, industry experts, and entrepreneurs for conversations on the issues shaping small business today. Watch session replays, catch key moments, and explore actionable insights on AI, cybersecurity, policy, retail, and business growth.
To be able to come into a room with other like minded individuals… It’s a beautiful experience that I wouldn’t trade.
Business owner & 2025 Small Business Day Attendee
Chrishawn Murray
Our 2026 Speakers
Bill Briggs
Deputy AdministratorU.S. Small Business Administration (SBA)
Lisa Plaggemier
Executive DirectorNational Cybersecurity Alliance
Joseph Carr
FounderJosh Cellars
Matthew J. Eggers
Vice President, Cybersecurity Policy, Cyber, Space, and National Security Policy DivisionU.S. Chamber of Commerce
Kris Thiessen
Senior Partner, Tax and AdvisoryBlock Advisors
Mike Morello
Chief Digital OfficerU.S. Chamber of Commerce
Dwayne Myers
Co-Owner & CEODynamic Automotive
Bill Briggs
Deputy AdministratorU.S. Small Business Administration (SBA)Lisa Plaggemier
Executive DirectorNational Cybersecurity AllianceJoseph Carr
FounderJosh CellarsMatthew J. Eggers
Vice President, Cybersecurity Policy, Cyber, Space, and National Security Policy DivisionU.S. Chamber of CommerceKris Thiessen
Senior Partner, Tax and AdvisoryBlock Advisors
Mike Morello
Chief Digital OfficerU.S. Chamber of CommerceDwayne Myers
Co-Owner & CEODynamic Automotive
Small Business Day 2026 | Recaps + Replays
Browse event highlights and replay sessions from the event.
Latest Content
Small Business Day 2026: The Small Business Talent Advantage
Mike Morello, Chief Digital Officer at the U.S. Chamber of Commerce, and Dwayne Myers, Co-Owner & CEO of Dynamic Automotive and a 2025 CO—100 Top Small Business, discuss how small businesses can attract and retain top talent in today’s workforce.
From Passion Project To Category Leader: Josh Cellars' Founder On Building America's Number One Premium Wine Brand
Josh Wines founder Joseph Carr shares his origin story from growing up in upstate New York to founding one of the nation’s leading wine brands. Interviewed by CO— Senior Editorial Director Barbara Thau.
Talking Taxes: A Small Business Perspective
Kris Thiessen, Senior Partner, Tax and Advisory at Block Advisors shares how the One Big Beautiful Bill impacts small business taxes and what businesses can do to take advantage of the new legislation.
Cybersecurity Simplified: Practical Protection for Small Business
Matthew Eggers, Vice President, Cybersecurity Policy, Cyber, Space, and National Security Policy Division, U.S. Chamber of Commerce, interviews Lisa Plaggemier, Executive Director, National Cybersecurity Alliance, on the practical actions small businesses can take to protect their data and financial information at Small Business Day 2026.
Small Business Day 2026: A View from the Small Business Administration
During Small Business Day 2026, SBA Deputy Administrator Bill Briggs discusses how the agency is helping entrepreneurs access capital, cut through red tape, and grow in an AI-driven economy.
Small Business Day 2026: Small Business Update
In this special 2026 Small Business Day update, Neil Bradley of the U.S. Chamber of Commerce discusses the economic uncertainty, policy shifts, and emerging opportunities shaping the outlook for small businesses.
Small Business Day 2025 CO—100 Panel on Growth and Success
Three CO— 100 Honorees explain how they’ve disrupted their industries, built loyal customer bases, and navigated challenges during a live panel at Small Business Day 2025.
Small Business Day 2025: Growth Insights from Tuckernuck CEO
Jocelyn Gailliot, Co-Founder and CEO of apparel boutique Tuckernuck, shares the brand’s journey from a bootstrapped e-commerce startup to a profitable omnichannel retailer.
Small Business Day 2025: Small Business Update
During Small Business Day 2025, Neil Bradley of the U.S. Chamber of Commerce discusses how issues like tariffs, the economy, and immigration are impacting small businesses.