Simply Business and Sky's the Limit Team Up to Launch 2026 U.S. Big Dreams Grant to Support Small Business Owners

With 87% of small business owners relying on personal funds to sustain operations, this $25,000 initiative delivers the capital and resources needed to scale

BOSTON, May 5, 2026 /PRNewswire/ -- Simply Business, an online insurance platform that helps small businesses compare quotes and buy insurance from leading carriers in one place, and Sky's the Limit, a digital business accelerator for early-stage entrepreneurs, today announced the launch of the 2026 Big Dreams Grant. 

"Small business owners don't lack ambition, and they certainly don't lack grit, but many lack the time, the resources, and a clear path to turn momentum into measurable growth," said Samantha Roady, U.S. CEO, Simply Business. "Through Big Dreams, we aren't just providing funding; we're equipping small business owners with the hands-on coaching and tools they need to break through revenue plateaus and build strong, sustainable businesses."

The Big Dreams Grant provides $25,000 in grants as well as mentorship and resources for the winners as part of Simply Business's global Big Dreams Project, which aims to help 10,000 small businesses start or grow by 2030. According to recent Simply Business research, 73% of small business owners feel more confident today than when they launched, but 57% have seen their revenue stay flat or decline in the past year. In addition, 80% noted spending significant hours on tasks like administration and finance rather than focusing on growth.

Bo Ghirardelli, CEO and Co-founder, Sky's the Limit, said, "Capital is important, but it isn't enough on its own. Together with Simply Business, we are combining funding with the support entrepreneurs need to grow their business."

About The Big Dreams Grant 2026 Program

• Direct Funding: Five business owners will receive $5,000 to fuel their next stage of growth.
• Mentorship and Training: Twenty-five finalists will join Sky's the Limit's structured business accelerator and mentorship program to sharpen their strategy and receive advice from proven business leaders.
• Tools and Systems: Finalists will gain access to Sky's the Limit's Launchpad platform, a suite of tools that helps businesses streamline operations, automate workflows, and focus on revenue growth.

How to Apply for the Big Dreams Grant

Applications for the Big Dreams Grant are now open to small business owners across the United States.

Application Deadline: June 18, 2026, 11:59 PM EDT

For more information and to apply, visit: https://www.simplybusiness.com/campaign/bigdreamsgrant/

About Simply Business
Simply Business helps small businesses compare quotes and buy insurance from leading carriers in minutes, and manage their coverage all in one place. The company is dedicated to making small business insurance simple and accessible by offering transparency, choice and value. Simply Business's product offerings include general liability, professional liability, business owner's policies, workers compensation, cyber insurance and more.

An insurtech pioneer, Simply Business has 20 years of experience supporting the needs of small businesses, with over one million active customers. Founded in the UK in 2005, Simply Business launched its U.S. operations in 2017. Simply Business is a subsidiary of The Travelers Companies, Inc. (NYSE: TRV).

About Sky's the Limit
Sky's the Limit is a nonprofit digital business accelerator that helps early-stage, underrepresented entrepreneurs gain traction, generate revenue, and build scalable businesses through mentorship, community, startup grants, and hands-on execution support. For more information, visit https://www.skysthelimit.org.

Research Methodology
The report is based on an online survey conducted on behalf of Simply Business by an independent research firm in March 2026. The survey gathered insights from 1,092 small business owners with five or fewer employees across the United States. The data collected was analyzed to identify their 'growth gap' by quantifying the specific operational hurdles that cause these businesses to plateau after reaching profitability. A detailed methodology is available upon request.

Contact: Jillian Reid, [email protected]

SOURCE Simply Business