#United States #Boston #Simply Business #Sky's the Limit #Big Dreams Grant

Simply Business and Sky's the Limit Join Forces for the 2026 Big Dreams Grant

Simply Business, a prominent online insurance platform, has recently partnered with Sky's the Limit, a digital business accelerator, to launch the 2026 Big Dreams Grant. This initiative aims to support and empower small business owners in the U.S. as they navigate the challenges of growth and sustainability in a competitive market. With a staggering 87% of small business owners relying on personal finances to keep their operations afloat, this grant offers a ray of hope by providing essential capital and resources.

In an announcement made on May 5, 2026, Samantha Roady, the U.S. CEO of Simply Business, emphasized that although small business owners are rich in ambition and perseverance, they often grapple with limited time and resources, which can hinder their ability to achieve measurable growth. "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," she stated.

The 2026 Big Dreams Grant is part of Simply Business's broader initiative, the Big Dreams Project, which aims to assist 10,000 small businesses in either starting or growing by the year 2030. According to recent research by Simply Business, 73% of small business owners feel more confident today than when they first launched their enterprises. However, 57% have reported stagnation or a decline in revenue over the past year, while 80% have been spending excessive time on administrative tasks rather than focusing on growth.

Bo Ghirardelli, CEO and Co-founder of Sky's the Limit, added that while capital is indeed vital, it is insufficient on its own. He believes the combination of funding and necessary support is what entrepreneurs truly require to foster growth.

Overview of the Big Dreams Grant 2026 Program

Direct Funding

Five fortunate business owners will be awarded $5,000 each to help fuel their next stage of growth, giving them the financial boost they need to invest in their vision.

Mentorship and Training

Twenty-five finalists will join Sky's the Limit's structured business accelerator and mentorship program. This will allow them to refine their strategies and gain invaluable insights from seasoned business leaders, enabling them to navigate the complexities of entrepreneurship more effectively.

Tools and Systems

Finalists will also gain access to Sky's the Limit's Launchpad platform, a comprehensive suite of tools designed to optimize business operations, automate workflows, and enhance revenue growth.

Application Details for the Big Dreams Grant

Applications for this prestigious grant are now open to small business owners across the United States, with a deadline set for June 18, 2026, at 11:59 PM EDT. Those interested in applying can visit Simply Business for more information.

About Simply Business

Simply Business specializes in simplifying the process for small businesses to compare quotes and purchase insurance from top carriers quickly and efficiently. The company is committed to making small business insurance straightforward and accessible, offering a variety of products, including general liability, professional liability, and cyber insurance. Founded in the UK in 2005 and launching in the U.S. in 2017, Simply Business has cultivated a customer base of over one million small businesses.

About Sky's the Limit

Sky's the Limit is a nonprofit organization dedicated to supporting early-stage, underrepresented entrepreneurs. Their mission is to help these entrepreneurs achieve traction, generate revenue, and build scalable businesses through mentorship, a supportive community, startup grants, and hands-on assistance. More information can be found at Sky's the Limit.

Research Methodology

The findings shared in this announcement are drawn from an online survey conducted in March 2026 by an independent research firm on behalf of Simply Business. The survey collected insights from 1,092 small business owners operating with five or fewer employees across the United States. This data sheds light on the operational hurdles each faces and how these obstacles contribute to revenue stagnation.

In summary, the 2026 Big Dreams Grant signifies a meaningful investment in the future of small businesses—a commitment to empowering entrepreneurs with not just funds, but the knowledge and resources to thrive in an ever-evolving marketplace.