Simply Business and Sky's the Limit Team Up to Launch 2026 U.S. Big Dreams Grant to Support Small Business Owners
Simply Business (TRV) and Sky's the Limit launched the 2026 Big Dreams Grant on May 5, 2026, offering $25,000 in grants plus mentorship and resources for small business winners.
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Rhea-AI Summary
Simply Business (TRV) and Sky's the Limit launched the 2026 Big Dreams Grant on May 5, 2026, offering $25,000 in grants plus mentorship and resources for small business winners.
The program is part of a global Big Dreams Project aiming to help 10,000 small businesses start or grow by 2030. Research cited: 87% of owners rely on personal funds, 73% feel more confident than at launch, 57% saw revenue flat or decline last year, and 80% spend significant time on administration and finance.
Positive
- $25,000 grant awarded to each winner
- Mentorship and resources included with grants
- Program target: 10,000 small businesses helped by 2030
Negative
- 87% of owners rely on personal funds
- 57% reported revenue stayed flat or declined
- 80% spend significant hours on admin and finance
Details
News Market Reaction – TRV
On May 5, the day this news came out, TRV closed 0.06% below the previous close.
Data tracked by StockTitan Argus for the May 5 session.
Key Figures
- Big Dreams Grant amount
- $25,000
- 2026 U.S. Big Dreams Grant initiative
- Owners using personal funds
- 87%
- Small business owners sustaining operations
- Target businesses helped
- 10,000
- Global Big Dreams Project goal by 2030
- Confidence vs launch
- 73%
- Owners feeling more confident than at launch
- Flat/declining revenue
- 57%
- Owners reporting flat or declining revenue past year
- Time on admin/finance
- 80%
- Owners spending significant hours on non-growth tasks
Historical Context
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Launch of AI-powered Claim Insights tool within e-CARMA platform.
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Voluntary participation in California SIS to expand homeowners coverage.
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Launch of Simply Business insurance app in ChatGPT for U.S. small firms.
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Publication of 2025 community report with about $24M in contributions.
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Excellent Q1 2026 earnings and higher dividend with capital returns.
24h Move is the share-price change in the day after each event; other market factors may also have contributed.
AI-generated analysis. How Rhea-AI works. Not financial advice.
With
"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,
The Big Dreams Grant provides
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 - 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
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
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
Contact: Jillian Reid, jillian.reid@simplybusiness.com
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SOURCE Simply Business
FAQ
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