Big Dreams Grant
We’re awarding $25,000 to help small business dreams take flight.
$5,000 to 5 small
business owners
Enter by 11:59 PM EST
on June 18
$5,000 to 5 small business owners
Enter by 11:59 PM EST on June 18
What Could Your Business Do With $5,000?
Through our Big Dreams Grant, we’re investing in 5 small business owners who are looking to scale. Each winner receives:
$5,000 each for their next growth move.
One-year membership to Sky’s the Limit’s Launchpad Program, a business accelerator and mentorship program, providing expert guidance and resources to grow your business.
Plus 20 runners up will also receive a membership to the Launchpad Program, a business accelerator and mentorship program, providing expert guidance and resources to grow your business.
Please review the “Entry Criteria – what we’re looking for” section below this application to understand the criteria that each answer will be judged on.
Win a $5k Business Grant
By submitting your application for the Big Dreams Grant, you agree to the terms and conditions. No purchase necessary. One entry per person and business. The Big Dreams Grant promotion is open to US residents ages 18+. Competition closes 11:59PM EST on June 18, 2026. Simply Business will announce winners on or before July 29, 2026. At Simply Business, we respect your privacy. For more information, see our privacy policy. California residents, please also see our privacy notice for CA residents for this contest, which includes the notice at collection and financial incentive notice.
About the Big Dreams Grant
Our latest research reveals a stark reality for small business owners: 87% are forced to use personal funds to stay afloat, while 80% are losing critical growth hours to administrative burdens. In short, many entrepreneurs are stuck in a cycle of survival. They have the drive and confidence to grow, but lack the breathing room and resources to do it. That’s why Simply Business is committing $25,000 to provide the capital, mentorship, and business tools needed to break through the small business growth plateau and turn ambition into measurable scale.
Entry Criteria —
What We’re Looking For
Our judges are looking for small business owners that are ready to take their business to the next level. Below are the two questions you’ll be asked, and the criteria your answers will be evaluated on.
1: Why should you win this prize? (500 words max)
Please address each of the following in your response:
Criteria 1: What makes your business unique and impactful?
Tell us about the special skill, the niche market, or the innovative way you serve your customers that sets you apart.
Criteria 2: A ‘Big Dream’ needs a solid foundation. How have you validated that your business is ready to scale?
Show us the demand through your numbers, customer feedback, or market research that proves you’ve found the right “sweet spot” in your industry.
Criteria 3: What is your plan for financial stability and growth?
A big dream needs a sustainable plan. How will you scale your current revenue, and what financial milestones are you aiming for to ensure your business continues to grow year after year?
2: How will you use the grant and the Launchpad program to grow your business? (250 words max)
Please address each of the following in your response:
Criteria 4: How do you plan to use the grant money?
Be specific. Is it equipment, marketing, operational systems? Give us a breakdown of how this cash will remove a specific hurdle to your growth.
Criteria 5: What do you need to learn to help you grow alongside your business?
Tell us what you want to gain from the Sky’s the Limit Launchpad Program. Financial planning and mastery? Leadership skills? Strategic planning?
Key Dates to Remember
April 29
Applications open
Share your story and tell us how the Big Dreams Grant will fuel your next stage of growth.
June 18
Application deadline
Final call to get your entry in before the window closes.
July 29
Winner announcement
Celebrating the five small business owners ready to scale.
October 19
The growth milestone
A strategic check-in to celebrate your progress and share your success stories.
The Big Dreams Project
This competition forms part of Simply Business’s social impact strategy – The Big Dreams Project—and our long term commitment to helping 10,000 small businesses start or grow by 2030. To read more about our work in this space, click here.
Sky’s The Limit’s Launchpad Program
In addition to the five winners, twenty finalists will receive access to Sky’s the Limit’s Launchpad, a structured business accelerator program. This includes 1:1 mentorship and an all-in-one digital platform designed to streamline operations, automate workflows, and empower business owners to move past the daily grind, sharpen their long-term strategy and drive revenue growth.
Meet our Judging Panel
Samantha Roady
U.S. CEO of Simply Business
Samantha is responsible for leading the strategic growth and overall operations of Simply Business U.S., driving the company’s mission to empower small business owners through a simple and accessible insurance shopping experience.
Bo Ghiradelli
Sky’s the Limit Co-founder
Bo Ghirardelli is the Founder and CEO of Sky’s the Limit, an innovative nonprofit that operates as a digital platform helping underrepresented entrepreneurs launch and grow businesses, and supporting more than 100,000 entrepreneurs,
Nic Cary
Sky’s the Limit Co-founder, Co-Founder of Blockchain
Nic Cary is an entrepreneur, investor, and technology leader committed to expanding access to opportunity through innovation, financial technology, and artificial intelligence. In addition to Sky’s the Limit, Nic is the Co-Founder and Vice Chairman of Blockchain.com.
FAQs – Everything You Need to Know
How do I enter the competition?
Fill out the form at the top of this page to enter our Big Dreams Grant contest. Make sure you read our entry and eligibility criteria section. Please also read the Big Dreams Grant Terms and Conditions before applying.
Who can apply and is there an age limit?
The Simply Business Big Dreams Grant is open to U.S. business owners ages 18+ at the time of entry who meet the following criteria:
- Are legal residents of the United States;
- Business must be headquartered in the United States;
- Business must have generated a minimum of $25,000 in gross revenue over the last 12 months;
- Possess a valid Employer Identification Number (EIN) or Social Security Number (for sole proprietorships) and able to provide a valid W-9 upon request to Simply Business;
- If the business is a registered business entity, it must be in good standing in the state(s) it is registered in; and
- If the business is a sole proprietorship, the applicant must be able to provide upon request proof of business activity, such as a DBA registration, a valid local business license, professional license, or permit, or a redacted invoice issued in the last 60 days (removing all client identifying information).
You can read the full terms and conditions here for more information.
When will I find out if I’ve won?
If your entry is successful and you’re a winner we’ll email you by July 29, 2026.
When and how will I receive the prize grant?
All grant winners must first pass OFAC screening and provide a valid W9 before any funds are awarded. Those who are selected for a grant but do not pass OFAC screening or provide the W9 will be deemed ineligible.
Once winners have been selected, and passed OFAC screening, and provided a W9, funds will be transferred to the winner’s choice of a U.S. bank account via wire transfer or to their PayPal account.For more information, please review the “Prize Receipt Details & Requirements” section in the Big Dreams Grant Terms and Conditions.
Winners will get access to Sky’s The Limit’s Launchpad program, where you can access a variety of tools and mentors to help to grow and scale your business.
How will Simply Business use my data?
We’ll use your personal information to run the Big Dreams Grant. This includes things like getting in touch about your application, checking if you’re eligible, rewarding prize winners, and to follow up with the five winners 3 months after to see how you used the grant to grow your business.
To do this, we’ll be sharing your information with Sky’s The Limit, who we’re working in partnership with. We handle personal data in accordance with our privacy policy. California residents, please see our contest privacy notice for CA residents.
If you choose to receive promotional emails from Sky’s the Limit or visit their website, please visit their privacy policy for more details on their personal data handling policies.
If you can’t see the answer to your question, you can reach out to us at [email protected].
About Sky’s the Limit
Sky’s the Limit is a digital business accelerator and mentoring platform that provides earliest-stage, underrepresented entrepreneurs with mentoring from peers and volunteer professionals, as well as entrepreneurship training and startup grants.
About Simply Business
Simply Business is dedicated to making small business insurance simple and accessible. The company’s robust digital marketplace allows small business owners to find and buy the insurance they need online, matching them with coverage from multiple top carriers to offer transparency, choice, and value. Simply Business’s product offering includes general liability, professional liability, business owner’s policy, workers’ compensation, cyber insurance, and more.
An insurtech pioneer, Simply Business has over 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 and has offices in London and Northampton in the UK and Boston in the U.S.