Simply Business and Sky's the Limit Announce Winners of 2026 Big Dreams Grant

Five trailblazing small businesses selected from more than 6,500 applications to receive funding, mentorship and resources

BOSTON, July 29, 2026 /PRNewswire/ -- Simply Business, the leading digital marketplace for small business insurance, and Sky's the Limit, a digital business accelerator for early-stage entrepreneurs, today announced five winners and an additional 20 finalists of the 2026 Big Dreams Grant. The grant is a part of Simply Business's global Big Dreams Project, which aims to help 10,000 small businesses start or scale by 2030.

After reviewing more than 6,500 applications from across the United States, five standout businesses were selected for their community impact, potential to scale, and clear, strategic plans.

The Big Dreams Grant Winners

• BirdieBlue is a Vermont-based sustainable outdoor adventure brand that upcycles hard-to-recycle outdoor gear into premium, American-made bags.
• KneadED NEO LLC is an Ohio-based worker-owned cooperative bakery and shared commercial kitchen space designed to empower aspiring local food entrepreneurs.
• Rise & Ritual is a Pennsylvania-based tea house and apothecary that blends plant medicine with preventative care.
• Select Auto Parts & Sales is a Wisconsin-based indoor salvage facility that services over 400 repair shops while offering community workforce training.
• Stereotype Co is a New York-based lifestyle brand and creative agency that empowers New York City public school students to design, manufacture, and launch merchandise-driven businesses directly from their classrooms.

"These entrepreneurs show us exactly what is possible when passion and commitment meet a big dream," said Samantha Roady, U.S. CEO of Simply Business. "We are proud to support them as they build strong, lasting businesses."

Boosting Small Business Growth

"The first thing I'm going to do with this grant is to hire someone who can do outreach," said Dave Nudelman, founder of Stereotype Co., "Right now, I'm doing everything. I'm doing the sales calls. I'm doing the zooms. On top of this, I'm in the schools throughout the week to run the programs and I'm preparing all of the orders for the projects. Yes, it's been fun and given me a good workout, but I feel the burn from it."

His experience reflects a common challenge. According to a 2026 Simply Business survey, 80% of small business owners reported spending significant hours on tasks like administration and finance rather than focusing on growth. Simply Business and Sky's the Limit designed this year's grant package specifically to counter those operational bottlenecks.

"A strong support system helps a small business endure," said Bo Ghirardelli, CEO and Co-founder of Sky's the Limit. "We're excited to welcome the finalists into our vibrant entrepreneur community and equip them with our Launchpad program, including mentorship and software tools to help secure long-term success."

For business owners on the ground, that sense of community isn't just a perk – it's essential for survival.

"Be in the community. Don't do this alone. It can be a lonely thing to be a business owner," said Natasha Broxton, owner of Select Auto Parts. "Talk about your business. Share your journey. You never know who might have a resource or solution that you don't even know about. There are so many people inside and outside the community who want you to succeed."

About the Big Dreams Grant 2026 Program

• Direct Funding: Five winners will each receive $5,000 to fuel their next stage of growth.
• Mentorship and Training: Winners and finalists will join Sky's the Limit's business accelerator and mentorship program, receiving strategic guidance from experienced business leaders.
• Tools and Systems: Winners and finalists will gain access to Sky's the Limit's Launchpad platform, a suite of tools to streamline operations, automate workflows and focus on revenue growth.

For more information on the winners and finalists, please 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, underestimated 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.

MyAnh Nghiem, [email protected]

SOURCE Simply Business