Enterprise Challenge
The Enterprise Challenge is an annual business plan competition for new and emerging companies within Kittitas County. We believe it is a great way for theĀ Kittitas County Chamber of Commerce to celebrate small business and support promising ventures in Central Washington. More than 250 entrepreneurs have competed in the contest since its inception and many of them have gone on to start their businesses in our community.
The 2025 competition runs from September 9, 2025 through October 29, 2025.
What is Enterprise Challenge?
The registration cost for the Enterprise Challenge is $200. The estimated value of this competition is $2,500 in professional services.
- Instruction on business planning, marketing, financing, technology, and related topics
- Individual help sessions with experts in finance, marketing, law, and other business topics
- Feedback on plans submitted by judges who have practical business experience
- Opportunities to network and collaborate with other great entrepreneurs
- Significant publicity for your business through local media and other channels
The biggest benefit is that participants get the counsel and support they need to get their businesses off to a strong start. We designed the competition so that it helps all participants even if they donāt advance into the winnerās circle. By offering in-depth business workshops and individualized counseling to everyone in the contest, we are confident that our participants gain traction with their enterprise and learn what it takes to launch a successful business.
Entrepreneurs from all parts of Yakima and Kittitas Counties have boosted their businesses with the help of the Enterprise Challenge. You may recognize Whipsaw Brewing, Pearl Street Optical, Claim Clothing, Basecamp Outfitters, Make Music Ellensburg, Gallivant Chocolate, Closet Maestro, all businesses that entered the competition.
- Contestants attend online classes and tutoring sessions that help them develop their business plans
- Plans are submitted to judges who evaluate each enterprise*
- Contestants with the highest scores move on through rounds of the competition
- The competition features a pitch your business trade show and a final presentation round
- Winners are announced at an awards ceremony or via video depending on our current local health measures
*Judges use scoring criteria to evaluate contestants on how well they have thought through and developed their enterpriseās marketing, financing, management, and operations plans. These judges provide contestants feedback on their ventures and business plans which is invaluable information for anyone launching a new business.
Again, please note that there may be schedule changes and different ways we approach each round of the competition during the 2025 Enterprise Challenge. If you have questions about the competition or want more information, please email Darby Grimes at darby@kittitascountychamber.com.
The Enterprise Challenge is for individuals, teams, or start-up companies that are located in Kittitas County.Ā Participants must comply with the following:
- Teams and/or businesses must be based in and have 50% of the partners located in Kittitas County, Washington.
- The business must have been in operation for less than two years with gross receipts under $1 million, or it must be a new business venture.Ā Franchise and chains are not eligible. A supporting business license number or status documentation must be provided at registration.
- Businesses must be āfor-profitā enterprises.Ā Non-profits are eligible to compete in the contest but are required to produce āfor-profitā financials and business strategies.
- Business plans may be submitted by individuals or teams.Ā Teams may have a maximum of three members.Ā All contestants must be over 18 years of age.
- The applicant and/or team member that is identified as the owner, or team lead, in order to advance to the final round of the contest, are required to attend the:
- orientation
- workshops, with one excused absence
- Enterprise Trade Show
- Final Presentation
- Contest judges will recuse themselves if he/she has a conflict of interest (i.e. family, financial, or business relationship).
- Judgesā decisions are final, including interpretation of the rules.
- Previous Enterprise Challenge participants may enter the contest with a different business; however, winners from previous Enterprise Challenges areĀ notĀ eligible.
- Winners will receive half their business investment following the awards ceremony and the other half at a mutually agreed upon business milestone noted in the business plan.Ā (i.e.- official opening of business, signed lease, payment system, website, etc).Ā An official agreement is signed by both parties prior to the investment distribution that includes the milestone that must be met during the current competition calendar year.
**In the event that the competition does not generate enough participants, Kittitas County Chamber of Commerce reserves the right to amend cash prize amounts or registration deadlines.
ROUND ONE:
Orientation | SEPTEMBER 9, 2025 | 6-8 P.M.
WORKSHOP: BASIC START UP | SEPTEMBER 10, 2025 | 6-8 P.M.
WORKSHOP: FINANCIALS 101 | SEPTEMBER 11, 2025 | 6-8 P.M.
WORKSHOP: MARKETING 101 | SEPTEMBER 16, 2025 | 6-8 P.M.
WORKSHOP: 1:1 Industry Professionals | SEPTEMBER 17, 2025 | 6-8 P.M.
SUBMISSION: BUSINESS PITCH |SEPTEMBER 18, 2025 | 12 P.M.
BUSINESS PITCH JUDGING ORIENTATION | SEPTEMBER 19, 2025 | 2-5 P.M.
JUDGES SUBMIT SCORES | SEPTEMBER 23, 2025 | 10 A.M.
ROUND TWO:
ROUND 2 ANNOUNCEMENT | SEPTEMBER 25, 2025
WORKSHOP: TRADE SHOW PITCH CLINIC | SEPTEMBER 30, 2025 | 6-8 P.M.
WORKSHOP: FINANCIALS 201 | OCTOBER 2, 2025 | 6-8 P.M.
WORKSHOP: MARKETING 201 | OCTOBER 7, 2025 | 6-8 P.M.
SUBMISSION: BUSINESS PITCH | OCTOBER 9, 2025 | 12 P.M.
TRADE SHOW | OCTOBER 14, 2025 | 9 A.M. - 5 P.M.
ROUND THREE:
ROUND 3 ANNOUNCEMENT | OCTOBER 15, 2025
WORKSHOP: BUILDING YOUR PITCH | OCTOBER 21, 2025 | 6-8 P.M.
WORKSHOP: FINANCIALS 301 | OCTOBER 23, 2025 | 6-8 P.M.
SUBMISSION: FINAL BUSINESS PITCH | OCTOBER 28, 2025 | 12 P.M.
FINAL PRESENTATION | OCTOBER 29, 2025 | 12-5 P.M.
AWARDS CEREMONY | OCTOBER 29, 2025 | 5:30-6:30 P.M.
Sponsorship
Interested in sponsorship? Let us know how you want to be involved with our annual program by contacting our Director of Events and Programs, Darby Grimes at darby@kittitascountychamber.com or by calling the Chamber office at (509) 925-2002.
2024 Enterprise Challenge Winners

1st Place Winner - $10,000
Simply Social
2nd Place Winner - $5,000
Cherry On Top Cart Co.
3rd Place Winner - $2,500
I LOVE CLE ELUM
2023 Enterprise Challenge Winners

1st Place Winner - $10,000
Closet Maestro
Kittitas County
2nd Place Winner - $5,000
The RT Advantage
Kittitas County
3rd Place Winner - $2,500
NEST+FLOW Handmade Goods
Yakima County
2022 Winners:
- 1st Place Winner - $10,000 - Sunny Family Medicine
- 2nd Place Winner - $5,000 - Gallivant Chocolate
- 3rd Place Winner - $2,500 - Make Music Ellensburg
2021 Winners:
- 1st Place Winner - $10,000 - Sunnyside Meat Packers
- 2nd Place Winner - $5,000 - Basecamp Outfitters
- 3rd Place Winner - $2,500 - The Tap
2020 Winners:Ā
- 1st Place Winner - $10,000 - Junk-Bros
- 2nd Place Winner - $5,000 - The Little Hopper
- 3rd Place Winner - $2,500 - Elite Tours
2019 Winners:Ā
- 1st Place Winner - $10,000 - Taqueria La Palapa
- 2nd Place Winner - $5,000 - Round Tuit Kitchen
- 3rd Place Winner - $2,500 - Ag Drone Data Services
2018 Winners:
- 1st Place Winner - $10,000 - Instar Naturals, LLC
- 2nd Place Winner - $5,000 - Gibabeam Internet
- 3rd Place Winner - $2,500 - Natalie DeHaven Cakes
2017 Winners:Ā
- 1st Place Winner - $10,000 - Whipsaw Brewing
- 2nd Place Winner - $5,000 - Sorbatto
- 3rd Place Winner - $2,500 - Wycked Hitch
2015 Winners:
- 1st Place Winner - $10,000 - Yakima Hop Candy
- 2nd Place Winner - $5,000 - Pearl Street Optical
- 3rd Place Winner - $2,500 - Mama Hogues Kitchen
2014 Winners:Ā
- 1st Place Winner - $10,000 - Claim Clothing
- 2nd Place Winner - $5,000 - Nana Kate's
- 3rd Place Winner - $2,500 - Chestnut Market
2013 Winners:
- 1st Place Winner - $10,000 - Spring Harvest Fiber Mill
- 2nd Place Winner - $5,000 - Active Life Chiropractic
- 3rd Place Winner - $2,500 - 4 Seasons Fresh
2012 Winners:
- 1st Place Winner - $10,000 - Selah Smiles
- 2nd Place Winner - $5,000 - The Drawing Board
- 3rd Place Winner - $2,500 - Yakima Coupons
2011 Winners:Ā
- 1st Place Winner - $10,000 - Washington Vision Therapy Center
- 2nd Place Winner - $5,000 - Hop Central Brewing Company
- 3rd Place Winner - $2,500 - Milt's Original Gourmet BBQ Pellets
2010 Winners:Ā
- 1st Place Winner - $10,000 - Tieton Farm & Creamery
- 2nd Place Winner - $5,000 - Jenny Mae's Gluten Free Bakery
- 3rd Place Winner - $2,500 - Cascade Animals Care Products
