Enter the #UnderdogChallenge

Does your small team run circles around much larger competitors? Do you compete against big teams and big budgets with scrappiness and creativity? You’re the Underdog, and Basecamp wants to hear from you! 🫵

Share your team’s underdog story below. The winning entry will be featured on The REWORK Podcast, where the winner will have the opportunity to share their story with our host Kimberly, and our founders Jason and David. Enter by September 15th!

That’s a wrap!

The entries are in. We’ll reach out to the winner by September 22, 2023.

Subscribe to the REWORK Podcast to listen to new episodes as they go live.

Contest Rules


August 22, 2023, to September 15, 2023


  1. The Basecamp “Underdog Challenge” contest is open to small teams, businesses, and startups worldwide.
  2. Participants must be at least 18 years old to enter.

How to Enter

To enter the contest, you must either:

  1. Share your story on your own LinkedIn or Twitter profile using the hashtag #UnderdogChallenge and tag the official @37signals account in your post; or
  2. Fill out the form on Basecamp’s official “Underdog Challenge” contest page at basecamp.com/underdogchallenge.

Contest Guidelines

  1. Entries should be original and authentic. Plagiarized, copied, or AI-generated entries will be disqualified.
  2. Keep your description within the 500-word limit.
  3. Ensure that your photo and description are suitable for public sharing and comply with all LinkedIn and Twitter content guidelines.
  4. By participating, you grant 37signals LLC the right to share your entry on their social media platforms and The REWORK Podcast.

Winner Selection

  1. All eligible entries received during the contest period will be judged by a panel of 37signals representatives.
  2. Entries will be judged based on the uniqueness and compelling nature of the underdog story, as well as the impact of the story on the growth and development of the business.
  3. The decision of the judges is final and binding.


  1. One (1) winning entry will be featured on 37signals’s official social media platforms.
  2. The winner will have the opportunity to share their unique underdog story on an episode of The REWORK Podcast.
  3. The winner will receive one complimentary year of Basecamp Pro Unlimited.


  1. The winner will be notified via LinkedIn, Twitter, or email within one week of the contest closing date.
  2. If the winner does not respond within seven (7) days of being notified, a new winner may be selected.

General Terms

  1. No purchase is necessary to enter or win the contest.
  2. Entrants do not have to be customers of Basecamp or 37signals.
  3. This contest is in no way sponsored, endorsed, or administered by, or associated with LinkedIn or Twitter (X).
  4. By participating in the contest, entrants agree to be bound by these official rules and 37signals’s decisions.

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