What’s Your Toughest Business Question? Ask and Enter to Win an iPad 3

by / ⠀Startup Advice / May 15, 2012

Every day at Under30CEO we publish articles to help entrepreneurs get answers and build better businesses. Now, we want to know exactly what your questions are.

  • What’s your biggest business challenge?
  • What do you need more advice on?
  • What do you need tips on to get your business to the next level?

Under30CEO has partnered with HighTable to collect these questions from the Under30CEO community. The HighTable community is made up of close to 300,000 consultants, executives, and top entrepreneurs ready to help get you the answers you need and foster your success.

We want your questions! These questions will help shape Under30CEO content, get you featured on Under30CEO, and enter you to win a brand new iPad 3.

How it works:

1. Create your HighTable account here.  If you already have an account simply login when you ask a question on the Under30CEO page.

2. Ask your small business question and MAKE SURE it is tagged “Under30CEO”. If it is not tagged the question will not enter you to win the iPad 3.

3. Email the link to your question to Jared(at)under30ceo.com

Questions will be judged on relevancy, responses from the hightable community and your continued engagement with everyone that answers your question.


  • You have until midnight on May 22nd to ask a question.
  • Each person can only enter 1 question.
  • The winner will be announced the following week.


Grand Prize:

  • A brand new iPad 3, valued at $499
  • Have your question and the answers featured on Under30CEO. The feature will highlight you and your business.

 First Prize:

  • A feature on Under30CEO.  Have your question and the answers featured on this website, highlighting you and your business.
  • Business book of your choice from Amazon.com.


  • Next ten best questions will be combined into an Under30CEO featured article with links to each winner and their business.

Congratulations to last months winner:

Last months winner is Jane Ny who asked “What are the 3 best treasures of wisdom that you found helpful in your startup ventures?”.

Jane’s questions saw a huge response with 49 answers and 750 views to her question. Jane took our advice from the last competition by going above and beyond to stay engaged with all of the experts who took time to help her out.

Enter today!

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.