Jesse J. Anderson

Twenty Bits I Learned About Design, Business & Community

by Dan Cederholm


Twenty Bits... is an easy read with lots of actionable advice for starting a business and being a better designer. There are some fun insights into what worked and what didn't work in building Dribbble and how they learned from that experience.


1. Start with a t-shirt

Creating a logo and t-shirt is a great way to visualize a new brand and claim its identity.

T-shirts are a great way to express who you are without having to talk to anyone.

— Jake Nickell (Threadless founder)

People love getting mail. Sending someone a free t-shirt is a way to standout in announcing a new product or brand. Accompany with it a hand-written note.

2. Your first members are critical

By curating a list of thoughtful designers for starting Dribbble, those designers were thoughtful and selective in who they invited, resulting in high quality content for the start of the community.

Dribbble's invitation was meant as a way to throttle scaling and support, but accidentally meant the quality of content was very high.

Friends and family are great, but don't be afraid to seek people that you respect (even if you don't know them), if you would love for them to use your product and provide feedback.

3. Pave the cowpaths

Allow natural paths to occur rather than trying to anticipate usage.

Many Twitter features came from natural community usage:

  • @ mentions
  • # hashtags

4. Choose your partner wisely

Co-founding a company requires you to be essentially married, and sometimes that isn't easy. Communication is paramount.

Tips for finding good partner:

  • How well do our skills mesh (broad coverage is better)?
  • How well do we get along?
  • Can we communicate efficiently?
  • Do we share the same values?

5. Find a good lawyer and accountant

Find them before you need them. Try to have several names written down already (recommended from friends and family).

6. Don't be afraid to throw things away

Don't be afraid to chalk it up to a learning experience, even if you're throwing out a lot of time an code.

When something isn't working... trash it, move on, and don't look back.

7. Persistent iteration over flashy launches

Slower, more subtle updates and tweaks are more likely to be embraced by the community.

Consider smaller private focus groups for testing new features with.

8. Not knowing what you're doing is okay

Laugh at your mistakes but don't be afraid to jump into thing you don't know how to do.

Don't classify anything as “things only experts can do”. Everyone is just winging it, so don't be afraid to tackle new endeavors.

9. Grow thick skin—quickly

  • Learn who to ignore. Separate the genuine from those who love to pick a fight and ignore the latter.
  • Celebrate the positive. Make sure the team reads the praise you receive. This should be your focus! Print out positive tweets, share them, save them. Keep the positive always in mind.

10. Typography is the bet skill you can learn

Essential typography skills:

  • hierarchy
  • vertical rhythm
  • line height
  • case
  • italicizing
  • grids

Good typography transcends trends and improves clear communication.

11. Trends come and go... and come back again

Don't worry about them too much, focus on what works for the design task at hand.

12. Everything is temporary and that's okay

The temporary nature of most design frees us for reinvention (and protects us from too much worry about trends)

(13 and 14 purposefully missing, read the book)

15. People and relationships are what's most important

Be kind. It's both the right thing to do, and opens the door for future opportunity.

16. Stay sharp with side projects

Side projects can move fast and allow you to try things you can't do in a full-time business.

17. Identify when you're being stubborn

Try to identify when you're blocking something that might ultimately help the business. When you unblock yourself and accept change, your team will be better for it.

18. Write, teach, & share while you're learning

Writing about what you know helps you to think about it in a new way. teaching I was actually learning because I was forcing myself to deeply understand how this thing works ... then I can explain it to other people.

— Pablo Stanley (designer, illustrator)

Many talented and successful people attribute teaching while learning to helping their career.

19. Take care of yourself first

Take mental health seriously. Self-care will allow you to be a good leader for your team.

20. Know when to let go

Moving on and letting things go is healthy, and gets easier over time.

I've always thought of myself as an 80 percenter. I like to throw myself passionately into a sport or activity until I reach 80 percent proficiency level. To go beyond that requires an obsession and degree of specialization that doesn't appeal to me.

— Yvon Chouinard (Patagonia founder)