One mistake I often used to make at Justin.tv was offering a potpourri of business models (virtual goods, product placement, chat ads, contests, etc..). I was embarrassed to say Justin.tv would monetize with advertising when clearly that was the only answer. Own the simple business model.
Really unpopular opinion for designers:
it's easier, more joyful and beneficial to do free work for someone you like, than design and release your perfect portfolio with case studies.
The only rule for free work is that you should be the one to offer it, and not asked to do it.
There’s an activity that the Barrel partners have been doing for a while: reaching out to a couple of contacts per week. These have typically been former clients, industry acquaintances, other agency operators, investor types, old friends and classmates, etc. It’s been a practice we’ve kept up weekly since 2017.