Jessica Livingston at Startup School 2012

Livingston says determination combines resilience, which helps founders withstand setbacks, and drive, which keeps them moving forward. She describes how rejection is common, even for startups that later succeed: Airbnb faced skepticism when it offered airbed rentals, and Pebble founder Eric Migicovsky heard no from more than 30 investors before turning to Kickstarter. Y Combinator itself also faced doubts when it began.

Startups encounter problems without a reliable playbook, so founders need to improvise. Examples include Lavu founder Rat Suri working as a waiter to understand restaurants, the Collison brothers using phone calls to get payment companies to hear them out, and Lockitron founders repairing used locks to fulfill an order. When Justin.tv’s video system went down, Michael Seibel got a message to an unreachable engineer through a pizza delivery shop.

Livingston cautions founders to choose co-founders carefully and address concerns about trust, effort, or competence early, since breakups can damage a startup’s morale and productivity. Fundraising can also be slow and demoralizing; she advises founders to meet many investors and create a competitive situation when possible. Early on, she says, founders should prioritize building, talking to users, and exercising, while treating corporate development meetings as a potential distraction.

Livingston calls making something people want the hardest startup challenge and says it usually takes user conversations, adjustments, and sometimes a major change in direction. Airbnb broadened from airbeds for conference travelers to entire home rentals, while OrderAhead was its founders’ sixth idea; Dropbox required many small execution details. She describes startup fortunes as volatile, contrasting a signed $7 million investment that fell through with Codecademy’s 200,000 users in its first three days, and advises founders to keep perspective through both extremes.