The NOW Not How Mindset
Replace overthinking with immediate action by starting before you feel ready
The NOW Not How Mindset is the foundational mental shift required before any entrepreneurial framework can work. Most people never start businesses not because they lack ideas, money, or skill, but because they are trapped in an endless loop of figuring out 'how' — how to build a website, how to incorporate, how to handle taxes, how to scale. The NOW Not How Mindset replaces this with immediate action: start NOW, figure out the 'how' as you go. This is not reckless — it is empirically proven through Kagan's observation that every major company traces back to a tiny experiment launched before the founders knew what they were doing. Apple started as two guys building a computer kit. Facebook started as a weekend project. Airbnb started as a way to crash in someone's living room. None of them had the 'how' figured out before they started. The mindset shift reframes entrepreneurship from a big, daunting thing into a series of small experiments that are supposed to fail.
- Start before you are ready — readiness is an illusion
- Small experiments repeated over time are the recipe for transformation
- The willingness to try more things, not expertise, separates winners from dreamers
- Business is an experiment, and experiments are supposed to fail
- Define yourself by the things you do each day, not by end results
- Take the Dollar ChallengeAsk someone you know for a one-dollar investment in you and your future business. This is not about the dollar — it is about breaking through the fear of starting and asking in the simplest possible way. The act of asking someone for money, even a single dollar, activates the entrepreneurial circuit in your brain and proves that the act of asking is not as terrifying as your imagination makes it. Thousands of Kagan's students report that this single exercise changed their relationship with entrepreneurship permanently.Pro tipDo this today, not tomorrow — the point is to act NOW, before you have time to overthink it
- Set Rejection Goals Instead of Success GoalsReframe rejection as something desirable by setting daily rejection targets. Instead of trying to get five yeses, try to collect five rejections. This inverts the psychology of asking — you succeed when people say no, which means every interaction is a win. The Coffee Challenge is a specific exercise: walk into a coffee shop and ask for 10% off your order. The goal is not the discount — it is proving to yourself that rejection does not kill you and that asking is a skill you can develop.Pro tipThe Coffee Challenge shows how fearless you actually are — most people discover that asking is far less painful than they imagined, and a surprising number of people say yes
- Apply the Law of 100Commit to doing your new venture 100 times before evaluating whether it is working. This eliminates the common pattern of starting something, hitting resistance after two or three attempts, and quitting. Write 100 blog posts before deciding if blogging works. Make 100 sales calls before deciding if your product sells. Create 100 pieces of content before evaluating your audience growth. The Law of 100 ensures you push past the initial resistance phase where most people quit and into the territory where compounding effects begin to appear.Pro tipTrack your progress visually — seeing yourself at attempt 47 of 100 creates commitment momentum that makes quitting feel wastefulWarningThe Law of 100 applies to execution, not planning — do not spend your 100 attempts refining your business plan
Kagan was employee #30 at Facebook, with 0.1% of the company (worth approximately $1 billion in 2022). He was fired after nine months for self-promoting and leaking company plans. He spent eight months on a friend's couch, devastated. But the firing liberated him from the fear of doing things his own way. He started telling everyone about his failure, which became a calling card ('the guy who was fired by Facebook'). His fears about what others thought were totally overblown. This liberation led to years of rapid experimentation that eventually produced eight million-dollar businesses.
In 2013, Kagan launched his first course with five beta testers — a programmer, a horse trainer, and three people with day jobs. All had the skills, information, and desire to start businesses. After two weeks, the entire group had made zero progress. Through group therapy, Kagan discovered the barrier was not capability but two fears: fear of starting (believing entrepreneurship is too risky) and fear of asking (unable to face rejection). This led to the development of the Dollar Challenge and Coffee Challenge as fear-breaking exercises.
After being fired from Facebook and spending eight months on a friend's couch, Kagan realized that his repeated 'almost successes' — Microsoft internship rejection, Google offer rescinded for failing long division, Facebook firing — all shared a common pattern: he kept waiting to feel ready rather than starting before he was ready. When he finally embraced experimentation without readiness, everything changed. He started random side hustles, consulted for startups, created conferences, launched websites — most failed, but the sheer volume of experiments eventually produced AppSumo and seven other million-dollar businesses. He distilled this into the NOW Not How principle after watching his first five beta testers (a programmer, a horse trainer, and three people with day jobs) make zero progress in two weeks despite having everything they needed.