Josh Kaufman on Creatively Navigating Entrepreneurship

Converge: The Business of Creativity Podcast with Dane Sanders

Background

Josh is a full time researcher and author who started off at a big company analyzing if their online advertising was actually working. His research developed into putting together a strategy of determining what works for the company when it comes to things of the advertising nature. Josh’s job eventually changed to advising entrepreneurs and small businesses primarily during their early stages.

Early Stages of Entrepreneurship

For an entrepreneur, Josh says that the early stages of development are most important in that during this time, you are an explorer and adventurer. This time period entails feeling lost and alone looking for the your path or hydra. All of the information you find during this time can be used to determine your next step. One thing that is needing is also practical wisdom which is learning to act and do things in a way that gets you good results but is also practical, grounded, and impacts your life in a meaningful way.

Each of us must ask four questions:

What do I want? 2. Why do I want it? 3. How am I going about getting it? 4. Is there a more straightforward and less stressful way to do it?

Josh analyzes these questions through looking at not just complex ideas but particular purposes or ends. He asks himself, “How are people approaching it?” and “Is that approach constructive or not?” As a researcher, these questions form the basis for what he studies and how he applies the answers through his writings and advising.

How to Fight a Hydra

How To Fight a Hydra is about a protagonist attempting to defeat a monster and also survive the experience. This concept can be parallel into the same demons all entrepreneurs face when it comes to starting a business or chasing an idea. In his book, the protagonist does not just face a single stage victory, but multiple of varying levels of size and impact.

One of the biggest things Josh mentions is how to get from knowing nothing about something you want to do to being good at it to then getting the result the you want. The next thing to look at it is being able to do all of these things quickly and with as little frustration as possible. Each of these concepts are analyzed through the story of the protagonist in his book.

Timeline

[02:50] Josh’s work experiences and their influences on him today.

[05:02] What is the best, most effective, most useful way to think about a particular area of life?

[06:30] 1. How are people approaching this subject? 2. Is that approach constructive or not?

[09:30] Going from knowing nothing to achieving your goals.

[10:22] His research and writing is more than complex ideas.

[10:50] Practical Wisdom

[11:09] The four questions every entrepreneur must ask.

[13:18] Influential authors on Josh are those that have written "how to think about ____” books rather than solely entertainment books.

[16:25] Why is it important to know the “bugs” in our thinking processes?

[16:41] The three kinds of books out there are entertainment, how-to, and worldview.

[20:30] What is an active barrier we must each individually overcome?

[21:00] You won’t know if something will or will not work until you do it.

[21:32] Factors that influence the success of something.

[25:27] Why are Josh’s writing based in behavioral and cognitive psychology?

[27:11] The protagonist in How to Fight a Hydra had multi-level victories.

[27:27] Experiences can change you.

[30:04] What is the most important time for an entrepreneur?

[30:54] Why am I feeling lost in this stage of starting a new business or chasing a goal?

[34:55] The importance of the ability to discern what opportunities are good for you.

[38:04] Differentiating between the different types of entertainments and their influences upon you.

[39:38] The easiest way to free up time in your life.

[40:00] “Is this improving my worldview, or is this primarily a diversion?"