Today, we'll help you think through a deceptively tough question - are you a freelancer or an entrepreneur? Every decision you make needs to nest neatly below this core decision for your business to work, but tons of founders are either trying to do both simultaneously or think they're one when they're really the other.

We clarify the difference between freelancer and entrepreneur, help you decide which will make you happier, and get you started on the path for whichever you choose. 

• BYLDD
• Tacklebox
• Seth Godin Conversation
• Kurt Vonnegut
• No Lunging

0:30 Why Entrepreneurs are unhappy
01:14 Do you want to be a freelancer or entrepreneur?
04:12 Seth Godin Conversation
04:58 Our definition of a freelancer
07:28 Our definition of entrepreneurs
09:07 Cuban’s Definition of Entrepreneurship
11:24 BYLDD
12:25 The Restaurant Startup
15:15 Rivers and Dams
19:19 No Lunging
22:44 Don’t Pretend
23:10 How do you want to spend your days?

Today, we help you become the type of founder who relishes uncomfortable things that lead to successful startups. There are no real secrets in the startup world - the hard, proactive, uncomfortable work leads to businesses that matter. This work doesn’t happen without a system.

Today we help you build that system, using The Costanza Swap, The Three Levers of Resilience, and The Failure Case.

Hoo ahh.

• Tacklebox

00:24 Doing Things You Don’t Want To Do
02:45 Why the Eisenhower Box Doesn’t Work for Entrepreneurs
03:30 The Al Pacino Problem
04:45 Creating Content
08:00 Smooth Jazz
08:30 The Costanza Swap
10:15 One Out, One In
11:20 The Three Levers of Resilience
12:40 Scheduling
13:24 Committing
14:30 Dissecting
17:40 The Failure Case
21:15 Happiness

Today, we'll lay out a framework to help you identify and kill bad ideas. It's hard to objectively evaluate your idea early on - this framework helps you rise above your idea to do it effectively. A side-effect is that the framework will help you find and pursue the good ideas.

We talk through 1) Finding and Evaluating the Real Risk, 2) Predicting Organic Growth Potential, and 3) Predicting the Likelihood of Converting Early Customers, using a startup idea from a listener as an example. 

• Tacklebox
• Kunal Shah Delta 4
• Dig out of a Hole Idea to Startup Episode - The Four Characteristics of Great Startup Ideas

00:25 - Killing Bad Startup Ideas
02:00 - The Three Pillars of the Will Your Idea Fail Framework
02:45 - The Startup Idea - AI Messaging for Plumbers and Electricians
03:15 - Dig out of a Hole Markets link to episode
05:56 - Smooth Jazz
06:24 - Part 1 - How to Find and Evaluate the Real Risk
07:35 - Flipping your biggest risk to your biggest strength
11:00 - Decisions aren’t made in a bubble
13:45 - Part 2 - Predicting the Organic Growth Potential
14:00 - Kunal Shah Delta 4 Scale
17:41 - Part 3 - Predicting whether you’ll actually be able to get first customers to convert
18:49 Managed by Q

Today is the last episode in the three-part series on an internal operating system for people working on startup ideas. We talk through the core pillars - Projects, Areas, Inbox - and the multipliers (like Keystone Actions) that'll make sure you're focused on the things that could be differentiators for your business. After today, you'll have everything you need to build your own system.  

• Tacklebox
• The PARA Method
• Getting Things Done
• Notion GTD Template

00:24 Your Startup System
02:18 The Birthday Email
06:34 Email System Prompts
08:26 Smooth Jazz
08:55 Structure - Projects, Areas, Inbox
10:06 Getting Things Done + The PARA Method + Notion Template
11:00 Projects
16:14 Areas
16:46 Inbox
19:55 The Multipliers
20:00 Keystone Species
23:12 Never Agains
24:39 Lottery Tickets
26:44 Doing the Thing
27:31 Reflection

Today is part 2 of our series helping you build an internal operating system. We identify the four things you'll need to have happen for your startup to gain momentum, then we organize those into a system that'll help you move fast based on inertia.

• Tacklebox
• Beehiiv
• Monkeys and Shakespeare
• 101 Essays That Will Change The Way You Think
• Delta 4 Status Level Jump
   

00:25 - Internal Operating System Part II
03:15 - Monkeys and Shakespeare
07:40 - Smooth Jazz
08: 05 - Reverse Engineering a System
10:45 - Where is the Monkey?
11:33 - The Four Things That Matter for an Early Stage Business
11:40 - Problem
12:01 - Delta 4 Status Level Jump
13:34 - Secret
16:35 - Optimize for Inertia
18:37 - 101 Essays That Will Change The Way You Think
20:00 - The Thousand Daily Votes
21:43 - The Last 15%
23:30 - Script the Beginning and End
24:30 - Feedback Loop Optimization

Today, we'll kick off a series that'll help people with jobs and startup ideas build an internal system that'll help them track progress and build momentum. Too many founders have no strategy or measurement system around how they pursue and test an idea - this series will help you do it.

In part 1, we go through what a strategy should look like and the three counterintuitive benefits to creating one. 

• Tacklebox
• Beehiiv

00:00 Jazz
00:25 What should you work on today?
02:29 Golf Clubs in Cities
4:20 The Danger of Unstructured Work
6:58 The Three Ideas, #1 - No One Does This
8:45 Change your Behavior to Change How You Think
10:22 The Magic Happens After You Start
15:55 The Four Questions to Anchor Your Week

Today, we'll help you find a differentiator powerful enough that it can support your business. We'll talk through what a differentiator actually allows you to do, five prompts to help you uncover and test one for your business, and Brian's favorite current differentiator - Popup Bagels. 

• Tacklebox
• Beehiiv
• Popup Bagels
   

00:00 Beehiiv
00:33 Differentiator intro
04:00 What do you hire a differentiator to do?
05:44 The Attention Pie
09:03 Smooth Jazz
09:28 Popup Bagels
16:30 Five Prompts for Your Differentiator

Today, we'll help you get out of your own way. We subscribe to the Charlie Munger school of "instead of trying to be smarter, try to be less dumb," and this episode digs into three ways to simplify your startup so that you can move faster. We talk through how to actually implement jobs to be done, how to build systems to amplify your willpower 100x, and how to be more courageous. 

Also, I'll watch Interstellar. Everyone calm down. 

• Tacklebox
• Idea to Startup Newsletter (Beehiiv)

00:34 Removing Yourself as the Bottleneck
2:33 Leverage Jobs to be Done to Focus (Fishing Story)
6:23 Elderly Relocation Idea
11:08 Smooth Jazz
11:37 Run Towards the Rain
13:45 Thrashing to find a Secret - The Plant Story
15:25 A System for the Uncomfortable Stuff (fiverr + IG DM’s)
17:13 The Process for Improving Willpower
18:31 What Would You Do if You Knew It Would Work?

Today, we'll talk through a framework that'll help you evaluate whether you're building something useful enough to anchor a business. Most startups fail because the thing they built doesn't make a big enough dent in their customers lives. We'll make sure you don't make this mistake with help from Habit Kangaroo, a startup Brian ran back in 2014, and a GMAT training program his friend ran that helped people get into Harvard. 

• Tacklebox
• Beehiiv (Idea to Startup Newsletter)
• Byldd
• Greenlights

0:30 Building a Wildly Useful Startup
2:12 Why Measuring Usefulness is Hard
7:00 Byldd
7:53 Habit Kangaroo
12:50 The Usefulness Framework
13:24 What is your Secret?
13:51 Three Categories of Secrets: Customer
14:45 Three Categories of Secrets: Acquisition
15:16 Three Categories of Secrets: Product
17:08 Rivers and Dams
19:00 GMAT over 700 Product
23:02 Hire Yourself

Today, we talk through four characteristics of great startup ideas (with a bonus fifth Brian thought of post-recording). We discuss organic growth, market innovation vs. product innovation, growing markets, product swaps, and happiness. The goal of this episode is to help shape fuzzy ideas and give you new ideas.  

• Tacklebox
• Beehiiv

1:27 The Personal Venn Diagram
5:18 Smooth Jazz
5:46 The Four Characteristics of Great Startup Ideas
6:48 Characteristic 1: Potential for Organic Growth
9:14 Characteristic 2: Market Innovation > Product Innovation
10:57 Characteristic 3: Prioritizing Around a Growing Market
12:40 Four Buckets of Market Growth
12:45 Hype Markets
13:36 Dig out of a Hole Market (nurses, agriculture, skilled trades)
16:23 Momentum Markets
16:56 Subsidized Growth
17:42 The Swap
21:19 On Happiness