Idea to Startup

Today we talk about two methods to help make your big startup plans for 2026 manageable. We borrow Short Assignments and Shitty Drafts from Anne Lamott, we get a little help from Martin Scorsese and a Bronx Tale, and we talk through a startup that's helping 40 year olds deal with loneliness. All in like 14 minutes. Not bad. Tacklebox WINTER2025 for 20% offBird by BirdThe To Do List MonsterThe Saddest Thing In Life 00:00 Tacklebox00:28 Actionable Motivation01:08 How to Actually Take a Swing at Your Potential04:15 The Two Best Ways to Make Progres05:59 The One-Inch Picture Frame10:20 Shitty Drafts12:55 The End: The Saddest Thing In Life

Today, we'll talk through how you'll find customers in-person. This is the single most important acquisition tool for early-stage founders, and there's no excuse - any business targeting any customer can do it. We use a few Tacklebox examples and give you a framework to make it happen.  Tacklebox CODE "HOLIDAY2025" for 50% off month one)Tacklebox Sunday EmailsTally (online form builder)Timestamps:00:45 Your In-Person Growth Strategy Intro01:30 Cropped04:20 For the People Who Can’t Do In-Person05:26 Your In-Person Acquisition Plan: A Date Wingman07:34 Places to Find Hard to Find Customers09:54 The Script11:42 The Media12:32 The End

Today, we're digging into the mailbag for your Thanksgiving commute. First, what idea would Brian start if he had to start an idea? We go deep on why a coffee truck idea is the best possible business for this moment. Next, we talk through how to get your spouse on board with your idea, and finally we hit on the best gifts for new entrepreneurs.Take that, Kyle. Tacklebox 50% off with code HOLIDAY2025Disciplined EntrepreurshipThe Personal MBAThe Power of HabitAtomic HabitsFour Thousand WeeksFocusmateWeber EG 1PluribusTimestamps0:30 Mailbag!01:25 Question One - What Idea Would Brian Start?03:05 The Four Idea Criteria06:40 Idea-Founder Fit07:51 A Coffee Truck14:50 Smooth Jazz15:25 Question Two - How do I get my spouse on board?19:26 Question Three - Best Gifts for Entrepreneurs

This episode is a toolkit for right-brain founders who get lost in ideas and struggle to execute. Brian shares three practical systems—AI as your left brain, the Regroup System, and the Ice Box—to help you make consistent progress, despite the whole right brain thing. This is a practical guide for turning creativity into momentum.Tacklebox (code HOLIDAY2025 for 50% off)The sailboat race I mentionTimestamps:00:30 How a Prolific Investor Invests04:47 Right Brain, Left Brain07:38 Jazz - CODE HOLIDAY202508:13 You Don’t Have a Goal11:30 Outsourcing your Left Brain to AI13:05 The Regroup System15:01 The Icebox16:59 The End

Today, we'll help you pick your startup's first customer segment. This decision dooms a huge percentage of first time entrepreneurs - if you don't understand what the job of your first customer segment is, you'll likely pick a customer incapable of doing it. Your first customer has a unique responsibility that no other customer will have - you need to choose them carefully.Conversely, if you choose the right first customer, you'll set yourself up for serious growth. We go through the five characteristics your first customer needs, give a preview of what your successful startup will look like, and help a listener find the first customer for their Myers Briggs startup. TackleboxGetting Real (museum curator reference)Everyman Espresso (☕️ 🐐)Timestamps00:27 First Time Entrepreneurs vs. Second Time Entrepreneurs03:20 The Idea: Personality-Based Management06:29 Why You, Why At All, Why Now08:55 Byldd09:55 The Story of Your Successful Startup15:35 The Five Necessary First Customer Characteristics16:41 Characteristic One: Pain21:51 Characteristic Two: The Knowledge Spectrum25:43 Characteristic Three: Measurement28:24 Characteristic Four: Influence29:48 Characteristic Five: Frequency31:45 The End