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 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 - Wher...
Jun 11, 2026•28 min•Season 5Ep. 216
Today, we'll talk about one of the most effective methods to do hard things we've found at Tacklebox: Scripting the start and end. Tacklebox Alternate Nostril Breathing Jr Jr - The Speed of Things
Apr 15, 2026•14 min•Season 5Ep. 215
Today we'll talk about thrust and drag, the components of momentum. Momentum is the lifeblood for startups, but most people leave it to chance. By focusing on the inputs of momentum - thrust and drag - you can build systems to ensure you keep moving forward. Gaps kill startups. This system removes them. Byldd Tacklebox Song where Taylor Swift burns Jake Gyllenhall...
Apr 08, 2026•21 min•Season 5Ep. 214
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 Byldd Greenlights 0:30 Building a Wildly Useful Startup 2:12 W...
Mar 25, 2026•25 min•Season 5Ep. 213
Today, we'll run through a Concierge MVP example live on the pod. Brian chooses an idea specifically because someone wrote in and said it was "un-Concierageable," which isn't a word but is the reason this podcast exists. We go through the four-part framework that'll help you build a Concierge MVP - The Three Components of Wild Success, Acquiring Customers, The Test, and Feedback Loops. And we get a little help from an alum helping people get grants and our old friend - the Monkey on the Pedestal...
Mar 18, 2026•24 min•Season 5Ep. 212
Today, we talk through the Silk Sheet Problem - how to do something new and hard when your life is fairly... comfortable. We help a listener get started on their idea - an AI tutor's assistant - with three shortcuts to set their life up in a way that makes it easier to start a startup than to not. We talk through Just-In-Time Prep, Forcing Functions, and life design. This episode is meant to be a blueprint for you to take action and keep momentum. Tacklebox Kevin running from the furnace 00:34 I...
Mar 05, 2026•22 min•Season 4Ep. 17
Today we'll talk through how to test out and build a startup idea in ~10 days by answering four questions. We'll use an idea that's oddly popped up a bunch lately: Kitchen Organizer. We do this with a little help from a story about a poker player and my good friend, Penne Vodka Pete. Join Tacklebox (CODE WINTER2025) Wix
Feb 19, 2026•23 min•Season 5Ep. 211
Today, we’re talking about startup identity—why you need one, and how it makes every decision you face way easier. We’ll talk swimming and nervous systems, walk through the Decision Equation, and help our good friend Carl figure out which customer to start with for his AI tool that helps adults learn Spanish. Then we’ll wrap with a simple framework to help you clearly define your startup’s identity. It’s practical, a little weird, and really important. On to it. Tacklebox Hero Timestamps 00:30 Y...
Feb 11, 2026•26 min•Season 5Ep. 209
Today, we'll help you get your first customers. We'll do it by learning how to use the trust to risk ratio - a way to identify the big risks that are holding your customer back and shoulder those risks early on to build trust. We talk through risk and trust with Find Your Lobster, Soona, and a finicky water pump. Tacklebox Soona
Feb 04, 2026•19 min•Season 5Ep. 208
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 Popup Bagels 00:00 Tacklebox 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 Differenti...
Jan 23, 2026•24 min•Season 5Ep. 207
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. Tacklebo...
Jan 14, 2026•23 min•Season 5Ep. 206
A 20(ish) minute skills episode on sales 101 for entrepreneurs who hate sales. We go through three tactics and a bunch of examples to help you build a system for sales that'll help you grow without making you feel slimy. We set up sales for a sabbaticals as a service startup. And we talk through why entrepreneurs hate sales and how to reframe the whole thing. Tacklebox (Code WINTER2025 ) Text Expander Streak Pipedrive...
Jan 07, 2026•28 min•Season 5Ep. 205
Today we'll talk about why people hand their keys over to random strangers on the street in New York City, how a person selling cures for baldness converts 80% of the people he speaks with, and how you can build a strategy to cultivate trust with your customers, too. Tacklebox (20% off with code WINTER2025)
Dec 31, 2025•18 min•Season 5Ep. 204
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% off Bird by Bird The To Do List Monster The Saddest Thing In Life 00:00 Tacklebox 00:28 Actionable Motivation 01:08 How to Actually Take a Swing ...
Dec 18, 2025•15 min•Season 5Ep. 202
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 Emails Tally (online form builder) Timestamps: 00:45 Your In-Person Growth Strategy Intro 01:30 Cropped 04:20 For the People Who Can’t Do In-Pe...
Dec 05, 2025•14 min•Season 5Ep. 201
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 HOLIDAY2025 Disciplined Entrepreurship The Personal MBA The Power of Habit Atomic Habits Four Thousand Weeks ...
Nov 26, 2025•22 min•Season 5Ep. 200
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 mention Timestamps: 00:30 How a Prolific Investor Invests 04:47 Right Brain, Left Brain 07:38 Jazz - CODE ...
Nov 20, 2025•18 min•Season 5Ep. 199
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 chara...
Nov 13, 2025•33 min•Season 5Ep. 198
Today, we'll talk about the big question - should you start with a focused niche? There are pros and cons to the approach, but the perceived cons - "what if I get tired of the niche in a few years?" , "what if the niche doesn't lead to a bigger market?" , "isn't a niche just hiding from the bigger problem I want to solve?" have gotten louder lately. So, we'll address them. We'll go over what a good niche looks like, how to get one, and how to grow. Podcast Insider Sign Up Tacklebox Kurt Vonnegut...
Oct 30, 2025•24 min•Season 5Ep. 197
Hard problems are the only problems worth your time. Today, we'll talk about how to identify them and build a business around them. We'll dig in on decisions customers avoid and using those decisions to anchor early traction. We'll talk through Brian's favorite current business - a guy who buys used cars for you - and how to approach helping people with chronic pain. Also, I'm writing a book! Want to help me? Sign up here . Tacklebox...
Oct 23, 2025•19 min•Season 5Ep. 196
Today, we talk about why you struggle so much with easy, seemingly straightforward tasks as a founder. You probably assume this is a productivity problem, but it's actually a nervous system problem - you've maxed out your Risk Threshold. We talk about how to navigate that and build a startup while being a human. Also, I'm writing a book! HELP BRIAN WRITE A BOOK Tacklebox 00:30 - Brian’s Writing a Book 02:34 - Why Easy Stuff is Hard 05:02 - Your Risk Threshold 07:15 - The Riskiness Equation 11:27...
Oct 16, 2025•15 min•Season 5Ep. 195
Most founders hope to get lucky. But luck isn't random - it can (and has to be) engineered. Today we'll break down exactly what luck is and how you can reverse engineer it. We'll help you identify Luck Gatekeepers and build your Luck Budget. You'll never think about entrepreneurial luck the same way again. Tacklebox (code Holiday for 50% off month one) Graham Weaver Timestamps: 00:30 How to get lucky 03:11 Story Time: Getting Press for 3Degrees 11:06 Tacklebox 12:32 The Five Types of Luck 15:05 ...
Oct 09, 2025•20 min•Season 5Ep. 194
Today, we'll help you build an SOP for testing startup ideas. We'll use an example from a listener - a startup in the homeschooling space - as a guinea pig. The best way to have a great startup idea this time next year is to test out a bunch of ideas in the interim. This SOP will help you do it, and scale the process. Tacklebox 00:00 Tacklebox 00:30 Pros and Amateurs 02:08 Homeschool Idea 05:47 The Story of Future You 06:16 Entrepreneur Pro Tactic Number One - Working Backwards from Dreams 07:42...
Oct 02, 2025•24 min•Season 5Ep. 193
Today, we'll talk about why so many entrepreneurs can't effectively explain what they're doing to their customers. The short answer is they speak the wrong language. Customers speak Problem, entrepreneurs speak Solution. It's like two people trying to have a conversation when one only speaks Latin and the other only speaks Dutch. We go through how to start speaking Problem, and show the power of Problem Language through a live idea test - two landing pages for an AI bot to help people get out of...
Sep 25, 2025•22 min•Season 5Ep. 192
Today’s episode is for everyone who struggles to summarize their startup in a sentence. We lay out a framework to do this well with help from a sticker on the street, a hedge fund, and a Vietnamese coffee shop. Tacklebox Idea to Startup Newsletter 00:33 One Sentence Marketing 01:10 Train to NYC 03:04 The best marketing Brian’s seen in a while 06:42 Smooth Jazz 07:28 Choosing a Customer and the Knowledge Spectrum 08:54 Air Quality Idea 13:07 Inflection Points + The Conference Exercise 14:09 The E...
Sep 18, 2025•16 min•Season 5Ep. 191
Today, we'll teach you how to name your startup. This is from No Whisper Ideas, a post sent every Sunday by Brian. Customer Interviews Workshop (Starts Sep 15) No Whisper Ideas Weekly Post
Sep 11, 2025•8 min•Season 5Ep. 190
Today, we build a machine to help you actually run customer interviews. We’ll use AI to tackle the big blockers—accountability, CRM setup, outreach, transcription, and even how to pick your first customer. You’ll hear the idea Brian is testing with the interview machine, and we’ll walk through exactly how AI can make the process faster, more uncomfortable (in the right way), and a lot more effective. Plus, a bit on creativity and being human. Tacklebox Customer Interview Workshop (starts 9/15) C...
Sep 03, 2025•25 min•Season 5Ep. 189
Today, we talk through a 4-part system to generate ideas - one that'll tap into your brain's natural ability to develop novel solutions rather than just waiting (hoping) inspiration will strike. We'll do it with a little help from a baseball training facility, a corked wine bottle, and an MRI startup. The Tacklebox Customer Interviews Workshop - Sept. Session is OPEN Idea to Startup Newsletter Fermenting Ideas Pod: Customers speak Problem Pod: How to Create a Strategy for your Startup Readwise I...
Aug 28, 2025•23 min•Season 5Ep. 188
Today, we'll help you tackle the big question for entrepreneurs with startup ideas and jobs - when's it time to quit the job and focus on the startup full-time? You should think about this question the second you start working on an idea, and you should use the Skeptical Startup framework - a goal of $8k per month in 10 hours per week - as a guide. The Skeptical Startup framework is magical, and Brian will show how it'll help you focus with an example startup. Tacklebox Idea to Startup Newslette...
Aug 21, 2025•21 min•Season 5Ep. 187
Today, we talk about the difference between Entrepreneur Brain and Normal Brain. Normal Brain is out to sabotage your startup. We teach you Entrepreneur Brain to make sure that doesn't happen. Tacklebox 10-Day Customer Interview Workshop Ali Abdaal - The Good Student vs. The Good Entrepreneur Mindset ( text , Ali's email signup ) Graham Weaver - How to Design a Winnable Game Daina Trout Episode Timestamps: 00:30 Entrepreneur Brain vs. Normal Brain 01:50 The $2 Million Dollar House 05:30 Customer...
Aug 14, 2025•20 min•Season 5Ep. 186
