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Recent episodes
15 Min(ish) Skill: Script the Start and End (ITS Classic)
Apr 15, 2026
14m 25s
Thrust and Drag, Part 1: A System to Keep Momentum
Apr 8, 2026
Unknown duration
A Framework to Make Sure You're Building Something Useful
Mar 25, 2026
Unknown duration
Running a Concierge MVP Live (feat. the four-step Concierge MVP framework) ITS Classic
Mar 18, 2026
Unknown duration
Three Shortcuts to Actually Help You Get Started On Your Idea
Mar 5, 2026
Unknown duration
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 4/15/26 |  15 Min(ish) Skill: Script the Start and End (ITS Classic)✨ | scriptingstart and end+3 | — | Tacklebox | — | scriptingentrepreneurship+3 | — | 14m 25s | |
| 4/8/26 |  Thrust and Drag, Part 1: A System to Keep Momentum | 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. | — | ||||||
| 3/25/26 |  A Framework to Make Sure You're Building Something Useful | Today, we'll help you make sure the thing you're building is wildly useful. Most startups fail because founders build stuff that customers don't care enough about to change their behavior for. We'll use The Usefulness Framework to ensure you don't do that, with help from Habit Kangaroo, a startup Brian ran back in 2014, and a GMAT training program his friend built to help people get into Harvard. | — | ||||||
| 3/18/26 |  Running a Concierge MVP Live (feat. the four-step Concierge MVP framework) ITS Classic | 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. | — | ||||||
| 3/5/26 |  Three Shortcuts to Actually Help You Get Started On Your Idea | 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. | — | ||||||
| 2/19/26 |  Start a Startup in Ten Days with Four Questions (ITS super-classic) | 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. | — | ||||||
| 2/11/26 |  Giving Your Startup an Identity | 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. | — | ||||||
| 2/4/26 |  How to Get Your First Customers (The Trust to Risk Ratio) | 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. | — | ||||||
| 1/23/26 |  The One Thing That Matters - How to Find a Differentiator That'll Support Your Business (ITS Classic) | 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. | — | ||||||
| 1/14/26 |  How to Identify and Kill Bad Startup Ideas Masquerading As Good Ones (ITS Classic) | 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. | — | ||||||
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| 1/7/26 |  The Three Pillars of Sales for Entrepreneurs Who Hate Sales (ITS Classic) | 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. | — | ||||||
| 12/31/25 |  Three Ways to Create Trust (ITS Classic - top 1%) | 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. An ITS classic. | — | ||||||
| 12/18/25 |  The One-Inch Picture Frame | Today we talk about two methods to help make your big startup plans for 2026 manageable. We borrow Short Assignments (The One-Inch Picture Frame) 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. | — | ||||||
| 12/5/25 |  How to Find Your Customers In-Person (Even If You're SURE You Can't) | 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. | — | ||||||
| 11/26/25 |  The Coffee Truck Idea I'd Start Tomorrow (Thanksgiving Mailbag) | 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. | — | ||||||
| 11/20/25 |  How to Finally Get Your Ideas Into the World as a Right-Brain Founder | 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. | — | ||||||
| 11/13/25 |  How to Pick Your First Customer | 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. | — | ||||||
| 10/30/25 |  How to Niche if You're Afraid of Niching | 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. | — | ||||||
| 10/23/25 |  How to Find and Solve Hard Problems (feat. a used car salesman and The Problem Hunters) ITS classic | 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. | — | ||||||
| 10/16/25 |  Why You're Struggling with the Easy Stuff as a Founder | 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! | — | ||||||
| 10/9/25 |  How to Engineer Luck (ITS classic) | 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. | — | ||||||
| 10/2/25 |  An SOP for Testing a Startup Idea (ITS top 1%) | 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. | — | ||||||
| 9/25/25 |  Customers Speak Problem, But You’re Speaking Solution (ITS Top 1%) | 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 debt: one with Solution Language, one with Problem Language. | — | ||||||
| 9/18/25 |  How to Nail One-Sentence Marketing (ITS Classic) | 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. | — | ||||||
| 9/11/25 |  How to Name Your Startup (a No Whisper Ideas pod) | Today, we'll teach you how to name your startup. This is from No Whisper Ideas, a post sent every Sunday by Brian. | — | ||||||
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Chart Positions
2 placements across 2 markets.