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    Business

    Idea to Startup

    A podcast for people working on startup ideas. We have 15-minute tactical episodes and occasional interviews with people who did the early things exceptionally well. We’ve helped launch hundreds of startups worth hundreds of millions of dollars, and these are the building blocks.

    “This is, without a doubt, the best podcast for people trying to build startups out there.”

    “If you aren’t listening to this podcast and you’re considering building a business (or you’re already building one), what are you doing?”

    “Must listen for first-time entrepreneurs – excellent storyteller.”

    Advertise
    • Apple Podcasts
    • Google Play
    • Spotify

    Latest Episodes:
    How to Get Your First Customers (The Trust to Risk Ratio) Feb 04, 2026
    Show notes

    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

    The One Thing That Matters - How to Find a Differentiator That'll Support Your Business (ITS Classic) Jan 23, 2026
    Show notes

    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 Differentiator


    How to Identify and Kill Bad Startup Ideas Masquerading As Good Ones (ITS Classic) Jan 14, 2026
    Show notes

    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


    The Three Pillars of Sales for Entrepreneurs Who Hate Sales (ITS Classic) Jan 07, 2026
    Show notes

    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

    Three Ways to Create Trust (ITS Classic - top 1%) Dec 31, 2025
    Show notes

    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)

    The One-Inch Picture Frame Dec 18, 2025
    Show notes

    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 at Your Potential
    04:15 The Two Best Ways to Make Progres
    05:59 The One-Inch Picture Frame
    10:20 Shitty Drafts
    12:55 The End: The Saddest Thing In Life


    How to Find Your Customers In-Person (Even If You're SURE You Can't) Dec 05, 2025
    Show notes

    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-Person
    05:26 Your In-Person Acquisition Plan: A Date Wingman
    07:34 Places to Find Hard to Find Customers
    09:54 The Script
    11:42 The Media
    12:32 The End


    The Coffee Truck Idea I'd Start Tomorrow (Thanksgiving Mailbag) Nov 26, 2025
    Show notes

    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
    • Focusmate
    • Weber EG 1
    • Pluribus

    Timestamps

    0:30 Mailbag!
    01:25 Question One - What Idea Would Brian Start?
    03:05 The Four Idea Criteria
    06:40 Idea-Founder Fit
    07:51 A Coffee Truck
    14:50 Smooth Jazz
    15:25 Question Two - How do I get my spouse on board?
    19:26 Question Three - Best Gifts for Entrepreneurs


    How to Finally Get Your Ideas Into the World as a Right-Brain Founder Nov 20, 2025
    Show notes

    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 HOLIDAY2025
    08:13 You Don’t Have a Goal
    11:30 Outsourcing your Left Brain to AI
    13:05 The Regroup System
    15:01 The Icebox
    16:59 The End


    How to Pick Your First Customer Nov 13, 2025
    Show notes

    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.

    • Tacklebox
    • Getting Real (museum curator reference)
    • Everyman Espresso (☕️ 🐐)

    Timestamps
    00:27 First Time Entrepreneurs vs. Second Time Entrepreneurs
    03:20 The Idea: Personality-Based Management
    06:29 Why You, Why At All, Why Now
    08:55 Byldd
    09:55 The Story of Your Successful Startup
    15:35 The Five Necessary First Customer Characteristics
    16:41 Characteristic One: Pain
    21:51 Characteristic Two: The Knowledge Spectrum
    25:43 Characteristic Three: Measurement
    28:24 Characteristic Four: Influence
    29:48 Characteristic Five: Frequency
    31:45 The End


    Previous 1 2 3 4 29 Next

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