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

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)

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

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

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

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

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

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 Shape of Stories
• Slice Podcast - How to Get Your First 1,000 Customers

1:00 Kurt Vonnegut - The Shape of Stories
2:38 The Niche Question
4:15 The Jiro Problem
5:20 Act 1 - A Chef's Startup
7:48 Smooth Jazz
8:15 Act 2 - What's a Niche For? 
8:44 A Niche is a Shortcut to Trust
11:49 A Niche to Seed Future Growth
13:40 What a Good Niche Looks Like
14:25 The Cook By Smelling Niche
16:38 Act 3 - How to Grow From a Niche
17:29 Grow Vertically or Horizontally?
19:20 Grow through Influential Customers
20:00 Spice Smelling Niche
21:14 Act 4 - The Real Villain, and the Real Hero
22:11 Trust in Future You

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

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 - Why This Is So Bad and What To Do
14:14 - The End