
The Three Pillars of Sales for Entrepreneurs Who Hate Sales (ITS Classic)
07/1/2026 | 27 mins.
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 ExpanderStreakPipedrive

Three Ways to Create Trust (ITS Classic - top 1%)
31/12/2025 | 17 mins.
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
18/12/2025 | 14 mins.
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

How to Find Your Customers In-Person (Even If You're SURE You Can't)
05/12/2025 | 13 mins.
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

The Coffee Truck Idea I'd Start Tomorrow (Thanksgiving Mailbag)
26/11/2025 | 21 mins.
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



Idea to Startup