How to Quit Your Job and Pursue Your Startup Idea

Things That Always Work and Things That Never Work: Today, we dig into the Always Work and Never Work Lists - a method that'll help entrepreneurs make good decisions through the constant second guessing and self-doubt that a startup brings. We talk through examples from the lists and apply them to a moment Brian had to deal with recently. We get a little help from Goodfellas and Taylor Swift. by Idea to Startup

21 min listen

How to Create Useful Content (for people who don't think they can create content): Today, we'll talk about content. Two of the most asked questions we get are "should I create content?" and "if I should... what the heck should I say?" Creating content feels daunting until you realize the best way to create content is to not create content. We go through how to do that, leaning on a few examples and a content generating framework. We also crown the best burrito in NYC. by Idea to Startup

22 min listen

A Mouse Pod (How to Stand Out in a Crowded Market): One of my favorite episodes in a while. Today, we talk about how you can stand out in a crowded market by looking at an exceptionally successful exterminator. We'll pull out four lessons that make a framework to create contrast between your business and your competitors. We'll talk through Customer Journey Mapping, the Feature Fold, how to take yourself seriously through pricing and the things other people stink at. And, we'll get a ton of help from the Mouse Man (and no help from Ruby). by Idea to Startup

24 min listen

A Weekly Prioritization and Audit Framework for Entrepreneurs (ITS Classic): One of the most listened to episodes in ITS history with an average consumption rate over 100%. Today, we go through a Weekly Prioritization and Audit Framework for entrepreneurs. We'll hit on three giant shifts you'll likely need to make - ditching a to do list and moving to your calendar, weekly progress reports, and environment design. We get a little help from our friends in Finland along the way. by Idea to Startup

27 min listen

Running a Concierge MVP Live (feat. the four-step Concierge MVP framework): 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. by Idea to Startup

24 min listen

How to Start the Business You’re Not Quite Ready to Start: Today we talk through a system to help you start the business you don't feel ready to start. We do this because that's the only type of business there is. You're never going to feel prepared so you can't let that fear paralyze you. We talk through the three main gaps that keep founders from starting - the Knowledge Gap, the Network Gap, and the Product Gap - and describe a method that'll help you navigate each. We get a little help from a startup idea Brian's been kicking around, a turtle swimming across the Atlantic Ocean, and the Backstreet Boys. by Idea to Startup

24 min listen

How to Take Yourself Seriously feat. The Entrepreneurship Handbook (ITS Classic): Most people's startup approach is haphazard. It's a combination of instincts and reactions and luck or happenstance. People who succeed are far more purposeful. Today, we'll help you take your idea and yourself seriously. We'll build your entrepreneurship handbook - the thing that'll let you make tough decisions at scale. by Idea to Startup

22 min listen

A Startup Storytelling Framework for Non-Storytellers: Today, we'll help all the non-storytellers tell a compelling story about their business. We've got a framework that'll walk you through the ingredients of a compelling story, and a mise en place-inspired approach that'll help you get to story market fit. We've got some rules, some variables, some accelerants, and an example about a service that helps Airbnb hosts launch their own interior design businesses. by Idea to Startup

25 min listen

When to Pivot and When to Stick (aka what to do with all your startup ideas) ITS Classic: Today, we'll talk about one of the most common hurdles entrepreneurs run into - getting tempted by a new idea a few months into working on their main idea. We lay out a framework to identify the first principles of the new idea fast so you can decide if it's worth a pivot. We also dig in on why the urge to pivot shows up, procrastination, and how to win a baking contest. And, English Lords from the 17th century. by Idea to Startup

24 min listen

How to Pick Your Startup's 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. by Idea to Startup

33 min listen

A System to Do Hard Things (ITS Classic): Today, we help you become the type of founder who relishes uncomfortable things that lead to successful startups. There are no real secrets in the startup world - the hard, proactive, uncomfortable work leads to businesses that matter. This work doesn’t happen without a system. Today we help you build that system, using The Costanza Swap, The Three Levers of Resilience, and The Failure Case. Hoo ahh. by Idea to Startup

23 min listen

How to Build the First (Magical) Version Of Your Product This Weekend (ITS Classic): Today's classic episode will help you get the first version of your product up and out this weekend. We use a three-part framework to help you focus in on the one core feature you've got to nail that can be built by someone with no technical or product building skills in an afternoon. We also find your customers inertia and ride that wave to make it easier to use your product than not. We get help from an airbnb for lawn equipment startup and move the ball forward on the chronic pain idea. by Idea to Startup

29 min listen

A System to Generate Ideas (aka how to let your brain be a brain): 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. by Idea to Startup

24 min listen

20-ish Minute Skill: The Concierge MVP (ITS Classic): Today's classic ITS episode discusses the Concierge MVP, an indispensable tactic early stage entrepreneurs can use to get the feedback of a full product without the money and time required to build one. We go through the 4-step method that'll get you data from customers you can use to raise funding, hire, or recognize the opportunity actually isn't worth your time. by Idea to Startup

26 min listen

How to Create a Strategy For Your Startup: Today, we'll talk about strategy - what good (and bad) strategy looks like for startups, and how most early-stage companies lack any strategy at all. Using a framework from Good Strategy/Bad Strategy, we'll explore the three core elements: diagnosis, guiding policy, and coherent action. We'll examine strategies from a stand-up comedian and GoPro as examples, before applying the framework to craft a strategy for launching a successful children's book. by Idea to Startup

23 min listen

How to Build a "Skeptical Startup" - 8k per month in 10 hours per week: 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. by Idea to Startup

21 min listen

What if the problem you're solving isn't "painful" or "urgent"? What if it's just something you think people will want? Should you still pursue it? (feat. Linguini): Today is an ITS classic - an episode that was listened to and shared a ton. It hits on a fundamental question for idea-stage entrepreneurs - what if the problem you're solving isn't an urgent, painful, bleeding neck problem? What if it's just something you think will improve people's lives? Should you still pursue it? How? We'll talk through Linguini, Yeti, gross margins and status level jumps and land on the answer - is that type of business worth your time? by Idea to Startup

22 min listen

The Magic of One-Sentence Marketing: 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. by Idea to Startup

16 min listen

Designing a System to Actually Prioritize Your Startup This Year: Today, we dive into a practical, resilient system to help you carve out and hold time for your startup amidst the craziness of your life. Most startups fail because the founders lose momentum when predictable life things pop up - you were supposed to work on your startup but your kid was sick or your job gets busy. You need to build a system that adjusts to this constant "failure state" - one that doesn't require Herculean willpower (wake up every day at 4am) and makes working on your startup easier than ignoring it. Today, we help you do that. by Idea to Startup

17 min listen

Seth Godin and Brian Go Through Startup Ideas (ITS Classic): Seth Godin (!) and Brian go through startup ideas. Seth gives his opinion on how he’d start everything from a pasta truck to an updated CSA program. We dive into risk, emotion, tension and doing things that matter. Seth talks about the distinction between entrepreneurs and freelancers and the danger of thinking you’re one when you’re really the other. We talk about marketplaces and domain expertise and knowing what it is you’re actually selling. This is Brian's favorite episode ever. by Idea to Startup

49 min listen

How to Think Bigger (feat. The Problems and Opportunities Method): Today, we’ll teach you how to avoid sabotaging your startup. Most founders think the best way to build a startup is to mitigate risks - to optimize for worst case scenarios. But the actual way to build a successful startup is to optimize for tasks with the highest ceiling - to do the things that might give you asymmetric gains, if they work. This is unnatural and hard - the Problems and Opportunities Method, the second in our Method series, will help. by Idea to Startup

23 min listen

How to be Different, Part 1 (feat. The Personal Venn Diagram Method): Today, we'll help you build a system to be different. We dive into the Persona Venn Diagram Method - a tool designed to help you identify and capitalize on your unique strengths - and we'll talk through how the path you might think holds the least risk actually guarantees the most. This is the first in a series of episodes on the Methods we use at Tacklebox to help our founders build differentiated businesses. by Idea to Startup

20 min listen

Testing Another Startup Idea Live Part 1: Picking the Idea, Nudging the Boulder: Today, we'll kick off a new series where we'll start an idea live on the pod. Actually, we'll start two. One in the healthcare space, one in the AI space. The hope is that you've got an idea and can follow along with us. Today we'll cover when your idea is ready to start, how to structure the first couple of weeks, and how to think about the giant boulder sitting in front of you. Also, there's a brief Ruby cameo because she's been absent for a few weeks. by Idea to Startup

23 min listen

The Quest for an Identity: Today we'll help you find an identity. An identity is something unique that you can organize your business beneath. A north star that can act as a lens for every decision you make. We talk through how to use category shifts and first principles to find and evaluate possible identities, and when to stick with an identity vs. when to jump ship. We use a bunch of examples - from an Italian restaurant to a skincare company called Jolie to the 1994 Arkansas Razorbacks basketball team. by Idea to Startup

21 min listen

How to Find a Differentiator (ITS Classic): Today we'll outline two frameworks that'll help you find a meaningful differentiator. We'll use a bunch of examples to show how Inversion + Before and After can change your business. A baseball academy, Krispy Kreme, and Nutrisystem help show us the way to a product your customers will happily overpay for. by Idea to Startup

19 min listen

Customers Speak Problem, But You’re Speaking Solution: 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. by Idea to Startup

22 min listen

An SOP for Testing a Startup Idea: 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. by Idea to Startup

25 min listen

Two Ways to Approach Your Startup Idea Like A Pro (ITS Classic): Today, we'll talk about pros and amateurs. Pros build businesses that have a shot - amateurs never leave the starting gate. Unfortunately, most amateurs don't know they're approaching their idea the wrong way. We talk through your vision and your internal system - the internal process you'll build, automate, and scale to help you execute that vision. We do it with a little help from the best run solo business I've encountered (an interior designer), and the best tool for your internal system (Zapier). by Idea to Startup

22 min listen

Writing Persuasive Copy to Test an Idea: Today, we talk through how to write compelling copy. We go through a few counterintuitive archetypes you can use to dramatically increase the clarity of your messaging, which will allow you to increase your conversion rate and get more people involved earlier in the process. Copywriting is an idea-testing superpower. by Idea to Startup

19 min listen

How to Embrace Risk, Uncertainty, and Chaos: Today, we'll help you embrace risk, uncertainty, and chaos. The only way to get asymmetric results in life is to spend a lot of time in what we call the "chaos" zone - the uncomfortable place where you're finding things no one else has yet. This type of work (life) is uncomfortable and stressful, so people don't do it. But, it's where all the potential asymmetric value is. So, we go through tactics to make this stage feel safer, allowing you to spend more time in it and increasing the chances you pull a life changing business out of it. by Idea to Startup

24 min listen

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How to Quit Your Job and Pursue Your Startup Idea

How to Quit Your Job and Pursue Your Startup Idea

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