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Things that Always Work and Things that Never Work
A System to Make Big Decisions
Brian Scordato
June 14, 2024
Things that Always Work and Things that Never Work
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Why This Episode Exists + Nerdy Stuff Not In The Pod 💡
This week, we talk about things that always work and things that never work.
I’ve been building a list of things that always and never work for years as a tool - whenever I have big decisions or reach some sort of self-questioning crossroads (“what the hell am I doing?”), I lean on these lists to get momentum.
Today, the episode runs through how to use and create these lists - specifically to help me decide whether to continue the podcast or not.
I’ll eventually publish these lists - respond “yes” if you’d like to get them when I do.
I’m always out for things to add to the lists, and grab inspiration from things like:
Hopefully this pod is useful for all the self-questioning I’m sure your startup is forcing you to do.
Pod References
Pod Timestamps:
00:30 Intro
02:54 Is My Idea Actually Good?
04:13 Goodfellas
05:44 Smooth Jazz
06:11 Should I Stop Doing This Podcast?
08:24 The Process
08:55 The Three Prompts
12:20 The Things That Always + Never Work Lists
17:27 The Plan
18:58 You
19:57 People Over 30 Don’t Sprint
Transcript - Feel Free to Read it Like a Long-form Article:
The Always Work and Never Work Lists
Today, we’re going to talk about an indispensable Method - the Always Work and Never Work lists. This method will keep you happy and moving forward despite the nasty little habit of startups and life to try to keep you from both.
The lists themselves are wildly straightforward, but using them practically is anything but.
I think of it like a hike my wife and I went on in the Catskills right after we got engaged. A ranger bounced up to us at the trailhead and said “hey - just a reminder you’re in bear country and we’ve seen a bunch of bears recently. If you see one, don’t worry - they’re way more scared of you than you are of them. Just hold your ground or even walk towards them and clap and wave your arms. They’ll probably just run away.” In a vacuum, walking forward and clapping and waving my arms is something I’m very confident I can do. But when there’s a 700 lb bear who will, quote, probably just run away…
And that’s entrepreneurship. You won’t have a 700 pound physical bear blocking your path, but that path will be littered with 700 pound mental ones. You’ve heard the trope about startups being a mental game but you don’t really know what that means until you’re in them. And once you’re inside you realize it’s not mental toughness in the - can you stay up for another 3 hours and work sort of way. That’s easy. It’s mental toughness in the constantly, relentlessly questioning yourself sort of way. Are you working on the right thing? Does anyone care? Who do you think you are, working on this, anyway? What are people saying about you? Is this thing actually going to work? Should you quit? Is Deloitte the one that Brian makes fun of in the pod? Should I just apply to a job there?
You know most of these questions are your subconscious needling you to stop doing what you’re doing because starting a business is uncomfortable and your instincts will always be to run away from discomfort. But that doesn’t make them any less real. Just like how I know on some level that a black bear is just a big raccoon and just as scared as I am, but reality isn’t rational.
And, sometimes your subconscious is right. Sometimes the thing you’re working on is systemically flawed and you should stop doing it. and sometimes you should run away from a bear.
So, we need a system to deal with the questioning.
We talk a lot about Methods on the pod, and to remind you, a Method exists to solve a hard problem. To answer a hard question.
In this case, this method can answer lots of questions. Startup or not.
But it’s a startup pod so we’ll tackle the biggest startup question it attacks:
Is this idea actually good?
Or, the more evolved, urgent version of that question. When you’ve come around and realize, firmly, that this idea, the thing you’re working on, as currently constructed, isn’t good. It isn’t going to work.
Now what?
I get asked both flavors of this question weekly from Tacklebox members. The “is this good” version and the “this isn’t good, now what?” version.
For the founders, this conversation is cataclysmic. This thing that’s so important to them, that they’ve folded their entire self worth into like strawberries into an angel food cake on the great british bakeoff - it isn’t working and maybe never will. How do they move forward with this knowledge? It’s heavy.
But for me, it’s Thursday. Every founder hits this moment and we’ve worked with hundreds and hundreds of them. So, this happens a lot and we have a process for it.
General life advice - find people who, to them, your biggest problems are a regular Thursday. Therapists, coaches, whoever. Find people with broad context for the big things we face in life once or twice.
Anyway, members show up to our meetings distraught, barely able to mutter that their idea isn’t working. It always reminds me of that scene in Goodfellas where a teenaged Henry Hill gets arrested for the first time for trafficking cigarettes and is despondent because he thinks he’ll be kicked out of the mob.
But, after he gets let off by a crooked judge, the whole gang is there - laughing and smiling and punching him on the arm.
Robert De Niro’s character shoves a wad of cash in his pocket and congratulates him. You took your first pinch like a man, he says, and you learned the two greatest things in life:
Never rat on your friends
Always keep your mouth shut
Getting pinched is part of being in the mob, and, while we got a bit off track, you can probably still follow the line I’m trying to draw.
That moment - when it feels like your idea is toast or when you hit any sort of wall where you’re questioning yourself - that’s part of it. A HUGE part of it. A massive opportunity. And you need a system for that moment because the hard moments are the moments you’re closest to something interesting. The moments where you’re ready to change and try something different. The moments where 95% of other people will quit.
And that’s where the always work and never work lists come in.
These exist for the moments when you’re stuck or frustrated or questioning what you’re doing. They help you get to the bottom of the problem. And they help you get momentum, one way or the other.
We’ll start with a story about how to use these lists, then we’ll lay out how to build and use your own lists.
So, let’s get into it.
After….. a little smoooooth jazz, which wasn’t in the episode last week and people were pissed. I got a bunch of emails about it. Sheesh. I forgot to edit it in. Won’t make that mistake again…
Should I Stop Doing this Podcast?
Today’s example was supposed to be about a founder that’s currently in the program and has run into the - this thing isn’t working, now what - wall. But, as I was mapping it out I realized there was a better example - me.
It’s easier to write about myself anyway, and, this shows that these types of moments - the ones where you question yourself and what you’re doing - are as regular a part of entrepreneurship as answering emails. I’m 9 years into Tacklebox and almost 4 into Idea to startup, and the self-questioning has increased, if anything. Which I wouldn’t put on a brochure trying to attract new entrepreneurs, but it’s true.
So, here’s the story.
I go through ebbs and flows with this podcast. I love writing it and thinking through it and I love that it attracts the right types of founders to Tacklebox. I love the emails I get from people saying it’s helpful or asking for pictures of Ruby. I love the way it helps me see the world - I apply our frameworks to everything - from coffee shops to penne vodka to exterminators. It’s fun.
But I hate the numbers. The numbers weigh on me.
Because no matter what happens, I’m upset. If they go up, I’m upset they didn’t go up more. If they don’t go up, I get upset about that, too. Since the ceiling is infinite it sort of messes with me. More is always better and more is always relative so you’re screwed.
I know I shouldn’t look at these numbers but, I do. And, practically, for advertising and our core business, because nearly every member comes from the pod, the numbers matter.
But apart from the number thing, I also think about the opportunity cost of the pod. It takes roughly two days a week to do the podcast. If I just… stopped… what could I do with those two days? Could I grow the business faster a different way? Do I even want that?
So, let’s rewind to a few weeks ago when I was wondering, for the 700th time, if the podcast was even worth it. If it’d ever grow to a place where I’d be happy with it. If that place even existed.
When I have these big questions, the doubts about my business, I turn to one place - the always and never work lists.
—
The Process
Linguini, my internal system, is completely run in Notion and has a specific section for the things that always work and the things that never work lists.
That main page has a bunch of subpages - examples of previous times that I worked through something hard using the system. They’ve got a date and a title. I look through them frequently, especially when I’m making the type decision I’ve made in the past.
When I launch a new page, for a new decision, a template pops up with three simple prompts to start the process.
Prompt 1 reads, “What’s the problem, big guy?” and there’s a pouting face emoji.
I don’t remember when I first added “big guy,” to the prompt, but I always forget about it and it always makes me smile because it lightens the mood. It makes me feel like a little kid with a silly problem. Which it usually is.
This is where I write a sentence or a paragraph. For the podcast decision, I was brief. I wrote:
“I’m just not sure I want to do the podcast any more. I’m not sure it’s worth it. I wonder if it’s actually holding the business back.”
On to prompt 2, which is actually a set of five prompts. The classic Toyota Five Why framework. It helps you cut through anything superficial and get to the root cause. The thing that’s actually upsetting you.
So, I started with the problem - I’m not sure the podcast is worth doing.
And I asked…
Why?
Because the pod isn’t growing in a way that could support a big business.
Why?
Because I don’t prioritize podcast growth and haven’t spent the time to figure out a coherent growth strategy.
Why?
Because I’d like to think the podcast is good enough to grow on it’s own without a bunch of marketing
Why?
Because I don’t like the idea of marketing and pushing myself out like a car salesman all over the place and joining podcasts and having people as guests and all that nonsense.
Why?
Because maybe I’m worried that if it gets bigger the fraud police will finally show up at my door and handcuff me and take me away. Or, people won’t like it and I’ll get lots of bad reviews. Or, something else equally as silly and unlikely.
—
If you go through all five whys, you’re almost certainly ending up at some sort of emotional blocker or some flavor of imposter syndrome, which is totally fine but usually not all that actionable for our purposes - though a therapist might help.
It is always good to know that the root of your inaction is usually self-sabotage - a fear of success for no reason other than success is scary and different from what you’ve historically had.
But, if we roll back into the more actionable whys, something kind of obvious jumps out. I’ve never had a coherent growth strategy because… I just… haven’t. I hoped the pod would grow on its own. And, it has grown a lot. But, if I want it to anchor the type of business I want to build, it’s got to grow way more. And I haven’t had a coherent strategy. So, it’s not that it can’t grow, it’s that I haven’t tried.
The first two prompts nearly always bring you to some sort of epiphany, and the one I wrote down was, quote:
“So, I’m upset about pod growth but haven’t ever really tried to make the pod grow? That seems dumb.”
And that’s why I say big guy. Because most of our biggest problems or insecurities or questions, when whittled down, are silly, fixable things.
I stare directly
Which brings us to prompt number three.
Prompt 3: What would you suggest someone who came to you with this problem do?
Again, this usually ends up being surprisingly straightforward.
And I wrote:
“I’d suggest they start trying lots of things to make the pod grow. To reprioritize growth as the number one priority for a month or a few months to see if the pod is capable of growing at a rate that can support a bigger business.”
Which brings us, to our lists.
The Things that Always Work and Things That Never Work Lists
Now, we get to the actual lists.
These lists started years ago as part of a journal prompt I’d use at the end of each day. It might’ve come from James Clear or Shane Parrish or maybe I made it up. It lived on my to do list and simply said - what worked today and what didn’t work.
I’d reflect on the day and put stuff down.
After a week or two, I started referencing the past few days each morning, looking for things I should and shouldn’t do. To make this easier, I compiled the best ones into lists. Those lists have grown and now have categories.
So, for example, I have a big list of general things that always work and never work, but then smaller sections with things that work for growth or product or diet or sleep or happiness.
A few years back I heard a line from Naval Ravikant that’s stuck with me and inspired these lists. I’ll butcher the quote but it said something like he’d want to create a life where in 1,000 parallel universes he’d be successful and happy in 999 of them.
So that was the hope - to find the things that, if you do them, lead to good outcomes.
This might seem silly, but as I look through the list I see things I should do and should think about, but don’t. We - or at least I - need reminders. Especially because most of these things are counter-instinctual. They’re uncomfortable so my mind and body are naturally pushing away from them.
So, back to the podcast. I’m frustrated about growth. Which means I need to look at the general section of the lists and the growth section of the list.
When I did, a few things popped out immediately.
First, from the general things that always work :
Work different rather than harder in the same way. Welp, I’ve just been killing myself to put out the same structure podcast for years, with no focus on growth. So, a different structure might push on growth. Next -
Fast forward to the end, describe the moment of wild success, then build a plan backwards from that moment. I haven’t ever defined what wild success is for the podcast, so I can’t possibly be building towards it. That’s probably why it feels unfulfilled.
Focus on raising the ceiling, not the floor. I’ve thought a lot about keeping existing listeners rather than finding pockets of new ones.
Take on ambitious projects with public accountability. Well, that’s what I’m doing right now.
Pay for momentum for something you’ve been stuck on for a while but know you need to do. I’ve known about marketing for this for a while - paying to get the ball rolling - overpaying for momentum to navigate the right blockers might make sense.
All the value is in the last 15%. Most people get 85% of the way there with marketing then stop because the last 15%, really sharing what you’ve created, is uncomfortable. Push through it to get 10x the results.
There were a ton of others that gave me ideas, but moving into the growth section of the things that always work, a theme popped out:
Use niche channels and painfully specific problem messaging
Help a few customers be wildly successful and then help them share that success
Find hub and spoke channels and give the hub something valuable they’d share with the spokes organically anyway
Use opportunity thinking - how to get hundreds or thousands of new customers irrationally excited with something big and unique
The fifteenth idea, not the first, will work - don’t get discouraged
Build structure - try one or two things different things in two week sprints over the course of 3-6 months. Track metrics that help you make decisions and move the bottom line - not vanity metrics. Understand the quality of customers you’re attracting and building towards a CAC < CLV ratio.
So, the takeaways - Be creative, be specific to customers, spend the time to get into niche channels, figure out ways to provide value, and do it in a structured, data-driven, long-term way.
And, on the never work list for growth a few stood out as well:
Waiting for people to come to you or notice the good work you’ve done
Building content that is, quote, so good, people just show up
Marketing agencies if you’re spending less than 20k per month
Social ads if you’re spending less than 20k per month
Getting upset when the first 5 things don’t work
There were a bunch more that resonated, but I know listing out stuff isn’t the best podcast. I’ll probably publish my lists of things that always work and things that never work at some point - email [email protected] if you’d like them when I do.
The next step is to think up a plan. A bunch of tests to try to navigate the problem.
For the podcast, I realized my big problem was getting 85% of the way there and stopping. I did all this work writing and recording the episodes, then gave them zero leash to grow.
So, I came up with 25 ideas for growth. Everything from cold emailing the head of the entrepreneurship club at every college in the country sharing the podcast and offering office hours to something a bit more radical that I might try.
Lots of founders have reached out after listening to the pod and sent their strategies after I’ve had an episode on growth or product or some other framework. Lots of these are really great. What if, instead of spending $5k on a growth agency, I just gave the $5k away to whoever I thought had the best idea for a growth strategy? Or, for whoever I thought had built the best approach for pursuing an idea? The $5k would help them sprint for a month, then I do a podcast episode with them to see how it went? Or maybe it’s $1k and we have 5 monthly winners?
To enter the contest, maybe you have to get some number of people to engage with a post or share an idea to startup thing or something I haven’t totally thought through yet.
But the idea hits a lot of the things that have worked in the past.
I’ve built out a structure to test these in two week sprints until the end of the year, with clear growth targets and the plan to test out 15 wildly different approaches. And, I’ve budgeted an amount of money each month to put towards making each test easier - whether that’s outsourcing design or copy or video tools or research.
You
There are three huge benefits of the always work and never work lists.
The first is awareness. They shift you from someone inside your business, struggling, to someone outside your business, consulting. You’re able to figure out the root cause of the problem.
The second is momentum. Once you’ve figured out the problem and seen a bunch of inspiration for what works, you can build a plan to navigate it.
And the third is reference. A catalog of decisions you’ve made.
Now, when I get frustrated with the pods growth in six months, I can go back and see my thought process around this decision. I can see if anythings changed. I can try different growth tactics or, maybe, decide to scrap the thing entirely.
This type of decision log gives you critical insight into your decision making process. It lets you build a system around decisions, rather than just making them haphazardly.
The End
I read a stat the other day that 90% of people over the age of 30 will never sprint again. They’ll never run onto a field and kick it into their highest gear.
This has stuck with me for some reason.
It just seems so.. upsetting, I guess. Because my son is 18 months old and literally all he wants to do is sprint. If he’s 10 feet away and has to come over to get some puffs, he sprints. I’m not sure he even knows how to walk. That might be the other side of that fact - 90% of people over 30 will never sprint again and 90% of the people under 3 have never walked.
The point of this type of framework is to help you sprint, in the startup or life sense. To figure out what you want and to go after it in a meaningful, purposeful way. In a way that can work.
Mixed into the lists are things I’ve noticed our most successful founders do - one of them stands out - they fear mediocrity more than failure. And that’s a good way to end here.
Most people won’t make lists of things that work and things that don’t. They won’t reference them to make hard decisions. They won’t log those decisions so they get better at them, recognizing how important they are.
but maybe you will.