Idea to Startup: The One-Inch Picture Frame

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This Episode

Today we talk about two methods to help make your big startup plans for 2026 manageable. We borrow Short Assignments (The One-Inch Picture Frame) 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.

Pod References + Timestamps

• 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

Transcript - feel free to read like a long-form article

Short Assignments and Shitty Drafts

Today, we’re doing the first in a series of end of year.. let’s call them actionable motivation episodes.

Todays is a holiday cocktail with one part motivation and two parts tangible methods that’ll actually help you translate that motivation into something real. A perfect combo for this time of year. The Moscow Mule of podcasts. And we’ve got a lofty goal.

We’re going to help you reach your potential.

We’ll get some help from Martin Scorsese and Anne Lamott and A Bronx Tale and short assignments and shitty drafts along the way.

But we’ll start, with where you’re at right now.

How to Actually Take a Swing At Your Potential

You’re a take stock of your life at the end of the year person because of course you are. You’re listening to this podcast. We’re a reflective bunch.

Maybe you do this through an email you boomerang to yourself every December 28th with goals and questions and predictions like me, maybe your kink is those end of year review templates that linkedin thought boys post and force you to comment on before they try to sell you creatime gummies, or maybe you just make a list of stuff you want to happen in 2026 and throw it into the fireplace on New Years Eve as the ball drops.

Whatever it is, you’re making a huge mistake.

I know this not because I’m some expert on life, but because I’m an expert on people taking stock of their lives. Tacklebox is ground zero for people taking stock of their lives. We get a bunch of you every January who have decided that this is the year you start a company and reach your potential and I love you for that. The desire to meet your potential is one of the qualities I most admire in a person.

But, you still make the mistake we’ll start with today.

As humans, when we decide it’s time to change, our instinct is to add. To add a gym membership or a coach or better running shoes or a morning meditation routine. Humans fix by adding. It’s how we think we grow.

The problem is that our instincts are, as usual, wrong. The best - only - way to add to your future life is to subtract from the current one. An old friend of mine named Wayne, who’s maybe the smartest person I’ve ever met and certainly the best designer, lives by the phrase Edit to Amplify. He uses it in every context of his life. And that’s the key here.

When you audit your life and decide you want something new, the first step is to remove what doesn’t serve you anymore.

The way to do this is with a very useful question:

Knowing what I know now, would I choose to do this again?

Ask this question about the things that take up the most time in your life. Start with your job. Knowing what you know now - not what you knew when you took the job 6 years ago - would you take it again? Would you apply today, happily, for the job you currently have now if you were out of work?

If the answer is yes or even “ehh, maybe,” it’s not necessarily the thing to change first. If you shutter at the thought of applying for your current job… well…

Next, ask the question about your hobbies and the chat groups you’re in and disney plus and your partner.

Knowing what I know now, would I choose to do this again?

Remove stuff that doesn’t serve you. Edit to amplify.

And, now that we’ve helped you make some space to add, we need to talk about the two most effective ways to actually make progress on something as big and hairy and wicked and overwhelming as “reaching your potential.”

And you know what? Let’s do it after some super quick jazz.

—

Hey!

We’ve changed Tacklebox a bit. It’s taken a long time, but we did it. It’s now a three month program built to help you test, build, and decide on an idea before you quit your job. Ninety days to get something up and out and find out if anyone cares.

We’ll give you a clear path and six coaching sessions along the way.

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Let’s build some stuff, eh?

Back to it.

Short Assignments and Shitty Drafts

Ok - back to the two ways for you to actually make progress on something big and hairy, which are pulled directly from me trying to make progress on something big and hairy.

I’ve been writing a novel on the side the past two months, which has required a ton of Tacklebox-y type of time management and accountability levers - so far, by far the best tool has been joining my towns local writers workshop - if you’re trying to write, do that first.

It’s also required a bunch of learning - writing a novel is different from anything I’ve done, so I built myself a curriculum. And, not surprisingly, a lot of the tools writers use to get something as gangly and multi-tentacled as a book into the world are useful for entrepreneurs, too. It’s all framed differently for writers, but a lot translates.

My favorite resource on writing so far is Anne Lamotts, Bird by Bird. It’s mandatory for writers and pretty close to that for entrepreneurs. I’ll pop it in the show notes.

Lamott talks a lot about the invisible barriers that keep people from writing books - mostly the same barriers that keep people from starting businesses.

She lists two practices that help with how intimidating a fresh idea can be and each are so relevant and useful we’ll go through them now. Short assignments and shitty drafts.

And, because why not, we’ll put these into practice with a fake startup idea I’ve been pitched weekly at Tacklebox that simply could not feel bigger or hairy or more intimidating to go after:

An AI tool that helps people in their 30s and 40s maintain and deepen friendships and stave off loneliness and depression.

What do you do when you sit down at 6am on a Tuesday for day one of hoping to make a dent in the problem of arguably the problem of a generation? You look at a one inch picture frame.

Short Assignments and the One-Inch Picture Frame Question

Lamott describes the overwhelmed feeling of sitting down and trying to tackle a massive book topic like, say, “the history of women” and how paralyzing it can be.

But she has a tool that helps. A one-inch picture frame that sits on her desk. This reminds her to find a one-inch piece of the story to tell, one small scene, one memory, one exchange. She says that this one-inch reminder makes a dent in the tremendous sense of being overwhelmed and often gives her writing students hope.

I’ve lived by the one-inch picture frame since, drawing one on a post-it and putting it on my monitor. When I’m overwhelmed with the novel, I think about one scene - how would my main character act in a coffee shop or how would he answer the phone when a telemarketer calls? I can write that. And then those scenes build into something real.

And I know we talk about this at Tacklebox, about building tests and sprints and all of that but this framing feels far more approachable and that’s the quality your work needs on day one.

So, what’s this look like for the AI for friendship startups?

And, by the way, if you have this idea, I’m not discouraging it. I love it. Join Tacklebox. We’ve got a few people doing it but there are 10,000 flavors of it an unending need and customer segments. This is market needs hundreds and hundreds of solutions, not one.

Anyway, what’s the one inch picture frame?

For startups, I’ve found it’s easier to think of the picture frame as a single question you’d really like the answer to.

With any startup, there will be a list of questions you need answers to before you can build a useful product.

So what’s a critical question?

If you’re helping 40 year olds keep up with their friends, maybe, how do 40 year olds keep up with their friends now?

Great one, but… it ain’t fitting in a one inch picture frame. Chatgpt tells me there are 2.2-2.5 million 40 year olds in the USA alone and they’re not squeezing into a photo the size of your thumbnail.

So, maybe, how do 40 year olds in your town keep up with their friends?

Getting closer, but ChatGPT estimates that my town has 1,100 40 year olds. Still a no.

So, maybe, how do your friends stay in touch? Or the friends of your friends to keep the feedback at arms length? Or, how to people who live in a town that isn’t driving distance from the place they grew up? Or ex pats in your town?

The inch picture has room for maybe 1 or 2 people to speak with. So, the goal for the day should be to talk to one and learn about their process.

Then, you do that. You speak with someone, and they tell you that they have a group chat but they rarely get together, even though they’d like to and they talk about it all the time. Great.

The next day, you’ve got some options for the picture frame. What questions do you want to answer? I’ve got a bunch, but here are the top two:

1. Do other people feel this way?

2. If I planned something for this person who said the barrier was planning… would they actually do it?

If I decide to answer question 1, my path is easy. Find another person to speak with who seems similar, at least on paper, to the first.

But, if you’re feeling sassy and want to answer the second question, you’ve got a path. And, the 1 inch picture frame gets more important. Because now, the activity you plan has to fit inside it. You can’t have them all go to madison square garden to watch the rangers in three months. But, you can organize a game night on zoom. Or a Friday lunch, if they’re in the same area.

This brings us back to my absolute favorite quote by el doctorow about driving at night - "You never see further than your headlights, but you can make the whole trip that way.”

Now, here’s where there’s a big difference between startups and writing a book. There are going to be opportunities to do things at scale. I just wrote a post on the to do list monster which I’ll pop in the show notes which teaches you how to think bigger.

Early days, the game is granular. Make something intimidating manageable by putting it into a one-inch picture frame. Which brings us to what to do with all those short assignments once you start producing them.

Which also means we’ve got to talk about martin scorsesee

—

Shitty Drafts

The second tip from Anne Lamott reminds me of a story a good friend of mine told me about one of his first days at NYU Film School.

Martin Scorseesee came in to speak, and a student asked him what he would do to get the most out of film school if he were sitting in the same seats as the students.

He responded that every great writer or director has 200 bad films in them. And you’ve got to get those out before you get to the good stuff. So, he’d spend his time producing as many of those 200 as he could.

If you’re, say, trying to come up with a customer acquisition strategy for your lonely 40 year olds, your first idea will probably be social media focused. Instagram ads or a linkedin boosted post or something like that. Then, maybe you’ll think about where you can find them in person. And on and on. Each idea gets you closer to something unique and specific.

The thinking for each is about reps. Most people don’t every make 200 films or come up with seven customer acquisition strategies. And, most people generally think the same. So, my first 5 ideas will be very similar to your first 5. You get to the interesting stuff after a bunch of reps.

Anne Lamott says the same thing about writing.

Your first draft of anything isn’t going to be good, and it probably won’t ever be read by anyone. The goal is to just get it out, so that you can see if there’s anything interesting in there that you can expand on.

She says you might write 10 pages on day one, then go to read it day 2 and realize there’s a paragraph in there with something really interesting. the rest is garbage, but that paragraph… then you expand on it. And write a bunch of other shitty pages, but the next day maybe there’s an exchange between customers you keep.

Our best founders have always been the most prolific. The ones that aren’t precious with every action. That’s not to say you can be flippant with your customers time or trust - that’s an absolute disaster. It’s more that you can run lots of little tests and see what comes from them. This goes nicely with the inch picture frame thought.

So, if we speak with a handful of 40 year olds looking to keep up with their friends and realize that, hey, maybe it makes sense if we take scheduling off their plate. And we decide to schedule something in person every other week.

What’s the absolute fastest version of this? How can we make this 1 of the 200 tests we’ll need before we get to a product that’s actually impactful?

The reps are what’s important. So, how do we condense them?

The first 10 attempts at anything - product, customer interviews, customer acquisition, investor pitches - are going to be shitty. Optimize for getting lots of reps.

The End - Colagero

My son has decided he’s a 2am guy. This is a problem, because neither me nor my wife are really 2am people.

The other day I was up with him while he was drinking a bottle and watching the snow and I turned on Youtube tv and got suggested a bronx tale. If you’re wondering, I’d go bronx tale, goodfellas, donnie brasco and the godfather in that order for my mafia movies rushmore. I know that’s heresy, but it’s the holidays. Gotta be honest.

Anyway, my son and I joined at the very best part of a bronx tale. Robert De Niro is with his son, Colagero, who asks if he has the talent to play for the yankees. De Niro says he has the talent to do anything he wants, as long as he acts right. But if he doesn’t, nothing will happen. And then the quote - “and the saddest thing in life is wasted talent.”

It’s powerful 5pm alone on a Tuesday, but holding my son in the middle of the night… it was a real moment.

I think this is really what all the outreach around January first is about. A bunch of humans who look back at their year and maybe aren’t sure they’re reaching their potential. And they really don’t want to waste it.

That’s something I feel all the time. It’s heavy. It’s tough to deal with. But I think these three tactics will help, no matter what you’re looking to do.

First, Remove to add. Edit to amplify. Your life is full - ask the question - Knowing what I know now, would I choose to do this again?

Next, short assignments. Break everything into the 1 inch picture frame to make it less intimidating.

And finally, get going on the shitty drafts. Don’t be precious with early work, because it almost certainly isn’t the work that’ll differentiate you. That’s 200 movies in.

And, have a great week. I’ll see you after the holiday, when we’ll floor it on how to start a startup in 2026.