Another Lesson at 40: Three Shortcuts for Getting Started

Podcast | Youtube

Sponsor: Tacklebox Customer Interview Workshop

If you’re struggling to kickstart your customer interviews, sign up for our Kickstart Your Customer Interviews workshop: Tacklebox Workshops

Want the Sunday Member Email?

We send a weekly thought to Tacklebox Members every Sunday. Sign up here (or just reply “Sunday” to this email) to get them, and see last Sunday’s post below.

• The Promise + The Complain Counter

Why This Episode Exists + Nerdy Stuff Not In The Pod 💡

Today’s episode exists because we get a bunch of emails from folks that are… comfortable. Everything is going well enough, but… they’re unfulfilled. They want to take a risk and try a startup but, as my dad always says, it’s hard waking up early when you’re sleeping in silk sheets.

Today’s episode covers some methods - shortcuts - to move from a life that doesn’t support you working on something new to a life that does.

It’s a fun episode where we help someone with this exact problem kickstart their AI for tutors idea.

But, this is the “nerdy stuff not in the pod” section, so, here’s some stuff that didn’t make it in but I think is still super interesting:

• The Zeigarnik Effect and Open Loops: I wanted to dive deeper into why reinforcing markers work. They tap into the Zeigarnik Effect - our tendency to remember uncompleted tasks better than completed ones. By constantly reminding yourself of your startup work, you're creating a productive "open loop" in your mind that your brain will work on subconsciously.

• Opportunity Cost of Prep: There's a fascinating economic concept called the "opportunity cost of capital" that applies to time spent prepping. Every hour spent reading general business books is an hour not spent talking to customers or building. The real cost isn't just the time, but the potential insights and progress lost. This is why Just-In-Time learning is so critical.

• Parkinson's Law and Time Blocking: I briefly touched on scheduling, but there's a whole framework around using Parkinson's Law ("work expands to fill the time available") to your advantage. By setting tight time blocks for startup work with clear deliverables, you can dramatically increase productivity. This pairs well with the Pomodoro Technique for sustained focus.

• The "Mere Exposure Effect" in Habit Formation: Forcing functions and reinforcing markers work partly due to the psychological principle of "mere exposure" - we tend to develop preferences for things simply because we're familiar with them. By consistently exposing yourself to startup-related tasks and thoughts, you're subtly reshaping your preferences and comfort zones.

• Dunbar's Number and Startup Communities: I wanted to explore the concept of Dunbar's number (the cognitive limit to the number of stable social relationships we can maintain) in relation to joining startup communities. There's a sweet spot for the size and intimacy of a group that will most effectively shape your behavior and mindset. This ties into why small, consistent accountability groups often outperform larger, less personal networks for early-stage founders.

That’s the nerd deep dive. Hope you enjoyed 🤓

Pod References

• Tacklebox Customer Interview Workshop

• Idea to Startup Newsletter

• Kevin running from the furnace

Timestamps:

00:34 Intro
03:30 The Idea: AI for Tutors
07:27 Jazz - Customer Interview Workshop
07:57 Just-In-Time Prep
11:55 Search for Hooks
14:14 The Three Step System
15:40 Forcing Function Examples
18:13 Reinforcing Markers
20:06 The End: Jump in the Ocean

Transcript - Feel Free to Read it Like a Long-form Article:

Today, we’re going to talk shortcuts.

A few weeks ago we talked about how I’d recently turned 40 and how it’d smacked me in the face like a sock full of batteries.

It turns out, that sock full of batteries struck a chord with people. I got a bunch of emails about listeners who’d recently turned whatever age, and this ranged from 25 to 65, and felt.. anxious.

Moreover, that anxiety didn’t seem to be rooted in biting off more than they could chew - it was rooted in not biting enough off.

They told me the questions that kept them up at night - were they too comfortable? Had they really reached their potential and, the interesting one - what if they’d gotten to a life that was good enough without reaching that potential? What if they were trapped in a life because it was, sort of, fine? Was that a bad thing or a good one?

I’m no therapist, but it seems like if you’re emailing me that question you’re probably looking for someone to nudge you into the deep end of the pool, and I’m more than happy to do it. And what I’ve learned about listener emails is that if 5 people write in with the same question, five thousand people are probably thinking about it.

The “am I too comfortable” crowd are plagued by what my dad calls the silk sheet problem - simply put, it’s tough to wake up early when you’re sleeping in silk sheets. And silk sheets don’t always mean you’re wildly rich and successful - you can get silk sheets on sale from brooklinen on prime day and they’ll keep you from getting up to do something interesting.

I realize these are high class problems. If you’re worried about reaching your potential you’ve probably steadied the floor beneath you. But that doesn’t mean it still isn’t a problem and, luckily, all the stuff we’ll talk about today works if you don’t have your ducks neatly aligned, too.

A big part of the 40 year old reflection stuff I did - and I didn’t like go eat peyote or ayahuasca or whatever other thing I have no knowledge of but occasionally see a headline about somewhere, I just did a few journal exercises - was pouring over the list of the hundreds and hundreds of founders we’ve worked with.

I searched for all the things that had helped comfortable but unsatisfied people change their course. People who liked the idea of leaving the castle before the walls got too high, but maybe wondered if they’d already waited too long.

This is a fun one, because I think this probably describes a lot of people. It’s probably you. It’s definitely me.

And to pull it all together into a tidy episode, a few weeks back someone reached out with an idea they wanted to go after. Because, in their words, “I recently turned 45, my kids are in school, my career is rock solid, but my life is a bit too… comfortable. I want to try something new. I feel like I’m coasting. But every time I try to start… I sputter out.”

Great.

So, today, we’ll help our friend try a thing. And, we’ll use the five best methods, or what I guess we’ll call shortcuts for the sake of a click baity title our podcast consultants wanted me to use, to help her do that. Methods that help you throw off those silk sheets every morning.

And we’ll start….

With the idea. There a shortcut in the title but no shortcut you can take to get to the jazz. You know that. Vegetables before desert.

Here’s the idea.

—

AI for Tutors

When someone pitches me AI for X these days my first instinct is to run away from them while screaming and waving my arms like Kevin when the furnace comes to life and growls at him in Home Alone.

But, I know that’s wrong. There’s potential for AI for x, sometimes. So, I’ve come up with a rubric for “AI for X” that I’ll consider.

I think of current AI as infinite processing power plus a generic perspective. So, if a hard problem seems like it might be aided by infinite processing power and a generic perspective, then, I’ll fast forward to the end of the movie where Kevin is no longer scared of the furnace and listen.

If there’s a scenario where a human would get tired of you asking them to do something over and over, but it’d really help if they would, AI is interesting. Robots don’t get tired.

That’s pretext for the email from the listener. Now, let’s jump in.

“Hey!

I don’t know what first time long time is, but it seems most people start their emails to you like that so I will, too. Editors note - nice. It continued.

I’ve got an idea I’d like to go after, but, I’m not sure I’m the entrepreneur type. I’m not endlessly obsessed with the idea and I don’t work on it and think about it every free second I have. I have a good job and family and I just turned 45 and I’m starting to feel a bit too… comfortable. My career is great, my family is in a good place, but I feel like I might need a new challenge. I’m antsy.

So, here’s the idea.

I’ve got a few kids in high school and they’ve each got a tutor for a few different subjects. One needs more help on the math and physics side, the other needs help with writing and softer skills. The tutor helps them with their schoolwork, then tries to figure out a personalized approach to help with whatever concepts they need support on.

The tutor comes for an hour each week with each kid, and it’s been helpful, but I can’t help but wonder how much more helpful it’d be if the tutor had more context. I’d love for them to know exactly what the teacher has gone over and all the assignments my kids have done in the past. This might help them see which methods of teaching resonated most and start to spot trends. I mentioned this and the tutor said sure, that’d help, but it’d obviously be an enormous amount of work, and they’d have to bill for it.

This strikes me as something AI could do.

I’m a lawyer and we’ve recently started using a tool at work that looks through huge databases of old cases to make suggestions for an approach in a new case. The AI tutor helper might do something similar. We could input all the work my son’s done and it could make suggestions to the tutor, or at least make all his work digestible.

The name is Short Circuit for now, after that movie from 1986 that you’ll probably remember.

So, the big question is, what would you do if you were me? How do I get going?”

Well alright. The first thing I’d do if I were you would be to pat myself on the back for the short circuit reference. And the second is to remind you that, while I do like this flavor of AI for X that focuses on processing power plus a generic opinion, we need to talk about problems and customers way before we decide if AI is the right solution.

But, for todays episode, we’re just focused on getting going. The nudge into the pool that kicks off the changes you’re reluctant to make.

The thing that seems easy but is monumentally hard. To shift your life from one that doesn’t have you working towards something new to one built specifically for that reason.

And we’ve got three methods..ugh… shortcuts.. that are incredibly effective at it.

And we’ll get to all five …. after… a little smooth jazz that’s got something a bit different today. A live workshop with me, if you’re interested.

Hey!

If you’re struggling at the customer interview stage - you know you should do them, you appreciate the value, you just… need some help. I’m running a customer interview live on zoom 3-day workshop. I’ll help you schedule your first 50 interviews, build the right questions to ask, and set up an internal system to make sure you’re continually running them.

Go to gettacklebox.com/workshops and click on get the details to sign up. We’ll send you dates and info once you do.

Back to it.

Just In Time Prep - Any preparation you do for entrepreneurship, or most things, is probably a waste of time

Before I had a chance to respond to our tutor friend’s email, she sent a follow-up.

“I’ve been prepping for the whole entrepreneurship thing for a while - I’m reading lots of blogs and listening to podcasts. I also just picked up the Personal MBA, which you’ve recommended. So, I’m going to run through that, and about five other highly recommended bookes, too.”

And that’s where we’ll start. With the first Method to get you moving - Just In Time Prep, aka, for the love of god, stop prepping for stuff.

Back in 2012, near the end of my time at business school but before I’d started working on Find Your Lobster, I decided that I wanted to learn to code. I wanted to be, quote, dangerous, when the big idea I’d been waiting on for a few years to strike finally did. So, I started taking computer science and coding classes. I spent like 5-7 hours a day on them.

A few months after starting, I went to a fireside chat with an entrepreneur who’d built and sold four companies. During Q+A I raised my hand, but before I could ask my question he asked what I was currently working on. I said I was focused on learning to code so that I’d be ready when an idea struck, and he pounced.

“This is a huge problem. Everyone, do not do this.” I was stunned. He continued. “I assume you don’t want to be a developer, right?” “Nope,” I answered, and before I could follow up with my whole - I just want to be dangerous spiel, he was talking.

“I live by Just In Time Preparation and you should, too. Do the thing you want to be doing until you hit a wall, then learn how to navigate that specific wall, and continue to move forward. With startups, and most interesting things in life, you can’t predict what skills you’ll need and what scenarios you’ll need them. The most direct route is to sprint, hit a blocker, figure out that blocker, keep sprinting.”

“What’s an idea you have,” he asked.

I said I didn’t have a specific idea, but maybe something about helping college athletes share video easier when they were getting recruited.

“Great,” he said, “every second you currently spend learning to code, instead just go talk to college coaches and players and learn their problems. Once you find a problem to solve, figure out what the technical hurdle you need to solve and learn how to solve it. Or, better, partner with someone who already knows how to solve it.”

The underlying advice here still cuts at me a bit. Because I’m a huge believer in venn diagrams. Learn a bunch of stuff, combine that stuff in a unique way, end up with something new. But, I think the prep people tend to do, especially when you aren’t sure exactly what you’ll need, is often a form of procrastination. ESPECIALLY at the start of a project. Reading the Personal MBA is easy. Cold calling tutors is hard.

In almost every scenario, it’s better to do the thing, make mistakes, hit walls, then go back and figure out how to navigate those walls then to spend a ton of time prepping for every wall you could potentially hit.

Learn just enough to get started - so, if you’re an early stage entrepreneur, the first step is always to learn more about the problem through customer interviews. Spend a few hours reading the mom test or going through the Tacklebox workshop to get a framework - gettacklebox.com slash workshops and click more details - then get going. Get out there.

It’s always better to do something before you feel ready to do it. Because, in the entrepreneurship world, you’ll never feel ready. It’s the land of making decisions with incomplete information.

So, when you lay out your work for the week, ask… is this necessary? Or am I prepping for something that likely isn’t going to happen? Am I using prep as a crutch?

Now, it’s time to move into some more tangible, tactical stuff.

And her response to the stop prepping advice was a good one.

“So… if no personal MBA, then…what do I do?”

Glad you asked.

Part 2: Search for Hooks to Put Yourself On

If you ask someone with a startup idea why they haven’t spent more time on their startup idea they’ll usually beat the crap out of themselves.

“Because I’ve been lazy, I can’t keep myself accountable, I try to work mornings but it gets so hectic, I try to work nights but after a long day of work I just want to watch Netflix,” and on and on.

But none of those are the real answer. The real answer is simply that their life, as currently constructed, isn’t set up for them to work on a startup. It’s set up to do what they normally do. Down to the most minute detail.

We’re all goldfish who grew to the size of our bowl, and no matter how comfortable you might feel, you don’t have an extra hour in the day to work on your startup. You need to purposefully create that hour and design it in a way that it can’t be usurped by your normal, as constructed life, which will have all the momentum. Everything in your life will be fighting for you to treat that hour the same way you did yesterday. So, we need a sustainable way to create and hold time. A life that’s designed so that you can’t not start a startup on the side.

To do that, we need to do three things:

1. Remove something that takes the same amount of time you’d like to spend on your startup. Like a bouncer at a club - one out, one in.

2. Build in mechanisms outside of your control to ensure you do not do the thing you said you wouldn’t do during your startup time.

3. Create reinforcing markers in your life to remind you that you’re a person working on a startup

To follow these steps, we’ll use forcing functions because there’s absolutely no reason to rely on willpower. You’ll need that to not eat oreos or hop on the peloton. Although we could build systems to make those automatic, too.

For the startup, we’ll need to find a bunch of hooks to put ourselves on until our new habits are ingrained and we no longer need those hooks.

Back to our Tutor friend. I asked her how she could get closer to the problem, and she said she’d love to speak with 10 tutors, 10 teachers, and 10 parents. I agreed.

But that’s 30 conversations and that’s a lot. Since she didn’t have 30 conversations with tutors, teachers and parents over the last few weeks, her life is not set up to do it in the next few.

So, we need to jump into the three-step system.

First, I asked her what she’d remove to clear the decks for an hour or two of startup work each day. She said she watched an hour of tv each night before she went to bed with her husband, so, she’d cut that hour out, go to bed an hour early, and shift that night hour to one in the morning. Instead of waking up at 645, she’d wake up at 545 and work. No one in the house would be awake and tempting her to do something else.

Great. Next up is step two. The question:

“How will you ensure you no longer watch TV at night, and ensure you work from 545-645 on your startup each morning? How can you make skipping that schedule impossible, or at least really painful?”

One answer, she said, was to tell her spouse she’d pay him $50 for every night she wasn’t in bed at 9pm. Not bad. Another route is to set up a timer on your wifi so that it shuts off at 9pm each night - easy to do in the settings. I always opt for things you have no control over. Your spouse can let you off the hook for $50.

In the mornings, she’d join a virtual accountability group. She found one online that met in a zoom and cost $100 a month. Not terrible. A good start.

Those first two steps, creating space and then creating forcing functions that make it harder to not do than to do can be done over and over. And you can get creative with forcing functions. You should always be searching for them.

Here are a few of my favorites:

• Host an expert event. So, for our tutor friend, she might host an event for parents who’s kids are in their first year of high school. This is when most parents get tutors, so maybe she organizes a q and a with local tutors, teachers and parents. This is a set thing that needs to happen, and off the back end of it, there will be enormous goodwill and connections that’ll lead to interviews and deeper customer intel. Once you send out the evites, you’re committed. A few years back we had a startup that was helping first time expectant moms prep for the coming baby. They wanted to figure out exactly how to help, so they organized walks around prospect park with experts - lactation specialists, doulas, etc. This ended up getting tons of feedback and actually just became the product. But it started as a forcing function.

• Outsource a future step. Hire a freelancer or someone off of Fiverr to send 250 cold emails for you the following week. Then, you’re on the hook to pull together the emails and the target list or you wasted your money.

• Offer a service. Offer to help parents find the right tutor. This will let you interview parents and tutors and put you on the hook to facilitate the connection. On our way to a concierge MVP.

• These are three of a dozens our founders have used to keep themselves accountable.

Constantly search for hooks to put yourself on, and make sure they’re at least mostly aligned with where you’re headed, but nothing will be perfect. An imperfect hook is better than no hook at all.

Now, for our tutor friend, we need to get to the final step. She’s created the structure and space to get those calls done, now we need to establish reinforcing markers.

But first, a quick interlude. You might’ve realized she lost an hour of tv with her husband each night. This is a huge loss and requires a shift in other parts of the schedule to make up for. They both ended up fixing their schedules so that they held an hour long lunch, in person on or zoom, together each day.

The bigger lesson is that the cost of your new life is your old one. Things have to change, and sometimes removing something you love forces you to figure out where there’s room to cut to ensure that thing you love is slotted back in. Change is good.

Back to reinforcing markers.

—

Reinforcing Markers exist to remind your subconscious what it should be thinking about. Your brain works continually in the background on open loops, and if you don’t push a preferred loop in front of it, it’ll focus on figuring out who the murderer in whatever netflix slash hulu show starring nicole kidman is currently popular when you listen to this.

So, remind yourself that this is a thing you’re doing constantly. I like a nightly journal with a few simple prompts, like - what’d you get done today, what’ll you get done tomorrow, what blockers did you face and how might you navigate them better tomorrow, and, most important, why is this idea so exciting?

The last prompt ensures you stay an optimist, which is the superpower of entrepreneurs. This journey is fun. You’re choosing it. Don’t forget it.

You can use whatever tool you like to make sure you answer these each night - put a journal on your pillow, create a recurring task in whatever task tool you use, or put a postit on your bathroom mirror. Doesn’t matter.

There are lots of internal reinforcing marker techniques - changing the background on your phone, sending yourself an email reminder each day with what you’re doing, and on and on.

But some of my favorite reinforcing markers are external.

The best forcing function for new behavior is the people you surround yourself with. The saying you’re the average of the five people you spend the most time with is absolutely correct.

If I were looking to pick up new behaviors, I’d find people who naturally exhibit those behaviors. People who do now what I’d love to do someday. Then, I’d spend a bunch of time around them.

If you want to be around people working on startups on the side, find a few people working on successful startups on the side and attach yourself to their hip. Figure out when and where they meet or work, and be there. Osmosis is an extraordinary thing.

If you’re single and you’re working on a media startup, move to LA. If you want to write a book, join a writing group with established authors. Put your butt where your heart is.

The End - Jump in the Ocean

Speaking of writing, I’ve been speaking with career authors as I’ve been plotting writing a fiction book, and one gave me some…interesting advice.

He told me that before I started writing a book, I should throw out my iphone.

Sure, I said, I know all about the screen time stuff and distraction and all that, but he cut me off. No no, that’s not why.

You need to remind yourself that all the things you do and have are temporary and optional. You have an iphone for a million reasons, but you could also not have an iphone. For 99.99 repeating percent of history, people didn’t have iphones and they did just fine. You could have a google phone or a flip phone or no phone and you’ll do great.

This, he said, is about reminding yourself that you’re in control of your life, even with stuff that you think is non negotiable. On day one of not having an Iphone it’ll probably be a nuisance, but by day 20, you’ll have moved on. That type of shakeup is important if you’re trying to change other parts of your life. Prove to yourself you’re the type of person who can change.

I loved this. And I loved his second suggestion, too. If you’re not going to throw away your phone, he said, at least go jump in the ocean. He knew I lived in Connecticut and was relatively close to the water, and he also knew that water was ice cold. Whatever, he said. You’ll be freezing, people will stare at the crazy person in the ice cold water, then you’ll get out and go home and write your book.

People tend to think startups can fit neatly into an hour here or there and the rest of their lives won’t be touched, but that’s missing a huge opportunity. Embrace this thing. Embrace that you’re capable of all sorts of change. Have fun with it.

Put yourself on the hook for stuff and see what you can do. That’ll be fun, too.

Remind yourself that those walls around the castle are made of construction paper.

And, if your kid has a tutor and that tutor would benefit from an AI overview of all the work that kids done? Email team at gettacklebox dot com. Because our tutor friend jumped in the ocean and she’s running concierge MVPs.

Have a great week.

Want to get started on customer interview? Join our our workshop on customer interviews. head to gettacklebox dot com slash workshops. First come first serve. We’ll send you dates and details once you sign up.