Idea to Startup: How to Finally Get Your Ideas into the World as a Right-Brain Founder

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This Episode

This episode is a toolkit for right-brain founders who get lost in ideas and struggle to execute. Brian shares three practical systems—AI as your left brain, the Regroup System, and the Ice Box—to help you make consistent progress, despite the whole right brain thing. This is a practical guide for turning creativity into momentum.

Here are some useable frameworks we talk through in the pod:

The “Left-Brain Injection” Prompt (Use AI as Your Structure)

Here’s a prompt that can work, from the pod. Pop it into ChatGPT or Claude or whatever you like:

The Regroup System (3-Minute Daily Reset)

After each work session, write only these three things:

1) What I finished today

Write in long-form narrative, not bullets. (This matters—narrative improves context memory.)

2) Where I need to pick up tomorrow

This creates “rolling momentum.”

3) What to ignore tomorrow

If you highlight what not to do, you pre-eliminate rabbit holes.

Pod References

• Tacklebox (code HOLIDAY2025 for 50% off)

• The sailboat race I mention

  
  00:30 How a Prolific Investor Invests
  04:47 Right Brain, Left Brain
  07:38 Jazz - CODE HOLIDAY2025
  08:13 You Don’t Have a Goal
  11:30 Outsourcing your Left Brain to AI
  13:05 The Regroup System
  15:01 The Icebox
  16:59 The End

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

Today, we’re going to talk about left and right brain. Specifically, I’m going to talk to right brain founders and help them navigate being stuck in a left brain world.

And we’ll start, with a story.

I got pretty close to a prolific venture capitalist who had been investing in NYC tech from the early 2000s, back when there was a very small, niche startup scene and Tumblr and Foursquare were doing everything they could to drag the city into tech relevancy.

He never invested in anything I did but he helped me a ton in other ways. Probably most helpful was him letting me in on how he evaluated super early stage companies.

Also, a totally random bit of color - he always wanted to meet at Pizzeria Uno up on the UWS, which I thought was the absolute strangest possible place to meet for pizza in new york freaking city but I must say the pizza isn’t bad. I always joked that everyone else in there must be having an affair because the pizzeria uno in NYC is the one place no one you know will ever be.

Anyway, back to how he evaluated startups.

He’d run them through what he called “the stack” - a batch of binary questions he’d come up with over the years. He said he’d “earned” these questions. Each came with a story of him either passing on a business that ended up being successful or investing in a dud. Since every question was binary, a startup either got one point or zero points for each and he had a threshold a startup had to meet for investment. It was a moneyball type of approach, one that, he hoped, took out emotion and would work in the long-term over a bunch of investments.

I’ll give you one quick example of one of the questions.

One time at pizzeria uno, while eating deep dish in the dead heart of August, I mentioned offhand about one of the hotter startups of the moment - ClassPass. I said I loved their model and half jokingly said I bet he wished he’d been in the angel round.

For everyone who isn’t familiar with ClassPass, it’s a subscription service that allows you to book lots of boutique fitness classes from different studios with one membership. So, you pay classpass $150 bucks or whatever per month and can go to ten classes a month from their marketplace of studios with things like yoga, cycling, pilates, high intensity, etc.

“Oh I had the chance - great founder and team. But I passed.”

He said it with no trace of regret.

“..why?” I asked

“Mostly because it failed the What if it actually works” question

He continued.

“This is my version of the famous quote from Jurassic Park - everyone was so preoccupied with whether or not they could, they didn’t stop to think if they should.

Let’s say ClassPass works exactly as it’s supposed to. Lots of end users and studios sign up and there’s a thriving marketplace. This looks great from the outside. But, if it works… it doesn’t work.

He started counting the points he was making on his fingers

• A studio charges $40 per class or $300/month for 10 classes.

• When a customer comes through ClassPass, they’ll get maybe $10

• And yes, some totally new customers will discover them and show up, but these, again, aren’t profitable customers. And, a bunch of their existing $300/month members will likely switch to ClassPass and keep showing up, but for 1/4 the margin.

• And, popular studios won’t join because if they do, their classes will get flooded with low margin customers

Overall, ClassPass says they want people to “discover” new studios, but this isn’t actually good for the studios. And the studios are hoping to use ClassPass to get new dedicated members, which is unlikely. The incentives directly oppose each other. That’s not a good marketplace.

And yes, absolutely it could work for a while and the team is great, maybe they’ll figure something out I haven’t thought of. But for a company to really, really grow, in a way that gives a venture return, the key parts of the company need to be aligned. The product working needs to be a GREAT outcome for everyone. And in this case, it just isn’t.”

And that’s how the questions work. Interesting enough.

But, the reason he has the questions in the first place is what we’ll really talk about today.

When telling me about them the first time, he said he invented them because he’s a right brain dominant person. Which means that he sees the world as a bunch of pieces that can be put together to build something interesting or beautiful or useful. And this perspective made him want to invest in every startup he met.

He created the questions as a left-brain check on his right-brain enthusiasm. As a filter.

He made it clear that left-brain and right-brain weren’t actually as distinct as most people thought - it’s a huge oversimplification, he said, that left brain is logical and right brain is creative.

Instead, he gave tendencies for each.

And, in this episode, we’ll use the terms right brain and left brain in a wildly unscientific way. If you want, you could swap “dreamers” vs “executors.” But lots of people talk about left brain and right brain so we’ll stick with it. The big thing is all about the tendencies each type of founder has, and their default processing approach.

The left brain is good at linear and analytical thinking, at breaking big things down into smaller, tackle-able parts. It likes precision and is, at all times, in a desperate search for and need of rules to be followed.

The right brain is good at nonlinear and contextual thinking. It sees the pattern-first and is good at integrating parts into a whole, good at reading emotion, and prefers flexibility over strict rules.

A good way to think about it is that the right brain sees the forest, the left brain organizes the trees.

For startups, and investing in startups, you obviously need both.

Our investing friend knew his default was right brain thinking, so he built a system to ensure he got the left brain structure in there, too.

For our founders, the awareness of your thinking type and a system to balance it out is critical. I’d guess maybe 60% of the founders I meet act in that right brain way, and for lots of them it’s their downfall. Right brain founders tend to run out of runway while making big plans. Most don’t ever launch anything.

So, today, we’ve got a three pack of tactics right brained founders can leverage to tap into their left brain and stop spinning around chasing their tale and actually get something out.

They stem from three catastrophic habits us right brainers - yes, I’m definitely one - suffer from:

1. Lacking a coherent goal, which means we don’t know what tasks to work on at any given moment

2. Not being able to get back on track after the inevitable rabbit holes we go down

3. Being hamstrung by your other ideas

Let’s get into em. Let’s create a system to actually get our stuff into the world.

And let’s do it…after…

a little smooth jazz - with a discount code! It’s that time of year.

Hey!

For the holiday season, I’ll be doing 50% off your first month of Tacklebox with code “Holiday2025” - If you’ve got a startup idea and a full time job and want to actually launch that thing, with me as your coach, let’s do it. Head to gettacklebox dot com and apply.

Also, just a heads up - our program usually fills up in January with all the resolution folks, and then you’d have to likely wait until march or april for a spot. So, good to reserve yours now if you’re interested. Holiday 2025.

Back to it.

Part 1: You Probably Don’t Have a Goal, and that’s not good

We’ll start with goals.

The blessing and the curse of us right brained folk is that we dream. A lot. We also believe in ourselves to reach those dreams, and both of those things are very important for entrepreneurs. The startup world is not kind to founders after incremental gains. Big vision is critical.

But, two things happen when you like to dream:

1. You spend too much time dreaming and not enough time on concrete actions moving you towards that dream, so your dreams get so big and ambitious they become functionally useless - you probably could’ve guessed that one, and

2. Since you dream so much, the goalposts are always shifting. The dream is never sturdy enough to build a plan around. It grows and expands and gets less attainable, like the helium balloon my son accidentally let go of at an outdoor birthday party last week.

Here’s an example

A founder applied to Tacklebox recently with an idea for an AI for the home tool.

He’d done a bunch of great customer work with home owners, knocking on doors and asking one question - if he was their personal contractor, if they could ask him to fix anything in their house right now, what would it be? He found the four most common issues that they’d been dragging their feet on were:

1. Something with plumbing - usually the water pressure in the shower was inconsistent, or the water didn’t get hot enough, or a toilet didn’t work or a drain was clogged.

2. Something HVAC related - heat didn’t get hot enough, AC didn’t get cold enough, seemed like bill was too high

3. A pest issue - mice, bugs, ants, whatever

4. A tree issue - they weren’t sure if a tree was in danger of falling on their house

So, he said, my plan was to pick one and focus on it.

the was scared me.

He continued,

But then I figured I could actually handle whatever task they wanted, because I could just find contractors for each. And I can start with an audit of their house - creating a dashboard with all their systems that I can update when they need attention, and it’s something they can use when they sell the place. Then, on the vendor side I can maybe start grouping projects to try and get bulk discounts. And, obviously, there’s a huge AI component.

He right brained for another minute or two before finally stopping.

“So, what are you doing right now?” I asked.

He shook his head and acted like I’d just asked him to explain quantum computing.

And this is the right brain problem. Absolutely everything he was talking about could, maybe work. But it’s a completely unapproachable vision. Especially for a right brained person who struggles building out a set of tasks and following them, which is all of them.

The problem with the right brain dreaming is that you know there’s always another dream coming, and that dream might be better than the one you’ve got right now. So, any time you sit down to work you’re working on something that, in the back of your mind, might be outdated tomorrow. So you get paralyzed.

The way to combat it is to build a system that jumps in, a more assertive left brain.

The beauty of the left brain is that it it’s much easier to fake than your right brain, especially now. What I do, and what I suggest you do, is outsource your left brain to AI.

The fear for right brained folks with this is that if you ask AI to prioritize your massive vision, it might pick the wrong stuff to focus on first.

But the beauty is that it literally doesn’t matter. Maybe ChatGPT says to focus first on what we’d call at tacklebox a concierge MVP - A full test where you help 5 different homes with plumbing issues actually execute on them. You find them, match them with a plumber, charge them a premium, and get feedback.

Maybe it’s actually better to focus on something else first, like the home operating system piece. But any goal is better than no goal when you start. You need to make progress and get some sort of validation and context, one way or the other. You need to move in a straight line for a while, then pick your head up and make a decision on continuing or pivoting.

So, type all of your thoughts and dreams into Chatgpt. Tell it that you’re right brained and you need some help setting a clear goal with tasks underneath it that pushes you towards validation of your big idea. Tell it how many hours you want to work and when you can work and what you’re good at. Have it set you a schedule and make a notion doc with a checklist for each day. Then, when you sit down to work, reference it. Make progress. Use it like a journal to say what you did and what you struggled with.

You’re outsourcing the left brain, because that doesn’t come natural to you.

Ok, on to the next right brain struggle: regrouping.

—

The Regroup System

A right brain calling card are rabbit holes. We see something interesting and we go after it. This is, again, a massive strength, but, when you’ve only got 45 minutes to work on your startup each day, it can be catastrophic for all the reasons we just discussed.

So, a skill all entrepreneurs need is what we call the Regroup System. A way to seamlessly switch from your regular life to your startup life with as little drag as possible. The first 15 minutes of your dedicated startup time can’t be spent on rabbit holes or on wondering where you left off or what’s up next.

The Regroup System is something you will have to force yourself to do, but it’s invaluable.

When you finish your startup sessions, building towards those firm goals we just established, spend 3 minutes writing out long form (no bullets) what you finished today and were you need to start tomorrow.

So, if you’re working on selling those plumbing services, you might write “I spoke with three families today. They each asked for more information and wanted to see a website, which, obviously, I don’t have. So, I started working on a template in squarespace. I was finishing up the H1 and was working on the H2. Start by getting back into that. I’ve got all the H2 ideas in Notion, and a Tacklebox article on problem language linked. Start by reading through that, then get 10 H2 ideas out. The goal is to finish the website by Friday, and to finish all the above the fold text tomorrow.”

That cadence and running diary will keep you on track. And your Right Brain needs that, because inbetween your working sessions you’re going to obviously come up with 15 more ideas and email them to yourself and be ready to test them. But to make any progress you’ll need to keep those at bay.

Which is the last critical piece for today.

The ice box.

—

The Ice Box

If you’re a regular listener you know about Linguini, my life operating system that lives in Notion.

One of the most important parts of that system is the Ice Box. I learned the phrase from a development shop I worked with over 10 years ago. The basic idea is anything that doesn’t fit into your current sprint - ideas on the current business, ideas on another business, random ideas - all go into the Ice Box.

You aren’t forgetting these things altogether or throwing them in the trash. You just can’t work on them now. You freeze em.

Here’s an example.

The other day I heard a story about a sailboat race from the 1960s where nine people all tried to get around the world without stopping. The fastest one would get a cash prize.

Apparently, of the nine people who set out, only six were actually sailors. One person was in a ton of debt to the mafia and was trying to win the race as a last resort to pay them back. Another was being blackmailed and was trying to pay off that person. One ended up trying to fake the whole race. The story is incredible.

I searched for books on it and there… weren’t any.

For two days I was obsessed with the idea of writing this book, and started mapping the whole thing out, before I realized I had to chuck it in the ice box. I’ve got other goals I’m working towards that are really important. It just isn’t the time.

So, I wrapped the whole thing up - described where I was at, why I was so excited about it, and where to pick up when I had time - and tossed it in the icebox.

For our Ai for homes founder, the ice box is where the 30 things he can’t start with go. It’s for your coffee startup idea and the bar named glory days you want to open with your college friends and the musical set in nyc about the guys on delivery bikes you want to write.

Every quarter I check the ice box to make sure I’m working on the right stuff, but it’s important to realize if you just jump from thing to thing you’ll never get anywhere.

The Ice box makes you excited to finish one thing so that you can get on to the next.

—

The End

As our listeners probably know, I’ve got two boys now. They’re the absolute light of my life and I want to spend as much time as possible with them.

But, I also want to make incredible stuff. I want tacklebox and the pod and the book to be great. I want to write novels and finish an ironman. Time is the thing.

So, I need systems. Because my right brain will just take me down rabbit holes on light roasted coffee and sailboat races from the 60s and I’m never going to remove that entirely, but I can build systems to get a left brain to keep it all in check a bit more.

Outsource your left brain to AI, create a regroup system, build your ice box, and, please, never go to pizzeria uno in august. Really don’t go ever, but especially not in august.

Have a great week.