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How to Flounder Effectively
Because extreme focus isn't all it's cracked up to be
Brian Scordato
July 24, 2025
Idea to Startup: How to Flounder Effectively
This Episode
Most founders think the key to a successful startup is laser focus on one thing. But there’s a problem - that’s not a sustainable strategy.
Today, I'll show you how to balance deep focus with productive exploration using what I call "floundering" - the art of following interesting threads without losing sight of your main thing. You'll learn why successful founders have the most unique personal Venn diagrams, how to turn your natural curiosity into a competitive advantage, and the specific system that lets you explore freely while building something real.
As always, we came up with a framework for you:
The Four Rules of Floundering
Give Yourself a Floundering Budget - Set sacred time for exploration (I suggest one hour daily)
Make Floundering Show and Tell - Turn wandering into tangible output with weekly accountability
Create Floundering Metrics - Test every interesting thread with simple experiments
Do Flounder Therapy - Distinguish between fear-driven avoidance and genuine curiosity
This was a fun one. Hope it’s helpful.
Pod References
The Let's Actually Run Customer Interviews Workshop - a 10-day program that'll help you actually, finally, run proper customer interviews. This will kickstart your business. $150 through July 31 with code "EARLY"
0:00 Let’s Run Customer Interviews Workshop01:12 Mailbag
02:44 How to Flounder
03:56 The Idea: Community Investment Circles
07:11 When is it time to become “maniacally focused”?
10:35 The Four Rules of Floundering
15:26 Floundering’s real value: longevity
Transcript - feel free to read like a long-form article
Today, we’re going to hop into the mailbag and answer a listener question. People seem to like these episodes - they get listened to and shared on average a bit more than the others - and I actually love doing them. I kill myself to try and make episodes that’ll help you get unstuck, and a great way to do that is to just…let you tell me where you’re stuck.
I never thought we’d be a mailbag every few months sort of show, but in the words of Richie from the Bear, the best character with the best arc from the best show of the past decade - I wear suits now. We do mailbags now.
One more note before we start - we’re back working with some podcast consultants because I can’t seem to quit them, and let me tell you, they were HORRIFIED that I don’t start every episode by saying if you don’t subscribe to the show please do, and if you like the show please give it a five star rating on apple and spotify. I told them I didn’t want to tell people how to eat their cheerios and they said that in their pretty vast experience people were 27x more likely to like and subscribe if you asked them to than if you didn’t. Over a year, this leads to a frankly shocking increase in listeners and ad revenue. Can’t fight math. Subscribe if you like the show and rate it five stars if you can. I wear suits now.
Anyway, we’ll hit one killer questions today. The goal was to hit four, but the first was so freaking important that we went deep on it. We’ll hit the other three next week.
And to introduce this wildly important question, I need to tell you why I’m not afraid of my son getting eaten by an alligator.
How to Flounder Effectively
There are a lot of things that worry me as a parent, but one thing that doesn’t is alligators. Because my son runs all the time, and the only route he takes would be categorized as an aggressive zig zag.
If you know anything about alligators, you know this is their kryptonite. They can run like 35 mph in straight lines, but it takes them forever to change direction because they’ve got those tiny little brioche legs. They’re like normal sized dinosaurs that got put in a pannini press.
If you ever find yourself being chased by an alligator, run zig zags and you’ll be fine.
My son zig zags because he’s endlessly interested in everything. He’ll be running to get a soccer ball but see a sunflower out of the corner of his eye, so he’ll change direction faster than lionel Messi and sprint towards it, shouting “thats a dandelion,” until a bird chirps behind him which will cause him to stop and sprint towards that instead, and on and on. He’s always sprinting but he never gets anywhere.
So, I can check being eaten by an alligator off the list of parental worries. It was pretty low, seeing as we live in connecticut, but parents worry lists aren’t all that rational.
A few weeks ago I chatted with a Tacklebox applicant who’d started out working on an idea that’d help local businesses get financial support from their community. The idea came from a lived scenario.
There’s apparently a beloved old movie theater in his small town that needed to upgrade all of their projection technology because new movies are in a format that’s no longer compatible with older rigs. The owner didn’t feel right about raising prices and the cost - something like $50k - was an amount he couldn’t take out a loan for. So, he was going to close.
Until our friend - along with other people in the town - helped him out. They helped create a membership program, where moviegoers could pre-pay for a yearly pass. This got them unlimited movies, popcorn, and access to the two best rows in the theater, which were now reserved for members. They set up a fundraiser, where locals donated items that went up for bid, with proceeds going towards the new equipment. Finally, the owner sold bricks with peoples names on them, which would become the sidewalk leading up to the theater. Like the handprints in hollywood.
The movie theater raised the money it needed, upgraded the tech, and continued to be a staple of the town.
Our founder friend’s initial idea was called Community Investment Circles. He’d create the infrastructure for neighborhood investment groups - where, say, 50 neighbors would pool capital to invest in hyperlocal opportunities that benefitted the community while generating returns. They’d invest in a coffee shop that needed a new espresso machine or they’d help bring a new daycare center to town. The hope was to help people lean into their communities with financial incentive. His product would be the tech platform that handled the deal flow and structure and all that.
That’s where it started.
But, then, in his words, “things got a bit nutty.”
He told me the story.
“Well,” he said, “I started by trying to find other examples of projects that’d worked - like our movie theater. This was difficult, so I switched to the other side of the market and interviewed local businesses - restaurants, cafes, auto body parts, etc. This led me to a deep interest in restaurant finances. But, after a few weeks of that, I got more excited about helping restaurants launch food trucks. This seemed like a huge opportunity. I started working with a restaurant that wanted to launch a lobster roll truck and realized that sourcing sustainable seafood was maybe the toughest part. So, I looked into that for a while. And that’s where I am today. Sourcing anchivoes, which are one of the healthiest foods on the planet and environmentally one of the best fish you can eat. I’m considering a tinned fish startup. I’ve got a good potential partner.
This whole process,” he continued, “has been super interesting. But… is this… ok? Is this good? Do I need to focus more? Or do I need to just keep chasing interesting things and trust that, eventually, an obviously good opportunity will present itself? I know I need to both be super curious and wildly focused. How do I balance those two? When have I niched down enough? When have I niched too much?”
It’s really nice to know that, at the very least, our anchovy friend is never going to get caught by an alligator either. But I do need physical therapy for the whiplash his 45 second story gave me.
So let’s get to the core of his question:
When is it time to stop exploring and to become, as most startup preachers put it, “maniacally focused” on one thing? What’s the balance of search vs sprint?
This one is difficult, because nearly every startup person you’ll talk to will preach focus. Find a niche, live in that niche, build systems to thwart your focus being pulled anywhere but that niche. The challenge and the goal are both extreme focus.
Which would mean the zig zagging is a bad thing.
BUT, the other side of that coin is that the more you zig zag, the further you go down a path, the more likely you’ll end up on that path alone. Meaning, other people who take the same path will get off it earlier. So, you’ll have a higher likelihood of finding an underserved niche the more you search.
When I look at the successful Tacklebox founders, lots of them searched longer than most. And, for the rest of the pod, we’re going to call that searching something more accurate - Floundering. This is the term Brie Wolfson used in her wonderful essay about Kevin Kelly, one of my heros, and I’ll adopt it.
Our best founders floundered a ton, but also focused intensely. They were able to zoom in and zoom out.
Moreover, these founders lives had been an interesting case study in floundering and focusing.
We’ve had a super successful founder that showed up to Tacklebox deeply passionate about finance, space, and teaching people how to DJ. Another was an actor on broadway who’d owned a gluten free muffin shop and was a freelance accountant. A few episodes ago I talked about a poison ivy eradication business run by a guy with a background in military contamination environments.
Our most successful founders have the most unique person Venn Diagrams. A mix of skills, interests, and networks that made them singular. This allows them to execute my absolute favorite startup strategy - take something that’s table stakes in one industry and port it to a new industry where it’s novel. This only works when you’re one of a very small group who have insight into both of those industries. It comes from floundering.
So, using our new terminology, the founder’s question - when should you stop floundering and start focusing? - is kind of the wrong question. ****
The right question is how to you get good at Floundering and Focusing? How do you get good at zooming in and zooming out?
I think the generally agreed upon startup premise that you flounder for a while until you find a niche, then you shift into maniacal focus on it and live and breath it for the next decade, is the problem here. I think that’s unrealistic and ineffective. It’s also a terrible way to spend your life - very few people will be endlessly fascinated by one thing. I think the right way to think about this is that both focus and floundering are skills. And both are needed indefinitely.
Now, when you position Floundering and Focusing as skills we need to get better at, it becomes clear that we just need some boundaries.
Some Floundering Rules.
Which from this point forward will be called The Four Rules of Floundering.
And I know that sounds a little too close to the Four Rules of Philandering, but that’s not what this list is at all. If you’re trying to Philander and you use this list you’ll just end up with a successful startup. Which is probably for the best.
There are lots of podcasts on how to focus, but very few on how to flounder. This list should help you build and cultivate that incredibly useful skill.
Rule Number One: Give Yourself a Floundering Budget and Recognize It As Such:
A key to happiness and sanity during a startup is to follow your interests. You’re doing this thing because you like pulling on threads, so let yourself do it. The key is to do it in a structured way. The first bit of structure is to set aside specific times for it. This is your time to explore the interesting threads from customer interviews or similar industries that might hold some answers to problems in your industry or unique business models. Or, vibe coding. Or learning to play piano. More on the specifics of Floundering in a bit. The point is to hold sacred time for it. I suggest an hour a day, and I suggest first thing in the morning, before the day finds you. And, your subconscious needs to know what this time is for. It’s exploration into genuine interests that might end up being useful and might not.
Make Sure Floundering is Show and Tell:
What you Flounder on can be unstructured, but the Floundering itself shouldn’t be. We have accountability groups within Tacklebox where founders meet each week for, quote, show and tell. You have to show up with something you’ve done. You can’t say you researched something or thought about something - you need to have a landing page you made after a conversation with a customer, or an email draft you’re planning on sending to trucking companies.
Every week - or every two weeks, if you’d like - produce something. Find a floundering partner if you’d like it to be a bit more fun, and commit to weekly or bi-weekly meetings.
Create Floundering Metrics for Customer Segments and Ideas:
A tricky part about Floundering is you’ll come up with a bunch of interesting startup ideas and customer niches and you’ll have to decide whether there’s actually something there or not. It’s really easy to fall into the all babies are cute syndrome. So we need to trade the dream of the idea for the reality of feedback.
For each interesting opportunity your floundering uncovers, define one simple test you can run in under a week. New customer segment? Send 10 cold emails with a value prop. Interesting product idea? Build a basic landing page and buy $20 of Google ads. Adjacent market opportunity? Schedule three phone calls with people in that space. The point isn't whether these micro-tests succeed - it's getting some data to get the baby ugly. And if it’s not, keep pulling. Trying to kill an idea is a really effective way to test it.
Do Flounder Therapy and don’t judge your floundering
A lot of times Floundering is actually just you avoiding working on the main thing. So, run a little Flounder Therapy with yourself every week:
Are you exploring new niches because you're genuinely curious, or because you're avoiding the hard work of going deeper with your current customers?
Is this fear driven or interest driven?
The other side of the floundering coin is judging your floundering. Trying to predict what’s going to be valuable before you do it. Don’t do that. Because your predictions will be the same as everyone elses, which means you won’t end up somewhere unique.
Need to scratch an itch for paleontology? I cannot tell you how useful this might be. Literally. I don’t know. It might be useless or it might be a breakthrough. But if your subconscious knows what the main thing you’re working on is, it’ll look at all your floundering through that lens. It might pick something up in paleontology that helps the core thing. So, follow your interests and don’t judge.
Those are the rules.
And yes, I did ask Claude what it’s four rules of philandering would be and my goodness was it haunting. I don’t even want to make a joke about it. Clean it up, AI.
Ok! Floundering and Philandering over.
We started with a metaphor about my son outrunning alligators and we’ll end with a metaphor of him outrunning alligators.
If you pick a thing to focus on, then only focus on it, you’ll get caught by the alligator. You’ll have a predictable product that’s easy to compete with. You won’t have a differentiator and likely won’t be able to shift and adjust when you need.
But, if all you do is zig zag, you won’t get eaten by the alligator but you won’t get anywhere.
The key is balance, and the balance is likely 80% main thing 20% floundering. The danger is to mess up those percentages, one way or the other. To flounder too much because you’re scared of the real work or to avoid floundering because you don’t see the immediate, obvious benefits to it.
My wife and I regularly default back to the show Alone for the 30 or so minutes each night we have for tv while one baby or the other has a bottle.
The premise is a bunch of survival experts are dropped into completely wild territory - like Mongolia - completely alone. The one who lasts the longest wins a million bucks. And, whenever you need to be picked up, you press a button on a walkie talkie.
You’d imagine that the hardest part of lasting 20, 30, 40 days is finding food or shelter or staving off the cold, but it’s not. People leave because they’re lonely. They miss their family. So they tap out.
The parallel to entrepreneurs is there.
This thing will be extremely hard and the key is to last the longest. To survive. And survival requires you to be well rounded.
Entrepreneurs are interested. We love to flounder. It’s our nature. It’s why we do entreprenuership in the first place - we pulled on a thread. You’ll last longer in this startup wilderness if you’re able to lean into that - to pull on threads to keep your soul happy and your business differentiated.
And if misread the title of this episode and thought it was on the rules of philandering… toss it into chatgpt. They’ve got you covered in the absolute creepiest way possible. seriously. clean it up ai.
Mailbag part 2, next week.