Idea to Startup: How I’d Start a Startup in 2025

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This Episode

Today, we'll talk about the four steps I'd take if I needed to start a startup in 2025. We'll also talk about idiots.

We begin by embracing the reality that both founders and customers are irrational. Then, we build out steps and a process to address this. We start with a life audit, increase our Luck Surface Area, tackle the unit economics of working with one customer, and build out a system for accountability. This is a fun episode - one of my favorites in a while.  

Pod References

• Tacklebox - code "MuchAdoAboutStuffing" for 20% off month one

• How to Engineer Luck

• A Weekly Prioritization and Audit Framework for Entrepreneurs

00:30 Intro - A Listener Email
02:59 A Note on Idiots
06:33 Part 1: Actually Make Time For A Startup
08:23 The Life Audit Exercise
11:33 The Budget Audit Exercise
12:23 Smooth Jazz
12:54 Part 2: Plan for Luck
16:38 Part 3: Focus on One Person
20:16 Part 4: A System
24:30 The End: Enthusiasm

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

Today, we’re going to talk about idiots.

We’re going to get back to our series on AI for parenting soon - it’s heating up. We’ve got a wedge product humming and emails coming in and if you haven’t listened, that’s what the last two episodes are on.

But, it’s early January. Lots of people are signing up for Tacklebox - code much ado about stuffing still works for another week if you want 20% off - and I want to kick the year off by answering my absolute favorite genre of listener email - passive aggressive.

After the Q+A episode a month or so ago, I got an email that said “I know you won’t actually do this, but it’d be great if you did an episode on how you’d start a company in 2025 if you were forced to.” Well, Derrick, it looks like you’re wrong. Despite basically every episode implicitly being how I’d start a startup if I had to, we’re going to explicitly do it today.

And I just realized that maybe Derrick meant I wouldn’t start a company in 2025 because I didn’t need to, not that I was scared to for some reason. If that’s the case, my sincere apologies, Derrick.

Anyway, I think it’s a good prompt for an episode. Because if you’re listening to this podcast, I can almost guarantee one of your resolutions or goals or promises to yourself for 2025 has been startup related. I know this for sure for some of you, as January 5th, the Sunday before everyone went back to work, was our biggest tacklebox application day ever.

If this is you, let’s set you up for success.

If I do an episode in January next year titled How I’d Start a Startup in 2026, let’s make sure you’re too busy with the business you started this year to listen to it.

Back to the question - Derrick said if I was forced to start a company in 2025, what would I do?

The answer is simple - set my life up in a way that I couldn’t not start a startup in 2025.

Since I didn’t start a startup in 2024, that means my life isn’t currently constructed to start one in 2025. I’ll need a serious shift in both strategy and levers that enforce that strategy if I’d like to start a business. My daily life would need to look drastically different.

And, as I said in the opening line, that strategy is almost exclusively about idiots. It’ll make more sense soon.

So, here are the four things I’d do - two strategies, and two levers to enforce those strategies - if I needed to get a startup up and running in 2025.

We’ll get into them, after, a quick note on idiots.

A Note on Us Beloved Idiots

When I look at why so many startups fail, I really do think it’s because people are idiots.

Both the people trying to start the startup and the people those startups are trying to sell to. And, to be clear, I use the term idiot in the most endearing way possible. I absolutely love us idiots. Because being an idiot isn’t my fault or your fault - it’s our nature. We’re hardwired to be irrational - to make decisions that aren’t in our best interest even when we know they aren’t in our best interest and we very clearly know what decision would be in our best interest.

Here’s an example.

You know and I know that meditating each day for 20 minutes would change our lives. We’d be happier and calmer and more creative and live longer. Like 80% of successful people credit daily meditation with their success. Jerry Seinfeld says that 20 minutes of meditation each day was the single biggest driver in him creating Seinfeld.

There are 72 twenty minute blocks each day. If you point out that we’re asleep for a third of that, great, there are still 48 20 minute blocks each day. Using just one of those 48 on meditation would be life altering. And meditation isn’t hard. You literally sit there and do nothing. And yet, we don’t do it. Because we’re idiots.

Which is why I love startups so much.

Because people think they’re about AI or venture funding or MRR or a CTO or some other three letter acronym, but they’re really just about people and all of our silly, irrational idiosyncrasies.

Idiosyncrasies even sounds like idiot and I’d imagine they share a latin root or something but I didn’t look it up because I’m an idiot who knows the pod flows better if they’re connected. I just did, and they are connected - idio refers to something or somebody that is so peculiar that it has little or no sense or reason.

So, to be successful the first thing we need to acknowledge is that we’re idiots, our customers are idiots, and any assumption of rational acting on either of our parts is a waste of time. To be successful we need to assume irrational behavior from ourselves and our customers, which means to build something they’ll use we need to study that irrational behavior. We won’t be able to predict it, so we’ll need to see it in action to understand the motivations behind it.

When you start working on a business you’ll assume your customer is motivated by money. Eventually you’ll realize they’re actually motivated by being cut by their second grade baseball team or by the linkedin posts of their college roommates startup which just announced a new fundraise or by the dwindling amount of money in their bank account that, when it runs out, means they’ll have to go back to deloitte with their tail between their legs.

One of our most successful founders once asked me - while his business was doing millions and millions of dollars in revenue - if I thought his experience as CEO could get him into Harvard Business School the next year. When I laughed at what I thought was clearly a joke and said they’d be more likely to ask him to give a seminar and hire a few of their grads, he asked if I thought his parents would be allowed to come to that seminar, not picking up on my joke. They’d always dreamed of him going to Harvard Business School, he said, and maybe giving a seminar would be the next best thing.

Idiots, all of us. In the best way.

—

Back to starting a startup in 2025.

If I were to start a business, the theme would be idiot proofing the process. Both internally and externally.

Here’s how I’d do it.

Part 1: Actually Make Time For a Startup

The first way I’m an idiot about anything new is assuming that I can just start doing it.

I can wake up earlier or stay up later or be more efficient with the things I do now to create pockets of time.

I’ve said this before on the pod, but it’s well worth repeating. We’re all goldfish who have grown to the size of our bowl. Our lives are at capacity. Actually, they’re probably over capacity. Adding something as substantial as a startup without removing something as substantial as a startup is just silly.

This is going to be uncomfortable, but startups require sacrifices.

Your new life will cost you you’re old one, and that’s ok. It’s a prerequisite.

So, the first step of idiot proofing my startup strategy would be to make sure I actually had time to go after it. The minimum for me is 7 hours a week. The reason I say 7 hours a week is that’s the threshold for your subconscious to take it seriously. We want your mind working on this idea in the background all the time, which means you need to work on it every day to remind your subconscious it’s the top priority. So, if you’re doing 7 hours a week, three hours Saturday morning and four hours Sunday morning and then zero time during the week will be far less effective than an hour each morning, because your subconscious will forget about your startup after a day without working on it. Startups are about momentum, and you can’t get it with breaks.

So, we need to find you an hour a day.

And I know what you just did. You thought - holy crap, I can just wake up an hour early! I don’t need to remove anything. I thought the same thing.

We can’t even go 3 minutes without us both proving the theory that we’re all idiots, huh.

Because it’s not just the hour - it’s the mental space.

Which brings us to exercise number one of making space: a life audit.

Grab a couple big pieces of paper and your calendar.

On one piece of paper, write out absolutely everything you’ve spent time on the past month or two. Put everything that’s on your calendar, and mark the rough amount of time you spent on it. Put anything that didn’t make it on the calendar but you spent time on, too. And, if you’re feeling particularly saucy, check the screen time on your phone. Write that down.

Finally, put all the projects you’d like to do but haven’t found time for. Stuff that lives in your head even if it hasn’t escaped to your calendar yet.

Now, we have a source of truth. What you spend time on is what you prioritize.

I’d recommend pausing the pod and taking 15 minutes to do this.

Welcome back to anyone who actually did that.

So,

How does it look?

If an alien saw this piece of paper, what would they think your life goals were?

If you keep doing the stuff on the piece of paper, will you get where you want in a few years?

And on that thread… What do you want? Tough to end up there if you don’t know.

The point here isn’t to be hard on yourself. The contrary. The more garbage you spend time on now, the easier it’ll be to find that startup hour.

Everything on that page is a choice. Think of it like a gift from a past version of yourself that you can choose to accept or not. I’d imagine that nearly everything on that page is something you do solely because you did it the day before and the week before and the month before and the year before.

Life works like that. The tide takes us out a little farther each day without us realizing. And one day, without us noticing, we’re out to sea.

Now, jump over to a blank piece of paper.

Port over the stuff from your old life that you’d like to have in the new. Leave the stuff that doesn’t serve you any more. And, I realize a lot of this stuff might not seem like it’s a choice. You might have to do a certain thing for your job each day. But, try framing it as a choice. What if you didn’t do it? Would you need a new job? Or, more likely, could you figure out a way to get it off your plate without there being a big hubbub?

Now, add your startup to the page and drive home the swap. What it’s taking the place of. Write it out so you can see it:

Quote -

Before, I spend an hour or two hours or three hours a day on X. I won’t do that again this year. I’m now spending that time working on a startup.

For me, the swap would require me to drop something important to me - writing a book. I spend an hour plus a day on that right now and I’d have to stop.

Adding a startup into your life will likely create some pain. You’ll have to drop something you like.

Your old life will cost you your new one.

If you aren’t sure you want to start a startup, set it up as a sprint. For the next quarter, you’ll do an hour of startup work a day. on March 31, you’ll pick your head up and see if you enjoy it. See if you’d like to swap it back.

Now, I want to tack one more quick exercise on here. We made time for the startup, but I’d suggest making a budget for it, too. To actually pursue your startup you’ll want to spend a bit of money on it. Not a ton. But a few hundred dollars a month will go a long, long way - both for testing or development or coaching or a community, but also in reinforcing your commitment. Behaviors drive mindset.

The audit process here is the same. Grab your credit card bill to find the source of truth. Write down everything you spend money on and figure out what job it’s doing for you. Create a swap - make a budget of $200 or $600 or $800 by stopping spending money on other things less important.

Simple, but really important.

Remember, you’re a goldfish. You’re already the size of your tank. Remove to add.

On to idiot proofing our startup life, step 2.

Part 2: Plan for Luck

I had a full pod on this a while back that I’ll link, but I can’t have a podcast on what I’d do if I were starting a startup without at least a section on Luck. Because Luck would be a huge part of my strategy.

The idiot in me misunderstands what Luck is.

He thinks that luck is something that just happens out of the blue.

There was a story floating around NYC when I first moved there about an actor who got his big break while a scene was being filmed in the west village. As he walked by, the director jumped out from behind the camera and said YOU - you’re perfect! I need you in this shot. And the rest was history.

That’s what most of us think of as luck. And, hopefully, it just happens to us.

Except, as you probably figured out, that’s not what really happened to the actor.

It turns out that first, he moved to NYC. Because he lived in the midwest and knew that was going to make his path harder. Then, once he got there, every Sunday he’d look up filming permits that had been filed for the upcoming week - these are, apparently, public. He’d then figure out what movies or shows were being filmed through some internet sleuthing, and pick out something appropriate to wear - the movie where he got his, quote, break was set in the 50s, so he wore his most 50s style suit and a fedora.

He’d then go to the location and try to understand the scene and ask if they needed specific help. He’d then show up the next day, and the next, and ask the same question. On the day of his break, it turns out he’d first bought a pizza for the crew because craft services had been stuck in traffic. And, he was given a small part.

You can’t force the director to choose you, but you can make it way more likely that they do.

Which is what we call Luck Surface Area.

If I were starting a company in 2025, I’d recognize what type of luck I needed and dramatically increase my Luck Surface Area for it.

This usually works well if you back into it.

So, first pretend you’re doing a podcast interview in 5 years about your super successful company. When the interviewer asks… what was your big break? What’s a plausible story for it? What could happen that might have asymmetric upside? … what’s your answer?

When something great has happened to you in the past, what was the lucky break that led to it?

A huge driver of luck are relationships. Nearly every asymmetric leap my career or life has been due to someone helping me make that leap.

If I’m starting a business in an industry I don’t already have a big network in, well, I sure need one. And I need to not act like an annoying transparent leech while building the network.

Which means my luck approach would be to find a way to help the people I needed help from. There are lots of ways to do this. My favorite is through events that they’d actually want to attend. Another, possibly easier way is to find the things they hate to do but need to do, and make them far easier.

A Tacklebox founder trying to enter a new space spoke with a few people high up in this new industry and learned that they struggled getting a specific set of industry data each week. So, this person started a newsletter that aggregated and presented that data. All the top people in the industry joined it because they now didn’t have aggregate it themselves - a thing they hated. And he struck up relationships.

To wrap luck up, I’d make sure that of the 100 things that need to go right for a super lucky break, I’d orchestrated 99 of them.

I never want to have to rely on something lucky to happen for me to have good luck.

—

Part 3 - Focus on one person, and enormous value, at a time

We’ve talked about how we, as founders, are idiots. Now it’s time to talk about how big of idiots your customers will be.

Your customers won’t act rationally. If you build something that can dramatically help their business or their life and show it to them, they probably won’t buy it. If you offer it to them for free, they definitely won’t take it. If they do take it, they won’t use it. When you ask them if they used it, they’ll say yes, even though they didn’t. If they did actually use it and got some value, when you ask them to pay for it they won’t. Then, six months later, they’ll email you - asking if they can have that thing from six months before. Or, maybe they won’t. They’re irrational.

If I’m going to build a business in 2025, I simply cannot put up with all of that bullshit. I don’t have the time, financial or mental bandwidth for all the false starts.

There is only one way businesses grow, and if I were starting a business, I’d make sure I was backing into it.

Here it is.

Your first customer has an extremely painful problem. They are trying desperately to solve it but can’t. You come along and solve it for them. This leads to a very successful outcome - one that’s obvious and loud and easy to visualize and to talk about. So, your customer talks about it to other customers who have the same type of problem. And because the first customer was successful, a second customer gets jealous of that success. And they buy, too.

Your first customer needs to take a leap - they’ve got to take a chance on you. The next customers just have to be envious of the first one. One reliable human trait is that we make decisions based on envy, not greed.

You help your first customer get out of a hole, other customers see this success and want you to help them get out of a hole, too.

Startups only work when they find a customer in a hole that every other competing solution, for some reason or another, has missed or purposefully ignored. This is usually because the customer has specific traits that aren’t worth building for.

So, maybe there are a bunch of digital legal solutions for restaurants. But, for a local restaurant that’s just bought a food truck and plans to use it for corporate events, none of those digital solutions work, because of the mix of types of contracts. But this restaurant already bought the truck. They’re in a hole. They have no other viable choice and urgency to solve the problem.

So, if I were starting a company in 2025, I’d do it one customer at a time.

Which is sort of obvious, but not. Because you’ll be tempted to focus on something that can scale early on, and you’ll be tempted to say that a certain type of customer won’t lead to scale. That’s your inner idiot talking.

Pick one customer. Deliver an enormous amount of value to them by learning their idiosyncracies. Then, see if that value is so strong it attracts other customers. Or, if you can take that value and find other customers with the same idiosyncracies as the first.

A customer segment is a group of people or businesses that share unique idiosyncracies. Find that and you’ll have a business. Start with one customer at a time.

The depth of idiosyncracy knowledge becomes your asymmetric information. What you know that others don’t that leads to a much higher quality product.

And quality is what I’m after. And you should be, too.

—

Part 4 - A system to keep you from being an idiot

All of the stuff we’ve talked about is great, except for that fact that you and I are, as I’ve maybe mentioned, idiots.

All the value in life comes from doing things other people won’t.

So, while our plan - the first three steps - are definitely things most other people won’t do, we need a system to ensure that we do them.

This has a number of levers for me. I’ve already built a system for this sort of thing, but if I didn’t have one, here’s where I’d start.

First, a Sunday Check-in that kept everything in order.

At that Sunday Check-In I’d have four items.

1. Hooks. What hooks am I currently on? What am I nervous about that’s coming up in the next two weeks that will increase my luck surface area or access to potential customers? What have I promised to people that I need to deliver on?

This could look like a million things - hosting a webinar with 20 target customers or committing to sharing progress at an industry meetup or… something.

When you’re doing something on the side, hooks are critical. It’s easy to fall into habits of researching and emailing people you know and relative safety. But, everyone performs better under pressure. So you’ve got to create it. Each week I’d be sure there were things I was on the hook for - things I wasn’t sure I could deliver and would have to push to figure out. 2. Accountability. This is different than a hook - it’s a way to ensure you're staying honest with yourself, and, just as importantly, keeping others accountable. The second part might sound odd, but helping someone with their startup is often the best way to recognize the strategy you need for your own. Humans are terrible at introspection but great at judgment.

Specifically, I'd have three people I send weekly updates to. One who knows the space I'm working in who can call BS on anything I’m not pulling directly from customers and tell me what I’m missing. One who's also working on something similar and is at the same stage. And one who just wants me to succeed and will check that I'm not burning out. Probably my mom. Each week, they get a quick update - what I did, what I learned, what's next. The key is picking people who won't let you off the hook with vague updates or reasonable-sounding excuses. And if you want these groups to be bigger, or want the accountability to come from other means, great. It just needs to exist. 3. Coaching. The best athletes in the world have coaches. Not because the coaches are better athletes, but because someone who’s done this thing before is helpful. I'd find someone who's helped other people like me go from zero to one before. This might sound like a Tacklebox plug and I guess it is, but it’s also just why I built the company. This kind of knowledge and a consistent touch point thing is extremely helpful for a beginner. And coaches do some pushing - they put you on hooks.
4. The Ratchet. Each week needs to move you forward in a way you can't easily reverse. Maybe it's telling ten more people about what you're building. Maybe it's taking money from a customer. The point is to make reverting to your old life harder than pushing forward.

A system is designed to improve your worst days.

We have a bunch of other system tricks - email team at get tacklebox dot com if you’d be interested in a workshop on setting these up - but there’s one I’ve got to mention.

Transitions.

When you work on stuff for an hour a day, you simply cannot have the first 15-20 minutes be you trying to figure out where you left off. So, at the end of each hour-long session, spend 5 minutes describing to future you exactly where you are and exactly how to start. Five minutes saves 15 minutes the next day and it adds up.

Which brings us to… the end. And the most important thing you’ll need to do.

—

The End: Enthusiasm

Way back in my brief venture days, I remember a pitch from an entrepreneur that didn’t make a whole heck of a lot of sense.

The guy left the room and my boss, as he always did, looked to me and my colleague and asked what we thought. We both shook our heads no. The entrepreneur was great, but the business was really far away.

We assumed our boss would quickly say the same thing, but he hesitated.

“The idea is a mess,” he started, “but….man. Enthusiasm is worth 10 points of slope. And that guy has endless enthusiasm.”

We were silent because we didn’t really understand what he meant.

“When I asked what he’d done in the past month, did you hear the sheer number of things? He’d been to three conferences, run 25 on site customer tests, pitched 50 companies, organized an industry fireside chat.. I mean… you just can’t teach that type of enthusiasm.”

Enthusiasm, he would tell us later, was the amplifier. An endlessly enthusiastic person would add, in his words, 10 degrees of slope to their trajectory - meaning their progress would be steeper than their peers.

We didn’t invest in that founder immediately, but eventually they did and my boss always kicked himself for not doing it right when he saw the enthusiasm.

People want to work with and for enthusiastic people. We root for enthusiastic people to succeed. We read books about enthusiastic people and pay to see people try to do really hard things. Everyone loves someone who’s enthusiastic.

Some people are naturally more enthusiastic than others, but, unlike my boss, I think it can be learned and improved upon. If you act like someone who’s enthusiastic enough times, eventually you’ll be that.

And that’s it. My idiot-proof path to starting a business in 2025: 1) Make space for it, 2) Increase your Luck Surface Area, 3) Solve for one customer’s massive problem, 4) Build a system to keep you moving forward, and be… super enthusiastic.

Looking back it’s a bit… wishy washy? Right? Enthusiasm? Luck? But, Derrick asked what I’d do, and that is it. These types of things dramatically amplify all the work you’ll do. And, I’m confident that if I did them, I’d be in a great spot in 2025.

So, take a stab at this stuff. And when the episode for starting a company in 2026 comes out, I hope you’re in such a good place with your business that you don’t need it.

Even if you’re an idiot.