Idea to Startup: Mailbag! Beating Idea FOMO, The Best Stories for Founders, and Simple Startup Math

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This Episode

Today, we're digging into the mailbag to answer some common questions. We hit on how to actually commit to a startup idea when you aren't confident it'll work (featuring the Discipline + Strategy Levers), the most frequent advice I give (feat. Monkeys and Pedestals and Sell the Position), and a question on the startup decision - should you do a thing that'll take 10 years? 

Pod References

• Tacklebox (test your startup idea)

• No Whisper Ideas (weekly newsletter, sign up to get a Notion copy of the ERP Rubric)

• Good Strategy Bad Strategy

  00:30 Mailbag
  01:53 Question One: How to Commit to an Idea
  03:57 Discipline - Levers and Hooks
  05:42 Marathon Programs
  11:30 Strategy - Where to Run
  19:00 Smooth Jazz
  19:21 Question Two: The Key Stories
  20:22 Monkeys and Pedestals
  23:00 Sell the Position
  25:07 The $10K Prompt
  25:53 Question Three: How Old Will You Be?

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

Mailbag! Beating Idea FOMO, The Best Stories for Founders, and Simple Startup Math

Today, we’re doing a looong overdue mailbag. Three great questions, each one has come up a bunch of times before, and honestly each is good enough to deserve it’s own episode. Maybe some day.

Today’s lighter episode will also act like a bit of a palette cleanser - a lemon sorbet in podcast form - to the dense ERP Rubric episodes we just put out, which you should definitely listen to if you haven’t. Responses for those ranged from “I listened three times in a row and furiously took about 20 pages of notes” to Kevin in Minnesota who said, “honestly, that was a bit too much.” Thanks for reaching out.

In fairness, he did try to soften the blow by saying Idea to Startup was his favorite podcast and then ended with what I think was just a joke he thought I’d like, because out of no where he wrote “By the way, if yogurt is so cultured, how come I never see it at the museum?” Then signed his name with no other explanation.

Every fiber of my being wanted to reply “that joke was honestly a bit too much,” but it wasn’t and I couldn’t pretend it was. I loved it. You’re ok in my book, Kev.

Anyway we’re way off track already.

Let’s get into the emails. And, if you’ve got a question, send it in to team at get tacklebox dot come as always.

We’ll answer one question, do a little jazz, then answer the other two and get you out of here on time.

Question one - How to Commit to an Idea aka Idea FOMO

Our first email comes from Shale in Wisconsin. Shale writes -

“Hi,

I’m having trouble with something you talk about all the time: committing to an idea and sprinting on it for a set period of time.

I’ve got a few ideas, but I don’t really like one any more than the others. Honestly, I think they all could work. So, when I try to focus on one, I have this heavy feeling in my gut that I’m missing out on the others, like Idea FOMO. So I always wind up kind of doing a little bit of work on each idea each week and I don’t get anywhere.

I guess the headline is I feel like I’m doing lots of random things on a few different ideas and not getting anywhere. I don’t really know how to have a firm direction or North Star.

How do I commit and stick to an idea?”

—

Whoooeeee is this a loaded one. And it’s a question we get a ton. How do you make early progress when you aren’t confident you’re moving the right direction?

There are two ways to answer this question.

The first way is to assume that committing to an idea, in Shale’s words, is a discipline problem. Helping her work harder. The second is to assume that commitment is a strategy problem. Helping her… have one. Most founders assume they’re struggling with the first - discipline - when it’s almost always the second - strategy.

Since I don’t have any more color on why Shale - very cool name by the way - can’t commit, and I’m not super interested in finding out because I think both discipline and strategy are interesting and relevant and usually wound together tighter than a Twizzler, we’ll just hit em both. Discipline and Strategy. The two levers of a successful… anything.

Each has a story and a framework.

We’ll start with discipline, because it’s quicker and relatively straightforward-ish. Although, as usual, a few parts are counterintuitve and always trip people up. Let’s jump in.

—

Discipline

For Shale to be successful, she’ll need to put her head down and sprint on one idea for long enough to feel the weight of it. To feel the idea sand between her toes. To understand the nuances between customers and their specific problems, to form opinions on the way customers solve those problems now, to create relationships with people up and down the trust stack to see how hard customer acquisition will be, to find out where her customers hang out now, both digitally and physically - to know what wild success looks like for them and how they measure it, to see who motivates them - remember, people are motivated by envy not greed, and to find a way to reliably find 20 potential customers in a pinch.

In short, Shale needs depth. If you don’t show up to your idea with depth, often referred to as domain expertise, you’ve got to earn it through interactions with your customers. This will help you find a secret - the thing you know that everyone else doesn’t that anchors your business. Every business that works is based on a secret, and finding it takes time and digging and effort. It takes… discipline.

You never know when a secret will show up - we’ve had founders run 10 totally surface level customer interviews before the 11th one blew their mind. We recently had a founder run 50 customer interviews with coffee shop managers that went absolutely nowhere before they shadowed a manager for a day and uncovered an insight that’s allowed them to build a very useful service over the past six months.

Discipline helps you wade through the early days because you won’t have signs telling you you’re close to that a ha moment.

Discipline requires two things - levers and hooks.

And with that, let’s tell a story.

—

I’m training to run the NYC marathon again, and the plan is for this to be the last time. There’s an aggressive time in my head I want to beat, and when I beat it, I’ll move on to a hobby that doesn’t require me to fling a toddler and a baby on my wife for three hour training runs every weekend.

The past few weeks I’ve been trying to pick the right marathon training program, which feels a bit like trying to pick the “right” cereal at the grocery store. There are hundreds of options with totally superficial differences.

And then, a few days ago, one program leapt off the page at me.

Nearly every program I’d seen to this point talked about helping you hit a goal time, and their specific mix of long runs and short runs and recovery runs and fartleks - an actual thing - would be better than someone else’s mix those because of…whatever.

But this new program had a totally different focus. Here’s their H1:

“A marathon training program built to make sure you don’t get injured and miss the race”

Some context - I’ve trained for the NYC marathon three times but run it once. Late injuries stopped me twice. I was intrigued.

The site continued:

“There are two reasons people who train for marathons don’t run them.

1. They get injured during training and physically can’t run on race day

2. They get injured during training and, while they continue training after, they aren’t prepared on race day

Our program is built to make sure you don’t get hurt. Which means you’ll do every training run. Which means you’ll be prepared on race day. Which means you’ll run the race and hit your time. Marathon training is all about preventing injuries.”

This reminded me of one of my favorite quotes by Shane Parrish - “the shortest path is the one you don't abandon.”

If you’re hurt, you can’t train, which means you won’t reach your goals. Simple.

The program then dug in on each of its two foundational elements - avoiding injury and sticking to the program.

They cite numerous studies that show that running injuries happen in two scenarios - on long runs over an hour and a half, and during aggressive increases in weekly miles. Nearly every other program has at least one run each week that’s well over an hour and increases miles aggressively week over week. This program doesn’t.

Instead, they focus on what they call the foundation of endurance - v02 max. This is the measure of your body's ability to use oxygen during exercise. If you increase that, you’ll be able to run for longer. The best way to increase Vo2 max is varied types of exercise and pace. So, their plan has a bunch of short runs, interval training, and sprints. But, it also includes swimming and strength sessions. You run way fewer miles than any other program.

There are only three runs over two hours in the whole program, yet pages of reviews saying that, on race day, running for four hours wasn’t a problem.

This training approach - removing injury and focusing on V02 max - is the lever.

The other huge part of the program is the hook - the way to keep you on track.

When you join, you're added to a Slack group with all trainees for your race split into teams of 5. Each Sunday, everyone posts their weekly schedule. At midnight on a random day each week, one runner from each team gets tagged and must post their workout or admit they skipped. Teams earn a point for completed workouts and lose a point for skipped days. A live scoreboard tracks all teams, with members of the winning team winning a hoodie.

Is this a bit silly? Sure.

But, do you feel awful if your name comes up, you didn’t do your workout, and your team loses a point? Absolutely.

Lever and hook.

Lever - do the stuff that moves you forward in the smartest possible way

Hook - create external accountability to hold you to it

The shortest path is the one you don’t abandon.

So, for Shale, and potentially for you, the goal is to create levers and hooks.

Begin by working backwards, like the running program. Start with the reasons you - or most founders - won’t end up getting anywhere with a startup idea. The startup version of a running injury. Here are a few ideas for Shale:

1. Never talk to enough customers, so aren’t confident enough in the problem to not second guess it constantly, and aren’t externally motivated because they just live in their own heads

2. Don’t set clear validation milestones, so always working in circles with no visual progress as a motivator

3. Try to validate everything - customers, product, pricing, etc. all at once instead of picking one core assumption at a time and tackling it so that they get the momentum of a closed loop

4. Jump between ideas so there’s never any real momentum

5. Give up on a strategy when they’re 85% of the way towards something interesting, because the closer to something real you get the scarier this startup thing gets

Pick your version of the injury and write it down.

Now, architect a program for yourself that’s oriented around making sure that thing doesn’t happen.

So, if your injury is not speaking to customers, what’s a program of levers and a hook for speaking to customers? Maybe you need to send 10 cold emails each morning before you have coffee, which means you’ll start to build out the system to make those 10 emails better and more targeted and increase response rates, and the hook - maybe you host an event or sign up to a conference or buy a summer slot at a farmers market or join a startup program - something you can’t get out of.

Now, to the more interesting side of the problem and the more likely reason you aren’t able to move forward: Strategy.

—

Strategy

These two are inextricably tied because procrastination, or not committing to an idea, is very rarely a pure discipline problem like most founders assume. It’s usually an emotional problem.

Startups are likely very different from anything you’ve done in your life. Even if you’re the first employee at a startup, your path has been laid out. There are goals and existing projects and probably KPIs and OKRs. You’re told, even if broadly, what to do.

When it’s your own thing, as my dad used to say, you can always scrap everything and make a toaster. Meaning, literally everything is on the table. That’s terrifying.

If discipline is the ability to run fast, strategy is telling you where to run. Running fast is hard to do if you aren’t confident you’re going the right way.

That’s why so many founders tell me they wake up early, get to their desk, and can’t do…anything. Discipline without strategy is worthless.

Intertwined like a twizzler.

The way to increase discipline is to clarify your strategy.

Which brings up what maybe feels like an obvious question, but very much isn’t.

…what is a strategy? Especially for a company at this stage?

I think about strategy as using your unfair advantage to make it outrageously hard for someone else to compete with you. If you’re making a coffee machine with no plastic, and all the other coffee machines have plastic in them, if you lean fully into the no plastic thing it’s really hard for existing competition to react. Because if they pivot and make a no plastic machine, they’re undermining all their current plastic machines which make up all their sales. Strategy is when your move benefits you and hurts competition.

But, again, at this stage - that isn’t all that helpful because you might not know what that unfair advantage is just yet.

As with most things that are hard to pin down, I find it’s best to start with what strategy isn’t.

Richard Rumelt, in his wonderful book Good Strategy Bad Strategy, defines bad strategy in four ways:

1. Fluff - In Rumelts words, ”fluff is a form of gibberish masquerading as strategic concepts or arguments. It uses “Sunday words” - words inflated and unnecessarily abstruste, and apparently esoteric concepts to create the illusion of high level thinking.” Damn. Take that, fluff.

2. Next is the most important one. Failure to Face the Challenge. “Bad strategy fails to recognize or define the challenge. When you cannot define the challenge you cannot evaluate a strategy or improve it.” I’ve got a post-it with this written on it on my monitor.

3. Next is Mistaking Goals for Strategy. Many bad strategies are just statements of desire rather than plans for overcoming obstacles.

4. And finally, bad strategic objectives. A strategic objective is set by a leader as a means to an end. Strategic objectives are bad when they fail to address critical issues or when they are impractical.

I think bad strategy boils down to avoidance.

Doing everything you can except explicitly stating the challenge and choosing a path to attack it that plays to your strengths.

Which means Good Strategy is about choosing a path.

Rumelt helps you choose that path with a framework he calls the Strategy Kernel - made up of three parts: diagnosis, guiding policy, and coherent actions.

Here’s Rumelt on the parts of the Kernel:

First, Diagnosis:

A good diagnosis simplifies the often overwhelming complexity of reality by identifying certain aspects of the situation as critical.

Next, guiding policy:

This is an overall approach chosen to cope with or overcome the obstacles identified in the diagnosis. A set of coherent actions that are designed to carry out the guiding policy.

And finally, coherent actions:

These are steps that are coordinated with one another to work together in accomplishing the guiding policy.

This is a somewhat verbose way saying you identify the real obstacle, pick an overall approach to attack it that plays to your strengths, and break that approach down to bite sized bits.

Rumelt’s strategy approach is effective for your actual business as well as your approach for validating and developing hypotheses around business ideas. Here’s what the process might look like:

1. Diagnosis

You’ll need to clearly define your real challenge here. That challenge is, almost always, something like “I don’t have enough conviction about my idea and what I’m supposed to do next.”

Some questions that might help are things like, what’s the actual obstacle preventing progress? or what characteristics would an idea I was confident was worth pursuing have?

If you’ve got challenges with a specific idea, that works, too. Maybe you’re worried about selling to B2B or entering a market where you’ve got no experience. Great.

Next is Guiding Policy. How you’ll overcome the challenge.

If the big thing preventing your progress is speaking with customers, maybe you’ll choose an idea where you naturally have the most access to customers. If the problem is you aren’t sure customers feel real pain, maybe you choose a problem you’re personally dealing with. If it’s insecurity about your ability to build an impactful business, pick an idea where your background gives you a serious advantage - an idea you’ve been subconsciously preparing to start for years.

Finally, Coherent actions. Your sprint plan.

Translate your guiding policy into two week sprints.

Maybe weeks 1 and 2 are 15 customer interviews. Weeks 3 and 4 are intent tests. Weeks 5 and 6 are a concierge mvp with one customer. And then the last day of week 6 is blocked off for your decision- is this idea worth another 6 weeks. What hypotheses do you have, what customers are most excited, etc.

There needs to be an end date where you step back and reflect.

You also want a kill switch - a clear scenario where you’ll ditch an idea. Maybe it’s if 90% of people you interview don’t see this as a problem or if you can’t get in touch with 10 people in a week. This doesn’t necessarily mean to kill the idea altogether, but to adjust assumptions or customer and start back at week one.

If I tell you to hop on a treadmill and sprint, you’ll tell me no. If I tell you to hop on a treadmill and sprint for 3 minutes, you’ll be able to do it.

Strategy for founders is about making the best with the incomplete information you’ve got. Moving forward in a world of uncertainty. This usually requires extra structure, something founders don’t anticipate, often buck against, and definitely have never set up for themselves before.

What feels like a discipline problem is likely a strategy problem. So.

Define the problem.

Build a set of actions to go after it.

Create an end date.

Create kill criteria.

Then, use the levers and hooks of discipline to get it done.

So, Shale, run through this system, strategy then discipline, and get to it.

WHOOOOO boy was that longer than I’d thought it’d be, but hopefully it was useful.

Time to break. We’ll get to a few more questions after….. a little smooooooth jazz.

—

Question Two: The Key Stories

The first question was long and startup strategy focused. The second one will be shorter and.. also strategy and startup focused. The pod is called Idea to Startup - what’d you expect.

Here’s James in Florida:

“Hey!

I’ve listened to like 200 plus episodes of this podcast and you tell tons of stories and give tons of frameworks - what piece of advice do you give founders the most? What are the stories to remember?”

Thanks, James.

There are two. One is my story, one isn’t. We’ll start with the one that isn’t - I’ve heard it’s from a guy named Astro Teller but my old boss used to use it all the time, too.

It’s got a fair amount of strategy in it, and it is, without a doubt, the thing our best founders do and our worst founders struggle with.

Let’s say I told you that in two months, you needed to get a monkey to recite Hamlet on top of a pedestal. How much time would you spend working on the pedestal?

It seems like a silly question because, obviously, you wouldn’t spend any time at all on the pedestal. On the day you needed the monkey to recite Hamlet you’d probably find a pedestal or use a chair or something. The pedestal doesn’t matter. Literally anyone can get a pedestal.

But, like 95% of founders I meet are spending most of their time chiseling a pedestal out of stone. Because making a pedestal makes sense. We can wrap our arms around it. We can tell ourselves that, hey, the monkey is gonna need a pedestal eventually, so we might as well start there. And then we get into it and decide to make it nicer, or taller, or Carolina blue.

The pedestal dilemma is a dilemma of sequencing.

“I’ll have to do this eventually, so I might as well do it now” is logic that will work exceptionally well in 99% of your life but absolutely torpedo your chances of building a successful business. When you’re building a company, your runway will be finite. Either the time you can spend or the money you can spend or both.

If a business is made up of 1,000 components, 995 of them won’t have the potential to create any separation or contrast between you and a competitor. Five will. So, obviously, you should spend absolutely all of your time on those 5. Especially early on. Because what you’re testing in the early days is your hypothesis that one of those 5 is actually a driver of contrast. So, spend all your time on it and see.

When I meet with our founders at Tacklebox, it’s pretty common for me to say “you’re working on the pedestal.” People know what I’m talking about.

If you’re building an AI tool that’ll help restaurants source sustainable seafood, and you spend literally any time on the UX of the tool early on, you’re working on the pedestal. The only thing that matters is finding restaurants that currently struggle to source sustainable seafood. And not just struggle - their whole business is being held back. This is the top priority for them. If a restaurant doesn’t see this as a top priority, they won’t be your first customer. So, find someone would immediately see enormous value from sourcing sustainable seafood and understand their process. Then, and only then, find suppliers who can help solve that customers problem. And never, ever, write a thought piece about sustainable fishing practices and post it to linkedin. Anyone can do that. Not anyone can dig in with customers.

So, for your business, what’s the monkey and what’s the pedestal? What’s the hard thing other people won’t be able to do? Are you spending 99% of your time on that? Or are you making pedestals?

The second is my story, and the framework is called Sell the Position.

This one comes up every week.

I’ll link to my longer story in the show notes, but the short version is that the wealthiest guy in my town growing up got that way by, in his words, selling the position.

He worked at a hedge fund and had a few traders underneath him - he was small potatoes to start. Whenever any of his traders positions had gone sour, they’d show up in his office and try to convince him that it wasn’t time to sell yet - the company would turn it around.

For years, every time this happened, he’d make the decision in a vacuum. Did he believe that, say, Apple, would turn it around?

Then, one day, he changed his approach. Now, every time a trader showed up and said that, say, the 5 million they owned in Apple stock, which was currently down 10%, he told them to sell the position. The next morning, he’d give them the 5 million and tell them they could buy back Apple if they wanted, or they could buy… anything else.

99% of the time, they bought something else. The spell had been broken.

He rode this approach all the way to the top, eventually becoming CEO.

I’m pretty sure that most of the things you do each day - we do each day, I’m no exception - we do because we did them yesterday. If we were picking from all the infinite options available to us, we’d choose something else. But, we suffer from loss aversion. We value what we have 2x more than what we don’t. Until the spell is broken, until we don’t have the thing, we can’t see clearly.

Sell the Position works best for early stage founders outside of their business. Looking at their non-startup life and figuring out where they can free up space. Would they actively choose what they spend time on now from a buffet with lots of other options?

Monkeys and Pedestals, and Selling the Position. Those get used every week.

Oh - and I just thought of one more. This is more of a prompt, but I think it’s as helpful a prompt as you can have.

What would a customer pay you $10k for?

This works for businesses that sell $25 winter hats or $5 lattes or $500 software or $2500 consulting packages, though that’s probably the upper limit. If you charge more than $2,500, change that number to $50k or $100k. The number should feel strikingly high.

So, you’re selling $5 lattes. What would a customer pay you $10k for?

This is a great way to think about who really values what you make.

Good question, James.

On to the last one, because this episode is getting long.

—

This is from a founder we’ll leave nameless and stateless:

“Hey!

I’m 50. I know that isn’t old, but I’m thinking of starting a company and companies take time. If I started a company today, and it took 7-10 years, that means I’d be 60.

So… should I do it?”

I’ve gotten this type of email a ton, and the specific age has absolutely nothing to do with it.

I’ve had people say “I’m 25, which means I’ll be 35 and will have missed prime earning years,” or “I’m 40 and my kids are 3 and 5, and that means I’ll be 50 and miss their formative years,” and on and on.

People are scared of ten year commitments, which I get.

So, when people hit me with math, I answer with math. And it’s complicated, so bare with me.

If you’re 50, and you start a company that takes 10 years to be successful, by the time it is successful you’ll be 60.

But, if you’re 50 and you don’t start a company that takes 10 years to be successful, after those 10 years of not working on a company, how old will you be?

My math tells me you’ll still be 60. You just won’t have built a company.

And I totally understand that this question is about opportunity cost and energy levels and a bunch of other feelings under the surface.

But I think it comes down to a regret calculation. If you’ll regret not starting a company, you should go for it. Moving purposefully towards something creates all sorts of positive benefits, even if they aren’t directly related to your startup. And, whatever you think is going to happen during those 10 years isn’t a guarantee, either. Just because you don’t start a startup doesn’t mean you’ll have time and money or whatever else. It only guarantees you won’t have a startup.

Piece of cake. Trying things is always better than not trying things.

—

Ok! Got a bit long, but hopefully it was helpful. And there are a bunch of other questions here I wanted to hit. Maybe I’ll do another one in a few weeks.

And, obviously, if you want to ask me these questions in person and build your startup with us, head to gettacklebox dot com and check out our programs.

Have a great week!

This was the idea to startup podcast brought to you by tacklebox. I kind of already did the ad in the last line, so… just some jazz…