How to Choose The Right Quest

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• The Future Story of the Current Setback

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

Today’s episode is about a hard lesson every entrepreneur eventually gets smacked in the face with: every startup is equally hard.

No startup ideas are “easier” or “more manageable” than others. There are certainly things you can do to make it more likely you succeed, but every problem worth solving will be, by definition, hard - otherwise it would’ve been solved already.

This means the “quest” you choose needs to be a worthy one. Because it’ll require a ton of sacrifice.

We talk through what a good quest looks like through three key lenses:

1. Visualizing the moment of success: Can you picture the exact moment when your product lifts a massive weight off your customer's shoulders? The intensity of their reaction is directly proportional to the importance of your quest.

2. Avoiding the 90 Yard Mistake: It's tempting to target customers who need the most help, but sometimes the best strategy is to focus on those who are just a few steps away from success. We'll discuss why this approach can lead to faster growth and better outcomes.

3. Zooming in on the unit economics - people: No matter how technical or complex your solution, at its core, every business is about serving people. We'll explore why keeping this human element front and center is crucial for tackling big problems.

Pod References

• Tacklebox

• Idea to Startup Newsletter

• Idea to Startup Bot

• Choose Good Quests

Timestamps:

00:24 Intro - Becoming a Parent
05:21 The Hard Stuff Is Easier
07:50 Smooth Jazz
08:16 How to Identify a Worthy Quest
12:44 The 90 Yard Mistake
19:06 How to Get Started - People & Success
21:40 How to Not Be Intimidated
24:16 Choose Worthy Quests

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

Becoming a parent forces you to think about stuff.

I remember looking at the little guy on our first day back at home after the hospital and thinking…man… this kid is … so small. He’s too small. He’s gotta double in size at least once or twice before anyone takes him seriously. Just can’t be weighing 7 pounds. That’s not enough pounds.

And then I slept a bit for the first time in a week and when I woke up I looked at my kid and thought some other, far more coherent things.

Interestingly, and possibly selfishly, most of those thoughts were about myself. Kids, even week old babies, make for great mirrors.

I realized my kid will - hopefully- graduate high school in 2039. He’ll be middle aged in the 2060s and 2070s. As that math washed over me like a confusing wave I thought… what am I … doing? How am I spending my time? Really, really good time. Time in my prime with a family I love and so many people I care about nearby physically or digitally. Time I can go do or try or build… anything. The only time I’ve got.

Am I doing the right stuff?

Surprisingly or maybe not surprisingly, lots of people join Tacklebox shortly after they have a kid or lose their job or have some other big shakeup in their life. This might seem counterintuitive - you’d think shakeups would lead to a decrease in risk tolerance. It certainly leads to a decrease in things like time and disposable income.

But there’s a stronger force at play. As I said, kids and shakeups are mirrors. And most humans will avoid mirrors as long as they physically can but when one is thrust in front of them they are, sometimes, willing to make changes. The mirror helps them realize that most of the stuff they do each day is a result of inertia, not a conscious choice they’d actively make amongst lots of other options.

Things like babies give shape to opportunity cost - usually hidden but suddenly painfully obvious. Each day becomes a clear swap.

I could be home with my kid watching him learn how to roll over and laugh and aggressively grab at my beard, but instead I’m at work doing this thing. And this thing seemed fine…until the other option got so much better.

It reminds me a bit of a Tyler Childers lyric - up til now there ain’t been nothing that I couldn’t leave behind. Yeah, I’m a country guy, too. It’s not just 90s and 2000s pop. Though it mostly is.

And since I, like just about everyone, needs to work to keep a roof over my head, I likely can’t choose to hang out all day with the little guy. So it becomes more important that the thing I’m leaving him for is worth leaving him for.

If you’ve been a listener of the pod for a while, you might realize something else happening here that causes the behavior change at a life event. This is a classic inflection point.

Behavior change is clustered.

When you have a kid there are seven thousand other decisions you need to make, things you need to buy, changes you’ll have to come to grips with. You’ve got decision making inertia so you make more decisions. When you get laid off, when you move or buy a house or get married - the flood gates for new behaviors are opened and the friction for trying something new decreases dramatically.

When you’re building for a customer, the best way to get early traction is to somehow latch your product on to existing behavior change initiated by someone or something else big and meaningful. Creating the momentum for behavior change is hard. Riding existing momentum is .. less hard. So, find it.

Which brings us…to Quests.

I read an article recently called Choose Good Quests. I’ll pop it in the show notes - it’s fine - mostly highlighting that our best and brightest are doing safe things, which I tend to agree with to a point. The article then says it’s a smart and capable person’s responsibility to devote their lives to problems that help humanity which I disagree with but understand the perspective.

Anyway, the thing I liked most about the article was the title. I just can’t get enough of framing your life’s work as a Quest. It’s perfect. Quests are big and hard and worthwhile and kind of playful and definitely mythic. They matter and they’re interesting. And that’s what I find most people who have been shown a mirror want - An interesting, meningful quest. Something they can devote their lives to that changes them, and the world, for the better.

Last week, in our Seth Godin interview - still can’t believe that actually happened - he talked about this when I asked what words he’d put on a billboard people had to drive past each day - his choice was… does it matter.

I loved this and it also immediately reminded me of another conversation I’d had years before with Jeff Engler, the founder of a company called Wright Electric that makes 100+ passenger electric planes - something he started from scratch nearly a decade ago.

Jeff and I met in a coffee shop in soho and I remember asking him how he wrapped his head around a problem so big and hairy and hard and, in the parlance of a good friend of the pod, wicked. He had to build an electric airplane, sure - something that’d never been done at that size. But also, he had to compete with boeing and, if he was building an airline - he was - delta and american and on and on. Then there’s the safety stuff and the pilots and regulations..

“Well,” Jeff cut me off. “I’ve started a few companies now, and I’ve learned that they’re all pretty much equally hard. The unimportant, iterative company will be just as hard to succeed with as the hardest company you can think of. No startup is easy. So, you might as well try to do something that matters.”

“And,” he continued. “In a way, the hard stuff is actually easier. Doing hard stuff that matters acts as a giant magnet for the types of people that are capable of and willing to go after hard stuff that matters. People want to talk about solving important problems. People want to help. They want to fund. They want to try. The less important, less complex stuff is harder, in a weird way. Because no one really talented is interested in helping you do something that, even if you succeed, won’t really matter all that much.”

I remember him thinking for a second, then finishing - “you’ll be in a better place if you try something big and fail than if you try something iterative and succeed. Because the iterative thing is guaranteed to not matter. The big thing, even if it fails, still might. Plus, you gotta look yourself in the mirror.”

When you go to the wright electric website, in big letters, you’re greeted by this statement: By 2040, Wright will eliminate carbon emissions from all flights under 800 miles.

That’s a quest.

Today, we’re going to talk about quests. How to identify quests that matter, how to wrap your arms around the big, hairy, wicked problems those quests will pose, how to get started on something so big and how to avoid being intimidated.

We’ve been lucky to have a handful of founders come through the program over the years and go after the big stuff. We’ll use some of them to talk through the approach.

And we’ll do it all… after… a little smooth jazz. Which I considered swapping for the lord of the rings soundtrack today, what with the quest talk and all. There’s no better quest soundtrack than lord of the rings. But I think we’re big enough now that someone might notice and certainly still small enough that if we got sued our quest here would be over. So. Just the jazz today… not a bad silver medal.

How to Identify a worthy quest - Visualize the moment of success

This is a tough place to begin our quest for quests because a worthy quest will always be subjective, and I think of this first section as more of a jumping off point into the far more relevant next sections - how to get started on something ambitious and how to avoid being intimidated and make yourself a force in a new space.

By the way, if you’re playing a drinking game where you take a shot of yager every time I say Quest, please stop. It’s not going to end well.

Anyway, there’s one important point I’ll start with here.

I think about good quests in terms of moments. Specifically, the exact moment you’ll create with your first customers when you lift this massive weight off their shoulders.

I like zooming in on that moment and thinking about the reaction the customer will have. Are they relieved, energized, excited to tell the story. What new options do they have? What can they do now?

Think about it for your problem - can you picture someone? How do they feel?

Zooming in on the impact and importance of that moment will give you a sense of the impact and importance of the quest.

The intensity of the reaction dances in lockstep with the wickedness of the problem.

Here’s an example.

I’ve been working on the chronic pain idea - if you haven’t listened to the past handful of episodes before Seth, there’s a huge portion of the population that suffers from debilitating chronic pain. In my interviews, I’ve met some people who kicked chronic pain - though this is the minority. Nearly all of these people had some combination of treatments, lifestyle changes, and extreme accountability, but each of them reached a place where they hadn’t thought about the pain in over a year.

When they told me that, I asked about the moment that they realized the pain was gone.

Each corrected me - saying that that wasn’t the moment they remember. That wasn’t a moment at all. The moment was when they were once again able to do something they used to love that had been taken away from them. For each person, this was different. One told me they went for a 5 mile run for the first time in 6 years and when he finished pain free, they collapsed in tears.

Another told me they finished a long day at work where they wrote for seven hours - they were a writer - and popped up from the desk and went and had dinner with their kids and were fully present with no pain for the first time in years. After dinner, this person excused herself and - yep - cried.

The side effect of a worthwhile quest is emotion. If you help people get over a serious hump- help them be successful, there should be a reaction.

This moment becomes a marker for us. The thing we work backwards from.

This might sound silly, but for lots of hard problems, defining success is hard. What’s it look like when you win?

This doesn’t mean you need to know the product right away - that’ll change. The key is understanding the impact you’ll have if you’re successful, and since I think of everything in terms of people I think of the impact in terms of the individual people that’ll be affected.

The throughline for everything we’ll talk about today is one I didn’t realize when I started writing this but now I’m supremely confident in: The important quests, the ones worth going on, also make the best fundamental businesses and give you the best chance at success, if you pursue them right.

If you can’t think of the specific emotion your customer will have in the moment you solve this big problem for them… there’s an issue.

That issue might be that you see this as an opportunity to help yourself rather than the customer. Maybe you see the potential for a marketplace where you take a small transaction fee and you love the business model and potential. Maybe you are jumping on a trend or being opportunistic or seeking out a b2b saas product or AI tool because that seems like the fastest way to get a venture check.

This exercise - visualizing your customer at the moment of success - will weed out the ideas that were secretely about you. Don’t feel bad - we all do this. But, customers will sniff it out a metric mile away and you’ll have no shot.

Any successful company is successful because they create the conditions for their customer, particularly their first customers, to be wildly successful.

make sure you know those mom

Drink.

How to wrap your arms around something overwhelming and avoid the 90 Yard Mistake

Now that we’ve agreed you’re going to do something that really matters for your first set of customers, we’ve got to deal with the fact that you’re trying to do something that really matters. That’s intimidating and, usually, overwhelming - because the stuff that really matters that hasn’t been solved yet is usually the hardest stuff. Lots of entrepreneurs default to solving problems with limited upside and downside because they subconsciously don’t want to be on the hook. Don’t let that be you.

Hopefully you’e got an unfair advantage here, and we’ve got tons of episodes on that. Hopefully the idea you go after is one that sits at the center of your founder venn diagram of unique skills, networks, and knowledgebases. Hopefully it’s one you’ve been subconsciously preparing to go after for years.

But maybe it’s not.

Either way, there’s one massive mistake people make here. I call it the 90 Yard Mistake.

The 90 Yard Mistake happens most with empathetic entrepreneurs driven endlessly by the big problem. I’ve been running into it with my chronic pain idea - here’s what it looks like.

Last week, I interviewed 5 or 6 people suffering from chronic pain. One messaged before, saying that while he’d like to do a Zoom call, his head hurts so bad he couldn’t. He isn’t able to turn the lights on bright enough that I’d be able to see him.

As we talked, I realized how much pain he was really in. He’d been injured 6 months earlier in a car accident and had lingering, brutal headaches. He hadn’t been able to go back to work yet. He knows he has a long road ahead, and he’s motivated to travel it. I’m confident he’ll get back to his old self.

Another call was with a woman who’d been injured in a surfing accident 2 years ago. She’d gone through a rough 6 month stretch directly after the accident, then found a clinic that was helpful. She’d kicked 90% of the chronic pain, but had one bump in the road left- working at a computer 9 hours a day. By hour 3, she was uncomfortable, by hour 5 she usually needed to take advil, and the last 45 minutes of the day were nearly unbearable. She was able to run and surf and do all the things she used to do, but the final boss of this injury was a 9 hour workday at a computer without serious pain by the end. She couldn’t solve it despite endless attempts at ergonomics and daily stretches.

I visualize most customers I find like they’re on a football field, with the end zone being them reaching their goals. The moment of success we talked about earlier. And for our beloved Brits - we’ve got a ton of you listening apparently - I’m talking American football.

If I plot these two customers on that field, one is on their own 10 yard line - a full 90 yards away from the end zone. The other is close - maybe 5 yards away from the end zone.

The mistake entrepreneurs make here is thinking that since they’re trying to do this meaningful thing, the product they should build should be for the customers that need the most help.

The first customer I spoke with, the one in so much pain they can’t turn on the lights - we can help them a ton. During all this customer discovery and research I’ve done I’ve found a bunch of doctors and clinics and practices this guy can and should try. We could move him 30, 40, 50, 60 metaphorical yards, hitting big milestones along the way. But even if we moved this person 60 yards, they’re still 30 away from the goal.

The second customer, we’d only push her those 5 yards. But that’s all we’d need to solve a serious problem for her - to get her into the endzone, kicking chronic pain altogether.

This section is about wrapping our arms around a hard problem, and the way to do that is to make the hard problem easier. To find the people who only need a hand getting off the bus - not the people who need help from square one of booking travel plans.

As we said, startups are about creating the conditions for success, so that the customers you help be successful can tell other people about what you did for them. So that adjacent potential customers look at the people you’ve helped and are jealous of their success. People make decisions based on envy, not greed.

So, we need to stack the deck and make sure our first customers are wildly, publicly successful.

Our products natural growth then would be from the people who have 5 yards to go to the people who have 10, then 15, then 20, and so on. As we move further away from the endzone we’d likely need to add new levels of service as the problems would expand and diversify, but this growth flow keeps the product as small and manageable as possible through that growth.

If we targeted the person 90 yards away, we’d have to build out all sorts of products and services to reach a goal that might be two years away and might be unlikely. It’s a feedback loop and product scope a business likely can’t survive.

The other option, if we really want to work with the customer 90 yards away, is to change where the endzone is. So, we might say “we’re going to get you to the place where you can have the lights on during the day.” If that success is uniform, compelling to similar customers, and something you can build a business around - great. But, “success” needs to be clear and obvious if it’s going to be shareable. Be careful about that.

If you’re the type of entrepreneur who wants to go after big problems you’ll be the type of entrepreneur who naturally tries to help the person 90 yards from the end zone. Make sure you either shift the field so that they’re close to some goal that’s meaningful and can anchor a business, or realize that the best viable path to them is to start with people who have bleeding neck problems but are close to solving them with your help.

I think about this a bit like storytelling. Some of the best writing advice I ever got was to start with the thing that mattered - the crucial point of the story - when your aunt spilled the casserole or your uncle got eaten by a lion - and roll back from there only far enough to set the most critical parts of the story up. The further back you move from the moment the story is about, the more skill you need as a storyteller to grab and keep attention and the less likely the story will land.

Startups are the same way. The further back you move from the moment, the harder you make everything for yourself.

How to get started - people + success

We’ve talked about people a lot this episode but the way to get started is to remember that everything is about people. The domain is always people and you need to be an expert in setting them up for success.

When you are solving huge problems, like building electric planes, it’s easy to forget about people. but it’s always the people that matter - the ones who benefit the most from what you’re making.

A few years ago someone came into Tacklebox with a ghost kitchen idea. The founder was super talented - they’d done ops and logistics at both Uber and Lyft. They thought that if they had a few strategically placed kitchens and a fleet of trucks with ovens to keep stuff warm, they could revolutionize delivery.

I thought the idea was interesting. So, I called in my resident chef expert, a Tacklebox alum.

“Yeah, you’ll never get any good food with the ghost kitchen concept over any period of time.”

“Why” I asked - “The trucks keep stuff warm, and you can even finish the dished in the truck if you”

he cut me off.

“it has nothing to do with the trucks, the trucks are fine. Why do chefs cook?”

I was quiet, assuming it was rhetorical, then realized it wasn’t and blurted “because they like food?”

“No.” He said flatly. “we cook because we like cooking for people. When you tell your waiter that you loved a dish and they relay it to the chef, or when you peek out and see people enjoying your food or you think up a recipe as a special and it sells out or when a cook from a restaurant nearby comes over and you make them something and they like it so much they’re jealous - that’s why we cook. No good chef will ever sit in a room without windows and customers and make nameless food for faceless customers.”

Thinking about people forces you to put this giant, seemingly unwieldy quest into clear terms. You’re helping this person solve this problem because it’s important to them that it happens. And, all the other people impacted feel it in this way.

This requires interviews and ethnographic research and choosing - all the good stuff. It helps you break down the big, scary thing into people - who are much less scary and much easier to build specific stuff for.

People make big ideas approachable. Which leads us into our last section.

How to Not Be Intimidated

If you’re choosing something hard and worth doing, there will be lots of people in that space that are good at stuff that’s hard and worth doing. That’s intimidating, often to the point of making these ideas non-starters.

Don’t let that happen.

There are two ways to not be intimidated. One’s silly and ones a tactic. We’ll start silly.

1. First, everyone is just a person, just like you. They were all kids, like you were. And the gap between you and them is way smaller than you think and way more manageable. The whole human population is in a pretty tight competency band.

The best thing to do is target why you’re insecure and build a plan to attack it.

If, say, you’ve got an idea in the solar power space because you think it’s a meaningful quest for the planet - and I agree - but you haven’t been in the space for the past 10 years and you don’t have a network… cool. Let’s build one. First, get someone off Fiverr to create a list of the top 250 thought leaders in the space. People who write about, work in, and invest in the top solar companies. Send them cold emails seeing if they’re up for a coffee. Have that same person compile a list of all the solar events, newsletters, conferences, and happy hours. Add one or two even each week, have 5 to 10 coffees or calls each week, and in 6 months you’ll be known in the industry.

Whatever you’re intimidated about, attack it with purpose and strategy. No one does this, but it doesn’t mean you can’t. It’ll work. And, as always, put your ass where your heart is.

That was actually pretty tactical. So I guess both are tactical. On to number two.

2. Push on the first principles of the industry and the problem and the customer. This is a great way to break the impenetrable facade of an industry.

Most first principles in an industry exist because they were easy at some point and then it was hard to change. Here’s an example - The Myth of the hour-long therapy appointment. WHy are therapy appointments all an hour? Is it because therapists need that hour? Is it because patients need an hour? Of course not. It’s because therapists bill by the hour and when there weren’t virtual appointments it didn’t make sense to drive to the therapist for less than an hour. It makes things simple.

What if therapy appointments were 7 minutes long and every day?

Getting familiar with a space is a combination of knowledge, network, and secrets. Lots of times, pushing on the first principles of the industry lead to secrets. you can build systems for the rest.

The End: Choose Worthy Quests

You can do just about anything you’d like. Some things might take some time and pressure and maybe a partner or two - and everything’s going to take luck - but what you work on is a choice. Whatever you’re doing now is likely due to, in some part, inertia.

Take a look in a mirror whether you’ve had a kid or not and see if it’s worth your time. We don’t have much.

And, maybe most importantly, I’ve found that our best, happiest, and most successful entrepreneurs - the ones that grow with their businesses and have just exploded as people - those are the ones that choose the things that seemed the hardest and least likely at the start.

The five or seven or ten or thirty year quests solving important stuff other people are scared to touch.

Hard, important things inspire and attract. They force you to focus and your business is better for it. And when they work - they matter.

And if you’re on a great quest, it softens the blow of recording a podcast while you hear your son giggle and squeal upstairs. The tradeoff maybe isn’t worth it, but at least it’s one I’d actively choose - a worthy quest … (drink).

And with that, time to go upstairs and get in on those laughs.

This was the idea to startup podcast brought to you by tacklebox. If you’ve got a startup idea and a fulltime job, head to gettacklebox.com and apply. We’ll help you throughu the early days and get back to you on your app in 72 hours.

Have a great week.