How to Engineer Luck

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• The Overpay Test

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

I said this last week, but this week is one of my favorite episodes of all-time.

There are a few ideas that some of our founders have grabbed and run with in here, the biggest of which is this:

Humans dramatically overestimate downside and underestimate upside.

It’s a core trait, and, if you can push back against it, you’ll create a ton of contrast with how every one of your competitors approaches their business.

I’m working on a Luck Workshop - something that’ll keep you accountable to the time you allocate to luck. I’ll push it here when it’s done.

Here are some other nerdy things that inspired the pod but didn’t explicitly make it in:

• 🧠 Dunbar's Multiplier Effect: While Dunbar's number suggests we can maintain ~150 relationships, research shows each "luck gatekeeper" effectively multiplies your network by 3-4x through what network scientists call "weak tie activation." This is why focusing on a few key relationships rather than broad networking can create exponentially more lucky moments.

• 🎯 The Information Asymmetry Principle: There's some game theory behind why reducing friction for gatekeepers works so well. It's related to what economists call "screening equilibrium" - when you provide pre-packaged value (like our article framework), you signal both competence and understanding of their incentives, making cooperation the dominant strategy.

• 🧪 Proximity's Paradox: Research on innovation clusters shows that physical proximity increases serendipitous encounters logarithmically. But here's the weird part - digital proximity (regular meaningful online interaction) shows almost identical patterns. This suggests you can engineer "digital proximity" to luck gatekeepers through consistent, valuable micro-interactions.

• 🌊 The Availability Cascade: Behavioral economists have found that people dramatically overweight easily recalled examples when making decisions. This explains why targeting specific "luck moments" (like our press hit) works better than broad exposure - one vivid success creates a self-reinforcing cycle of attention and opportunity.

And that’ll do it 🤓 

Have a great week!

Pod References

• Tacklebox Workshops

• Graham Weaver

Timestamps
00:30 How to get lucky
03:11 Story Time: Getting Press for 3Degrees
11:06 XLR8dev.com
12:32 The Five Types of Luck
15:05 Luck for a Date Planning Service
16:25 Luck Gatekeepers
17:45 Luck Routines and Luck Budget

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

Today, we’re going to help you get luckier as an entrepreneur.

I have to specify as an entrepreneur, as the original script said today we’re going to help you get lucky and when I tossed it into ChatGPT to proofread it strongly suggested I add “as an entrepreneur,” to make sure no one thought this was, quote, relationship advice. It appears ChatGPT has found out about 1990s slang and thought I was buggin. As if.

Anyway, today we’ll be helping you get lucy in a totally non-sexual, entirely entrepreneurial way.

The good thing about helping you get luckier is that while it seems totally different than if I said I’d help you get fitter or healthier or better at content marketing, it’s not. Luck is as tangible as all of those things.

You’ve heard people talk about how important luck is for entrepreneurs and you’ve probably just thought, well, I hope that happens to me.

And I won’t blame you for that. Let me channel my inner high school class president giving a graduation speech for a second so we can acknowledge how people are taught to think of luck: Websters dictionary defines luck as success or failure brought by chance rather than ones own actions.

Chance, not actions.

But for entrepreneurs, that’s not what luck is at all. So even using the word luck is misguiding.

Luck is tangible. We can optimize for it, plan for it, and nearly guarantee it, to some degree. Luck is maybe 90% action, 10% chance, when you do it right. Create the 90/10 scenario a bunch and you’re going to get, quote, lucky.

Practically, I think about luck as an amplifier - an exponent that sits outside the parenthesis that hold what you do each day. That exponent isn’t guaranteed and is variable in size. It can dramatically amplify your work or, sometimes, do nothing to it. But it’ll definitely do nothing if you don’t strategize for it.

So, today, we’ll help you optimize for luck. We’ll sort out Luck Gatekeepers, Luck Hooks, Luck Routines, and we’ll build out your Luck Budget.

And we’ll start by visualizing luck. Making it tangible. And the best way to do that is to take an event that seems lucky, and work backwards to pinpoint what was actually lucky about it, to figure out what luck actually is.

So, lean back in your office chair and pretend to work on an excel doc when your boss walks by and let me tell you a story about Brian getting lucky - not like that, chatGPT, ya freak - in the entrepreneurial way. And to do that, we’ll hop in a mini-time machine, and go all the way back to 2012.

<Time machine sound>

To set the scene, a quick google tells me that the biggest things that happened in 2012 included a government shut down, a total solar eclipse in parts of Australia, and the act of filibustering becoming, quote, popular again. Riveting stuff.

Aside from all that intrigue, I was working on 3Degrees, the business that preceded Find Your Lobster, my Facebook driven dating app.

The general idea for 3Degrees was that the job market stunk and lots of people were unemployed. I’d just left business school, and a lot of my classmates hadn’t gotten the jobs they’d been promised when applying to business school because those jobs no longer existed. And the students looking for them were a bit…frantic.

To find opportunities, they scoured their friends’ Facebook and Linkedin accounts to try and piece together some sort of connection to a possibly vacant job, like detectives trying to solve a murder on one of those giant corkboards with all the red string.

I got countless emails that said something like - hey, you went to high school with Jeremy, who went to college with Erika, who now works at Deloitte and I think they have a role on their tech strategy team. Could you ask Jeremy to intro me to Erika?

So, I built 3degrees, which synced up facebook and linkedin and public job boards to make this sort of expert level snooping easier.

For those scoring at home, this solved both a teleporter and a hole problem, the two best types of problems for entrepreneurs to solve. A hole problem in that the customer was literally at the bottom of a well. Absolutely nothing mattered until they got a job. They were open to try anything. And a teleporter problem, in that their current process required them to spend hours searching for connections and writing emails. We removed that step entirely for them. Our bus picked them before the connection searching and dropped them off after it. The bones of the idea were sound.

But, to get it going, we needed enough concentrated users to get the network effects churning. I figured the best way was press, which felt like some combo of luck and a PR agent, so I hired one.

This person took a shocking percentage of my funding to do a shockingly small amount of work. She emailed the pitch that I’d put together to hundreds of her contacts at various tech places, wrote a few articles on PR newswire - which sounds fancy until you realize anyone can post there -and at the end of our engagement, after zero articles from journalists and about 25 total pageviews from the PR newswire stuff, she sent me an email asking for final payment and saying that, unfortunately, we didn’t get…quote… lucky.

I told a friend of mine this story, who introduced me to one of their friend’s - a journalist at a tech outlet. She said she got hundreds of those annoying PR pitches every day and had set up a filter to automatically delete them all. She hadn’t looked at one in years.

Sweet.

So, how do I get an article written about the business, I asked?

Easy, she said. Make it harder for a journalist to not write the story than to write it.

This seemed a little Yoda-y, but she continued.

Forget about pitching a thousand outlets, she said, what are the 10 that, if you were featured, would make a serious impact? We’re talking thousands of the right new users.

It was tempting to pick tech places that wrote about startups, but MBAs didn’t read those. So, we found the stuff MBAs read and made a list.

Now, she said, find the last 10 posts in those outlets on new startups.

I did some digging and found that this type of feature was… very rare. Actually, only two of the outlets had written about new startups recently, and it was in a monthly article that had a roundup of a number of startups they’d, quote, noticed doing something unique.

Ok, my new friends said, so when the author is writing those stories, what do you think they’re hoping to get from them?

I remember nodding because it was a smart question, but apparently it wasn’t rhetorical. She went on;

Dig into the past articles and figure it out - what are the titles? What’s in the first paragraph? When the author posted the story to social media, what was their caption? Did the post get traction? Was the article successful?

She paused and asked a more pointed question:

What do you think a successful article looks like?

I didn’t know.

Well, you can’t pitch someone an idea if you don’t know what them being successful with that idea would look like.

The answer, she said, was reach. An article is written because the author thinks a lot of people will read it and share it.

She then listed out why readers share an article, which is the biggest indicator of that article’s reach:

• If they’re controversial, which wouldn’t likely be useful for us. But the next three would:

• If they’re counter-intuitive to public opinion - meaning everyone always thought X, but X is actually not true

• If they’re helpful - people share generic, broadly helpful things on social channels and specific helpful things directly to the person who’d benefit

• And if they create emotion

So, she said, if we convince an author that the article you’re suggesting is a no brainer for a few of these, they’ll believe it can spread and are more likely to pursue it.

Great.

Now, there’s one more variable, she said.

How hard it is to write. That’s the friction that exists and keeps them from helping you. We needed to remove that by pitching the idea in a way that’s already done 90% of the work for publishing an article.

So, we wrote emails to the two outlets that wrote about new startups. We included three potential titles for the article, highlighting something counterintuitive - “this startup believes you’ve already got a warm intro to your dream job, you just need to use it” something specifically helpful, “if you’ve got a friend looking for a job, this startup will help them get a foot in the door,” and something emotional, “Your friends and family want to help you get a job - this startup lets them.”

We then drafted out the three questions that would anchor the article. These were based on the sharing archetype, too. We even suggested a few other startups that could be featured alongside us, in case the article became one with a hiring theme.

Turning our email into a post that got traction was, in the words of my new friend, unbelievably simple.

The traditional view of luck is, man it’d sure be lucky if a writer at a tech publication somehow noticed my company, decided to write something about it, and lots of people read it and shared it.

The real view of luck understands what luck is: It’s when someone who can help you grow decides to.

If you find the friction for that moment and eliminate it, and create enormous thrust for the person to help, you dramatically increase the chance that the lucky thing happens.

Two weeks later, one of the two people we wrote to ran an article with the exact headline we’d suggested. The body of the article was the three questions we’d written with. The answers were the ones we’d drafted, barely edited. And a few of the other startups we’d suggested to feature, were featured. It was easier to write that article than to not write it.

We got hundreds of downloads day one and over a thousand within the week.

And I remember a friend who was also working on a startup texting me - “dude, you’re so lucky they wrote about you!”

Sure. Sorta.

Luck has a formula, and we’ll jump deeper into it today, with luck gatekeepers, hooks, and finally, your luck budget - the counterintuitive way to spend your time and money on luck.

And we’ll do it all, after… a quick word from our new friends at XLR8 Dev.

The Five Types of Luck and Your Luck Story

Press is a pretty obvious type of luck. That’s why I used it for the example - it’s easy to see how thinking critically about press could give you a better shot at getting it.

The trickier part of luck is figuring out what it is you’re actually looking for. What does luck look like?

If I ask you what’s the luckiest thing that could happen for your startup right now, what would you say?

I’ve found the best way to wrap your arms around luck is to start writing stories.

It’s a trick from our old friend Graham Weaver - I’ll pop his talk in the show notes and if you haven’t watched it yet.

You take 20 minutes or so and write out, long-form, what wild success looks like. Describe that success in detail - customers, revenue, team, funding. Don’t worry about how any of this happened - just describe it.

Then, identify where you’ll need a big jump.

If you say you want to have a vibrant community alongside your product, you’ll need at least one key jump - an extraordinary community builder and manager. You’d be lucky to find one.

There are five types of luck that usually emerge from these stories, and we can build strategies to target each.

1. Serendipity Luck - right place right time. You can't force these, but you can stack the odds by constantly being where your luck gatekeepers hang out.

2. Preparation Luck - the elevator pitch moment- when you do find yourself at the right place at the right time, having a message so clear and compelling - or something tangible you give or do - that people can't help but understand it, remember it and pass on.

3. Network Luck - when your network introduces you to someone key. This isn't about knowing everyone - it's about making sure your existing network knows exactly how they can help you. Because they’ll want to.

4. Creation Luck - you build the stage that attracts the right people. Host a conference, start a podcast, write the perfect article template. Help luck gatekeepers be successful.

5. Persistence Luck - show up consistently where your people are until you become part of the furniture. When they need what you offer, you're the obvious choice.

Each type takes a different strategy, but they all share one thing: they turn "getting lucky" from hoping to engineering.

As I wrote these out, memories from my work and our founders came flooding back to me.

Let me show you how this works.

A few years ago one of our founders built a date-planning service for new parents after discovering a wild stat: happiness in marriage drops 70% after having kids. It’s a perfect foundation - counterintuitive, sort of taboo, and the kind of insight that spreads the second people hear it.

To get initial traction, she combined Serendipity and Preparation Luck. Every weekend in Central Park, she'd hand out postcards to parents. The cards led with that 70% stat in huge font, followed by a simple promise: "We plan and book your dates. You show up, and get your happy marriage back."

After weeks of chatting with dozens of couples each weekend day, she happened to give a card to a momfluencer with 800k followers on Instagram. The person posted about it and our founder got 250 paying customers that day.

For a business built on trusted word of mouth, this was the perfect customer seeding.

I shared the post on LinkedIn, and a friend commented - “she was SO lucky that she happened to hand a card to that person!”

Sure. Lucky.

Luck Gatekeepers

I mentioned Luck Gatekeepers briefly in the previous section and I want to expand quickly now.

Every business, every book, every cafe, every student applying to college every person trying to do something interesting should have a list of the 10 or 20 people who could have outsized impact. The gatekeepers of the luck.

If Guy Raz from How I Built This said on his podcast, hey, you all should be listening to idea to startup if you’re actively working on an idea, we’d likely get tens of thousands of new subscribers and advertisers would flock and my business would change. If Malcolm Gladwell listened to the pod and gave me feedback, or decided it was good enough to be under his umbrella at Pushkin, the business changes. There are another 15 to 20 people like this that could dramatically amplify the past 10 years of Tacklebox and 5 years of Idea to Startup if they chose to. If I helped them choose to.

So, I should be working towards that constantly. Both figuring out who the people are, because they aren’t all obvious, and spending time trying to get in front of those people.

To get lucky, you need to know who the luck gatekeepers are.

Which brings us to, your routines and your budget.

Luck Routines and Luck Budget

The problem with luck is a human one. We’re terrible at prioritizing it.

Humans dramatically underestimate upside and overestimate downside. We think if a feedback loop isn’t clear and obvious, it’s unlikely to make a positive impact and guaranteed to make a negative one.

We spend our days answering emails and making small product fixes - stuff with clear, immediate outcomes but low ceilings. Necessary work, sure, but it won’t ever lead to anything extraordinary.

The opportunities - the, quote, lucky stuff - that's where uncapped upside lives. But because most attempts don't work immediately, we deprioritize them. That press pitch might have a 10% chance of success. You might spend hours on five that fail. But the sixth one hits and creates more value than 100 hours of incremental work ever could’ve.

So, the question is, how do you make luck systematic?

Two ways:

1. The Luck Budget Create a "luck portfolio" with 15% of your resources - time and money - dedicated to high-upside opportunities. These are your 10% probability plays that could 10x your business if they work. Think of it like you’re on little venture capital fund - most won't hit, but you only need one to transform everything.

2. The Luck Routine Every Sunday, ask yourself:

• What's one thing that, if it worked, would make my entire to-do list obsolete? That’s our old friend we call the To Do List Monster.

• What could I commit to that would force me to engage with luck gatekeepers? Put yourself on the hook for something.

• When's the last time I told my network exactly how they could help? Let Network Luck happen.

We’re not trying to get lucky once. We’re trying to build a system that makes it inevitable.

Stick with this, and you’ll get lucky.

In an entrepreneurial way, chatgpt. Ya freak.

This was the idea to startup podcast, brought to you by TB. We’ve got a few slots opening up for the small group program. Codle holiday