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Stacking the Bricks - Real Entrepreneur Confessions on Smash Notes

Stacking the Bricks - Real Entrepreneur Confessions podcast.

December 28, 2019

If you're tired of all the buzzwords, boosterism, mythologizing, the cult of overwork in the world of startups, it's easy to feel like the oddball in the room.

We're here to share the real stories of today's business bootstrappers: the makers who make their money with products and launches instead of client pitches and hourly consulting.

Episodes with Smash Notes

Donovan picked up JFS in December. Read it over Christmas. By the end of February, he'd grown his mailing list to 1,500 people. He created a landing page and JFS'd an email course on CSS animation, with a price tag of $49. In the first 7 days, he made 50 sales — for a total of over $2,000.


To learn more about how Donovan did it — including specific techniques for getting traffic to his blog posts — listen in right now…

Updated on August 21

Nathan Johnson left a corporate gig to bootstrap an affiliate business to 100,000 users. But to get it any bigger - and profitable - he would have to give up the very thing he left his corporate gig for: freedom. Ouch.

Find out how he changed course to build a different business that DOES let him travel and spend more time with his family, while helping an audience of professional photographers.

I've been wanting to do an episode with Brennan Dunn for a LONG time. He's one of our most successful students, having built an empire of resources and products for freelancers at But freelancing rates aren't the only thing Brennan has figured out how to he's mastered the art of personalizing on-page content to boost conversion rates, often 2x or more!

Brennan has come a long way since he joined 30x500 with the idea to build and AirBnB for homecooked meals...and in this episode you're going to learn how he built his empire by stacking the bricks.

Dave Ceddia knew how to ship, but none of his projects had ever made a sale.

Today, $15,000 in sales of his book "Pure React" later, he knows how to create new, bigger products for his loyal and growing audience.

In this episode, you'll find out how he stopped thinking of himself as a "lifer" at a cushy job to being in control of his professional future.

Here is the double-edged sword of the software business:

All the “features” in the world will not matter if you don’t have the customer pipeline.
It is better to lose many customers over a missing feature than spend a month on a feature that people say will make them sign up.
Yet there really are features you’ll require in order to get and retain your best customers.

OK, so maybe it’s a triple edged sword. Or maybe a citrus reamer. Shut up.

Adding people - partners, employees, contract staff - is one of the hardest parts of growing a business. It doesn't get talked about enough, and partly, because it's hard to talk about openly.

In this episode we talk about the reasons why working with people falls apart so often and some things we've learned along the way to make wise decisions when adding people to the team.

2015 was the best ever for Amy's SaaS business Freckle, with $625k of gross receipts, and so far we’re on track to hit close to $800k annual run rate (ARR) before this year is out. Those are some big numbers, but we didn’t start out there, and it hasn’t been all smooth sailing.

In this episode we talk about the first of five things I wish I’d known when I started Freckle, things that would have made my life so much more profitable and pleasurable.

Up first: "Inflection Points," aka the myth that "everything gets easier when..."

When Kai Davis sends you an email, there's a good chance he's asking for something.

Let us show you how most of the "risk" in starting a business isn't really risk at all.

Got 5 minutes? Then let Amy give you a swift kick in the ass.

Learn why "accountability" doesn't work the way you think it does, and how to change your mindset to get more done.

Got 5 minutes? Then let Amy give you a swift kick in the ass.

Listen to this quick, bite-sized episode to learn why business is unlike any other game you've ever played.

If we're honest...some of the most crucial parts of our business are a mess. A mess that makes money, but messy still.

Amy has talked about starting Freckle. Alex has talked about starting Indy Hall. But NEITHER of these were our first brushes with business.

To get our true origin stories, you'd need to see what we were doing to earn money while we were still in grade school. And it wasn't from babysitting...

Jump into a time-traveling DeLorean with us to go back, back back in time and learn how our EARLIEST experiences with business, making sales, and understanding customers and their behaviors shaped the businesses we run today.

Scott Hurff - who you met back in Episode 2 of this show - just released a new hit book through O'Reilly called "Designing Products People Love."

But Amy and Alex aren't interviewing Scott about his book or his launch in this episode. In fact, the opposite.

In this episode we turned the tables and Scott interviewed us, digging REALLY deep into our combined backgrounds in business and how we do research, conduct "Internet Ethnography" a.k.a. Sales Safari, and how we build learning systems to help our customers and students.

We didn't plan to make this a podcast episode so the audio quality isn't perfect, but when I found this recording buried in some folders a few nights ago I realized that there wasn't anything this comprehensive anywhere out there.

So it's time to change that. Click play to tune into this fun, fast-paced, and multi-layered conversation with an alumni we're very proud of, as we share what goes into creating the products that people love, and how we help others do the same.

The right motivation is a fire under your ass, not a Happy Place you retreat to in your mind when things are hard.

The right motivation is enduring, meaningful, and personal — and often times, painful.

Here's what the right motivation is not:

fantasies of acclaim
fantasies of riches and luxury
fantasies of retiring early to a Mojito Island

They're fun, but actually destructive to your ability to keep going.

Why? Why can't these shiny Lamborghini Goals keep you going? What will?

Listen to the latest episode of Stacking the Bricks to find out!

Why are we talking about pants on a business show? There's a connection, we promise.

"The idea that, oh well, I shouldn't charge money for this because… some reason.

Justin spent years noodling on side projects. He made every excuse in the book for not charging for them, including some we haven't often heard:

At the time, it seemed like, 'Why should I charge money for this? This is a passion project of mine.' So I should just release it for free."

But last year, he decided to make a change.

Click here to watch the video of the ebomb that you hear in the intro of this episode ->

ebomb, noun -
our special 30x500 term for "actionable educational content marketing". Yeah, cuz that's a mouthful. So drop a knowledge bomb on 'em. Ebomb 'em.**

Sooo… you've got some Sales Safari data, you've got some quality ebombs under your belt, now what?

How big should your ebombs be?
What if it feels like you're exhausting a small watering hole?
How do you go from ebombing to a product?
What thing should you try, if your ebombs aren't getting great traffic or signups?
What's the best way to open up (and sell) a (free) ebomb?
When's the right time to start on the product, anyway?
Ummm soooo… if you hear things over and over in the watering holes, what do you do with it?
What if the pros in your audience… uh… aren't in love with you?
How is it actually kind of magical and productive to be annoying?

"I just need someone to hold me accountable."
"If only there was a community where I could get advice…"
"Let me tell you my plan…"

Have these phrases ever passed your lips? And then you failed to 1. execute
your plan, 2. take action on the advice you received, or 3. be accountable?

I'm going to assume the answer is "Yes," because it's a mistake we've all made before. Although some of us longer than others.

That's what I did for about a decade before shipping Twistori, before Freckle, before JavaScript Performance Rocks! — before 30x500. I used to talk about the business I would build, some day. The software I would design, some day. I had HUGE ambition.

I was always looking around for something that would make me do it.

And I learned: There's no such thing.

There is no force on earth that can make you do something. Really — nothing.

Even if a moustachio'd highwayman held you at gunpoint and demanded "YOUR LAUNCH DATE OR YOUR LIFE," you would still be choosing between consequences: Do I ship? Or do I take the bullet? You get to choose. You cannot be truly forced.

And why would you want to be, anyway? Why would you want to put yourself in that position?

Nobody does, not for long.

So you say you want "an accountability partner," and that lets the pressure off, and then… nothing gets done. No surprise there: you relied on the pressure, and then you let it escape. Accidentally on purpose.

This is a pattern I've seen over & over in myself, before I decided to get over it. And in the last 5 years I've seen it in so many of our students.

It's one of the core causes of failure and if you want to succeed, you need to address it.

To help you, I recorded a little Amy Productivity Psychology Story Time for you. I explain the why, the wherefores… and what to do about it.

Newsflash: Lean Startup and Customer Development are inherently broken.

If you ask me, the whole process is functionally bankrupt. Why? Let me answer your question with a pair of questions:

Why do you create good things… but nobody buys?

Worse: Why do you feel the thrill of a great idea, then get stuck before you even finish the damn thing?

In short: Why all the struggle? And why do people worship the struggle?

This lil mini-episode I made walks you through the problem, and the solution. It’s only 13 minutes. It could just be the 13 minutes that’ll end the idea-fail cycle for you forever. This mini-episode is from a video that appears here, if you'd like to "see" what Amy is talking about:

Jim Gay is a busy dad. A REALLY busy dad, with 4 kids.

He really wanted a product business so he could spend more time with his family instead of working endless stressful hours to pay the bills.

But this episode isn't actually about making time at's about clearing a path for success.

Do you remember the approach to tidying we talked about in episode 6 and 7? We learned that the path to a tidy home is deceptively simple...and part of the process involves letting go of things that are holding you back.

In this episode, 30x500 alum Jim Gay talks about going through exactly that process, and how hard but important it was to start his product business with a clear perspective.

You'll learn how he rebooted his approach, immersing himself in the community to learn what they care about most.

Jim did so many smart, strategic things to build his audience: from turning his most popular ebombs as talks for conferences, to being really intentional about the KINDS of blog posts he wrote in the first place. And he's done very well for himself - his launch weekend topped $10k and he's earned over $60,000 from his first product since the first beta release.

But Jim made some mistakes, too. One mistake in particular had big emotional costs in additional to delaying his financial success for over 2 years.

It's a mistake that Amy and I have seen countless people make, and we've even made ourselves. You're going to have to listen to see what that mistake was, and how he recovered from it, and how selling products is helping him achieve his goal...having more time to spend with his family.

Links mentioned in this episode

Interested in being part of our 30x500 Pioneers program? Sign up here and we'll send you details about the launch next week:

Amanda has learned the hard way that publishing beautiful books on the Kindle and other e-readers is a pain in the ass.

In this hour long masterclass, Amy and I help Amanda through her first steps in turning this deep vein of pain into her first product.

We talk about:

Choosing and narrowing an audience (including some critically counterintuitive lessons)
How to spot evidence of a market (where's the proof that lots of people have the same itch you're trying to scratch)
Designing who your product will resonate with first
How to develop marketing content (we call them ebombs)
How to use audience jargon to connect with your audinece
How to figure out what your audience already knows (and use that to your advantage)

...and a lot more

This recording originally appeared on:

Want a different result than you've been getting? Then you need a different approach.

Enjoy part two of our 2-part conversation to learn the revolutionary approach that Japanese organizing expert Marie Kondo teaches for tidying, and how those lessons apply to your startup, too. Bonus: life (and business) wisdom from ancient Chinese philosophers, 500-year-old French noblemen, and the Bible.

If this is your first episode of Stacking the Bricks, we'd recommend going back to Episode 6 to listen to the first'll help set the stage for this episode. But...if you don't mind your listening to be a bit more of a jigsaw puzzle then by all means...keep listening. :)

Get BOTH parts, all of the background on this show and all of the show notes in one place:

Links mentioned in this episode

Managing the Absurd on Amazon
Alex's guide to writing for your audience

Right now I'm reading a book called The Life-Changing Magic of Tidying Up, by Japanese organizing expert Marie Kondo.

It's amazing. I can't recommend it enough. Already, I'm feeling an increase in lightness, beauty, and joy in my home. But that wasn't the reason I started reading it to Alex during one of our Skype calls last week. Nope, I shared it with him because of a deeper truth, and its masterful presentation.

The Life-Changing Magic of Tidying up isn't just about tidy homes, it's about life.

The book itself is so good because it throws out every traditional piece of advice. Marie proves it: Little by little won't solve the problem. Storage won't fix the problem. Fancy boxes and shelves and "one thing a day" won't get you there, ever.

You have to do something radically different to get a radically different result.

Most startup advice is on the day-to-day level: the little tactics. Try this, try that. Pivot. Split-test. But like tidying, the problem occurs upstream. These tactics will never fix the broken strategy.

The lessons from this book? Virtually the same lessons we have learned ourselves in business, and what we do our damnedest to teach our students. The previous failures, the negative self-talk, the self-perpetuating cycle, the backsliding that terrifies our students… it's all exactly the same as Marie describes in her students. Only the implementation details change.

Sound at all familiar? It sure sounded familiar to me.

Listen to part one of our 2-part conversation to learn the revolutionary approach Marie teaches for tidying, and how those lessons apply to your startup, too. Bonus: life (and business) wisdom from ancient Chinese philosophers, 500-year-old French noblemen, and the Bible.


Links mentioned:

The Life-Changing Magic of Tidying Up on Amazon
Why running a consultancy doesn't prepare you for building products
Amy's 500-years-ago essayist doppelganger, Michel de Montaigne
The 7 steps to failure - How do you create a product that people want to buy?

This recording originally appeared at:

Earlier this week, Alex and I were stuck. Hard. I was crazy unhappy with the lessons I'd been trying to design. What I was doing… wasn't working.

Why was I stuck? What did we do to get unstuck? What on earth is the "voicemail effect" and why is it the source of so much writer's block?

If you find yourself stuck in a project — and therefore avoiding it — then this episode might give you the inspiration you need to figure out why. That kind of thinking can save your project.

More insider peeks at

Are you a procrastinator?

Don't feel bad about it - DO something about it.

On this show, you’re going to be hearing a short story from my business partner and co-host Amy Hoy admit something....there was a time when she wasn’t so great at shipping. That's right, the author of Just Fucking Ship ( used to be a serial procrastinator.

As she describes, "I could ship work and projects for other people - bosses, clients - but when it came to shipping my own things I was the worst." Amy goes on to describe the sequence of events that snapped her out of her nasty habit and started her down the path of shipping, including one of her most famous projects, including the story behind one of her most famous projects and how it helped her career.

This episode is just a tiny excerpt from a longer interview hosted by one of our friends and alumni, Sean Fioritto, who has been writing a series called “Github Ghost-towns” ( where he’s been talking about all of those side projects that we spin up…and then leave to rot.

You know what I’m talking about. ;)

The FULL LENGTH interview with Sean is action-packed with stories and advice from Amy and I, including a bunch of tips that we use every day to make sure we keep shipping the products and ebombs that you all seem to love so much. So go check it out at

Get your own copy of Just Fucking Ship

There are 21 principles that we used to Just Fucking Ship the book Just Fucking Ship. You can learn what they are here and pick up a copy for yourself:

We didn't hit our goals (which was mostly our fault).

We let deadlines slip, and probably let some people down.

Amy got really sick. :(

So of course, looking back on 2014 feels like we didn't get all that much done.

But when Amy and I sat down and spent an hour going over the stuff we did do...we realized that holy cow, it was a lot.

A bit further down on this post, we've put together our comprehensive review of 2014. It's complete with revenue and subscriber numbers, where we have them readily share-able. You'll see that 2014 might not have been as unproductive as we'd felt.

After pulling this list together, Amy and I sat down again to talk about how the year went, and talked about the difference between how we felt... and what the facts actually showed.

And this time, we recorded that conversation so you can listen in! You can expect more audio stories and conversations like this one in 2015! That'll include interviews with successful bootstrappers (and not just our own students) and more chances like this one to peek "behind the curtain" and see how Amy and I truly work together, using our unique strengths and differing approaches to actually compliment one another.

This recording originally appeared on in an article titled "2014 Year In Review – The year that sucked, or did it?":

30x500 Alumni Scott Hurff joins Alex Hillman. They talk about how Scott's approach to building products has changed, and what he's learned from both of his launches.

By his own measures, Scott's first product - a technical course for designers wanting to use Quartz Composer - was far from "perfect". But even without perfection, his launch still exceeded his expectations and earned him $10k on launch week.

Then, when he improved his launch by incorporating ebombs & our 30x500 launch sequence technique, Scott more than tripled his launch revenue.

Also, like a lot of us, money isn't the only motivator. Scott's learned that there's some amazingly good feelings that come from being in the business of helping people succeed.

Tune in and learn a whole lot from Scott's experience. Check out his blog at

This recording originally appeared on in an article titled "What if your product launch fails? This interview will give you $10k reasons to do it anyway.":

30x500 Alumni Pat Maddox joins Alex Hillman. They talk about how Pat used the 30x500 process of Sales Safari and dropping ebombs.

Then Pat shares how he ruthlessly followed just three steps every day for 10 days to get from from barely making rent to having over $3000 in MRR from paying customers and over 1000 subscribers on his mailing list.

Tune in and learn from Pat. Check out his blog at

This recording originally appeared on in an article titled "From zero to $3k MRR in 10 days, the story of RubySteps":