Stacking the Bricks - Real Entrepreneur Confessions

Stacking the Bricks - Real Entrepreneur Confessions
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.

EP29 - What are you optimizing for?
Sep 13, 2017 • 38 min
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…
EP28 - Double your Conversion Rate with Brennan Dunn
Aug 30, 2017 • 33 min
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…
EP27 - You can ship. But will anybody buy?
Aug 16, 2017 • 19 min
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…
EP26 - Don’t wait 18 months
Oct 9, 2016 • 26 min
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…
EP25 - Features, or marketing? (Part 3 of a series)
Jul 15, 2016 • 24 min
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…
EP24 - Teamwork is harder than you think (Part 2 of a series)
Jul 8, 2016 • 37 min
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…
EP23 - “Everything will get easier if…” (Part 1 of a series)
Jul 1, 2016 • 30 min
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…
EP22 - How to make an offer they can’t refuse (Outreach Masterclass with Kai Davis)
Jun 10, 2016 • 40 min
When Kai Davis sends you an email, there’s a good chance he’s asking for something.
EP21 - The most dangerous room in the house
Mar 25, 2016 • 36 min
Let us show you how most of the “risk” in starting a business isn’t really risk at all.
EP20 - Swift Kick in the Ass (Accountability)
Mar 18, 2016 • 3 min
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.
EP19 - A Swift Kick in the Ass (The Game of Business)
Mar 11, 2016 • 4 min
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.
EP18 - Our Profitable Mess (and how we’re cleaning it up)
Feb 21, 2016 • 40 min
If we’re honest…some of the most crucial parts of our business are a mess. A mess that makes money, but messy still.
EP17 - Kids Incorporated
Feb 12, 2016 • 52 min
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…
EP16 - How do you design products people love?
Feb 5, 2016 • 50 min
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…
EP15 - Why “Lambo Goals” never keep you motivated
Jan 29, 2016 • 24 min
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…
EP14 - What are your New Years Pants?
Jan 26, 2016 • 24 min
Why are we talking about pants on a business show? There’s a connection, we promise.
EP13 - Justin Weiss’s shift from side projects to successful product launches
Mar 9, 2015 • 42 min
“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,…
EP12 - “I’m shipping ebombs, now what?” - From Pain to Product with Nick Piegari
Mar 5, 2015 • 43 min
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…
EP11 - “I just need someone to hold me accountable.”
Mar 4, 2015 • 9 min
“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…
EP10 - Why do people worship the struggle of entrepreneurship? And how to avoid it.
Mar 3, 2015 • 13 min
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…
EP9 - How to clear a path for product success
Feb 26, 2015 • 57 min
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…
EP8 - From pain to product Masterclass with Amanda Thomas
Feb 23, 2015 • 56 min
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.…
EP7 - Part two of “The Life-changing Magic of Shipping”
Feb 17, 2015 • 21 min
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…
EP6 - “The Life-changing Magic of Shipping”
Feb 16, 2015 • 29 min
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…
EP5 - The evil voicemail effect
Feb 15, 2015 • 7 min
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…
EP4 - Shipping is a skill
Feb 5, 2015 • 9 min
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…
EP3 - We didn’t hit our 2014 goals. But…
Jan 12, 2015 • 56 min
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…
EP2 - Scott Hurff’s first product launch was “wrong”, but $50k later he knows it didn’t matter.
Jan 8, 2015 • 51 min
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…
EP1 - How Pat Maddox went from 0 subscribers to over $3k MRR in 10 days
Jan 8, 2015 • 45 min
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…