Hackers Incorporated

By Ben Orenstein and Adam WathanBusiness Entrepreneurship Technology

Hackers Incorporated episodes

September 12, 2023Q&A: Starting over, the ideal employee, success and happiness, and selling the company
In this episode, Adam and Ben share some personal updates on lake houses, gym equipment, and luxury electric vehicles, and answer listener questions on topics like things they'd change when starting over, how to be more valuable as an employee, the point in their businesses that had the biggest impact on their happiness, and would they ever sell their companies.
Discuss this episode on Twitter →
Timestamps
(00:00) - Personal updates
(27:18) - "How come you've never released a trailer for Hackers Inc. on Art of Product?"
(30:44) - "What's something you'd do differently if you were starting a business today?"
(41:42) - "What would you do the same if you were starting a business today?"
(45:24) - "What does your ideal employee look like?"
(53:40) - "How often do you reflect on how far you've come?"
(59:28) - "What was your biggest change in net happiness while running your businesses?"
(01:10:56) - "Would you ever sell the company?"
Links
Adam on Twitter
Ben on Twitter
1 hr 22 min
August 30, 2023Predictable mistakes of the developer-turned-founder
So many developers (your podcast hosts included) make the same mistakes when trying to turn an idea into a business for the first time. In this episode, Ben and Adam talk through a bunch of these mistakes, why they matter, and what you should do to avoid them.
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Timestamps
(00:00) - Ben's Laracon talk "Predictable Mistakes of the Developer-Turned-Founder"
(02:57) - Mistake: Starting with SaaS
(15:21) - Mistake: Selling to consumers
(17:40) - Mistake: Selling to struggling businesses
(24:24) - Mistake: Not pre-selling your product
(25:52) - Mistake: Assuming people are rational
(26:58) - Mistake: Not choosing a customer you like
(28:05) - Mistake: Being comfortable with your pricing
(33:37) - Mistake: Raising VC
(40:09) - Mistake: Overfocusing on legal and compliance
Links
Adam on Twitter
Ben on Twitter
"Predictable Mistakes of the Developer-Turned-Founder" on YouTube
50 min
August 15, 2023Losing 70 lbs, getting in shape, and 15-minute workouts
Last year, Adam got very serious about losing weight and getting in shape and lost 70 pounds, getting to about 12% body fat and maintaining enough strength to still bench 315. In this episode, Adam and Ben talk about Adam's weight loss story and all the specific tips and tactics he used to overcome a lifetime of bad eating habits, change his relationship with food, and kick ass in the gym.
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Timestamps
(00:00) - Introduction
(01:16) - Adam's weight loss story
(03:27) - Working with an accountability coach
(10:17) - How to eat less food
(22:11) - Macros aren't your biggest problem
(24:27) - Tracking what you eat
(30:20) - Protein shakes
(33:20) - A day of eating in Adam's life
(37:35) - Adam's training background
(41:37) - Adam's current training routine
(47:17) - Using a training partner or personal trainer for accountability
(48:37) - Adam's morning routine
(50:30) - Training to build muscle vs training to maintain
(53:53) - Mobility
Links
Adam on Twitter
Ben on Twitter
MyBodyTutor
Lose It!
1 hr
August 01, 2023Hiring is hard
When you're running a small company, hiring is simultaneously your highest leverage opportunity and the scariest thing ever. In this episode, Adam and Ben share some lessons learned, how they think about hiring for their teams now, and talk through some of the things they're still trying to figure out how to get right.
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Timestamps
(00:00) - Hiring
(02:02) - Why hire at all?
(06:41) - Avoiding hiring altogether
(11:44) - Vetting people
(24:45) - Finding people
(36:22) - How Ben got recruited at Thoughtbot
(37:53) - Evaluating hires
(43:23) - Fears and anxieties around hiring
(50:50) - Unfair hiring advantages
(57:36) - Levels of management
Links
Adam on Twitter
Ben on Twitter
1 hr 7 min
July 19, 2023Enterprise sales for reluctant founders
Enterprise sales gets a bad rap amongst indie founders, but at Tuple it's become an important part of their business model. In this episode, Ben shares all his tips and tricks on how to sell to enterprise customers as a small startup without letting it slow you down.
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Timestamps
(00:00) - Ben's notes on enterprise sales
(02:58) - Ben's first time
(04:56) - Tactic: Build a product that can grow bottom-up
(07:12) - Tactic: Ask buyers to answer their own questions
(08:34) - Tactic: Say no to more than you think
(16:11) - Tactic: Your pricing should make you uncomfortable
(25:38) - Tactic: Charge more for SAML single sign-on
(27:50) - Tactic: Don't sign something without charging a lot
(28:34) - Tactic: Put an expiration date on your quotes
(29:12) - Tactic: Dodge pricing pushback with quarterly payments
(31:06) - Tactic: Make sure you lose some deals because of price
(33:26) - How procurement works
(37:54) - How important is enterprise sales for Tuple?
(47:59) - Tactic: Ask procurement, "what helps this deal get done faster"
(49:49) - Tactic: Have a /security page on your website
(53:07) - Tactic: Use Y Combinator's sales agreement template
(55:47) - Tactic: You probably won't be sued
Links
Adam on Twitter
Ben on Twitter
Tuple's /security page
Y Combinator — Sales Agreement
1 hr 1 min
July 07, 2023How to not suck at project management
Most people are way too comfortable letting a project run for 12 weeks before ever getting it into a shippable state. In this episode, Adam and Ben share the strategies they use to make sure the projects they work on are shippable within the first few days, and stay shippable until the decision is made to finally cut the release.
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Timestamps
(00:00) - If it's not done, it's not done
(03:54) - Example: Building an example app for Catalyst UI
(07:01) - Tracer bullets
(11:11) - Tactic: Thinking from the perspective of "what could I demo"
(11:43) - Example: How Tuple spins up standalone demos
(13:00) - Feature flagging and continuous integration
(14:19) - Example: Migrating the Tailwind UI website to React and Inertia
(18:30) - Tactic: Derisking projects with "save points"
(19:07) - The infamous "how to build an MVP" skateboard to car analogy
(20:07) - Example: Shipping the Tailwind Connect event website
(29:17) - Tactic: Don't be afraid of waste
(31:41) - Tactic: Compare your work to what's in production, not your wildest dream
(33:42) - Tactic: Do a great version of the simple solution
(36:48) - Tactic: Make work in progress visible to avoid taking on too much
(39:23) - Example: Designing the "Is it Tailwind" tool
Links
Adam on Twitter
Ben on Twitter
50 min
June 09, 2023Minimalist management with David Heinemeier Hansson
After over 20 years in business and despite being responsible for a larger-than-ever team, David still finds plenty of time to get his hands in the code and build new products himself. We run significantly younger companies and significantly smaller teams and even we can't seem to find the space to do that, so we talked to DHH about how he makes it possible.
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Timestamps
(00:00) - “Why the fuck did I do this?”
(06:20) - What is minimalist management?
(10:56) - Should you need to be a trained life coach to be allowed to hire people?
(16:12) - Using systems to provide career progression guidance
(18:50) - What do David’s days usually look like?
(27:13) - What are David’s responsibilities at Basecamp, and what are people counting on him for day-to-day?
(29:38) - How David and Jason use their Shape Up framework to give people more responsibility at Basecamp
(36:30) - Getting comfortable with being uncomfortable when giving people more responsibility
(45:54) - Letting people go when they can't live up to the responsibility
(47:14) - What systems do the 37signals team rely on that that haven't already been talked about publicly?
(50:04) - Letting people make decisions you may have to correct and being comfortable correcting them
(55:03) - Radical candor and redirecting feedback
(01:00:55) - How to say no to opportunities and being willing to take risks
(01:11:22) - Learning to stop worrying when you finally do succeed
Links
Adam
Ben
David
1 hr 24 min
April 21, 2023Lifetime pricing is underrated
Last summer, Tailwind UI moved from selling individual content packages and upsells to a one-time purchase, lifetime access pricing model. Since then, the business has doubled. Having seen this in action, Adam recently convinced his friends Sam and Ryan to try lifetime pricing for their product Build UI, and the results are starting to come in. In this episode, Adam and Ben dive deep into the world of lifetime pricing, why it's not something to be afraid of, and how it can be an absolute game-changer for the right type of business.
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Timestamps
(00:00) - Intro
(00:14) - Why are we talking about this?
(03:28) - Moving from package pricing to lifetime all-access pricing for Tailwind UI
(06:03) - What about when you run out of new customers?
(10:17) - "Everything You've Learned at MicroConf is Wrong" by Chad DeShon
(13:33) - The myth of starting from zero every month
(16:04) - Would Tailwind UI work as a subscription model?
(18:09) - Characteristics of a lifetime-suitable product
(20:50) - Subscription LTV vs. lifetime pricing
(22:47) - Subscription friction and the death of the impulse purchase
(25:42) - The brutality of churn in content businesses
(27:21) - Why your lifetime price can actually be higher than your subscription LTV
(29:01) - Ben's experience running Upcase at thoughtbot
(32:42) - The hidden costs of the content treadmill
(36:20) - Hitting a subscription plateau with Upcase
(38:34) - Cookie Clicker game — how to make perceived value go up over time
(42:31) - Why aspirational, impulsive purchases are more likely with lifetime deals
(45:22) - Pricing decisions aren't forever
(49:13) - Turning Build UI from a grind into an instant success by flipping the switch on pricing
(54:17) - Using lifetime pricing to buy yourself flexibility and time to focus
Links
Adam on Twitter
Ben on Twitter
Tailwind UI all-access
Everything You've Learned at MicroConf is Wrong, Chad DeShon's lighting talk at MicroConf Growth 2018
Build UI, Sam and Ryan's new UI training site that recently switched to lifetime pricing
1 hr 1 min
March 25, 2023Revisiting "The Ideal Bootstrapped Business" with Jason Cohen
Jason Cohen’s talk “Designing the Ideal Bootstrapped Business” from 2013 is a classic in the bootstrapper canon. In this episode, Jason joins Adam and Ben to see how the talk holds up a decade after its creation.

Timestamps
00:00 Intro
00:27 Designing the ideal bootstrapped business
06:53 Recurring revenue vs one-off sales
13:30 Getting all the LTV up front
18:31 Product validation
24:56 Creating a cash machine
26:05 Where does growth come from?
41:25 Annual prepays
46:41 Increasing your prices
51:56 What new advice is there since this talk?
59:00 What about freemium?
01:03:39 What happens next?
01:08:58 Picking an idea that's compatible with the life you want to live
01:12:16 Ideas for Tailwind
Links
Adam
Ben
Jason
1 hr 25 min
March 25, 2023Running your business like a band
“How come Dave Grohl is still playing guitar and writing songs and singing but I'm filling out DMCA takedown notices, answering customer support emails and responding to GitHub issues?”
Timestamps
00:00 Intro
03:05 Bringing on a band manager
07:34 Why the band metaphor works
11:54 Make things for your fans, not for your critics
14:49 Always do the things you want to do
18:04 Turning over your rep over time
19:33 A band needs a frontman
22:14 Showing behind the scenes
25:23 Doing one thing at a time
30:57 Don't interview people, audition them
35:38 We don't make movies to make money, we make money to make movies
Links
Adam
Ben
37 min