“And then you also have your Substack.”
Substack
By Substack Inc.
27 recommend/use · 34 sourced episodes
Every sourced reference
Short attributed excerpts only. Timestamps are approximate.
“So execsinthesity is my Substack.”
“I decided, I'm going to move to Substack. I'm going to write every week.”
“this is a huge part of like the Substack phenomenon and the newsletter phenomenon and the podcast phenomenon”
“You can find me on LinkedIn and you can find me on Substack.”
“I have my blog, The Looking Glass. It's on Substack.”
“You hitched yourself to Substack super early. You took a focus.”
“they were engineers leading up the growth team at Substack”
“Oh my god, what if all of those people who have signed up to my Substack suddenly disappear?”
“I did the exact same thing with my substack no none great”
“DM me on LinkedIn or just reply to my Substack newsletter email.”
“leave a comment either on YouTube or on substack”
“I have a uh subsat called practical intelligence”
“if you actually subscribe to my substack you can just reply to the first email”
“I have a newsletter called on background it's on substack”
“I spend a lot of time with the Substack teams. Been a very active advisor there.”
“leave a comment on YouTube or in substack”
“I do have a substack newsletter”
“when I joined substack I thought it was too late”
“at this point over 80% of my subscribers come from substack Network”
“it's on Substack. So you can find it there.”
“some of the top growth companies like block versel ramp retool uh Mercury and substack are are building with lineer”
“lane. substack”
“the reason I called my newsletter Lenny's Newsletter is because that was the default recommendation Substack gave me when I signed up”
“I publish on sub stack when I have time”
“I have that experience myself with Substack, which is a subscription newsletter.”
“search sub Stacks directory of newsletters for specific things you're dealing with”
“the other one is this sort of newsletter that I have on sub stack”
“longer form explanations in my sub stack”
“with that story in mind when I was chatting with a sub stack people early on”
“eighty percent of my new sign ups are coming from sub Stacks Network the recommendations feature and their onboarding”
“I met Lulu while she was head of comms at sub stack”
“that was the default recommendation when I was signing for substack”
“your newsletter is the number one technology newsletter on sub stack”
“sub Sac introduced recommendations which has been a massive growth engine”
“Substack as a product and a company has changed my life and allowed me to do the work that I do now.”
“I joined Substack around a year ago now exactly through an acquisition.”
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The Keeper Test
Ask monthly: if this person quit today, would I fight to keep them? If not, have the conversation now.
The Learning-Impact Ladder
Alternate between roles where you have mastery and roles where you're the newbie — zigzag, don't climb.
The Lightweight-First Outreach Opener
Open cold with a one-line 'are you open to ideas?' instead of a full pitch, to earn a reply.
The Lindy Commitment Test
However long you've sustained something is roughly how much longer you can trust it to last.
The Made-Up Name Reset
Give a team or feature a name nobody recognizes, so nobody can skip the argument about what it should be.
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A five-step, repeatable loop that converts helping your manager into leverage for your own goals.
The Marketplace Priority Stack
Pre-commit an explicit ranking of who you serve first, so thorny trade-offs resolve themselves.
The Meeting Operating System
Version your team's meetings like a product — ship a new rev every 90 days.
The Negative-Growth Rehearsal
Growth masks all problems — so ask what you'd do if growth went negative, before it does.
The One-Month Experimentation Rule
If you can't collect the sample size in a month, don't A/B test it; ship it and measure pre vs. post.
The PM-Engineering Alignment Operating System
Run product and engineering as one leadership unit with clear ownership and async, iterated reviews.
The Product-Led Sales Escalator
Convert self-serve usage into large enterprise contracts by bridging individual, team, and enterprise value.
The Reboot Leadership Equation
Practical skills + radical self-inquiry + shared experiences = better leadership and resilience
The Relentless Iteration Loop
Read-through, add, repeat 50-100 times, set aside, return — then hand to editors. That's the secret.
The Repeatable Idea Test (Put the Pill in the Cheese)
Engineer a message people repeat for their own reasons — memorable, effortless, and never an inside joke.
The Scaled-Liquidity Smell Test
Before calling yourself a marketplace, prove you have scaled liquidity on both sides.
The SEO Staffing Stack Rank and Impact Clock
Internal expert, then a relentless doer surrounded by advisors, then agencies — and 3 to 12 months to prove it
The Setup-and-Follow-Through Sales Pitch
Structure a sales pitch as market setup then differentiated value, not a feature walk-through
The Shared-Fate EM/PM Pair
Give the eng manager and PM the same performance rating, and make them understand before they argue.
The Sidecar Model of Management
You don't take the wheel or hand it over — you ride attached, and you have to be invited in first.
The Skip: Career as a Product
Plan for the job after next, not the next job — and treat promotion as a means, not the goal.
The Skip — Plan the Move After Next
Optimize career decisions for the job two moves out, not the next job.
The Soft Pushback
The one-line, zero-aggression ask that recovers ~20% of comp almost every time
The 'So What?' Ladder to Differentiated Value
Ladder a differentiated feature up through repeated 'so what?' until you reach value rivals can't match
The Superpowered Individual (Combination-of-Skills Career Moat)
Go deep in one craft, then use AI to add adjacent crafts until you become un-replaceable
The Team Is the Product
Choose the company you want to build first, pick a problem worthy of it, then treat every hire as a product launch.
The Three Acts and the Next North Star
The greyhound that catches the rabbit never runs again — pick your second North Star before you catch the first.
The Three-Chapter Hiring Playbook: Find, Assess, Close
Hire the top 1% by hunting signs of excellence, then closing with the whole exec team and the family
The Three Lead-Attribution Channels (PQA / PQL / MQL)
Route leads by whether usage and a buyer exist, because each channel has different conversion rates and playbooks.
The Three Modes of Customer Understanding
Separate targeted Discovery, always-on Continuous Conversations, and passive Customer Listening — each needs its own machinery.
The Three Network Effects (and Why Social Products Must Evolve)
Classify defensibility as direct, cross-side, or data network effects — and know social products must add the latter two
The Three Pillars of Self-Serve Monetization
Lift free-to-paid conversion by fixing awareness first, then checkout friction, then the model itself.
The Time-Boxed Leap Bet
De-risk a scary career leap by treating it as a fixed-length experiment with a fallback
The Tomorrow Test for Saying No
Decide whether to accept a distant commitment by imagining you had to do it tomorrow
The Two-Bucket SEO Fit Test
Does your product mint pages by itself? The answer decides your entire SEO strategy
The Two-Question Introvert Diagnostic
Two thought experiments that reveal your true temperament preference, cutting through learned behavior
The Two-Year Publishing Cadence
Write a post several times a week for two years and an audience will find you
The Waterline Model (Snorkel Before You Scuba)
Diagnose team problems from the top down: structure and dynamics, not the people, cause 80% of issues.
The YOLO Rule: When Not to Run an Experiment
Experiments have a cost — sometimes shipping 40 things fast beats testing 10 things properly
The Zero-to-Seven-Day Retention Sprint
Concentrate experiments and flexibility on the first 7 days, where loss aversion actually locks in.
The Zone of Benefit (3x Rule)
A product must make the customer at least 3x better before they notice enough to switch and pay.
Throwaway Prototyping To Discover The Product
Build disposable prototypes on real data to feel what works before writing any production code.
Timeless-Customer Team Structure
Organize teams around customers and problems that never end, not around product surfaces that do.
Two-Way Write-Ups
Make written docs conversational with done-reading, Dory questions, and a sentiment table.
Use AI As Leverage On Your PM Time
Assign the model a role, feed it more context than you could read, and iterate the prompt until it works.
Values as a Mirror
Don't author values. Interview the whole team, harvest their exact words, and write them back as a story.
Virality as Customer-Augmented Marketing
Real virality is high-quality word of mouth from a great product — not synthetic referral traps bolted on top.
Visibility Signals Importance
Users care about a feature in proportion to how much the product visibly cares about it.
Where to Fish for a Unicorn: The Workflow Quadrant
Score a B2B SaaS idea on two axes — workflow breadth and frequency — to predict billion-dollar potential.
Work Alone Together (Note-and-Vote)
Replace group brainstorms with silent individual idea generation, a quiet vote, and one designated decider
Workshop-First Advisor Hiring
Vet an advisor with a paid working session on a real problem, then re-evaluate their value every month.
Write What You Repeat
If you say it more than once, write it down — then get an accountability partner to enforce a monthly cadence.
Your Problem Isn't Unique
Never start from scratch; find who already solved your problem and patternize the solution.
People in these episodes
- April Dunford
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