Dru's Notes

40 Episodes
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By: Dru Riley

One mental model each day in a few minutes. Habits, business, building products and thinking clearly. From Dru Riley, founder of Trends.vc.

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How to Attract the Right Clients With Your Price | Daily Essay
Yesterday at 11:50 PM

Cutting the price of Trends Pro changed who signed up. Support rose, engagement thinned, the room shifted. Raising the price back filtered for people who arrived ready. Price selects your market before anyone reaches your inbox.

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Customer Lifetime Value: What ConvertKit Got Wrong | Daily Essay
Last Wednesday at 11:09 PM

ConvertKit auto-upgraded my bill the hour my list crossed a tier, then held the higher price when it dropped back under. Their own logs later admitted about $936 in overcharges across eight months. The math from the vendor's side is the real story.

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How to Adapt to Change Fast Enough | Daily Essay
Last Wednesday at 2:35 AM

For years I built businesses that went nowhere. Then one took off, once I held a daily floor of experiments. Below the floor your work falls behind a drifting world. Above it, it compounds.

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Consistency Over Intensity: What Pushing Harder Costs | Daily Essay
Last Monday at 11:42 PM

Pushing one habit harder than it needs steals from the habits still below the line. The durable move is the smallest version that still compounds.

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Think on Paper to Keep Your Principles Sharp | Daily Essay
Last Sunday at 5:07 PM

After a month without rewriting my principles by hand, the impulses they keep in check started winning. Copying them onto a fresh page each week is what keeps hard-won lessons from fading.

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Get More Done by Counting What You Finish | Daily Essay
Last Saturday at 5:08 PM

I count my output by what I finish, not the hours I sit. Flannery O'Connor watched the clock; Stephen King counted words. A 17-day launch burnout taught me which one to trust.

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Analysis Paralysis Is a Bundling Problem | Daily Essay
06/12/2026

Most plans stall because several separate problems got bundled into one decision. Split them, ship the piece that stands alone and the freeze breaks.

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I Stopped Taking Rest Days. The Binges Started. | Daily Essay
06/11/2026

I made the case for cutting rest days. Then the binges started: every two weeks or so, a Thursday ending at 3am, with the brain collecting the rest I refused to schedule.

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How to Get Startup Ideas: Build the "Dumb" One First | Daily Essay
06/10/2026

The great idea shows up after you start. Build the "dumb" one and the problems you hit along the way become your next products.

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Why Comfort Will Ruin Your Life: The Turkey Problem | Daily Essay
06/09/2026

One day the turkey wakes up and it's Thanksgiving. Comfort feels like safety, but it lets risk pile up quietly until it hits all at once. The fix is to take small risks on purpose, while a miss still costs little.

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To Achieve Your Goals, Aim at Your Habits | Daily Essay
06/08/2026

A goal doesn't have a hurdle rate. Habits do. Break the goal into the habits that feed it. Find each one's input level. Make experimenting the habit that carries you when the destination is uncertain.

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Fail Fast, Fail Often: My 1-in-20 Hit Rate | Daily Essay
06/07/2026

Most experiments fail, and that's the point. About 1 in 20 becomes a material win that keeps paying, and you can't tell which before you run it. So run more.

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Why Achieving Goals Doesn't Make You Happy | Daily Essay
06/06/2026

You hit the goal and the win fades by tomorrow. The target was never fixed: reach it and you want the next one. Chess ratings and jiu-jitsu belts turn out to be the same trap in different clothing.

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Turning Failure Into Success: 7,000 Subs, Zero Sales | Daily Essay
06/05/2026

A pre-sell to 7,000 subscribers got zero sales. The failure forced a free-plus-upgrade model that broke a three-year income drought and became Trends.vc. The target I missed was smaller than what the miss handed me.

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Don't Hard-Code Trauma: How to Let Go of the Past | Daily Essay
06/05/2026

A fraud alert in a foreign country almost became a permanent rule. The real fix was a backup card. Most bad experiences don't deserve a lifetime policy.

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Not All Trade-Offs Are Real | Daily Essay
06/04/2026

I cut from two operations days a week to one and watched email slow down while support got faster. That gap exposed a trade-off that was never real, and a way through it.

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Why Smart People Stay Broke | Daily Essay
06/02/2026

There are two ways to be careful with money. One group tracks what they pay. The other tracks what they get back. Only one builds wealth.

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Your Morning Habits Work. The Order Doesn't. | Daily Essay
06/01/2026

I drank tea before I meditated and the day went sideways. The habits were identical. Only the order changed.

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Don't Hate the Player, Hate the Niche | Daily Essay
05/31/2026

The anger you aim at a public figure is aimed at the wrong target. The role was open and the pay was good, so someone was going to take it. The person is replaceable. The game stays.

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How to Get Good Ideas | Daily Essay
05/30/2026

A single curious question became Multi and the biggest payoff of my year. You can't tell how much an experiment will pay off before you run it, so run more of them.

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Why Good Habits Get Boring | Daily Essay
05/29/2026

Day one of a habit is an inertia problem. Day 89 is a boredom problem. The challenge changes as a habit ages, and naming the level you're on tells you which fight you're actually in.

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The One Minute Rule for Habits That Stick | Daily Essay
05/29/2026

Three weeks of planning a habit I never started. The first step felt too steep. I set a timer for one minute, worked on the launch, and did it again the next day.

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Warren Buffett's Ovarian Lottery: Are You Born Lucky? | Daily Essay
05/27/2026

John Rawls wrote a thought experiment about the original position. Imagine you're behind a veil, about to be born, but you don't know where.

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Consistent But No Progress? It's the Hurdle Rate | Daily Essay
05/26/2026

You can be consistent and still be dying. Every habit has a hurdle rate: the minimum input it needs to clear the entropy working against it. Show up below the rate and you lose ground daily, even while the streak holds.

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How to Make Habits Stick When Life Pushes Back | Daily Essay
05/25/2026

I ran for half an hour and ten minutes became my new normal. Most habits break because the daily target has no room above it. Put the habit on a range with a floor and a ceiling, and the ceiling buys the buffer that keeps the habit alive on bad days.

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Substitute, Don't Subtract: How to Break a Habit | Daily Essay
05/24/2026

Every rule I set to stop scrolling at night broke until I added jazz. Imperfect substitution beats failed abstinence because it leaves you with progress while pure willpower leaves you with nothing.

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Engineered Addiction: Why I Deleted the App | Daily Essay
05/23/2026

I sat down to play one game of chess. Twelve hours later, I deleted the app.

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Habits of Great Writers, Founders and Investors | Daily Essay
05/22/2026

Great operators run two stacks every day: the work stack and the distribution stack. This episode maps how writers, founders and investors build both, and why one stack alone leaves great work unseen.

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What a Mastermind Group Actually Does | Daily Essay
05/21/2026

Three years of zero income ended in two hours because someone in a room saw what I couldn't. The five things a mastermind does that solo work can't replicate.

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Charlie Munger's Learning Machine (In Plain English) | Daily Essay
05/20/2026

Charlie Munger said this when asked how to live a good life. Your learning rate is your investment rate.

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Don't Believe Everything You Think. Test It. | Daily Essay
05/19/2026

For 15 years I believed meditation had to be the first thing after waking. One experiment with sun exposure dissolved that 15-year belief in 48 hours. The more experiments you run, the more fit you become to your environment, and the more accurate your model of the world.

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5 Things Chess Teaches Us About Life | Daily Essay
05/19/2026

I sat down to play one game of chess. Twelve hours later the day was gone. Five lessons from the board that run my work and my life.

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Build Systems So Your Work Runs on Easy Mode | Daily Essay
05/17/2026

I draft most posts on walks now. One experiment, voice-to-text, changed how much leverage every post gets.

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We Are All Investors | Daily Essay
05/17/2026

Say the word investor and most people picture money. Money is one resource among several you trade every day to close the gap between where you are and where you want to be.

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The Optimization Trap That Broke My Meditation Habit | Daily Essay
05/15/2026

I broke my meditation practice many times over fifteen years. The pattern was always the same. A working practice, the impulse to make it more efficient, and a feedback loop too delayed to catch in time.

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How to Get Out of Your Comfort Zone, Faster | Daily Essay
05/14/2026

Three types of experiments — mental, physical, social — cost different amounts of energy. The type you avoid most is usually the one to lean into next.

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Lee Kuan Yew: Engineered Sovereignty | Biography
05/14/2026

Lee Kuan Yew built one of the most efficient states in modern history and engineered the legal toolkit that kept his party in office for fifty-six years.

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Why I Rewrite My Principles by Hand | Daily Essay
05/13/2026

Each day I'd open my notebook and copy yesterday's principles to a new page by hand. Some lines I wrote without thinking. Others slowed me down.

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The Minimalist Philosophy of a Jellyfish | Daily Essay
05/12/2026

Each day I remove three things. A physical item, an app off my phone, a subscription on autopay. A jellyfish has no brain and has lasted 500 million years.

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Why Some Habits Stick: 12 Tardigrade Traits | Daily Essay
05/11/2026

I came up with a term to describe something I value. If tardigradity is the probability a thing keeps going, it has to come from somewhere.

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