Will Hill (@heywimo) header
Will Hill (@heywimo) profile picture

Will Hill

@heywimo

A man in the city

 Duluth, GA
Joined June 2025
  • Tweets66
  • Following23
  • Followers13
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Photo by Will Hill (@heywimo)Photo by Will Hill (@heywimo)Photo by Will Hill (@heywimo)Photo by Will Hill (@heywimo)Photo by Will Hill (@heywimo)Photo by Will Hill (@heywimo)Photo by Will Hill (@heywimo)Photo by Will Hill (@heywimo)Photo by Will Hill (@heywimo)Photo by Will Hill (@heywimo)
At one of our civic discussion meetings, we showed the Not Just Bikes video on the @strongtowns "Growth Ponzi Scheme" with our mayor, city manager, and planners in the room. Both officials argued vigorously that the premise was completely inaccurate, sparking an intense back-and-forth debate. Disagreement is part of the work. The point of gathering isn't unanimous agreement—it's getting local leaders and residents in the same room talking seriously about the systems shaping our town.
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3 AI Prompts That Turn Your Messy Financials Into An Approved Commercial Loan

3 AI Prompts That Turn Your Messy Financials Into An Approved Commercial Loan

Article · @heywimo
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Cars were speeding down our wide street right where a dozen neighborhood kids play outside, so I tried a bit of tactical urbanism. I spent $130 on a heavy-duty, road-grade pedestrian crossing sign with a rubber base and placed it directly in the middle of the road to force traffic to slow down. Public works confiscated it. But after a phone call and kicking up some fuss, I picked it up from the dump—and put it right back in the street.
Image from Will Hill (@heywimo)
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3 reasons you should talk to strangers: - You open yourself up to chance encounters - You broaden your horizons - You never know, you may make a friend. One strangers book recommendation changed my whole life.
A screenshot essay titled 'That book recommendation I took from a stranger on the street that changed my whole life.' The essay recounts a chance encounter in Duluth in 2025, where the author meets Jonathan, who introduces them to Nassim Taleb's work. Initially dismissive, the author later buys Taleb's 'Fooled By Randomness' and struggles to engage with it during a camping trip due to its complexity. However, after giving it another chance, the author finishes it and the entire 'Incerto' collection in 3 months, finding immense value in the ideas presented. The essay explores themes of randomness, risk, and personal growth, highlighting the transformational impact of Taleb's writing on the author's perspective.

ALT A screenshot essay titled 'That book recommendation I took from a stranger on the street that changed my whole life.' The essay recounts a chance encounter in Duluth in 2025, where the author meets Jonathan, who introduces them to Nassim Taleb's work. Initially dismissive, the author later buys Taleb's 'Fooled By Randomness' and struggles to engage with it during a camping trip due to its complexity. However, after giving it another chance, the author finishes it and the entire 'Incerto' collection in 3 months, finding immense value in the ideas presented. The essay explores themes of randomness, risk, and personal growth, highlighting the transformational impact of Taleb's writing on the author's perspective.

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When starting a local civic group, attendance will swing wildly at first. Some people RSVP immediately. Some come once and never return. Others ignore the invites entirely. The real key is consistency: 1. Keep sending out the invitations 2. Show up every single month to greet whoever walks in 3. Give conversations room to deepen Over time, the noise clears and a dedicated core group emerges.
Graphic: 3 things I've learned starting a Strong Towns Local Conversation

ALT Graphic: 3 things I've learned starting a Strong Towns Local Conversation

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3 morning habits that shape my life: - Getting up at 5:30am - Shunning my phone - Embracing solitude If you're a father of young kids, these will be game changers for you.
Screenshot essay titled '3 Morning Habits for Young Dads That Will Change Your Life'. The essay discusses the challenges of balancing family and personal life as a young dad. It highlights three key habits: getting up early at 5:30 am to gain an uninterrupted hour for personal reflection, avoiding phone use until after spending time with God, and embracing solitude in the morning to clear the mind before daily demands. Each habit is explored in detail, emphasizing their impact on daily life and mental clarity.

ALT Screenshot essay titled '3 Morning Habits for Young Dads That Will Change Your Life'. The essay discusses the challenges of balancing family and personal life as a young dad. It highlights three key habits: getting up early at 5:30 am to gain an uninterrupted hour for personal reflection, avoiding phone use until after spending time with God, and embracing solitude in the morning to clear the mind before daily demands. Each habit is explored in detail, emphasizing their impact on daily life and mental clarity.

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People like to think they are in control of what happens in their lives, but being outnumbered by kids shatters that illusion fast. It reminds me of the Three-Body Problem in physics: When you have two inputs into a system, you can predict outcomes relatively easily. But the moment a third body enters the system, predictability disappears. Small shifts create massive, unexpected ripples. With three kids, you don't control the system—you just learn to navigate the unpredictability.
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Lawns are pretty but they're mostly wasted, expensive space. Think additionally about the amount of money and time we spend maintaining them. We'd be better off using our lawn space to build cottages and ADUs to alleviate the housing affordability crisis
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When you have a five-year-old and a two-and-a-half-year-old, the baby is actually the lowest maintenance child in the house. The older two are the hard part. The difficulty comes in short, intense bursts. Sometimes all three kids melt down at the exact same moment and there's nothing to do except look at each other and laugh. Caring for three kids can feel like moving mountains at times, but you adapt and figure out how to manage the chaos.
Image from Will Hill (@heywimo)
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AI ushers in a new golden age of entrepreneurship. 1. Quicker deployment of ideas. 2. Upfront professional costs basically zero. 3. Regulatory expertise becoming commoditized. Opportunities are coming that we can't imagine.
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Queenstown is beautiful and sad: - Most places sit empty with absentee owners - Employees of businesses can’t afford to live there - Losing some of the down home kiwi culture I’d still love to visit though.
✶ (@echoesofworld) profile picture✶
@echoesofworldOct 30
Queenstown, New Zealand
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Once you read Black Swan, you will begin seeing model error everywhere and these things will cease to surprise you. You can instead position yourself for positive convexity.
Nassim Nicholas Taleb (@nntaleb) profile pictureNassim Nicholas Taleb
@nntalebOct 28
Every time I hear "10 sigma" event...
Image from Nassim Nicholas Taleb (@nntaleb)
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3 reasons relationships still matter in banking. 1. You need someone there when things go wrong. 2. Building trust with a bank will afford you more flexibility in the long term. 3. The more a banker knows your business, the better they can represent you when it matters. You can invest in technology and platforms all day long, but at the end of the day it's all about trust.
A screenshot of a text essay titled '3 reasons the bank turned down your commercial loan request.' The essay discusses common pitfalls that may lead to loan rejection, illustrated through three main reasons: 1) Funding the wrong thing, emphasizing mismatched loan terms and a lack of clear financial application. 2) Lack of dependable history, highlighting the importance of stability, predictable margins, and consistent spending patterns. 3) Taking too much out, stressing the need for reinvestment in the business and warning against distributions exceeding net income. The author concludes that banks prioritize their ability to be repaid and that business owners must showcase their repayment capability.

ALT A screenshot of a text essay titled '3 reasons the bank turned down your commercial loan request.' The essay discusses common pitfalls that may lead to loan rejection, illustrated through three main reasons: 1) Funding the wrong thing, emphasizing mismatched loan terms and a lack of clear financial application. 2) Lack of dependable history, highlighting the importance of stability, predictable margins, and consistent spending patterns. 3) Taking too much out, stressing the need for reinvestment in the business and warning against distributions exceeding net income. The author concludes that banks prioritize their ability to be repaid and that business owners must showcase their repayment capability.

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Three reasons financial statement quality matters: 1. Underwriters will find your inconsistencies 2. It helps your credibility with the bank 3. You get better visibility in your own business Messy books will be your achilles heel when looking for credit.
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3 reasons the bank turned down your commercial loan request: 1. You're funding the wrong thing. 2. Lack of dependable history. 3. You're taking too much out. Banks want to see steady cashflow staying in your company.
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3 tips for executing change in your neighborhood. Find a quick solution. Go for it. Iterate. Small steps will build upon each other.
Screenshot essay titled 'I put a $130 crosswalk sign in the middle of my street, here's what happened.' The essay discusses a resident's frustration with speeding cars in their Duluth, GA neighborhood, prompting them to place a large, reflective crosswalk sign in the street as a tactical urbanism experiment. It details the features of the sign, its immediate impact on traffic, and the city's response that led to the sign's confiscation. Despite initial setbacks, the author shares positive feedback from neighbors and highlights the increased safety for children playing in the area and improved community morale.

ALT Screenshot essay titled 'I put a $130 crosswalk sign in the middle of my street, here's what happened.' The essay discusses a resident's frustration with speeding cars in their Duluth, GA neighborhood, prompting them to place a large, reflective crosswalk sign in the street as a tactical urbanism experiment. It details the features of the sign, its immediate impact on traffic, and the city's response that led to the sign's confiscation. Despite initial setbacks, the author shares positive feedback from neighbors and highlights the increased safety for children playing in the area and improved community morale.

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3 reasons why I helped start Duluth's Strong Towns Local Conversation: 1. I believe in the city. 2. Staff and elected officials care. 3. Duluth has great bones. "Never doubt that a small group of thoughtful, committed citizens can change the world; indeed, it's the only thing that ever has."
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Day 15 of 🚢 Ship 30 for 30 Here’s my Digital Brain inside of Typeshare. Based on my data-driven niche selection, I am committing to writing more about Community Building.
Image from Will Hill (@heywimo)
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How I used ChatGPT to win an $80,000 Defense Contract and almost lost my shirt.

How I used ChatGPT to win an $80,000 Defense Contract and almost lost my shirt.

Article · @heywimo
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Is it really that hard to have another kid? 3 lessons I've learned since having our third baby.

Is it really that hard to have another kid? 3 lessons I've learned since having our third baby.

Article · @heywimo
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