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Jonathan Stern

Hi, I'm Jonathan Stern. Now: Thinking through that... Previously: I was a software engineer (employee #6) at Topline Pro. Before that: I wrote about...

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Old People

On Sunday, I was reminded of how wonderful it is to spend time with old people. I went to breakfast with my landlord and his wife. We talked about my time in Boston. What it’s like to be married for 55 years. Travels to Egypt and Peru and China. Boston’s parks. Why the new Copley Square is such a disaster. What it was like to live through the Big Dig. We talked about love. I'd never met M & A…

The San Francisco corner store

I've been living in SF for two months now -- going to this corner store called Rudily's nearly every day for four weeks. It's been my go-to shop for everything. Protein bars, apples, Gatorade after long runs, Ben and Jerry’s ice cream. And most of all: the famous “Gus Special” sandwich. Today being my last day in SF, I decided to have a longer conversation with the guy in charge. He’s this gruff…

It’s not goodbye, it’s see ya later

For the last 2.5 years, Topline Pro has been the thing I couldn’t wait to jump out of bed to work on. The thing I dreamed about, woke up in the middle of the night excited about, complained about, screamed about, laughed about, argued about. I was obsessed. I’ve always been ambitious but until I started at Topline Pro, my ambition was theoretical. Abstract. I knew I had it in me but was unsure of…

I'll miss the locals

In just one week, it will be time to say goodbye to Boston's North End, the neighborhood I’ve called home for five years and one of the most magical paces on earth. As I prepare to leave, I’ve been reflecting on all that I’ll miss -- the skinny alleyways and cobblestone streets, the smells of garlic on summer evenings, the rich history. Once, I even convinced a girl to go out with me by telling…

Learning to code

Growing up, I never wanted to be “technical”. I never thought I could be. The problem was self-perception. I didn’t see myself as “the sort of person” who grew up to be a software engineer. Sure, I placed top three at state math competitions and went to summer camps for game theory + physics. But that was nothing compared to people who could TALK TO COMPUTERS ... they were another species! Then,…

A theory of ambition

In January, I posted the following question on Twitter. “What makes a person high-ambition vs. low-ambition? Is it more nature or nurture?” I tagged Paul Graham and Rob Henderson, thinking at least one might respond. Neither did! So I decided to come up with my own ideas. Mostly they're the result of introspection plus thinking about friends from high school, college, and here in Boston. Extreme…

Polymarket is company of the year

I predict Polymarket will be the most important company to go mainstream in 2024. Polymarket is a prediction market that allows users to bet on world events: politics, news, culture, tech. It's been said that Polymarket is “the next generation of news”. This is true, but with a caveat. Twitter is where the news happens . Polymarket is the 24/7 marketplace that predicts the news and sets the odds.…

Writing online

I recently asked myself: why the hell am I doing this? I don’t have an Instagram. I haven’t posted to Facebook in a decade. Sharing my inner thoughts with the world feels unnatural. Almost icky. Plus, I'm worried it may be feeding something unhealthy. A longing for approval, likes, love. And yet here I am putting more words out there. Why? I’ve long thought of the best writers as magicians. They…

What if engineers had incentives, too?

I’ve yet to meet an engineering team that over-delivered on its commitments. -Praveen Seshadri (ex-Google) Given this, I think engineers should be open to experimenting with different incentive schemes, with a goal of boosting either quantity or quality. Quantity is the obvious one. Say an engineer is given 15 points of tickets at the beginning of a sprint. If that engineer delivers 20 or 25…

$7/month

$7 isn't good for much these days. Maybe a couple coffees. A pair of socks. Half of a sweetgreen salad... And yet, if spent wisely, $7 can change your life. I was reminded of this yesterday upon encountering essayist Henrik Karlsson's three-part series about love. I’ve read a lot of essays this year. And a lot of essays about love: Tim Urban on how to pick a life partner Scott Alexander on why we…