§ 01 — Writing
Writing
Mostly ecommerce and software. Some of it is what worked. A fair amount is what didn't, which tends to be the more useful half.
shopify12exposely11liverecover10platform risk7acquisitions5ecommerce5media buying5vigilance5bootstrapping4careers4distribution4marketplaces4sms4fundraising3influencer marketing3shutting down3business models2data2exits2founders2internet research unit2learning2myspace2operations2orderbump2pricing2sales2app store1attention1categories1competition1demand1disintermediation1growth1hiring1launch1liquidity1los angeles1luck1marketing1meta1portfolio1press1process1products1reputation1scale1writing1
Note — 40 of these are marked [archive]. I've been writing about this work since 2013, but almost all of it went into X threads that I can no longer find. Those posts are dated to when the thinking happened and were reconstructed in 2026 from notes and whatever I could recover. They weren't published at the time, and each one says so at the top.
2026
4 posts- 3 min
The platform can change its mind
Vigilance was working. Then Shopify deprecated the one file the whole product ran on. Here's what I'd price differently next time.
shopify · platform risk · shutting down
- 2 min
I sold OrderBump four months after I bought it
Bought it in October, sold it by February, then spent months handing it over. I've had people ask me how to repeat this. You mostly can't.
acquisitions · shopify · luck
- 2 min
What bootstrapping actually bought us at LiveRecover
We were one of the only SMS apps at that scale without investors. The advantage wasn't the equity. It was who was allowed to call us.
bootstrapping · sms · exits
- 1 min
Why this site exists
I've been posting on X since 2009. Nothing I wrote there survives, and none of it is mine.
meta · writing
2025
2 posts- 3 min
[archive]I took a job at Shopify
Seven years building on a platform, and now I work for it. The obvious question is what happens to the way I write about platform risk.
shopify · careers · platform risk
- 3 min
[archive]A portfolio of small apps
Three Shopify apps at once instead of one company. It's a worse story and, so far, a better structure.
shopify · portfolio · products
2024
3 posts- 3 min
[archive]The compounding return on staying put
Six years in one ecosystem. The advantage isn't expertise — it's that deals get shown to you before they're deals.
shopify · reputation · careers
- 3 min
[archive]Selling data to people who think they have data
Every buyer for IRU already has dashboards. The sale isn't about more data. It's about the difference between your numbers and the market's.
internet research unit · data · sales
- 3 min
[archive]Building something that isn't a tenant
Four companies on someone else's platform. This one takes data from across the whole industry instead of through one company's permission slip.
internet research unit · platform risk · data
2023
3 posts- 3 min
[archive]Offering the money back
We shut Vigilance down and offered our investors their money back. Several people told me that was a mistake. Here's the reasoning.
shutting down · vigilance · fundraising
- 3 min
[archive]How to read a deprecation notice
Shopify is deprecating checkout.liquid. I'd been reading that roadmap for a year as industry news. It was a countdown.
platform risk · vigilance · shopify
- 3 min
[archive]The first good month
Vigilance is working. Plus merchants are signing up and the math isn't a stretch. I've been here before and I know what it does to your judgment.
vigilance · shopify · growth
2022
3 posts- 3 min
[archive]Shipping into the app store in December
We launched Vigilance publicly in November and hit the Shopify App Store in December. Launching into peak season is either the best or worst timing available.
vigilance · shopify · launch
- 3 min
[archive]Raising money for the first time
Two companies, no outside investors, and then this year I raised about $250,000. I wanted the names more than I wanted the cash.
fundraising · vigilance · shopify
- 3 min
[archive]What a handover actually costs
I've now been on both sides of a transition. The sale date is a milestone in the deal and it's the beginning of the actual work.
acquisitions · orderbump · operations
2021
3 posts- 3 min
[archive]I just bought a Shopify app
Buying a small software business is a different skill than building one. Here's what I actually looked at before closing on OrderBump.
acquisitions · shopify · orderbump
- 3 min
[archive]A year of answering questions
We sold LiveRecover this summer. The process started in Q3 of 2020 and I was not prepared for how much of it was just documentation.
acquisitions · liverecover · exits
- 3 min
[archive]Three years of humans in the loop
We bet that a person having a conversation beats an automated sequence. Here's what actually held up and what I'd concede.
liverecover · sms · operations
2020
3 posts- 3 min
[archive]When acquirers start emailing
Every founder with any traction gets these. Most of them are not offers, and learning to tell the difference is worth doing before you need to.
acquisitions · liverecover · process
- 3 min
[archive]Getting outfunded in your own category
SMS marketing got funded. We didn't. Watching companies with tens of millions enter your market teaches you what money can and can't buy.
bootstrapping · competition · liverecover · sms
- 3 min
[archive]The month ecommerce changed shape
Everyone in this industry just got handed a demand shock they didn't earn. The interesting question is which part of it stays.
ecommerce · liverecover · demand
2019
3 posts- 3 min
[archive]Hiring when it's your own money
I've under-hired at every company I've run. It isn't caution and it isn't discipline. It's that a salary feels like a personal expense.
bootstrapping · hiring · liverecover
- 3 min
[archive]Charging for performance
Taking a cut of recovered revenue is the easiest thing in the world to sell and the hardest thing to run a company on.
pricing · liverecover · business models
- 3 min
[archive]The app store is a search engine
Most app developers treat their listing as a brochure. It's a ranked result page, and the ranking is most of your business.
shopify · distribution · app store
2018
3 posts- 3 min
[archive]Picking Shopify as a landlord
I've watched every platform I ever relied on change the rules. I just built a company inside one on purpose, and I want to write down why.
shopify · platform risk · liverecover
- 3 min
[archive]Selling to merchants instead of marketing directors
At Exposely I sold to people spending someone else's money. Now I sell to people spending their own. It changes every part of the pitch.
sales · liverecover · ecommerce
- 3 min
[archive]Abandoned carts are a people problem
Everyone treats cart abandonment as an automation problem. We started LiveRecover on the theory that it's a conversation someone didn't have.
liverecover · sms · ecommerce
2017
3 posts- 3 min
[archive]Media buying is a window, not a career
The best media buyers I know are worried about the same thing, and they're right to be. The platform is coming for the job.
media buying · careers · platform risk
- 3 min
[archive]What a million a month looks like
I consult on about $1M a month in ad spend. The surprising part isn't the scale. It's how few of the decisions are about advertising.
media buying · ecommerce · scale
- 3 min
[archive]Going back to a job after being the CEO
I ran a company for three years and then took a media buying seat at an agency. The ego part was real and it was over faster than I expected.
careers · media buying · founders
2016
3 posts- 3 min
[archive]Every platform I built on is gone
I started on MySpace. I've since watched the ground move under every channel I've relied on, and I keep acting surprised.
platform risk · myspace · distribution
- 3 min
[archive]What marketing school got right
I was a marketing major for two years at two community colleges and I've spent a decade being smug about it. Some of it was load-bearing.
learning · marketing · media buying
- 3 min
[archive]The quiet part of winding something down
Nobody writes the post about the company that didn't die dramatically. It just stopped being the best use of everyone in it.
shutting down · exposely · founders
2015
4 posts- 3 min
[archive]When your supply side outgrows you
The best people on the marketplace stop needing the marketplace. That's not churn. It's the business model reaching its ceiling.
marketplaces · exposely · disintermediation
- 3 min
[archive]Building this in Los Angeles
Everyone told me to move to San Francisco. For this specific company, LA was the correct city and it wasn't close.
exposely · los angeles · distribution
- 3 min
[archive]We never raised money for Exposely
Not out of principle. Nobody was funding this category, and by the time I could have raised I'd built a company shaped like it never would.
bootstrapping · exposely · fundraising
- 3 min
[archive]The cold start problem nobody warned me about
Everyone tells you a marketplace is hard to start. Nobody tells you the hard part is that it looks like it's working.
marketplaces · exposely · liquidity
2014
4 posts- 3 min
[archive]Pricing a market where neither side knows the price
Sellers guess. Buyers guess. I built a marketplace on top of two guesses and spent a year finding out what that does.
pricing · marketplaces · exposely
- 3 min
[archive]Press is not distribution
Fast Company put me in a story this year. It was great for my mother and it did approximately nothing for signups.
press · exposely · distribution
- 3 min
[archive]I was the product before I sold it
I came up on MySpace with an audience. Now I sell access to people in that position, which gives me one advantage and one blind spot.
influencer marketing · exposely · myspace
- 3 min
[archive]This category doesn't have a name yet
Half my sales calls are spent explaining what the thing is. That's a cost, and it's also the only reason there's room for us.
influencer marketing · exposely · categories
2013
3 posts- 3 min
[archive]Four years of running my own stores
I didn't go to school for this in any way that counted. I bought traffic with my own money until I understood what it was doing.
ecommerce · media buying · learning
- 3 min
[archive]Why Exposely is a marketplace and not an agency
The agency version of this business would make money faster. It would also make me the bottleneck for every deal, forever.
marketplaces · exposely · business models
- 3 min
[archive]The follower count is the wrong number
Every brand that emails us asks how many followers they can buy. It's the one number that tells you the least about whether anything will happen.
influencer marketing · attention · exposely