Insights
Analysis and observations on WealthTech strategy, product leadership, and commercial execution.
The Business of Building
Where technical decisions meet the P&L.
The Onboarding Problem Is a Revenue Problem
Wealth management spends billions optimizing portfolios and basis points — then loses clients to a PDF intake form. The highest-leverage moment in the client relationship is the one nobody has redesigned.
The 5-Month and $5M Button
Why the real constraint on wealth management innovation is not the front end — it is everything beneath it
Bodies and Buried Treasure
I see hype about how cryptocurrency frees people from a malicious government seizing your assets.
Deprived of Agency
I’ve had experience working on the phone and in the management of call centers.
Keeping government simple
I spend a lot of time thinking about user experience. When I build something, I want it to be simple and clear for the people using it.
Vanguard, Wealthfront, and the Fight for the Future of Retirement
For the average investor, investing in the stock market is pretty similar now to the 1950’s — it’s faster and cheaper, but not too different.
Robin Hood and His Merry Robo-Advisors
(image removed - originally hosted on Medium) There are a lot of young brokerage and wealth management companies starting today with a modern technology...
The Commercial Edge
Market structure, pricing power, and the anatomy of a deal.
Bye line
Journalism is going through a fascinating transition.
Replacement Level Marketing
Small teams have more reach than ever before, and can build huge businesses with very few resources.
The spice must flow
It’s been an amazing month for business news.
Thoughts on keys to career success post 2019
Some thoughts about what skills are becoming more valuable: The best jobs are getting more cross-functional: know business, marketing, product, design,...
We go for the uncompromised
“The compromise part of the market is very well serviced,” Burmeister says. “So we go for the uncompromised.
The Lab
Hands-on builds, applied to business problems.
What Would You Say You Do Here?
The articulation gap limits both your career and your AI effectiveness. A structured interview tool built for context engineering revealed something unexpected about self-knowledge.
The Best I Could Build in a Week
A week-long prototype proves the advisor desktop is the easy part — and the $5M infrastructure beneath it is the real constraint
Taste and Connection
AI commoditizes replacement-level work. The winning move is taste — and building an audience that trusts yours.
The Knowledge Gap in AI Finance Tools
Workflow automation and domain knowledge are two different layers in AI-assisted finance. Most teams are building one. Almost nobody is building both.
Mental Muscle Memory
Parenting makes you think a lot about your outlook on the world, especially as your kids come to you with things they hear from their friends that may not...
My take on coaching a team
Some quick thoughts on coaching a team: give people clear ownership and get out of the way give people room to stretch outside that area of ownership, so...
The end of truth
We think we are already in a post truth world, but we are barely starting down the path. There are tools that can already fake anyone’s voice or face.
Slow News
The “old” adage on the internet is that “information wants to be free”.
More Writing
Essays on media, policy, and working life — written along the way.
Bad Policies for the Cash Poor
Space war
Slow News Revisited
How to win with persistence
Reshaping our environment reshapes our behavior
Lessons on Writing from Michael Lewis
How 2018 Changed my Media Consumption
Strong verbs, short sentences
What a $3 Million Campaign Donation Buys
Bannon, ISIS, and the Clash of Civilizations
Trump’s America: What I am Watching
A reflection on the peril of raised expectations as I wait for my Verizon repairman
Universal Basic Income and Exploding Knowledge
A robots native tongue
Foundations for the Future
Debt We Must Pay
Archive: 2009–2013 — early writing on economics, policy, and whatever caught a student’s eye.
2010
- Battle of the Bulging Middle Class
- Shooting Ourselves in the Foot
- Privacy is a Thing of the Past
- Data is Changing Everything
- Estate Tax and Meritocracy
- Imaginationland and Intellectual Property
- Information Tech and the Future of Government
- Moderates Make Man-Bear-Pigs
- Political Polarization
- A Look Inside the Tea Party
2009
- If something can’t happen, will it?
- Putting It All Together
- The Passion of the Banks
- Requiem For A Firm
- Creative Destruction and Government
- Trading in the Fast Lane
- The Black Swan by Nassim Taleb
- Could We Change Finance?
- I Must Be Taking Crazy Pills…
- The Big Bad Wolf in Finance
- Freedom to Act (like an idiot)
- The Fat Tail by Ian Bremmer and Preston Keat
- Financial Fix
- The Perils of Paying for Handholding
- Banking Reform Proposal
- A History of God by Karen Armstrong
- Why Finance (Salaries) Won’t Change