How Aussie Founders Can Tax-Effectively Make the Jump to the US
The structures that can deliver a tax-free US$10M+ exit. Flipping up, QSBS, the E3 visa, and leaving Australia cleanly after the CGT changes.
Latest
Insights from a Boomerang
Insights from a Boomerang - Sunrise 2026 Talk
Boomerang Mode: Engaged
I'm heading to Sydney this week to talk at Sunrise about the experience of building a startup in the US. But this is my last trip as a visitor to my homeland because after 15 years away, I'm moving back home.
The Death of Story Points - How AI Finally Makes Agile Work
In the last month I shipped more working software than my team used to ship with five times the developers in six months. Here's why story points are finished, why Agile is finally about to work, and who's on the right side of the bifurcation that's coming.
How I Used AI to Pivot a Company in a Week
The thinking took weeks. AI compressed the execution into days.
The Signal That Made Me Pivot TeamScore Into WorkSights AI
Why I pivoted TeamScore into WorkSights AI - a founder’s lesson about product-market fit, revealed preference, and discovering the real opportunity.
Building with AI: Everything Except the Code
How I’m using AI to design, plan, analyze, and build a tech company - and why the most exciting things aren't happening in engineering.
75 Books in 12 Months
Today is Election Day in the US, and after the “shoot-self-in-the-other-foot” results came out this time last year, I decided the news - which for me was mostly podcasts - didn’t deserve my attention anymore. I’ve always been a news junkie - from being an early user of
The Corrosive Spiral of Poor Performance
In remote teams, poor performance isn’t just bad — it’s contagious. One disengaged person can corrode trust, effort, and culture faster than you think. Here’s what I learned the hard way about stopping the spiral before it spreads.
Fifteen Years of Paying It Forward
Every few months, I’m reminded just how special Startmate is - and Demo Day for the Winter 2025 cohort today is another one of those moments. It’s a celebration not just of another set of ambitious founders, but of the community that has quietly shaped the startup landscape
Chapter 4: Building Ascendius in Public with AI
After two decades building and running technology companies, I wanted to approach Chapter 4 differently - not by forgetting what I’ve learned, but by questioning everything I thought I knew, because I believe with AI, the rules have changed. That’s what Ascendius is about - and this post
The Analytics Trap
Analytics sounds smart and data-driven. But for most people, it’s just homework they’ll never do. Here’s why analytics is a trap for founders who build it - and for the leaders who buy it.
Fixing the Machine: The False Trade-Off Between Health and Success
It took me twenty-five years to realize that sacrificing health for business isn’t ambition - it’s a lose-lose deal.
Entrepreneurship
Kicking off Chapter 4
When I sold Accelo a year and a half ago, I promised myself something I’d never really given before: a break. Truth is, I wasn’t great at it. My family will tell you I failed miserably at "learning how to sit still." But spending more time
Entrepreneurship
The End of Chapter 3: Expert Mode
Earlier this month we sold Accelo, a company I co-founded 15 years ago, and last Friday was my last day at the company. With this transition, I wanted to share a few reflections on a massive journey, appreciation for the work of our amazing team and thanks for support of
Uncategorized
Deeply rooted in this Nation's (dark) history and tradition
The decision by the Supreme Court last Friday to overturn Roe vs Wade and eliminate a fundamental right of women in the world's leading democracy for almost 50 years is a shock but not a surprise. * To say that this is a massive deal for the United States
Personal
COVID Comparisons
Throughout the COVID-19 Pandemic there's been plenty of scary headlines, statistics and tragic individual stories. One thing I've rarely seen, though, is a comparative base for understanding the statistics that drive the scary headlines. To help with my own understanding, I've compiled a couple
E-3 Visa Renewal without Travel via I-129
Update March 2022do notrequires I'm the US right now in the midst of the COVID-19 pandemic and lockdowns/shutdowns across most of the economy. One of my friends and colleagues happened to have his E-3 visa expiring next week, and so the usual options of a visa dash
How to get useful feedback on your business idea
A startup mailing list I'm on recently had a customer-development survey link posted to it for an idea I thought was absolutely terrible. It is another "buy food from an app and have it delivered to you" product, but in this case they take inputs from
Apple Stole My Music. No, Seriously.
Apple. It just works.
Stopping Autoplay Videos on News Websites with Adblock Plus
Like many Aussie and Kiwi ex-pats I know, checking in on the news in the old country is both a habit and an escape, but the constant attempts by the old print media to "reinvent" themselves as broadcast/video media had lead to an irritating and increasingly prevalent
Uncategorized
Watching ABC's iView from outside Australia without a VPN
As an Aussie expat, it is a shame that all the awesome stuff on ABC's iView site is locked away. Aside from wanting to keep across what's going on back in Australia, there's truly world-class content produced regularly for 4Corners, Foreign Correspondent and stacks
Watching NBA without Blackouts or a VPN (and much more!)
As a big fan of the NBA (and particularly my adopted home town team, the Golden State Warriors) I was pretty excited to get into this year's season. While previous seasons have been aided by borrowing the Comcast credentials from a friend and streaming games via the CSN
Uncategorized
Advice for folks "putting my feelers out to find opportunities" in SF/Silicon Valley
From time to time someone will email (or be introduced via email) who's exploring career opportunities in San Francisco or Silicon Valley. Here's a variation of an email I recently wrote to answer this question - hopefully by putting this somewhere Google can find it I