Founder advisory
For when the hard decision is yours alone.
I advise a small number of startup founders on the decisions that don’t fit anyone’s job description—executive hires, board conversations, broken orgs, or big bets about what comes next.
The decision is yours. It doesn’t have to be lonely.
Founders are surrounded by smart people, but almost everyone has a role to play and an outcome they want. Your board has a governance job. Your investors have a portfolio. Your team needs conviction and clarity. Some decisions don’t belong cleanly to any of them.
Alex stays on top of AI in ways that are hard to do when you’re running a company, and brings the experience of building and scaling businesses to make sense of what matters. He also gives me a place to work through the things I can’t discuss with my board or team, with the technical depth to make those conversations useful.
I stay close enough to understand how the product, people, capital, and narrative fit together, then help you make the decision that’s actually yours.
What that looks like
You choose the problems we tackle. My mission is to make our time the most useful hour of your week. Here are a few examples of where that work has led.
Was there a bigger company hiding inside the product?
I proposed Duckbill’s first MCP integration so AI agents could hand off real-world tasks to Duckbill assistants, then worked alongside the team through the soft launch. That experiment has become central to Duckbill’s evolving B2B strategy, opening a new path for growth.
Taking on marketing through the Series B and C
When Wheel’s marketing leader left as I joined as Chief of Staff, I took on marketing and communications for more than a year. I led the fundraising narrative through the Series B and C and built the strategy and planning function. During that period, monthly bookings grew nearly 6× and the organization grew 4×. I recruited the permanent CMO and handed her the function.
Forging a strong, sustainable path for the founder
At Firesale, I helped shape a crowdfunding campaign, worked through hard team changes with the founder, and supported bringing in a fractional product leader. When a merger became the stronger path, I pressure-tested the terms. The deal preserved meaningful founder ownership and paired him with a compatible co-founder.
Pattern recognition, without the playbook.
Before advising founders, I spent more than six years at Uber, joining as employee 35 and leaving after it had grown past 25,000 people. Since then I’ve been a Chief of Staff, a marketing leader, an operator, and an advisor inside companies navigating growth, fundraising, leadership changes, and strategic pivots.
I don’t work from playbooks—the world is moving too fast for off-the-shelf advice to keep up. What my 16+ years have given me is pattern recognition.
Outside my advising, I’m also an operator and investor. I’m building software and AI projects, blending my own vermouth, and even tinkering with hardware. You can see some of what I’m building here.
Alex wasn’t someone I talked to once a quarter and got a polished deck from—he was in the trenches with me every week, texting, pushing, challenging assumptions, and helping me work through the ugly parts of building a company. More than once he told me something I didn’t want to hear but absolutely needed to hear, and that’s what I valued most—he wasn’t trying to make me feel good, he was trying to make the business better.
How I work
Most of my work is ongoing founder advisory: weekly conversations, async access when something can’t wait, and enough continuity that I don’t spend the first half of every meeting relearning your business. You get a fraction of my brainspace, all the time—not a consultant showing up cold.
I don’t filter by funding stage or revenue. What matters is whether you’ll let me see the messy parts. Not the board deck version, the real thing. That’s how I give good advice.
Sometimes the right starting point is narrower: a concentrated decision sprint around one consequential choice, or a short audit and build focused on how AI could change the way your company operates.
Start with a decision.
Tell me one of the big decisions you’re facing and why it matters now. I read every note personally.