Entrepreneurship
Founding, scaling, and stewarding companies built to last.
“Helping founders build enduring companies and lives of consequence.”
Over the last two decades, I have founded four companies, advised more than a hundred leadership teams, and spoken to audiences in twenty-three countries about building work that matters.
I grew up in a small town outside Boston, the son of a schoolteacher and a carpenter. My first business was a paper route with twelve clients and a hand-drawn logo. Everything I've built since has followed the same three rules: work you'd be proud to sign, people you'd trust with your family, and a purpose worth the years it takes.
Today I lead Northwind Capital, sit on four boards, and spend the rest of my time writing and speaking on leadership. My work has been covered by The Financial Times, Forbes, and the BBC, but the metric I care about most is the founders who tell me, years later, that something we discussed changed the shape of their company.
Build enduring institutions that outlive their founders.
A generation of leaders measured by the health of what they leave behind.
Craftsmanship, candor, patience, and quiet excellence.
The best leadership feels ordinary from the inside and inevitable from the outside.
Bootstrapped a research studio serving early-stage founders across New England.
Joined the executive team and led product across three continents.
An investment firm backing patient, founder-led businesses.
A book on leadership, hospitality, and the craft of building companies.
‘Why the best companies feel like homes,’ viewed more than 2M times.
A residency for underrepresented founders across four continents.
Founding, scaling, and stewarding companies built to last.
One-to-one work with CEOs navigating consequential decisions.
Keynotes on leadership, craft, and the long game.
Board seats and quiet counsel to founder-led businesses.
Patient capital for companies that treat quality as a discipline.
Books, essays, and letters on the practice of leadership.
Patient capital for founder-led companies in hospitality, media, and consumer goods.
Visit website →A research and strategy studio for early-stage teams navigating their first inflection.
Visit website →An independent press for books at the intersection of craft, leadership, and place.
Visit website →A residency and grant program for underrepresented founders in emerging markets.
Visit website →A yearly residency for twelve underrepresented founders across four continents.
Learn more →A quarterly print journal on craft, leadership, and the businesses that outlive us.
Learn more →A private gathering of thirty founders held twice a year in the Scottish Highlands.
Learn more →I speak to executive teams, industry associations, and universities on leadership, craft, and building companies that endure. Recent audiences have ranged from thirty CEOs in a private dining room to twelve thousand at a global summit.
On leadership, hospitality, and the craft of building companies.
Twenty years of notes on patient capital and enduring institutions.
A collection of correspondence, published annually.
An annual survey of 600 founder-led companies worldwide.
Alexander is the rarest kind of advisor — one who improves the caliber of your thinking without ever raising his voice.
His counsel changed the trajectory of our company, and the tenor of how we lead it.
Few speakers leave a room quieter than they found it. Alexander does, in the best possible way.
For 'Quiet Compounding'.
Recognition for contribution to founder-led capitalism.
For contributions to leadership practice.
For patient-capital returns in consumer sectors.
Full-tuition residency and grant program for underrepresented founders.
Environmental restoration across 3,200 hectares in the American Northeast.
Books, teachers, and libraries for rural schools in East Africa.
Pledge of 20% of lifetime carry to education and healthcare.
For speaking, advisory, and press inquiries. My team reads every message and responds within two business days.