What does it take to build a meaningful business and a fulfilling life? For Max Monks, it comes down to embracing the grind, staying curious, and treating people well along the way.
In this episode, Ben Rodgers sits down with Max Monks, Founder and Managing Partner of Keeper Bay Real Estate, to explore the experiences and philosophies that have shaped his approach to business, leadership, and life. From an early ambition to join the CIA and an unexpected career path to building a business at the intersection of real estate, healthcare, and private equity, Max shares how curiosity, preparation, and a willingness to pursue new adventures have opened doors.
Show Summary
This episode of At Depth welcomes Max Monks, founder and managing partner of Keeper Bay Real Estate, a fellow Mainer who grew up in a real estate family and spent the early part of his career trying to do something else. Max shares the story of his youthful plan to join the CIA: studying Arabic, spending a year in Jordan, and living in Spain and Geneva before business school, a consulting career, and the start of the pandemic led him back to the family business with a very different perspective. Host Ben digs into the idea of visualizing a "dumb, fun" idea, falling in love with it, and then chasing it — from earning a pilot's license to sitting in a major investor's office and realizing how far he was from Vassar.
From there the conversation turns to the grind. Max explains that the journey is the grind — the boring, mundane work that fills ninety-eight percent of the time — and that you have to genuinely like it without being masochistic about it. He and Ben talk about humor as a remedy for stress, why "the graveyards are filled with indispensable men," saving the real worry for the truly big things, and how staying calm helps a whole team stay creative instead of going into fight-or-flight. Max also shares how he balances work and family in Maine and why variety makes the daily work enjoyable.
In the second half Max explains Keeper Bay's niche: owning the real estate underneath private-equity-backed veterinary and other clinical practices, and juggling the very different worlds of investors, vets and bankers. He credits luck, preparation and a client-first mindset — treat everyone, from the banker to the vet to the limited partner, as you would a client. The two close on how the world changes incrementally, why money and time are our "votes," and why the answers are often simpler than we think: be nice, treat people with dignity, and control what you can touch.
Show Notes & Links
Links
Investment Concepts & Strategies Referenced
Relationships first, real estate second — Keeper Bay's service-first philosophy: treat everyone like a client.
Visualize it, chase it, then enjoy it — take a "dumb" idea out on a few dates, and after enough reps you start to smell which visions can become real.
Keeper Bay's niche — real estate beneath veterinary and clinical practices, serving private equity, vets and bankers at once.
Money and time are our votes — small incremental choices change the world, like a forest growing inch by inch.
Cultural / Conceptual References
The CIA daydream — a youthful fantasy to test his mettle led Max to Arabic, a junior year in Jordan, and an adventure that built lasting confidence.
The journey is the grind — most of life is mundane, and epiphanies come inside the grind; you have to like it (but don't complain about it).
The graveyards are filled with indispensable men — a reminder not to take yourself too seriously.
Humor as a remedy — work is a bit of a play; save the real worry for the big stuff.
Stress shrinks creativity — staying calm keeps you able to see many options instead of just A or B.
Reduce other people's stress — a manager's key job; don't try to be happier than happy.
Habit or personality? — a high tolerance for uncertainty and a knack for managing anxiety.
Balance and variety — keeping work and family separate, and variety in the day, makes the grind enjoyable.
It's better to be lucky than good — preparation meets opportunity.
Be nice, treat people with dignity — even when firing someone; the answers are simpler than we think.
