Michael Boguslavskiy
[§]About · The long version

[§] Who I am

Hello.I'm Michael.

Twenty years across web, marketing, print advertising, paid, email, and now AI. I run businesses, build the systems behind them, and write notes about the work from the airplane seat. NYC. Husband. Father.

Based
New York · 40.71° N
Working since
2006
Disciplines
Web · Marketing · Ops · AI
Portrait of Michael Boguslavskiy
⌘ M.B. · NYC

[§ 01] The arc

Twenty years, four hats, one desk.

The discipline I'm running on a given day is whatever the work in front of me needs. The path that got me here was never a straight line. It's an integration story, told in four eras.

  1. 2006 → 2012

    [01]

    Generalist

    Learning the whole stack the hard way

    Started building websites for small businesses out of New York under my own brands, Next Designs (free web hosting included) and then Rapid Purple. LAMP, WordPress, classic ASP, my own servers, whatever the work needed. I wrote about it publicly the whole time, hundreds of posts from PHP and C tutorials to candid host reviews. The pattern that stuck with me from those years: a site is never finished, it's adopted. The businesses that won were the ones whose owners actually used what we built. The rest collected dust no matter how clean the code was.

  2. 2012 → 2020

    [02]

    Marketer

    Media Explode and the agency years

    Media Explode was, and still is, a marketing shop running campaigns for SMBs across NYC and beyond. Print, social, email, paid, promo. Restaurants, retail, professional services. Over a decade of running marketing for owners who read every receipt taught me what actually moves the needle versus what looks good on a slide.

  3. Long before the brand

    [03]

    Operator

    Caballeros Vacations and the operator hat

    For years I sold travel as an independent agent under my own name, mostly for friends and family, before I ever made it a brand. Caballeros is what happened when I grew it into a real agency and went full-time. That is where I learned what it actually feels like to run an operating business instead of marketing someone else's: complex logistics, real-time vendor coordination, customers who notice the second anything is wrong. Running my own books changed how I work with everyone else's.

  4. 2024 → now

    [04]

    Integrator

    AI-augmented, all four hats

    Now I consult with business owners who want AI in their work without becoming engineers themselves. The work draws on every previous era: web for the substrate, marketing for the audience, operations for the workflow, AI for the leverage. I run all of it inside my own businesses too, the same way I set it up for clients. I use what I sell.

[§ 02]

Outside the work.

Husband. Father to a young son who has already taught me more about systems thinking than any framework. We're a Disney family, which is why there are Hidden Mickeys scattered through this site and why my son's first international trip was a Caballeros booking (I get a discount).

Born, raised, and based in New York. Outer-borough sensibility, Manhattan tolerance for traffic. The kind of New Yorker who actually likes the subway and has opinions about cross-bridge routes. The 40.71° N · 74.01° W you keep seeing in the corners of this site is the desk these systems get built from.

Outside the desk: a serious automotive enthusiast (the kind who reads spec sheets for pleasure), a cycling fanatic when the weather and the calendar allow, and someone who genuinely enjoys travel even when it's for work, particularly the part where I get to see how other places run their operations.

I build my businesses to be the kind I want to run for the next twenty years, not the kind that fund the next exit.

[§] Let's work together

Have a project? Let's talk.

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