A stranger at a San Francisco bar once looked Michael Bolognino up and down and said three words: cute, weird, cute. He's been living by them ever since. This conversation is about what happens when you stop explaining yourself and start trusting that verdict. It's also a philosophy of taste built on one idea: buy less, hunt more, and never be too much for the sake of being too much. Today’s conversation is all about Michael’s taste, references, approach to coaching, mid-life career pivots and more. It is available in audio, video and transcript.
On this page:
Who Michael is, in one paragraph.
The video version of the conversation.
The rabbit holes, every reference from the conversation, linked.
Chapters, timestamped, so you can jump to what pulls you.
About Michael Bolognino
Michael Bolognino spent twenty years in tech, the last thirteen at Google, before a quiet but total reckoning led him to coaching. He works with people who got what they thought they wanted and discovered something got lost along the way, helping them reconnect with themselves and use the careers they’ve built as a foundation rather than a cage. He and his husband spent two years renovating a falling-down house in the Berkshires, a project that became the unexpected origin point for both of their current careers. Michael describes his taste as “cute, weird, cute,” is a devoted thrifter and eBay obsessive, and is, by his own admission, a huge Mariah Carey fan.
The video
The rabbit holes
Everything we referenced, for your own falling-down:
Rec League, the whisper network for great recs. Human recs only, on everything. Michael's collections run from vintage high-heeled Frye boots to a discontinued Comme des Garçons Dover Street Market cologne he tracks on eBay. Follow Kima while you are there too.
Mariah Carey, as vocalist, writer, and lyricist. Michael singing one of her songs is here, and yes, it holds up.
The Filomena, Architectural Digest feature on Michael’s house renovation
Michael's inspiration list: Pee-wee Herman, Elsa Schiaparelli, Björk, tarot, Rossy de Palma, Pedro Almodóvar. More arriving on his website in autumn 2026.
Thrifting and Goodwill as a regular practice. No link here, go outside and do your research.
Uncompromising curation the Substack I brought up mid-conversation, but didn’t remember the name. Amazing resource by Martha Stewish. Martha writes essays on money, identity and the art of building quiet wealth while living beautifully. Check her work out.
Conversation chapter list
00:00 Meet Michael Bolognino, golden handcuff breaker
02:38 Thirteen years at Google, then the crash
05:45 Quick hits: vintage, vintage, vintage
08:46 "Cute, weird, cute" and the discipline of restraint
11:36 Goodwill as ritual: the treasure hunt
14:23 Fifty eBay emails a morning, and his dad's Frye boots
17:34 The Mariah Carey confession
21:53 On not over-explaining your work
22:40 Why AI won't replace coaches: the fresh pasta argument
26:20 Sharing the quote vs. absorbing the nutrients
32:23 The Filomena: raccoons, two years of Thursdays, two new careers
39:24 "I make money serving humans"
