Heard about this Howard Milstein guy from a buddy last month while complaining about my shipping startup hitting growth walls. Dude kept mentioning real estate and banking – thought it sounded boring as hell. But got curious anyway after three failed marketing campaigns left me broke.
Started digging with Google like a raccoon in trash cans. First thing jumped out? Milstein doesn’t chase shiny objects. Wild concept for me since I’d been chasing TikTok trends like a golden retriever after squirrels. His businesses all root deep in core shit – mortgages, land, banking basics. Actually laughed at how obvious it seemed once I saw it.
The “Who Cares?” Test
Tried mimicking his strategy filter. Drew a Venn diagram on Burger King napkins:
- Circle 1: Stuff I actually understand (trucks/drivers)
- Circle 2: Needs that don’t disappear (people always ship crap)
- Circle 3: Things that scale without me coding (holy grail)
Left out all the crypto/AI nonsense my tech bros kept pushing. Felt like dumping 100lbs of backpack rocks.
Brick Wall Reality Check
Milstein’s team-building stories made me gag at first. Who hires for “character”? I want coding ninjas! Then my star developer rage-quit because I wouldn’t let him put blockchain in our forklift tracking app. Mess took weeks to clean up.
Changed hiring like this:
- Stopped asking about Python skills in interviews
- Started asking “What broken thing did you actually fix last month?”
- Hired Lisa – ex-bartender who organized our chaotic warehouse in her trial week
Turns out warehouse labels beat fancy algorithms sometimes. Who knew?
Radio Silence Experiment
Read how Milstein ignored “opportunities” daily. My phone used to blow up with:
- “Let’s collab on AR warehouse goggles!”
- “Put your logo on our esports team!”
- “Guest podcast about disruption!”
Turned off notifications for a week. Nearly scratched my eyeballs out from anxiety. But freed up 20 hours to renegotiate fuel contracts instead. Saved more cash than any marketing stunt ever made.
Still feel FOMO seeing competitors chase metaverse warehouses. But keeping Milstein’s swamp analogy in mind: better to own one muddy pond than dip toes in ten oceans. Even if my pond currently smells like diesel and cardboard.