Free Friday: Operator in the trenches (ask me anything about broken businesses, ops, scaling chaos)
Remove if not allowed, wanted to post and help some people as I have quietly looked in here for years on my main. Thanks for all the cool people in this sub.
I’m an operator out of West Palm Beach.
I’ve been doing this for a little over 10 years across MSPs, IT, healthcare, multi-site operations, PE-backed situations, and post-acquisition cleanups. Basically anything where growth or bad structure starts breaking things.
Roles have looked like:
• Director of Operations in an MSP that exited
• COO, CRO, interim COO type work across different businesses
• healthcare operations across multiple markets
• global IT deployment (6500+ devices across 3 countries)
• manufacturing and retail multi-location scaling and exit work
Most of the work I end up doing is walking into businesses that are growing but the inside does not match the outside.
On paper it looks fine. In reality it is usually:
• leadership is stretched or unclear
• managers are executing but not really owning anything
• nobody trusts the numbers
• communication is inconsistent
• founders are still in everything even if they hired people not to be
• things get done but nothing feels controlled
Then it all slowly compounds…
My job is figuring out what is actually happening and rebuilding structure so the business can run without constant fire drills. (everything is fine, on fire meme)
Fix accountability. Fix cadence. Fix ownership. Fix visibility.
But honestly, the real work is people.
I talk with everybody in the business from bottom to top. People on the floor, managers, directors, all the way up through ownership, president, C-suite, investors, board. I want the full picture, not just one layer.
I will take people off site and just talk. Real conversations. No agenda.
I want to understand them as people first. What they actually like, where they want to go, what they want out of life, what they are trying to build for themselves.
Their frustrations matter, but so do their goals, their ambitions, what they think they are capable of if the business actually supported them instead of just using them.
And I always ask the same question at the end:
When we go back, this is your company and you can change 3 things, only 3, what do you change first?
It‘s fascinating to me how often the answers line up across levels. That is usually where you start seeing what is really broken versus what leadership thinks is happening.
Hiring is a big part of it too.
A lot of companies hire people who can do the job technically, but they are not always a fit for how the team actually has to operate. Can they work with others, take ownership, train people, not just execute in isolation.
That is really where things start breaking…
A lot of what I end up putting in place is structure around:
• clearer expectations for what good actually looks like in the role
• quantified scorecards so performance is not subjective
• hiring standards beyond can they do the work
• onboarding that does not assume people will figure it out
• real development cadence so people are not left to drift
And quantify able, ongoing reviews that are scorecard based:
• 30 / 60 / 90 day reviews
• 180 day checkpoints
• 365 day full cycle performance
It is not about being fancy or corporate. Without it, most orgs just drift over time and nobody really notices until it is really a big problem…
What I have actually been in the middle of:
• took a 1.2M operation to a 4M exit
• helped build and scale a 10M multi-site platform strategy with 3.3M investor consortium capital and ~700k personal co-investment
• cut an 8M infrastructure plan down to under 2M while improving control and execution
• stabilized a 90+ person healthcare org across multiple regions and protected recurring revenue
If you are an owner or operator dealing with stuff like:
• we are growing but everything feels messy
• I do not trust my team to execute consistently
• I am still the bottleneck
• we have KPIs but no real control
• everything works but barely
Ask me anything.
I will answer what I can when I can.
No pitch. Nothing to sell here.
Just figured I would be useful if anyone is in the middle of it.