Doctor turned 3x bootstrapped founder in highly regulated industries. Over $50m lifetime revenue.
Miami, FL
Joined March 2023
- Tweets630
- Following65
- Followers13.3K
- Likes67
Years ago, I spent 18 months and $250,000 on a software project that was going nowhere.
Every month, I heard that we were close.
Every month, another roadblock pushed the timeline out.
Walking away felt painful because of everything already invested.
Keeping it alive would have been more expensive.
The project was consuming capital, attention, and mental energy that belonged in businesses with real momentum.
So I shut it down.
Founders talk a lot about persistence.
Persistence matters when the underlying opportunity is still there.
When the facts change, continuing to push can become avoidance disguised as discipline.
Knowing when to stop protects your ability to commit fully to what deserves it.
I watched a new employee redo a task nobody asked them to redo.
It wasn't wrong the first time. It was just slightly below the standard the team held, and they knew it, so they fixed it before anyone said a word.
That moment told me more about the culture we'd built than any metric could.
"Excellence is normal" is easy to put on a wall.
It's much harder to build into the daily reality of a team.
What it actually looks like isn't dramatic.
It's quiet and constant.
It's the person who catches their own error before it ships.
The team member who flags a problem instead of hoping nobody notices.
The manager who holds the bar on a Tuesday afternoon when it would be easier to let it slide.
None of that comes from a slogan.
It comes from consistent standards, applied by leaders who model them, until meeting the bar becomes the default instead of the exception.
You can't demand excellence into existence.
You build an environment where falling short feels abnormal, and then you protect that environment relentlessly.
The culture isn't what you say in the all-hands.
It's what the newest person does when nobody is watching.
If someone owns the responsibility but needs your approval for every meaningful decision, you've just created a slower version of yourself.
The gap usually shows up when something unexpected happens.
The person knows the outcome they're accountable for.
They don't know what they can decide without you.
So they wait.
The work slows down, small issues become escalations, and everyone assumes the person needs more training.
Usually they need clearer decision rights.
Before handing over a responsibility, define what they can decide independently, what they should flag, and what must come back to you.
The clarity takes time upfront.
It gives the person a real chance to operate instead of manage up.
A manager came to me ready to let someone go.
The person had been underperforming for weeks, and the frustration was obvious.
My first question wasn't whether to fire them.
It was why they were underperforming.
We looked closer.
The expectations for the role had never been clearly defined. The person was optimizing for what they thought mattered, which turned out to be the wrong things.
That's a clarity problem wearing a performance problem's clothes.
We reset the expectations, gave it 30 days, and the person turned it around.
Sometimes the answer really is to let someone go.
But you can't know that until you've ruled out the causes that have nothing to do with the person.
Diagnose before you decide.
Good decisions and good discipline are not the same input.
Most people think decision quality comes down to intelligence or experience.
A large part of it comes down to what you put in your body.
My decision quality runs on inputs I control, not willpower.
When I eat poorly, my afternoon thinking degrades in ways I can measure against my own baseline.
When my nutrition is consistent, I hold focus longer and make sharper calls late in the day, when most consequential decisions actually happen.
I treat diet the same way I treat sleep and training.
Not as a health habit sitting off to the side.
As a direct input into the quality of every decision I make that day.
The founders optimizing their calendars while ignoring their inputs are leaving judgment on the table.
When I open a P&L, I don't start at the top.
Revenue is the number everyone looks at first, and it's rarely where the story is.
I go to the margin lines first, before anything else.
Gross margin tells me whether the core model is healthy.
Operating margin tells me whether we're running the business well or letting costs creep.
Then I look at the trend, not just the month.
A single month lies. Three months in a row gets closer to the truth.
Only after that do I look at revenue in context.
Growing revenue with declining margin is often a warning, not a win.
The founders who only watch the top line get surprised by problems that were visible in the margin lines months earlier.
The P&L tells you everything.
You just have to read it in the right order.
I onboard an EA completely differently than I onboard an operator.
Most people run both through the same generic process.
That's a mistake.
An operator is being onboarded to own outcomes. The first 90 days are about handing over decision rights and getting out of the way.
An EA is being onboarded to extend my capacity. The first 90 days are about understanding how I think, what I prioritize, and where my judgment lives.
For an operator, I document outcomes.
For an EA, I document reasoning.
Eventually, I want them to make the call I would have made, which means they need to understand the why behind my decisions, not just the what.
Different roles need different onboarding.
Running everyone through one process guarantees at least one of them starts slow.
If you hire fast in a high-turnover industry, you'll spend all your time replacing people instead of building a team.
Hospitality churns.
Taproom and kitchen roles turn over constantly.
People leave for school, for other industries, for reasons that have nothing to do with you.
The instinct is to hire quickly just to fill the gap.
That instinct is how you end up in a permanent cycle of backfilling.
We still hire deliberately, even for high-turnover roles.
A slightly longer search for someone who actually fits produces someone who stays longer and raises the bar for everyone around them.
The cost of a fast bad hire in a churning environment isn't just the replacement.
It's the standard that erodes every time someone marginal walks through the door.
Speed feels efficient.
Consistency is what actually saves you time.
A weekly scorecard is only useful if the right numbers are on it.
Here's how I decide what earns a spot:
1 - It's a leading indicator, not just a lagging one. It tells me what's coming, not only what already happened.
2 - It's tied to an outcome I care about. Revenue, margin, and retention over vanity metrics that feel good and mean little.
3 - Someone owns it. Every number on the scorecard has a person accountable for the trend.
4 - It changes a decision. If the number moves and nothing about how I operate would change, it doesn't belong there.
Most scorecards are cluttered with numbers nobody acts on.
The discipline is cutting the ones that don't drive a decision.
Most founders think an ops meeting is where work gets reported.
The ones who run it well know it's where drift gets caught.
Between meetings, small things slip.
A process bends slightly.
A standard gets applied loosely.
A metric drifts a point or two.
None of it is dramatic enough to trigger an escalation.
That's exactly why it's dangerous. Undramatic drift is the kind that compounds unnoticed.
My biweekly ops meeting earns its place by catching drift early, when it's still a two minute correction instead of a two month problem.
The agenda is consistent: what's on track, what needs a decision, and what's drifting and why.
A status update tells you where things are.
A well-run ops meeting tells you where things are heading before they get there.
When I started my first company, I spent a lot of energy worrying about the wrong things.
Whether people took me seriously.
Whether the timing was right.
Whether I had enough experience to pull it off.
By the third company, those questions were gone.
Not because I had more confidence in some abstract sense, but because I had actual evidence.
I knew what hard stretches felt like and that they didn't mean failure.
I knew which early signals mattered and which ones were just noise.
I knew what I was capable of building and roughly what it would take.
What stays the same across every business are the fundamentals.
Clarity on what you're building and who it's for.
Hiring people well.
Building operating systems that don't depend on you personally.
Staying solvent while you figure out what works.
What changes is the internal experience of doing it.
The first time, uncertainty feels like a warning sign.
By the third, it just feels like the beginning of something.
The work doesn't get easier, but your relationship to the discomfort does.
That shift is worth more than most people realize when they're still on the first one.
For deeper-dives on business and life optimization, check out my newsletter:
seanewenventures.beehiiv.com…
The biggest improvements rarely come from one breakthrough, they come from small, consistent actions repeated over time.
Whether it's your health or your business, long-term success belongs to those who focus on trends, not daily fluctuations.
I've never sold a business, and I don't plan to.
That's a deliberate choice, not a default.
The conventional path for a founder who's built something valuable is to sell it, take the payout, and start again or invest the proceeds.
I think about wealth differently.
I think about wealth as architecture, not an exit event.
Multiple businesses that generate consistent cash flow, combined with real estate and a portfolio of public and private investments, compound in a way that a single liquidity event can't replicate.
The exit gives you capital once.
The operating businesses give you capital, optionality, and leverage continuously.
Selling also resets the clock.
You lose the the team, the systems, and the relationships.
In other words, everything that took years to build.
What I'm building toward is a structure where the assets work together.
Cash from the businesses provides stability and investing capital.
The portfolio provides diversification.
None of those legs is the whole thing.
But the architecture is.
Building for that outcome changes how you make decisions along the way.
If you want to optimize, automate, and delegate more in your business and life, you'll love my newsletter:
seanewenventures.beehiiv.com…
Family businesses don't succeed because everyone thinks alike… they succeed because everyone trusts each other.
Clear roles, complementary strengths, and mutual trust turn potential conflict into a lasting competitive advantage.
I review a weekly ops report for each business every week, and the first thing I scan isn't revenue.
It's what's blocked and who owns it.
Revenue tells you what happened. Blocked items tell you what's about to happen.
My reports follow a consistent structure:
- What's on track
- What needs a decision
- What's blocked and unowned
Every item in that third category is a decision I need to make or a handoff I haven't completed yet.
The discipline of reviewing that list weekly means nothing stays invisible for more than seven days.
Most operating problems build slowly over time.
Creating a list of blocked items surfaces them before they create bigger problems across the organization.
Crisis demands focus. The best leaders narrow their attention to what matters most, seek information firsthand, and protect the habits that keep their judgment sharp when the stakes are highest.
For deeper-dives on business and life optimization, check out my newsletter:
seanewenventures.beehiiv.com…
I started ITphysicians because I kept seeing the same problem from the inside.
Healthcare organizations needed technology talent, and the people doing the recruiting didn't understand the clinical environment the candidates would be walking into.
They were matching on technical skills while the actual friction was cultural and operational.
I'd spent years in medical training. I understood how healthcare systems think, how they're structured, and what it actually takes to operate inside them.
That context was the edge.
Building ITphysicians wasn't about being a better technology staffing firm in the traditional sense.
I wanted to approach the problem from a different vantage point than anyone else in the space.
The companies that hired us weren't just getting a recruiter. They were getting someone who had been inside the environment they were trying to staff.
That turned out to matter considerably.
Every business I've built came from the same starting point: seeing a gap that others in the space couldn't fully see because they were looking at it from the outside.
The physician background that didn't lead to a clinical career has been the source of two separate competitive advantages in two completely different industries.
The skills compound.
The perspective travels.
If you want to optimize, automate, and delegate more in your business and life, you'll love my newsletter:
seanewenventures.beehiiv.com…