Tag: Founder Compass

  • Cash Flow Is Not a Finance Problem

    Make My Mess My Message · Issue 1 · Friday 12 June 2026

    You don’t fix cash flow by working on cash flow.


    Robert asked. The Collective Brain answered.

    Last Friday’s essay, The Boat or the Crew, landed three “bolt” stories from my businesses. The cash flow one was the bolt that hit hardest. The deepest reaction came from Robert Neyens, a B2B sales expert I have worked with and who knows the territory cold.

    He left a comment that ended with a question I want to spend the next thousand words on:

    “I have had multiple times where we ran record months, inventory was down, and I am pretty sure cash was stretched thin, but nobody ever told me about it. I assume you share sensitive information like cash flow in general terms? How can each A-team player adapt to a potential cash-flow situation? Do you turn away potential business because you know stock won’t last? How do you slow down sales from wanting to sell everything?”

    Four questions in one paragraph. Each one is sharper than most quarterly board prep I have sat through.

    The honest answer is that in most companies Robert’s experience is the default. Sales is the tip of the spear, and the last people in the building to know what cash flow actually is. That isn’t malice. That’s structure. You can’t fix it by sharing more reports. You fix it by changing the structure that makes the question invisible in the first place.

    Here’s how we run it in our businesses today.


    Start with the Collective Brain.

    Wednesday’s post named this, and several of you wrote in. The Collective Brain isn’t a metaphor. It’s a daily mechanism. Everyone has access to the numbers, the knowledge, and the strategy. Everyone is asked for input on what they see. The brain stays fed because the brain stays asked.

    The proof you have actually built one is that a junior in fulfillment will spot a cash-flow risk before a VP, because the junior has access, context, and dignity. If your junior can’t, you don’t have a Collective Brain. You have a dashboard.


    Question 1: how do you share sensitive cash-flow information?

    Three things.

    → Everyone has access to the business dashboard. Always. Not gated. Not “ask your manager.” The files live where every employee can open them.

    → Monthly walk-through plus Q&A. Across departments: engineering, sales, accounting, fulfillment. The goal is to connect the business to the numbers first, then dive into what the numbers might say versus what reality actually says.

    → Frame every number against what’s happening. A cash-flow dip in one month? Could be product mix: a large low-margin order, a misdirected sales push. Could be discounting. Could be an accounting anomaly. Could be cyclical. Could be a correction from a previous month that was exceptionally high. Always look at things and periods as connected. We do not live in a vacuum. Nor in a still picture.

    The data is nonsensical without framing. Andy Grove wrote that a manager should do two things: motivation and training. Sharing the dashboard without training to read it is neither.


    Question 2: how can each A-team player adapt to a cash-flow situation?

    This is the question most companies refuse to answer, because the honest answer requires admitting that almost every role affects cash flow. Here are the obvious levers:

    → Sales. Payment terms. Down-payments on built-to-order. Adjusted terms by deal size and customer profile. Discount discipline. The sales role isn’t just to close, it’s to structure business deals and partnerships in a way that’s good for cash.

    → Purchasing. Supplier payment terms (longer is better, within trust limits). Right products on stock. An order that ships in 24 hours becomes cash 30 days faster than an order that ships in three weeks.

    → Fulfillment / shipping. Same-day shipping. Every order that leaves today can be invoiced today.

    → Finance / admin. Every day you invoice sooner is a day less in receivables. Sounds trivial. It isn’t. A two-day improvement in invoicing speed across a year is real money.

    → Marketing. Campaign timing. Promote what has stock, margin, and shipping speed, not what’s old or what someone wants to clear.

    → Customer service. Faster issue resolution reduces credit notes and returns. Better customer satisfaction means faster renewals, and renewals are cash flow with no cost of acquisition.

    → Engineering / product. Design for cost. Reduce custom work where it can be standardized. Standardization keeps stock predictable and invoicing fast.

    → Operations. Inventory turnover. Less WIP. Faster cash conversion cycle.

    Every single one of these levers belongs to a person, not a department. Once each person sees their lever, the whole business starts breathing differently.


    Question 3: do you turn away business because stock won’t last?

    The traditional answer in most companies is: no, never turn business away. And then they over-promise and miss delivery and burn the customer.

    Our answer: you almost never turn business away. But you almost never over-promise either.

    The sales team is the tip of the spear. They need to know exactly what is in stock and exactly when it can be delivered if it isn’t. Promises kept reinforce future business. Over-promised, under-delivered orders are the opposite of cash flow: they are returns, credits, and churn.

    The thing that makes this possible isn’t a sales script. It’s the Collective Brain. The sales person on the phone needs to know what the warehouse looks like in real time AND what’s in the supply pipeline AND what the customer’s actual deadline is. If those three pieces of information live in three different heads, sales over-promises by default.


    Question 4: how do you “slow down” sales from wanting to sell everything?

    The most overlooked answer in business, and the simplest: change the reward structure.

    Reward structure determines behavior more reliably than coaching, more reliably than training, more reliably than reorganization. If your salespeople are rewarded on volume, they will sell everything. If they are rewarded on margin, they will sell margin. If they are rewarded on customer lifetime value, they will sell to fit.

    Don’t ask sales to slow down. Restructure the comp plan so the right pace IS the most rewarded pace. It will take a quarter or two to land. It will land more powerfully than anything else you do.

    The second lever: marketing. Pull the customers toward the offers that are good for the business. Push them via reward structure on the inside; pull them via positioning on the outside. The push-pull is what makes the system self-organizing.


    The bigger point under all four answers is the same.

    You don’t fix cash flow by working on cash flow. You fix the structure that creates the cash flow.

    Collective Brain. Dashboard transparency. Role-specific awareness. Reward structures pointing in the right direction. None of these is the work of a CFO. All of them are the work of the operator who decides the business will be one where the answer to “how is cash flow this month?” can be given by anyone in the building.


    I made a video on this during Covid for small business operators trying to survive. The whole project here, the newsletter, the eventual book, the OSBB philosophy, is built on the same belief: the knowledge of how to build and run a business sustainably should be openly available, like reading or swimming.

    If you want to go deeper on the cash flow piece, watch it here:

    https://youtu.be/klbPqEfHUo4


    Thanks to Robert Neyens, MBA for the question that became this issue. The book is being written in public partly so readers can co-create the chapters they want to see. He just did.

    Be water, my friend. 🌊


    Make My Mess My Message is a book written in public, one Friday at a time. This issue first appeared on LinkedIn. Every issue lives here.

  • The Boat or the Crew

    Make My Mess My Message · Issue 0 · Friday 5 June 2026

    Most things called failure are just adventures whose beauty hasn’t been seen yet.


    Three bolts I missed, from my own businesses.

    The wind was howling. We were both quiet.

    We had red headlights on our caps so we wouldn’t blind each other. Food everywhere. Ropes everywhere. The boat slamming into waves on the nose. We strapped the boom, secured the sails, tied down the mess. It was night and the deck looked like someone had tipped the kitchen onto the cockpit floor.

    For forty-five minutes we tried to motor ahead. We were barely moving. Current against us. Waves against us. Burning fuel for no ground.

    So we turned around. Surfed the waves home. Used the tidal current to push us back.

    That’s when the guilt came.

    The diagonal spreader that came loose, the bolt that almost cost us the mast? I’d fixed and tightened that spreader myself before the race. I’d forgotten the piece of tape on top.

    My friend, owner of the boat, never said a word about it. He saw the whole thing the way I would learn to see it later. As an adventure. As a thing we were doing not against the other boats, but against ourselves.

    By the time we entered the harbor, we had already reconfigured the regatta. Day 2 would be fixing the boat: McGyver mode, twelve hours, unmount and clean and rebuild. Day 3 would be sailing her home together.

    In the Uber afterward, my friend turned to me and said, “What a great adventure, hey.”

    There was fire in his voice.

    That was the moment I knew. Most things called failure are just adventures whose beauty hasn’t been seen yet.


    We didn’t break. The boat did.

    We trained ourselves for years. We trained the boat for a few months.

    Every founder I know lives the same split. They read every book on leadership. They go to every offsite. They hire coaches for themselves and their team. They obsess over culture, hiring, communication.

    And meanwhile, the systems quietly miss a piece of tape.

    The crew gets the credit. The boat decides the result.

    Heavy weather is on every forecast. Eventually. The only question is whether you remembered to tape the bolt.


    Three bolts I missed, from my own businesses.

    The first bolt: cash flow as a one-person system.

    For the first decade of my business, I was the only person who really understood cash flow. Felt fine. I knew the numbers. Finance brought me reports. I made the calls.

    Then one quarter changed it. Our finance director was on extended leave. A junior was in the seat. The quarter had been massive, and a massive quarter, by the way, is when cash swings the most. Big revenue, big receivables, big stock orders, big variability. Not bad. Just big.

    The leadership team called me in. We need to inject a few hundred thousand to get through. Panic. Despair. “How could this be?” After ten profitable years.

    There was no problem. The numbers were fine. What we had was financial illiteracy: a whole leadership team reading symptoms as the disease, because only one person in the building had ever been taught the difference.

    The small fix: train everyone on business fundamentals. Cash flow. Margin. Receivables. Payables. The cyclicality of the business. Every employee. Every quarter. Make them all think like owners, not just be paid like employees.

    Real cash flow problems come in disguise. And good cash flow swings get mistaken for crises. Only training fixes both.

    The second bolt: the A-team that couldn’t scale.

    I’ve started every business of mine with three or four people who could do anything. Sales, engineering, marketing, negotiation, customer service: pick your hat in the morning. The A-team. Heroes.

    And every time, when growth came, we couldn’t onboard a fifth person. There was nothing to onboard them into. No roles. No systems. No processes. Just heroes winging it 100% of the time.

    The hardest phase wasn’t making the business viable. It was the transition from heroes to systems. I had to learn this in every single business I built.

    The fix is calm energy. Roles. Responsibilities. Simple “formulas of success”, not strict rules. The crew stops doing each other’s jobs and starts doing their own well.

    It is exactly what happens on a boat. When everyone is a good sailor and everyone tries to do everything, all of it fails. When there is a system, when each crewmember has their seat and trusts the others to hold theirs, a calm energy descends. And the boat starts pulling away from the competition.

    The third bolt: leadership teams that weren’t ready.

    I’ve made this mistake more than once in my career. I assemble a leadership team. I pick the people. I figure out the seats. I give them autonomy. And I forget two things until it’s too late.

    I haven’t applied an honest filter on each seat: high energy, team-first, mission-driven, accepted by the team. I’ve picked on merit and history. Not on the four that count.

    And I haven’t created a context where the team can disagree with me, or with each other, on whether to actually BE a team. So they don’t.

    Months later, the team falls apart. Patterns I should have seen earlier finally surface. The strongest voice in the room has been quietly setting the temperature; the others have been letting it happen. I gave autonomy to people who weren’t ready for it. And I didn’t know for months.

    The fix is always the same. A reorg. Honest conversations about who can be on the team and who can’t. New filters. New seats. A new context where disagreement is the price of entry, not a sign of disloyalty.

    A leadership team is the most important boat-system you build. The bolt you forget here doesn’t drop sails. It drops trust.


    The Boat Audit.

    Pick a Saturday morning each quarter. Walk through your business as two people: the captain about to take it to sea, and the buyer doing due diligence on it. Both lenses surface different bolts.

    Five sections:

    → Systems and tooling. What would break first under three times the load?

    → Contracts and legal. What’s verbal, expired, or unread?

    → Single points of failure. Who or what, if removed today, would stall the business?

    → Documentation. What lives only in someone’s head?

    → Pricing and financial assumptions. When did we last revisit each one?

    Fix the smallest bolt first. Tape it.

    The audit isn’t the work. The habit is.


    The crew that walked off that boat had trained together for years. That’s why the storm didn’t break us.

    The boat that failed had had one piece of tape forgotten on a critical bolt. The bolt I tightened myself.

    That’s why the storm broke it.

    Most founders don’t crash on a boat they ignored. They crash on a boat they thought was ready, minus the small final detail that mattered more than they knew.

    The good news is what my friend said in the Uber, with fire in his voice. “What a great adventure, hey.”

    Most things called failure are just adventures whose beauty hasn’t been seen yet.

    Be water, my friend. 🌊


    Make My Mess My Message is a book written in public, one Friday at a time. This issue first appeared on LinkedIn. Every issue lives here.