A few years back, Jay told me to stop shitting on his ideas. Not in an email, not in Slack, just straight to my face, after one too many meetings where he pitched something he was excited about and I started poking holes in it before he had even finished the sentence.
I deserved it. He is the visionary of the two of us, and every time he floated something, I would go straight into how do we execute this mode instead of sitting with the idea for a minute. He was losing the fun of it. I adjusted how I delivered pushback, and we moved on. But I have thought about that moment a lot since, because it is where the real story of our partnership lives. Jay and I have been running StringCan together for ten and a half years, and we are still having the same argument, over and over, without ever fully settling it.
The argument is about effort. Our work is custom because our clients are not templates, and scoping a project honestly takes real hours from real people before a contract even exists. We eat that cost up front so nobody gets nickel-and-dimed six months into the engagement, and almost none of that time is billable. We tell ourselves we make it back over the life of the relationship. I have actually looked at the numbers. We do not.
It has gotten worse lately too. Our friend Susan Baier shared research with us that stuck: prospects now walk into a first conversation already distrusting you, a different problem than just not trusting you yet. Between AI-generated content flooding every industry and years of agencies overpromising, the starting line moved on all of us, and you end up spending unbilled hours just climbing back to zero before you have built anything real on top of it.
So my position, every time, is that we should be efficient, protect our internal time, and stop giving away so much free work. Jay agrees with every word of that, out loud, and then goes and does the extra work anyway. He is not running a profitability model in his head during a business development call. He is thinking about what the relationship could look like in five or ten years. He compares it to remodeling a house, where moving a window five inches sounds easy until the drywall comes off and you find out what is actually back there. He has sat on the client side of consulting before, and getting nickel and dimed mid-project by a firm that should have caught the problem early felt bad enough that he refuses to run our company that way.
We have hashed this out publicly, on our own podcast, on purpose, in front of an audience. Spicy is the word we have landed on for what those conversations sound like.
For years I assumed one of us had to be wrong, since that is usually how an argument works. What I have come around to instead is that we are not even answering the same question. Mine is whether the project is profitable. His is whether the relationship is still producing value five years from now. A business that only answers my question goes cold and transactional. One that only answers his eventually runs out of money, exceeding everyone's expectations. If you have read Traction, you will recognize the shape of this: Jay is the visionary, I am the integrator, and Gino Wickman would probably tell you the friction between those two roles is the entire point of pairing them up.
I have watched versions of this same disagreement play out at other companies, and it usually does not sound like a disagreement at all. It sounds like sales quietly complaining that delivery is too slow, and delivery quietly complaining that sales sold something that does not exist, with nobody saying any of it in the same room. Jay and I decided a long time ago we would rather say it out loud, and over the years that decision grew some actual structure around it.
Every engagement ends with a retrospective, where we go through whether the process worked, whether we hit our profitability targets, and whether the client actually got what we promised them. Jay's anxiety spikes walking into those meetings, right after he has spent weeks being proud of the work and he knows I am showing up with numbers, but the meeting happens on schedule regardless. That is the part worth stealing if you are leading a team: give the argument a container, so it lives inside a scheduled retrospective instead of leaking into hallway conversations and Slack threads, where it rots into resentment nobody addresses.
We also built internal budget sheets that nobody enjoys filling out, and they force my question to get answered before the work gets sold instead of after. At every handoff inside the company, sales to operations to customer service, we hold one rule steady: the definition of done does not get renegotiated along the way. Most of the revenue leaks I have seen in businesses trace back to that definition eroding a little at each handoff, like a long game of telephone played with your margin.
When Jay pushes back on me, or I poke holes in something he is excited about, we both start from the same assumption, that the other person is coming from a place of care. He has told me his first reaction to my pushback is disappointment, and that once he steps back, he can actually see the care underneath it. Without that assumption, pushback starts to feel like an attack, people stop offering it, and eventually you are running a company full of people who only ever tell you yes, which is its own kind of expensive.
Jay says he is grateful for the friction even when he does not act like it in the moment, because he is not a mind reader, and without it neither he nor the company grows. I have told him he takes feedback well. He says I give it well, which is generous coming from a guy who once had to ask me, out loud, to stop shitting on his ideas.
We are still arguing about biz dev effort, the same argument, a decade in. I used to think we would eventually land somewhere and put it to rest. Lately I am hoping we do not, because the argument is doing real work, and both of the questions buried inside it need someone in the building who refuses to stop asking them.
If you have a business partner, a co-founder, a leadership team you argue with more than you would like to admit, I would ask where your version of this argument actually lives, and whether anybody has ever given it a container.
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