It was November, and Russ and I were sitting across from each other for the first real meeting after he’d signed on. He ran a real estate investment company in the DFW metro — $5 million a year in revenue, twelve employees, five rehab crews, twenty-five bird-dogs scouting deals across the metroplex. Ten-plus years in business. By any external measure, the man had built something real.
He hadn’t hired me because the business was struggling. He hired me because he was bored.
“My favorite part of all of this,” he told me that day, “isn’t the deals. It’s the dinners.” He lit up describing it — the gin get-togethers, the Top Golf outings, the way he’d sit across from two people who didn’t know each other and realize, halfway through a conversation, that one of them had exactly what the other one needed. A contractor and a capital source. A property and a buyer who’d been looking for eighteen months. He wasn’t really a real estate investor. He was a connector who happened to make his money in real estate, because that’s where he’d started.
I asked him if I could pray with him before we got into strategy. He said sure — he was used to it from me by then. So we sat there, in his office, and we did something I call listening prayer: we asked God a direct question about the direction of his business, and then we got quiet and waited to see what either of us heard.
I want to be careful here, because this is the part people either lean into or roll their eyes at, and I understand both reactions. But this is what happened: we both heard the same thing, independently, without comparing notes first. Stop pouring yourself into the real estate. The gathering is the gift. Build that, and more doors will open than you can build yourself.
When we said it out loud to each other, Russ got that look — the one where someone’s body believes something a half-second before their mind catches up. He was enthusiastic. He talked about what it could look like. A meetup organization, built around exactly what he was already best at: rooms full of the right people, on purpose, instead of by accident.
He agreed to it. Genuinely agreed, in that room, with no hesitation I could see.
The next day, Russ called me and backed all the way out.
“I can’t do this to my team,” he said. “We’ve spent too much time and effort building this version. I couldn’t do that to them.”
I want to sit with that sentence for a second, because I think it’s the most common sentence in Christian business that nobody preaches on. He wasn’t rejecting God. He’d have told you, and meant it, that he believed what we heard in that room was real. He was rejecting the cost of being obedient to it — the sunk cost of ten years, the optics of telling a team of twelve that the thing they’d built was a detour, the fear of looking, in his word, crazy to people whose respect he’d spent a decade earning. Sunk cost dressed itself up as loyalty to his team. It’s a very convincing disguise.
This is the gap I think almost every Christian founder lives in, and most don’t know it has a name. It isn’t unbelief. It’s worse, in a way, because it’s sneakier: you believe in accountability to God in the abstract — you’d say yes if someone asked you, “should a Christian business be led by God?” But the actual practice of it gets front-loaded into one big moment — a founding prayer, a commissioning, a crisis-point Hail Mary when the bank account gets scary — and then it goes quiet. You asked God about the direction once. You don’t keep asking. You check in when things are bad, not as a rhythm, not as a structure, not as something your business is actually accountable to on a recurring basis. The first conversation is sacred. The eleventh one — the one three months later asking “is this still the direction?” — never happens.
He went back to the real estate. Business as usual. We kept working together on strategy, growth, hiring — the parts of the job that look like a normal fractional executive engagement. And on the surface, nothing was wrong. The business didn’t collapse. It didn’t even shrink dramatically. It just... stopped being alive.
By the following September — ten months after that meeting — the erosion was unmistakable. Revenue was flatter. People were leaving — not in a dramatic exodus, just a steady, quiet bleed of the kind of people who notice when an organization has stopped moving toward anything. The business is still “successful” by the numbers most people would use to judge it. It’s still making money. It’s just smaller than it was, smaller than it could have been, and noticeably less alive than it was the day he described dinners and golf outings with his eyes lit up.
We still talk. But there’s something different in it now. He gets quiet in a particular way when the subject gets near that meeting. I think Russ is ashamed — not of me, not of the business, but of himself, for knowing what he heard and choosing the safer, smaller thing anyway. I think some part of him is afraid to bring it up with me again, because bringing it up means admitting he’s still living downstream of a choice he made in a single afternoon ten months before things started slipping.
Here’s what that story taught me about the work I actually do, underneath the title on my invoice.
Most founders have access to one half of this. They have a coach or a consultant who’s sharp on strategy, unit economics, hiring, growth — someone who can tell them what’s smart. Some have a pastor, separately, who can speak into their character, their marriage, their walk with God — someone who can tell them what’s faithful. Almost nobody has both in the same room, on the same conversation, applied to the same decision. I’ve started calling that combination a Business Pastor — not in the sacramental sense, but in the functional one: someone who carries real operating fluency in your industry and who will also sit across from you and ask God a direct question about your business, then hold you accountable to the answer past the day you heard it.
That combination is rare for a reason. It requires someone who can read a P&L and also sit in silence with you without rushing to fill it. It requires someone willing to ask the uncomfortable follow-up six months later — “did you do what you said God told you to do?” — instead of letting the relationship slide back into being purely tactical once the spiritual moment has passed. Most coaches won’t go there because it’s not in their lane. Most pastors won’t go there because they don’t understand the business well enough to know what’s actually at stake in the decision.
I don’t know if his business would have thrived if he’d built the meetup organization instead. I can’t prove that. What I can tell you is that the version of him sitting in that office in November — lit up, certain, already half-building it in his head — hasn’t shown up in a meeting since. And I think that’s the actual cost of sunk cost: not just the dwindling revenue or the people walking out the door, but the slow disappearance of the man who heard something true and was, for about eighteen hours, brave enough to believe it.
This is the first of five things I keep seeing founders discover, almost always too late, about what it means to have someone in your corner who’ll tell you what’s smart and what’s faithful — and won’t let you stop asking after the first conversation.
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