Strategy
Learn From the Source
Brant DeBow
Written on July 29, 2026
Years ago, listening to Horace Dediu’s podcast, I heard Bob Moesta interviewing Horace about a car he’d recently bought. Bob was walking through the purchase the way he does, when Horace mentioned something about gas mileage. Bob paused the interview. “Did you see what just happened? Horace just tried to tell me he got a Porsche because of the gas mileage.”
That moment hooked me. Not the gotcha, but what it revealed: people cannot tell you why they buy things. Not because they’re lying, but because the real reasons sit underneath the rationalizations, and it takes a specific, learnable skill to get to them. Bob had spent decades building that skill. He ran the famous McDonald’s milkshake research with Clayton Christensen. He is, as much as anyone alive, the source of the Jobs-to-be-Done interview.
So when Joe and I learned that Bob was teaching a hands-on workshop, actually training people in how he does interviews rather than a simple keynote, we had a decision to make.
The debate we’ve had more than once
When you run a small, bootstrapped company, margin always feels tight, and there is always a good argument for not doing the expensive thing. This workshop meant both founders away for days. Flights, hotels, workshop fees, time not billed. The extraction logic writes itself: do we really need this? We’d both read the books. We knew the theory. Would a workshop truly differentiate us in a way the market would reward?
But we’re paid to be the best at what we do, to connect strategies and ideas that others don’t. JTBD and BDD aren’t garnish for us; they’re foundational to how BiTE thinks and operates. And there is no replacement for learning a practice directly from the people who established it. So we went. Twice in six months, as it turned out, and both times that reasoning paid for itself.
Watching a master up close
The Moesta workshop was in Chicago, at Basecamp’s offices, in April 2015. Bob’s method for teaching interviews is to do them, live, because the skill is easiest to absorb when you watch it work. He’d start each interview with his phone face up on the table. Phone up meant a normal interview. When he turned it face down, everything paused, and he’d point at what had just happened: something striking the person said, a rationalization sliding by, a question he chose not to ask yet and why.
In one of those interviews, he was talking with an attendee about a watch he’d recently bought. Somewhere in the middle, Bob asked how big the box was that he stored his watches in. It seems like a throwaway question. It isn’t. Watch collectors grow their collections to fit the box: six slots means six nice watches, and a new watch means selling one to make room, because buying a bigger box carries a cognitive weight all its own, and deep down the collector knows the bigger box means the collection will grow to fill it. One question, and you understand the real constraints on this man’s next purchase better than a focus group ever would.
We learned the deeper mechanics too. Asking “where’s the old one?” and reading the energy of the answer, because the person who threw out the old product the day the new one arrived is telling you something completely different than the person keeping it in the garage as a security blanket. The four forces that govern whether anyone actually switches. The timeline of first thought, trigger one, trigger two. And through all of it, Bob had us take our own notes during each interview, then compared them against his afterward: why he labeled a moment the way he did, what half the room missed and why they missed it. You cannot get that from a book, because the book can’t tell you what you specifically aren’t hearing.
Getting busted by the source
The Chicago trip wasn’t even our first run at this calculation. Six months earlier, November 2014, the same debate had sent us to Atlanta for BDD Kickstart, taught by Aslak Hellesøy, the creator of Cucumber, along with Julien Biezemans.
That trip was ostensibly for Joe. I’d been doing BDD for a while, loved it, and considered myself pretty proficient. Which made it all the more useful when Aslak caught me, mid-exercise, building something I didn’t have a test for. Getting busted by the creator of the tool, on the practice I thought I had down, was a well-timed reminder that proficiency is not mastery and there is always more to learn.
And the trip did exactly what we hired it to do. Joe walked in thinking BDD was a thing Brant loves a lot, and walked out having caught the bug for real: seeing that executable specifications were how he, as a product owner, could directly shape the design of the system rather than lobbing requirements over a wall. That shift in one founder’s head changed how we’ve run projects ever since. The relationships compounded too. Through Aslak and Julien we later ended up on the product advisory board for Cucumber Pro, working with Matt Wynne, Seb Rose, and Steve Tooke, the best of the best in the BDD world and, to a person, extremely kind and thoughtful people.
What it actually bought us
Nobody has ever hired BiTE because we know Bob Moesta or Aslak Hellesøy. That’s not how this works. What the market rewarded was everything downstream of those rooms.
We’ve gone on to teach JTBD and BDD to product and software teams as part of our consulting, and depth is what makes teaching possible: when you’ve learned something to its foundations, explaining it to others gets dramatically easier. Watching how the best teach their own practice also taught us how people learn these concepts, which mistakes are predictable, and which moments make it click. We went to learn a practice, and came back having also learned how to transmit it.
The generosity compounded too. Bob offered to help when we hit real-world walls applying this, and he meant it. Later, while starting our engagement with Prudential, we faced a JTBD problem that was genuinely hard: selling to multiple stakeholders who weren’t the end users. Bob got on a call and helped us think it through. The source, still teaching.
So this is partly a thank-you note, to Bob and to Aslak and all the others, and it’s partly a recommendation. When the people who established a practice are willing to teach it, the extraction math will always tell you to stay home. Go anyway. The books teach you the theory. The source teaches you what you, specifically, keep getting wrong. That second thing is the one you can’t buy any other way.
