Jason Droege

The strategic frontier of AI is moving from knowledge retrieval to agentic action and decision-making.

"The general trend right now is going from models knowing things to models doing things. The next question becomes, what can it do for me? How does the agent make decisions for you?"

Enterprise AI automation requires significant 'operational chiseling' and time (6-12 months) to reach production-level reliability.

"These things take 6 to 12 months to get them truly robust enough where an important process can be automated. Like with any of these major tech revolutions, headlines tell one story and then on the gr..."

The complexity of data needed for LLM training has shifted from simple preference ranking to high-level expert tasks requiring professional expertise.

"18 months ago, you would get a short story and it would say, 'Is this short story better than this short story?' And now you're at a point where one task is building an entire website by one of the wo..."

Evals are the primary tool for establishing quality benchmarks in enterprise AI implementations.

"A lot of it's evals, and within enterprise customers and government customers, it's mostly evals because somebody's got to establish the benchmark for what good looks like. That's the simple way to th..."

Gross margin serves as a litmus test for whether a product is adding enough value and is sufficiently differentiated.

"I take gross margin is just a very coarse instrument, not a perfect instrument to think about, am I adding enough value? Am I differentiated?... If the response is gross margin is super low right now,..."

In fast-moving markets, interviewing for core traits like problem-solving and humility is more effective than checking specific experience boxes.

"I just interview for three things... are you a curious problem solver and can you articulate that verbally? Can you work across people? Are you humble enough to work across and are you a good leader?"

Team cohesion and the ability to compensate for each other's weaknesses are more critical for scaling than hiring individuals with 'scale experience.'

"I was trying to compose almost like an organism of strengths and then minimize the conflicts. That management team for the most part... was the same management team from day one when we had nothing to..."

In uncertain markets, the primary goal is survival to ensure you are still present when the timing becomes right.

"Survival is just part of the game, and most people just give up before they get their timing right... Survival is a precursor to that. So let's not put ourselves in position that could potentially com..."

A strong product vision must be built on a unique, independent insight that differentiates you from the rest of the market.

"From an entrepreneurship standpoint, it truly is about what insight do I have? Why am I so lucky to have this insight? Why in a world of a million entrepreneurs who are thinking, who are smart, who ar..."

Effective problem definition requires understanding the personal and professional incentives of the buyer, not just the business problem.

"I look at the underlying incentives of the customer. And the underlying incentives of customers are not always financial. Sometimes it's ego, sometimes it's career growth. If you're selling enterprise..."

To define a problem accurately, triangulate 'ground truth' data independently rather than relying solely on what customers tell you.

"We ordered just a bunch of food from these places, and we got a restaurant supplier to give us a base catalog, and we just matched up how much does the ham weigh? How much does the cheese weigh? How m..."

Strategic patience and the willingness to say 'no' to a major partner can lead to better deal terms and exclusivity.

"McDonald's actually approached us and they said, 'We'd love to do food delivery with you.' And I said, 'No.'... I pushed them off for four or five months... I think it actually ended up being in net b..."