EP119: The Jagged Edge of AI and Why 95% of Pilots Fail and How to Beat the Odds
Mon Feb 02 2026
Dan Hou didn't plan to become an AI consultant by accident. After getting "professionally bamboozled" by the iPhone launch while working at Motorola, he made himself a promise: catch the next technology wave, but this time, own the outcome.
That decision led to Eskridge, an AI consultancy built specifically for mid-market companies—the ones competing in the same arenas as enterprise but without McKinsey budgets or tolerance for bloat.
We dig into the shift from "what is AI?" conversations in 2023 to tactical implementation pilots today, and why most companies are still treating AI adoption as a checkbox exercise rather than a competitive positioning tool. Dan breaks down the three-part framework his team uses: strategy (identifying high-value use cases), implementation (standing up pilots with measurable outcomes), and change management (the piece most engineers initially overlook).
The change management conversation gets real. Job descriptions are being rewritten. Performance reviews are shifting from "how many times did you use ChatGPT this week?" to "what evidence shows you're experimenting and adapting?" Teams need budget autonomy within guardrails, not six layers of approval to try a $50/month tool.
Dan also tackles the hard question: is AI actually a competitive advantage? His answer—yes in the near term, no in the long term as it commoditizes, but the proprietary context and instruction sets you feed it can sustain differentiation.
We close with what's next: portable jet-turbine power generators for data centers and world models that could unlock physical robotics applications by training AI to understand three-dimensional space and physics.
About Dan Hou:
Dan is a founder and partner of Eskridge, an AI consultancy that deploys practical applications of AI for mid-market companies, and has worked closely with senior executives to unlock value from their AI initiatives. Previously, Dan led Amazon Ads Creative Studio, supporting advertisers through technology and scaled services. He has spent over a decade partnering with Fortune 100 clients on digital transformation initiatives at Huge, founded and successfully exited a SaaS startup and held product management roles at Microsoft and Motorola. Dan holds economics and computer science degrees from UPenn.
Connect with Dan on LinkedIn
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Dan Hou didn't plan to become an AI consultant by accident. After getting "professionally bamboozled" by the iPhone launch while working at Motorola, he made himself a promise: catch the next technology wave, but this time, own the outcome. That decision led to Eskridge, an AI consultancy built specifically for mid-market companies—the ones competing in the same arenas as enterprise but without McKinsey budgets or tolerance for bloat. We dig into the shift from "what is AI?" conversations in 2023 to tactical implementation pilots today, and why most companies are still treating AI adoption as a checkbox exercise rather than a competitive positioning tool. Dan breaks down the three-part framework his team uses: strategy (identifying high-value use cases), implementation (standing up pilots with measurable outcomes), and change management (the piece most engineers initially overlook). The change management conversation gets real. Job descriptions are being rewritten. Performance reviews are shifting from "how many times did you use ChatGPT this week?" to "what evidence shows you're experimenting and adapting?" Teams need budget autonomy within guardrails, not six layers of approval to try a $50/month tool. Dan also tackles the hard question: is AI actually a competitive advantage? His answer—yes in the near term, no in the long term as it commoditizes, but the proprietary context and instruction sets you feed it can sustain differentiation. We close with what's next: portable jet-turbine power generators for data centers and world models that could unlock physical robotics applications by training AI to understand three-dimensional space and physics. About Dan Hou: Dan is a founder and partner of Eskridge, an AI consultancy that deploys practical applications of AI for mid-market companies, and has worked closely with senior executives to unlock value from their AI initiatives. Previously, Dan led Amazon Ads Creative Studio, supporting advertisers through technology and scaled services. He has spent over a decade partnering with Fortune 100 clients on digital transformation initiatives at Huge, founded and successfully exited a SaaS startup and held product management roles at Microsoft and Motorola. Dan holds economics and computer science degrees from UPenn. Connect with Dan on LinkedIn