Digital Patient Podcast

TDP 172: U of Rochester’s Dr. Michael Hasselberg & Catholic Health’s Michael Mainiero: Why Most AI Pitches Fail, Startup Red Flags, and the One Word That Will Get You Blacklisted from Health Systems

March 27, 2025
By
seamless

Subscribe on: RSS | SPOTIFY | APPLE PODCAST | GOOGLE | BREAKER | ANCHOR

In this dual-guest episode of The Digital Patient, Josh Liu and Alan are joined by two brilliant digital leaders in healthcare: Dr. Michael Hasselberg and Michael Mainiero. Together, they break down what startups get wrong when pitching health systems, why most AI pitches fall flat, and how the real winners are those that act like partners—not vendors.

From cold calls and bathroom pitches (don’t do it) to co-development and shared equity models, this episode is packed with real talk and tactical advice for vendors, digital health builders, and health system innovators alike. Click the play button to listen or read the show notes below.

Audio:

Guest(s):

  • Dr. Michael Hasselberg, Chief Digital Health Officer at University of Rochester Medical Center
  • Michael Mainiero, Chief Digital and Chief Information Officer at Catholic Health
  • Dr. Joshua Liu, Co-founder & CEO at SeamlessMD

Episode 172 - Show Notes:

[00:00:07] Episode preview

[00:04:45] Startup Saturation & AI Overload

[00:07:04] Why Health Systems Are Cautious in 2025

[00:09:02] What Scares CDOs: Not Lift, But Interoperability & Ownership

[00:11:07] Predatory Sales Tactics That Gets You Blacklisted

[00:17:03] Why Internal AI Development Beats Vendor Solutions

[00:20:22] Epic-First Strategy and the Case for Simplicity

[00:23:00] Why Health Systems Avoid Seed-Stage Startups

[00:26:02] Why Culture & Product Team Stability Matter Most

[00:29:03] “We’re Already Integrated with Epic” (No, You’re Not)

[00:33:36] What Health Systems Want in Startup Partnerships

[00:36:44] Sales “First Date” Red Flags: What Not to Say

[00:39:30] Never Start by Telling Me My Problems

[00:43:34] Don’t Pitch After a Talk (Especially in the Bathroom)

[00:47:16] The Smartest Strategy? Win with Your First Customers

The Digital Patient has been recognized as Feedspot's #1 Patient Engagement Podcast of 2025. Thank you to our listeners for making this happen!

TDP 172: U of Rochester’s Dr. Michael Hasselberg & Catholic Health’s Michael Mainiero: Why Most AI Pitches Fail, Startup Red Flags, and the One Word That Will Get You Blacklisted from Health Systems

Posted by:
seamless
on
March 27, 2025

Subscribe on: RSS | SPOTIFY | APPLE PODCAST | GOOGLE | BREAKER | ANCHOR

In this dual-guest episode of The Digital Patient, Josh Liu and Alan are joined by two brilliant digital leaders in healthcare: Dr. Michael Hasselberg and Michael Mainiero. Together, they break down what startups get wrong when pitching health systems, why most AI pitches fall flat, and how the real winners are those that act like partners—not vendors.

From cold calls and bathroom pitches (don’t do it) to co-development and shared equity models, this episode is packed with real talk and tactical advice for vendors, digital health builders, and health system innovators alike. Click the play button to listen or read the show notes below.

Audio:

Guest(s):

  • Dr. Michael Hasselberg, Chief Digital Health Officer at University of Rochester Medical Center
  • Michael Mainiero, Chief Digital and Chief Information Officer at Catholic Health
  • Dr. Joshua Liu, Co-founder & CEO at SeamlessMD

Episode 172 - Show Notes:

[00:00:07] Episode preview

[00:04:45] Startup Saturation & AI Overload

[00:07:04] Why Health Systems Are Cautious in 2025

[00:09:02] What Scares CDOs: Not Lift, But Interoperability & Ownership

[00:11:07] Predatory Sales Tactics That Gets You Blacklisted

[00:17:03] Why Internal AI Development Beats Vendor Solutions

[00:20:22] Epic-First Strategy and the Case for Simplicity

[00:23:00] Why Health Systems Avoid Seed-Stage Startups

[00:26:02] Why Culture & Product Team Stability Matter Most

[00:29:03] “We’re Already Integrated with Epic” (No, You’re Not)

[00:33:36] What Health Systems Want in Startup Partnerships

[00:36:44] Sales “First Date” Red Flags: What Not to Say

[00:39:30] Never Start by Telling Me My Problems

[00:43:34] Don’t Pitch After a Talk (Especially in the Bathroom)

[00:47:16] The Smartest Strategy? Win with Your First Customers

The Digital Patient has been recognized as Feedspot's #1 Patient Engagement Podcast of 2025. Thank you to our listeners for making this happen!

Recent news from SeamlessMD

TDP 171: UofU Health’s Laura Marquez: Dark Green v. Light Green Dollars For ROI, Why Healthcare Leaders Need to be More Comfortable Killing Old Tech, and How Patients are the Most Underutilized Care Team Members
March 21, 2025

TDP 171: UofU Health’s Laura Marquez: Dark Green v. Light Green Dollars For ROI, Why Healthcare Leaders Need to be More Comfortable Killing Old Tech, and How Patients are the Most Underutilized Care Team Members

Learn More
TDP 170: HIMSS 2025 Debrief: Riding the Epic Banana, The "Cream Incident", and Revealing the Most Provocative Ideas we Heard
March 18, 2025

TDP 170: HIMSS 2025 Debrief: Riding the Epic Banana, The "Cream Incident", and Revealing the Most Provocative Ideas we Heard

Learn More
TDP 169: Allegheny Health Network’s Joseph Seliski & Dr. James Solava: Piloting 3 AI Scribes at Once, Reducing Friction for Clinicians to Use AI, and Rethinking Medical Education in the World of AI
March 13, 2025

TDP 169: Allegheny Health Network’s Joseph Seliski & Dr. James Solava: Piloting 3 AI Scribes at Once, Reducing Friction for Clinicians to Use AI, and Rethinking Medical Education in the World of AI

Learn More