
Founder building AI healthcare | Scaled @Microsoft & @Instacart eng teams | Focused on curing complexity in healthcare IT with better systems @prettygoodai
San Francisco Bay Area
Joined November 2008
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In 2013, we built an email app with a small team.
18 months later, Microsoft bought it for $200M.
But after we signed the deal, they made one simple request that changed everything.
Here's the untold story of how we built (and sold) our startup:
Demoed our voice AI to a urologist this week.
I played the hard calls. Prior auth lookups. Referral checks. Insurance verification mid-call.
He stopped me.
"Do you have a simple one where a patient's just trying to make an appointment?"
I was showing off. He wanted the 90%.
If you’ve dealt with this, you’re not alone.
Pretty Good AI: Total Practice Automation for athenaOne
Take a look: prettygoodai.com/
7:42 pm: appointment rescheduled by voice.
10:05 am: prior auth approved through the portal.
10:11 am: co-pay balance collected by text.
And everything else on your list.
Your front desk closes at 5. Your patients don't stop calling. Pretty Good AI handles the work in between and writes it all back to athenaOne.
If you’ve dealt with this, you’re not alone.
We’re building solutions for the operational gaps in healthcare.
Take a look: prettygoodai.com/
"I can't tell you how many times I walked past the booth and I heard people just diving right into the pitch." - Max Alsgaard-Miller
His fix: be curious first. Ask what they're struggling with before you tell them what you do.
Watch the full episode: youtu.be/HkjyvbYHLpw
Half of the companies on the athenaOne marketplace joined after ChatGPT launched. Not athenahealth employees telling me that; data.
I sat down with Max Alsgaard-Miller, who spent eleven years inside athenahealth before spending the years since tracking 550-plus marketplace partners and publishing quarterly reports on who is actually winning.
Max walked me through where the marketplace actually came from: Jonathan Bush and Clayton Christensen's more disruption, please experiment to invite athenahealth's own competitors onto the platform instead of fighting them. That bet is still paying off years later.
We got into why Chrome extension and RPA-based integrations stay fragile by design, why athenaOne's 800-plus APIs reward companies that go deep on one EHR instead of claiming to support all of them, and what actually happens when athenaOne builds a feature your startup already sells.
Then we pulled up his live Q3 numbers together. AI phone agent connections nearly quadrupled quarter over quarter. A revenue cycle management surge was hiding behind one partner's churn. And most marketplace ratings tell you a lot less than the sheer volume of recent reviews does.
CHAPTERS
00:00 – A decade inside athenahealth, then a career tracking the marketplace from outside
02:42 – The origin of the athenaOne marketplace, Jonathan Bush, Clayton Christensen and more disruption please
04:55 – Why half of marketplace partners joined after ChatGPT launched
07:44 – Why Chrome extensions and RPA are fragile by design
10:28 – Navigating 800 plus APIs without breaking a practice's workflow
13:48 – What happens when athenaOne builds the feature your startup sells
17:50 – athenaOne owns the ledger, startups own the edge
20:43 – Why going deep on one EHR beats claiming to support them all
23:48 – The origin of the Athena Collector Rules Engine and why RCM startups are challenging it
25:49 – Q3 data, AI phone agents like Pretty Good AI explode and RCM hides a quiet surge behind one partner's churn
31:32 – Why marketplace ratings do not mean what practices think they mean
35:41 – Where the marketplace goes next: RPA, regulation, and the race between payer and provider AI
If you’ve dealt with this, you’re not alone.
We’re building total practice automation to close the operational gaps in healthcare.
Take a look: prettygoodai.com/
Everyone writes the after-hours post.
Nobody writes the 12:40 post.
The front desk goes to lunch. The phone does not.
Not emergencies, not after-hours, so nobody is built for them.
Pull your answer rate for noon to 1:30. That is the honest number.
Asked a prospect last week how she found us.
"I actually asked ChatGPT about who might be able to help us in our practice."
Then she asked her athenahealth CSM the same question directly.
The rep said: nothing yet.
Two answers, same week. Only one of them had us in it.
AI is getting better at solving problems.
It’s also getting better at finding ways around the rules.
This week on Founder Mode, @jasonshafton and I dig into what happens when AI agents become powerful enough to do things their creators didn’t expect.
The technology is moving fast, and the opportunities are enormous. But as agents take on more responsibility, founders have to think harder about security, control, and what makes their businesses worth building.
The goal isn’t to slow down innovation.
It’s to move fast without losing control of what you’re building.
CHAPTERS
00:00 – Cold Open
00:43 – Jason’s First Marathon and the AI Agent That Ordered His Carbs
04:42 – 2026: The Year AI Agents Hacked Real Companies
06:18 – How Worried Should We Be?
07:35 – Inside the Incidents: RubyGems, Gemini, Medicare and More
12:09 – Emergency Brakes: Who Gets to Pull Them?
15:40 – Will the AI Labs Eat Your Business?
19:28 – Is the Age of the Consultant Over?
20:49 – The $23 Million Navier-Stokes Heist
23:52 – Has a Robot Run a Marathon Yet?
24:50 – Founder Mode Top Five
Build smarter. Operate better. Stay in Founder Mode.
Subscribe free: gofoundermode.com/subscribe
Scheduling. Referrals. Smart Forms. Prior Auth. Collections. Appt Optimizer. Reputation. And more.
One platform, every workflow, all directed from a single Command Center.
Your team isn't juggling seven vendors, seven logins, and seven versions of the truth.
Put your busywork on autopilot: prettygoodai.com
I've spent the last 18 months watching people interact with AI tools. The single best predictor of who's winning isn't technical skill. It's not budget. It's not team size. It's curiosity.
There are three types of people in every organization right now:
Type 1: The Overwhelmed
They know AI is important. They're vaguely anxious about it. But they don't know where to start, so they wait. "I'll figure it out when things settle down." Things aren't settling down.
Type 2: The Dabbler
They've tried ChatGPT. Thought it was cool. Used it a few times, then went back to how they used to do things. They mention it in meetings. They're not using it daily.
Type 3: The Obsessed
The moment a new tool drops, they've already tried it. They're running agents, testing builds, breaking things on purpose. Every week they find two or three things that save them hours. They're not waiting for permission.
The gap between Type 2 and Type 3 is compounding every month. Because every tool you adopt early means you're a year ahead of the people who adopt it late.
The engineers running Cursor two years ago are miles ahead of the ones just now learning Claude code.
Curiosity isn't a personality trait you either have or don't. It's a practice. Go try the new thing. Break it.
Ask "what else can this do?"
That question is worth more than any technical credential right now.
Which type are you right now, and which type do you want to be?
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I hope you've found this thread helpful.
Follow me @KevinHenrikson for more.
Like/Repost the quote below if you can:
I've spent the last 18 months watching people interact with AI tools. The single best predictor of who's winning isn't technical skill. It's not budget. It's not team size. It's curiosity.
There are three types of people in every organization right now:
Type 1: The Overwhelmed
They know AI is important. They're vaguely anxious about it. But they don't know where to start, so they wait. "I'll figure it out when things settle down." Things aren't settling down.
Type 2: The Dabbler
They've tried ChatGPT. Thought it was cool. Used it a few times, then went back to how they used to do things. They mention it in meetings. They're not using it daily.
Type 3: The Obsessed
The moment a new tool drops, they've already tried it. They're running agents, testing builds, breaking things on purpose. Every week they find two or three things that save them hours. They're not waiting for permission.
The gap between Type 2 and Type 3 is compounding every month. Because every tool you adopt early means you're a year ahead of the people who adopt it late.
The engineers running Cursor two years ago are miles ahead of the ones just now learning Claude code.
Curiosity isn't a personality trait you either have or don't. It's a practice. Go try the new thing. Break it.
Ask "what else can this do?"
That question is worth more than any technical credential right now.
Which type are you right now, and which type do you want to be?
Watched a practice this week; plan to turn on patient self-scheduling.
Then the catch-22 showed up.
Self-scheduling in the portal needs a portal login.
To get a portal login, most patients have to call the office.
So the feature meant to stop calls starts with a call.
A healthcare practice I spoke with recently had 2+ hour patient hold times. Not 2 minutes. 2 hours. Their staff was drowning. Patients were furious. No-show rates were climbing. We got the hold time down to under 5 seconds. Here's how.
This is a universal problem dressed up in a healthcare uniform. Every service business has a version of it: high-volume, repeatable customer requests that are routed to expensive humans rather than systems.
In healthcare, it's especially acute.
Healthcare practices aren't bad at patient experience because they don't care. They're bad at it because they're solving a systems problem with headcount.
More staff. More phone lines. More training. And the calls keep coming.
Because 70-80% of the calls coming into a specialty practice don't require a human at all:
"I need to reschedule my appointment."
"Can you refill my prescription?"
"What's the address of your office?"
"Do you accept my insurance?"
These are not clinical decisions. They're administrative tasks handled by phone.
Yet most practices have trained, expensive human beings answering these questions all day long. Meanwhile, patients are on hold. Staff is burned out. Physicians are frustrated.
The fix isn't more people. It's the right system.
At Pretty Good AI, we build voice intelligence platforms for healthcare practices. We integrate directly with athenaOne EHR. We go live in about 30 days. And we consistently see 50%+ of calls handled automatically from day one.
If your practice is dealing with this, reach out. It's a solvable problem.
Company culture isn’t what you say you believe.
It’s what you’re willing to stand behind when it gets difficult.
This week on Founder Mode, @clairewaves joins @jasonshafton and me to share what 12 years inside Google and YouTube taught her about culture, leadership, and the gap between a company’s promises and its actions.
She helped tell Google’s story, believed in its mission, and later helped organize a walkout when that story no longer matched what she was seeing.
It’s a reminder that building a great company isn’t just about creating a mission people believe in.
It’s about making sure your decisions still reflect it as the company grows.
CHAPTERS
00:00 – Cold open
00:41 – Is culture load-bearing or just marketing?
04:07 – Selling meaning as a perk
05:42 – Ghostwriting Larry Page and the cure-death era
08:35 – Google+ and the corporate bonus
10:29 – When the story cracked: Creative Lab
13:18 – YouTube and the brand vulnerability briefing
15:54 – Was advertising the real mission all along?
18:10 – Marketing to executives instead of the public
21:31 – Maven, the walkout, and why workers went quiet
25:21 – Would she organize the walkout again?
28:08 – The subway ride home
32:06 – Where to find Claire and Don't Be Evil
33:13 – The Founder Mode Five
Real conversations. Hard-earned lessons. Better companies.
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