What does it actually take to build a healthcare company from scratch?

In this episode of #TheShot, Eugene Borukhovich and Jim Joyce sit down with Daniel Kivatinos, co-founder of DrChrono, to unpack a real founder journey — from growing up in Queens with blue-collar parents to bootstrapping a healthcare startup through the 2008 crash, betting early on the iPad, and building DrChrono over 13+ years before selling in 2021.

This is not a “how to get rich quick” story.
It’s about persistence, timing, relentless shipping, and ignoring most advice.

We talked about:

🧱 Start painfully small - One doctor who loves your product beats 1,000 lukewarm users

🔁 Release fast, fix faster - Daily shipping built trust doctors didn’t get from incumbents

🕰️ Timing is earned, not predicted - Years of grinding made the iPad moment possible

💸 Bootstrapping builds discipline - Scarcity forced focus

🚫 Ignore most advice - Especially from people who aren’t where you want to be

🏃‍♂️ Just do it - Overthinking kills more startups than bad ideas

If you’re building in healthcare, fintech, or any regulated industry — this one’s for you.

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00:00 – Intro & JP Morgan recap
01:30 – Why Eugene can’t do the show without Jim
02:10 – Meeting Daniel at Health 2.0 in NYC
03:10 – Growing up in Queens
05:00 – Blue-collar parents & elevator mechanic stories
07:00 – Stony Brook, choosing computer science, brutal CS class
09:30 – Art, music, and coding
11:00 – Early startups that failed
12:30 – The 2007–2008 reality check
14:00 – Why Daniel didn’t chase “safe” jobs
16:00 – Watching friends raise money & choosing a harder path
18:30 – Saving $50k and deciding to start a company
20:00 – Why healthcare
21:00 – Founding DrChrono
22:00 – What DrChrono originally solved (scheduling)
23:30 – Printing flyers & knocking on doctor doors
25:30 – One doctor who truly loved the product
27:30 – “10 users who love you beats 1,000 who don’t”
28:30 – Expanding into EHR, billing, and practice management
29:30 – Hearing about the iPad
30:30 – Building the first iPad-based EHR
31:45 – Overnight growth after the App Store launch
33:00 – Releasing faster than Epic and Cerner
35:00 – Why speed mattered more than strategy
36:00 – Cold-emailing Y Combinator
37:00 – Alexis Ohanian visits NYC
38:30 – Startup School & mindset shift
39:30 – The YC interview experience
40:30 – Getting the first real check
41:30 – Life inside Y Combinator
43:30 – Growing DrChrono over 13+ years
44:30 – Selling to EverCommerce in 2021
45:30 – Why the buyer mattered more than the price
46:30 – What Daniel is building now (JustPaid)
48:00 – Why starting SMB beats selling enterprise first
49:30 – Final question: advice to younger self
52:00 – “Just do it. Don’t stop.”