On this podcast we've explored many dramatic post exit stories. Tales of existential crisis, addictions to drugs, alcohol, sex and obsessive money chasing, extreme sports, mind blowing adventures and long spiritual journeys to faraway lands. Daniel Kivatinos journey is different and just as important to hear. His pause after selling his company didn't push him into a new path. It gave him clarity that he was already on the right one. Daniel built and sold DrChrono, one of the first mobile medical platforms processing billions in medical billing. His work even took him to the White House to help shape healthcare data policy. Today, Daniel is building JustPaid, an AI powered platform changing how businesses manage accounts receivable. In our conversation, Daniel shows us how he built that conviction about who he is and what he truly wants to do. In his case, to keep building highly impactful tech companies right in the heart of Silicon Valley.TIME STAMPS:00:00 – Fulfilment: “Some days I’m a five, some days a six”00:19 – What would it take to feel like a 10?00:58 – The illusion of a “perfect place” in life01:17 – Mountain after mountain: why satisfaction always moves01:37 – Introducing Daniel Kivatinos & his journey from DrChrono to JustPaid02:14 – Can a life ever feel fully “satisfied”?03:11 – Starting the conversation: Daniel joins the show03:17 – How he discovered the podcast & why it resonated03:36 – He sold DrChrono… and then started a new company within a year04:05 – Why founders can’t take long breaks without losing their edge05:40 – Did one year off give enough space for clarity? (Short answer: no.)06:21 – Why entrepreneurs struggle with taking real time off07:57 – The addictive nature of building companies08:40 – Is the second company easier? (Spoiler: no, just “different hard.”)10:10 – Is it ever easier the second time? Unrealistic expectations10:43 – “You can’t hire people to build it for you”11:40 – Even Steve Jobs struggled with his second company13:07 – Why second-time founders often fail14:33 – What Next actually gave Steve Jobs later15:19 – Connecting the dots only works backward15:44 – What Daniel did during his year off16:40 – The Reddit founder told him to move to California17:22 – Early Y Combinator days & why he never returned to NYC17:39 – Considering moving away after the exit18:01 – Missing family and exploring other states23:15 – “What should I do with a year off?” His advice23:59 – Driving across the U.S. twice — unstructured freedom25:05 – The joy of having no plan26:25 – Driving across the Great Salt Lake (the slightly risky part)27:11 – Why unstructured time matters after a big exit27:31 – Realizing he wasn’t “done” with tech or Silicon Valley27:57 – Three years later: is he happy?28:07 – Business as a game, not just work29:32 – Creator vs operator: early-stage founders must be both32:41 – Did his son influence the decision to start another company?33:58 – Modeling meaning and fulfilment for children36:08 – Why he became an entrepreneur in the first place36:14 – Graduating into the 2008 crisis36:40 – Discovering startup life and loving the creative chaos38:23 – It wasn’t about money — it was about people40:49 – Two failed startups in a row: learning without financial reward41:11 – Motivation after exit: still driven by curiosity, not fear or money42:13 – Curiosity as the true engine behind building companies43:17 – Why no single motivator is enough to build a company45:01 – “Stay hungry, stay foolish” — Daniel’s interpretation46:36 – Work-life balance vs. work-life integration46:45 – How he designs balance in his second company48:40 – Why remote culture supports family life49:26 – How much he actually works49:35 – Comparing work intensity: first company vs second50:16 – Why he set up the company so co-founders push each other50:22 – Returning to fulfilment: the moving target51:00 – The mountain metaphor: why fulfilment never stays52:07 – What a “10 day” looks like for Daniel53:42 – Finding joy in the small things53:59 – Why the end goal will never create long-term fulfilment54:18 – “How do you want to be remembered?”54:29 – Family, impact, and acceptance56:16 – Graveyards, billionaires, and perspective on legacy57:13 – Closing reflections & farewell

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