Is the Second Startup Easier?

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 life
01:17 – Mountain after mountain: why satisfaction always moves
01:37 – Introducing Daniel Kivatinos & his journey from DrChrono to JustPaid
02:14 – Can a life ever feel fully “satisfied”?
03:11 – Starting the conversation: Daniel joins the show
03:17 – How he discovered the podcast & why it resonated
03:36 – He sold DrChrono… and then started a new company within a year
04:05 – Why founders can’t take long breaks without losing their edge
05:40 – Did one year off give enough space for clarity? (Short answer: no.)
06:21 – Why entrepreneurs struggle with taking real time off
07:57 – The addictive nature of building companies
08:40 – Is the second company easier? (Spoiler: no, just “different hard.”)
10:10 – Is it ever easier the second time? Unrealistic expectations
10:43 – “You can’t hire people to build it for you”
11:40 – Even Steve Jobs struggled with his second company
13:07 – Why second-time founders often fail
14:33 – What Next actually gave Steve Jobs later
15:19 – Connecting the dots only works backward
15:44 – What Daniel did during his year off
16:40 – The Reddit founder told him to move to California
17:22 – Early Y Combinator days & why he never returned to NYC
17:39 – Considering moving away after the exit
18:01 – Missing family and exploring other states
23:15 – “What should I do with a year off?” His advice
23:59 – Driving across the U.S. twice — unstructured freedom
25:05 – The joy of having no plan
26:25 – Driving across the Great Salt Lake (the slightly risky part)
27:11 – Why unstructured time matters after a big exit
27:31 – Realizing he wasn’t “done” with tech or Silicon Valley
27:57 – Three years later: is he happy?
28:07 – Business as a game, not just work
29:32 – Creator vs operator: early-stage founders must be both
32:41 – Did his son influence the decision to start another company?
33:58 – Modeling meaning and fulfilment for children
36:08 – Why he became an entrepreneur in the first place
36:14 – Graduating into the 2008 crisis
36:40 – Discovering startup life and loving the creative chaos
38:23 – It wasn’t about money — it was about people
40:49 – Two failed startups in a row: learning without financial reward
41:11 – Motivation after exit: still driven by curiosity, not fear or money
42:13 – Curiosity as the true engine behind building companies
43:17 – Why no single motivator is enough to build a company
45:01 – “Stay hungry, stay foolish” — Daniel’s interpretation
46:36 – Work-life balance vs. work-life integration
46:45 – How he designs balance in his second company
48:40 – Why remote culture supports family life
49:26 – How much he actually works
49:35 – Comparing work intensity: first company vs second
50:16 – Why he set up the company so co-founders push each other
50:22 – Returning to fulfilment: the moving target
51:00 – The mountain metaphor: why fulfilment never stays
52:07 – What a “10 day” looks like for Daniel
53:42 – Finding joy in the small things
53:59 – Why the end goal will never create long-term fulfilment
54:18 – “How do you want to be remembered?”
54:29 – Family, impact, and acceptance
56:16 – Graveyards, billionaires, and perspective on legacy
57:13 – Closing reflections & farewell