In this conversation, serial entrepreneur and exited founder Omar Haroun reveals the hidden emotional cost of success, the identity collapse many founders experience post-exit, and why wealth alone often fails to deliver fulfillment.

Omar Haroun is a multi-exit entrepreneur and investor who has spent years exploring and trying to understand the psychological and emotional realities of life after selling a business.

He explains:
◼️Why financial freedom often triggers confusion, guilt, and emptiness
◼️The “wealth lag” founders experience after an exit
◼️Why money buys safety — but not security or fulfillment
◼️The most dangerous financial mistake founders make post-exit
◼️How to rebuild purpose, clarity, and meaning after success

After selling her bootstrapped company in a 9-figure all-cash exit, Anastasia Koroleva expected freedom, joy, and the end of struggle.

Instead, she encountered something no one talks about—the Wealth Lag.

In this deeply honest and research-backed breakdown, Anastasia reveals the emotional crash that happens after financial freedom: the confusion, cognitive dissonance, identity loss, and the quiet dissatisfaction that haunts even the most successful founders, investors, athletes, and creators.

For 15 years she's studied hundreds of post-exit lives, and today he shares the patterns, tools, and stages that determine whether wealth becomes leverage for a deeply fulfilling life… or a trap that slowly suffocates us.

This episode is for anyone who has created wealth, is on the path to it, or wants to understand the psychological reality behind “success”.

Anastasia explains:

◼️ What the Wealth Lag really is — and why it hits every rich founder
◼️ Why the brain rebels against sudden wealth (cognitive dissonance explained)
◼️ How comfort becomes a silent addiction that drains purpose and identity
◼️ The 5 stages people must move through to adapt to wealth
◼️ Why most wealthy people stay stuck for decades
◼️ The emotional, intellectual, and spiritual work required after an exit
◼️ How to build a tribe that accelerates growth instead of stagnation
◼️ Why financial freedom does NOT create fulfillment — and what does

This is the real conversation that elite founders, ex-CEOs, wealth creators, and next-gen inheritors have behind closed doors. Exit Paradox brings it into the light.

If this episode helped you, please share it with someone who needs it.

TIMESTAMPS
00:00 – What Happens After Financial Freedom
00:22 – The Hidden Problem No One Warns You About
01:01 – The Wealth Honeymoon: Cars, Jets & New Toys
01:43 – Why Wealth Eventually Stops Feeling Good
02:15 – “Wealth Has Arrived… But I Haven’t”
02:58 – The Wealth Lag: Why Your Inner World Falls Behind
03:38 – Cognitive Dissonance: Your Brain’s Wealth Alarm System
05:00 – Why Most People Never Adapt to Wealth
06:39 – The Trap of Comfort (and How It Quietly Destroys Ambition)
07:28 – Step 1: Reframing Wealth as Leverage, Not the Goal
08:24 – Step 2: Building a Fulfilling Life Strategy Post-Exit
09:50 – Step 3: The Skills You Need After You Get Rich
10:42 – Step 4: Building a Tribe That Pulls You Forward
12:16 – Step 5: The Decision That Changes Everything
13:24 – The Real Mission: Clarity, Conviction & A Life Worth Living

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