Episode Details

In this powerful conversation, I sit down with Mat Lewczenko — entrepreneur, coach, and author of The Entrepreneur's Regret — to unpack what it feels like to be winning on paper while quietly losing at home. Mat shares his story of growing up as a Polish political refugee, building success through grit and discipline, and eventually finding himself at the top of his professional game… but emotionally empty, disconnected, and on the verge of self-sabotage.

We talk about the silent epidemic facing high-performing entrepreneurs — entrepreneurial drift — and what it takes to reclaim your nights, weekends, relationships, and sanity. This episode is a wake-up call for any man chasing more while feeling less.

Timeline Summary

[0:00] The concept of "Rock Top" — succeeding outwardly while unraveling inwardly

[1:41] Mat's family escaping Poland as political refugees before martial law

[3:02] Growing up in an immigrant household built on pride, discipline, and ownership

[10:10] Early lessons on earning what you want and respecting what you own

[17:47] The tension between giving kids a better life without raising them soft

[24:58] Mat's pivot from theater professor to real estate entrepreneur

[30:29] The breaking point — winning at work while losing at home

[31:31] The porch conversation where his wife said, "You don't get to do this"

[35:29] Realizing he couldn't even name his core values

[36:33] The North Star Values process and regaining alignment

[40:52] The three pillars — Leadership, Love, and Life

[41:30] Why being "all in" where you are eliminates guilt and fragmentation

[45:28] The danger of climbing the wrong mountain

[47:06] Why you must go back through the clouds to choose a new summit

[54:28] Small hinges swing big doors — 15 intentional minutes a day

[58:32] Presence over presents — how to win back connection at home

Five Key Takeaways

1. Rock Top is real — you can be crushing it professionally while quietly collapsing personally.
2. Clarity of core values simplifies decision-making and eliminates internal friction.
3. Entrepreneurial drift happens gradually, then suddenly — awareness must come before crisis.
4. Being fully present where you are removes guilt and fragmentation.
5. Small, consistent intentional actions create massive relational change.

Links & Resources

• The Dad Edge Business Boardroom: https://thedadedge.com/mastermind
• Mat Lewczenko on LinkedIn: https://www.linkedin.com/in/mat-lewczenko/
• Mat Lewczenko on Instagram: https://www.instagram.com/mat.lewczenko/?hl=en
• Mat's Podcast (Buzzsprout): https://www.buzzsprout.com/1956169/episodes
• Mat Lewczenko — Additional Resource: https://ifgrxppecbxjqjkoyvl7.app.clientclub.net/courses/offers/82985e7c-be3c-41c2-b004-8e703e688431?fbclid=IwRlRTSAP-xitleHRuA2FlbQIxMABzcnRjBmFwcF9pZAo2NjI4NTY4Mzc5AAEe9kqpb3eiIFwdvocjWzIhjjxamujPzRooAIc