About this episode
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 Rock Top is real — you can be crushing it professionally while quietly collapsing personally. Clarity of core values simplifies decision-making and eliminates internal friction. Entrepreneurial drift happens gradually, then suddenly — awareness must come before crisis. Being fully present where you are removes guilt and fragmentation. Small, consistent intentional actions create massive relational change. Links & Resources The Dad Edge Business Boardroom: https://thedadedge.co
