Dads Starting Businesses: Risk, Purpose & Building a Legacy

In this powerful and unfiltered episode of The Dad Compass, Dmitry and Patrick dive deep into what pushes dads to finally start their own businesses — and what stops most from ever trying.

Fresh off Thanksgiving, the guys talk family moments, leftovers, gratitude, and the pressure many fathers feel to create something bigger than themselves. From sober-living entrepreneurship to creative media startups, they unpack the real reasons dads dream about being their own boss: freedom, legacy, purpose, frustration with corporate life, and the desire to show their kids a different path.

Through raw stories and well-earned lessons, they explore:

The moment they realized traditional work wasn’t enough

How fatherhood completely reshapes ambition

Why side hustles turn into hobbies when fear takes over

Managing money, risk, and the weight of providing

What starting a business actually teaches you about yourself

How one bad seed can destroy culture — in business or life

The legacy they want to leave for their kids

Why being terrified is normal — and why you should still do it

Patrick opens up about 24 years in the corporate world, real estate investments, building Mad Gap Sober Living, and the emotional impact of helping people rebuild their lives. Dmitry shares how creativity — and a moment with his daughter — pushed him to launch his own media company and choose purpose over perfection.

This is an episode for every dad who has a dream sitting on the shelf.

Stay for the laughs, the holiday chaos, the “unscripted” segment… and a surprisingly philosophical question that hits harder than expected.

If you're a father thinking about starting something of your own… this one’s for you.

📌 CHAPTERS 

00:00 – Opening banter & post-Thanksgiving chaos
01:40 – Family time, leftovers & holiday nostalgia
05:40 – What pushed us to start our businesses
06:00 – Patrick’s journey: 24 years at one job → real estate → sober living
10:20 – Building Mad Gap Sober Living & the emotional impact
14:00 – The moment you realize your current path isn’t enough
18:00 – Risk, authority struggles, and wanting autonomy
20:00 – Why dads crave more than a paycheck
23:00 – “Go all in or it becomes a hobby”: hard truths about entrepreneurship
28:00 – Culture, integrity, and building something meaningful
32:00 – Dmitry’s creative spark & why capturing moments matters
36:00 – The fear of failing… versus the fear of staying stuck
39:00 – Teaching kids entrepreneurship & building generational change
46:00 – Managing people, boundaries & leadership lessons
50:00 – How creativity and struggle shape a dad’s purpose
54:00 – Final message to dads: Be terrified — and do it anyway
58:00 – Unscripted segment: road trips, kids & connection
01:06:00 – The philosophical “would you intervene?” question
01:08:00 – Closing thoughts on risk, fear & new beginnings
01:10:00 – Broncos, Christmas chaos & sign-off



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