Guest: Mike Henley – Financial Analyst | Entrepreneur | First-Gen College Grad
@mikehenley_
Topics: Career Pivots | Acquisitions | Social Media Branding | External Judgment | Is College Worth It?
This week on David’s Saturday Night Sit Back, I’m joined by Mike Henley, a low-profile powerhouse who’s redefining what it means to pivot, grow, and take ownership of your life.
From underwriting and financial analysis to building a personal brand, running half-marathons, and networking around the world, Mike brings the mindset of a high-performance operator. As a first-generation college graduate from St. John’s University and a self-made entrepreneur, Mike's story is full of practical insights and bold life choices.
We dive into whether college is really worth it in 2025, how to break free from the fear of external judgment when building your online brand, and what it takes to walk away from the corporate world and pursue acquisitions and ownership.
If you're in your 20s or 30s and thinking about your next move, this episode is packed with real talk, strategy, and motivation.
⏱️ Episode Chapters:
(0:00) Mike’s early life in a 20,000-person city
(22:00) Leaving behind sports, discovering fitness & “the iron church”
(31:45) Mike’s college journey, first-gen struggles, and first jobs post-grad
(44:00) Would Mike still go to college? His pivot from corporate life to acquisitions
(55:00) Performance optimization tactics for 2025 + Mike takes the “agency quiz”
(1:20:00) How to build a social media brand without fear of external judgment
(1:32:00) Mike’s future goals, his superpower, and what he wants to master next
🎯 Career & Education:
should I go to college in 2025
first-generation college graduate
college vs no college debate
how to pivot your career in your 20s
career change after college
leaving corporate America
do you need a degree to succeed
💼 Business & Entrepreneurship:
how to start acquisitions
entrepreneur mindset 2025
building a business after corporate
finance career pivot
business strategy for young professionals
becoming your own boss in your 30s
📱 Social Media & Branding:
how to build a personal brand
overcoming fear of external judgment
personal branding tips 2025
social media growth mindset
authentic branding for millennials
how to grow your brand with confidence
🧠 Self-Development & Lifestyle:
performance optimization tips
developing agency over your life
personal growth podcast
mindset shift in your 20s
fitness and mindset for entrepreneurs
how to take control of your future
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