Outside The Corporate Box cover art

Outside The Corporate Box

Outside The Corporate Box

By: J Squared
Listen for free

Outside the Corporate Box is for leaders, builders, and thinkers who knew they were never meant to stay inside someone else’s blueprint.

Hosted by JMan and Jeffrey, this show explores what happens when ambitious professionals step beyond traditional titles, rigid systems, and inherited definitions of success to build a life and business that actually reflects who they are.

These are conversations about reinvention, courage, identity, entrepreneurship, leadership, and the messy, beautiful work of becoming fully yourself.

From executives who walked away from the boardroom…
to creators who turned expertise into influence…
to entrepreneurs who chose freedom over comfort…

This is where modern thought leadership gets honest.

Because sometimes the most powerful move isn’t climbing the ladder.

It’s realizing the ladder was leaning against the wrong wall.


© 2026 Outside The Corporate Box
Economics Leadership Management & Leadership
Episodes
  • She Had the MBA, the Six-Figure Salary, and Was Crying in a Parking Lot at 10 PM | Tezeta Roro
    Jun 29 2026

    Tezeta "Tez" Roro had everything the blueprint promised: the MBA, the six-figure salary, the recognized company name on her badge. She was so proud of that job she wore her badge to the grocery store. Then came 10:00 PM on a corporate campus, nine months pregnant, working through a capital budget crunch, and the moment she realized the structure she had spent 12 years climbing was fundamentally incompatible with the life she was actually trying to live.

    What she did next took two and a half years of calculated planning, a Forbes article documenting every step, and the courage to go from a guaranteed salary to 100% commission as a first-gen immigrant with a toddler, a newborn, and a husband consulting out of state three weeks a month. Today Tez is a broker-owner, speaker, and founder of Yourtopia Realty Partners. This is her story.

    What You Will Learn:

    1: Why the "golden handcuffs" of a six-figure salary are often worth less than they appear once you calculate taxes, commute, stress, and lost time
    2: How Tez structured a deliberate two-and-a-half-year exit strategy as a risk-averse introvert with no safety net behind her
    3: The difference between mourning a corporate identity and finding confidence in a new one
    4: Why she used a six-month maternity leave to test whether she could actually sustain the real estate lifestyle before fully committing
    5: Practical financial strategies for leaving corporate when you have a mortgage, kids, and no trust fund
    6: What it really means to define success on your own terms, and why middle schoolers gave her a standing ovation

    About Tezeta Roro:

    Tezeta "Tez" Roro is a broker-owner, speaker, and founder of Yourtopia Realty Partners. A first-generation Ethiopian-American with a biology degree, MBA, and 12 years in corporate operations, Tez documented her exit strategy in Forbes and has since built a brokerage and property management company simultaneously. She speaks nationally on entrepreneurship, real estate, and building a business that aligns with your values.

    TIMESTAMPS:
    00:00 — Introduction: The parking lot moment
    01:00 — Painting the picture: 12 years inside corporate
    03:00 — The risk-averse introvert and what that actually means
    04:30 — The immigrant path: biology, MCATs, and the pivot to business
    07:00 — The cracks appear: parenting inside a corporate structure
    10:00 — The RSV hospitalisatio and the conversation that changed everything
    14:00 — Nine months pregnant, 10:00 PM, hitting a deer in the parking lot
    17:00 — The second maternity leave that became her launch runway
    19:00 — "We get married to the top-line salary" -- the real numbers breakdown
    22:00 — What to do if you have no partner safety net
    24:00 — The rebuild: identity shifts, isolation, and finding the new version
    28:00 — Why real estate and the ding-ding moment during her own home purchase
    31:00 — The introvert-extrovert misunderstanding and entrepreneurial risk appetite
    35:00 — Letting go vs. mourning: how to leave without grief
    38:00 — Lightning Round
    41:00 — The Last Question: advice for anyone about to bet on themselves

    Connect with Tezeta Roro:

    LinkedIn: https://www.linkedin.com/in/tezroro/
    Forbes Article: https://www.forbes.com/sites/ellevate/2019/07/31/plotting-your-corporate-exit-strategy/

    FOUNDING SPONSORS:
    1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

    2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

    3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% off

    SUBSCRIBE to Outside the Corporate Box for new episodes every Monday.

    Outside the Corporate Box is part of J Squared Podcast Productions — a premium media network built for professionals who want more than entertainment.

    Show More Show Less
    43 mins
  • From Fortune 500 to Founder: Why Staying Comfortable Is the Biggest Career Risk
    Jun 8 2026

    Jackie Phichith spent nearly two decades inside Fortune 500 boardrooms helping McDonald's, Merck, and Pfizer navigate transformation. Then she realized the framework she had been teaching organizations was the same one she needed to apply to herself. What she learned next might change how you think about the career decision you are sitting on right now.

    What You'll Learn:

    1: Why 70% of enterprise transformations fail and the one thing companies keep cutting that guarantees it
    2: The SHINE framework: a 5-step method for moving any team through change without losing people
    3: What the Midnight Rambles of Teddy Roosevelt teach us about effective leadership in 2025
    4: How to do a quarterly business review on yourself when you're a founder of one
    5: Why employee engagement scores are not soft data and what happens when leadership ignores them
    6: The identity shift nobody talks about when you leave a corporate title behind

    About Jackie Phichith:
    Jackie Phichith is a change management strategist, keynote speaker, and founder of Inspiration Your Way. With nearly 20 years inside Fortune 500 companies including McDonald's, Merck, and Pfizer, she has developed the SHINE framework to help leaders and organizations move through transformation without losing their people. She now brings that expertise to a broader stage, working with executives and founders across industries.

    TIMESTAMPS:
    00:00 — Cold open and episode introduction
    01:00 — What 20 years inside Fortune 500 companies actually looked like
    03:30 — Why only 27% of employees trust their leaders to guide them through change
    07:00 — The real reason companies cut training during transformations
    08:30 — The moment Jackie knew she had to step outside the corporate box
    13:00 — How staying comfortable becomes the biggest risk
    15:00 — The identity shift of going from corporate employee to founder
    20:00 — How to protect your focus as a solo founder
    24:00 — Running a quarterly business review on yourself
    28:00 — The Teddy Roosevelt Midnight Rambles story and what it means for CEOs
    31:00 — The organizations that will be left behind by AI and rapid change
    38:00 — The SHINE framework explained step by step
    44:00 — Lightning Round
    46:00 — The Last Question: What would you go back and tell yourself on day one?

    Connect with Jackie Phichith
    Guest LinkedIn: https://www.linkedin.com/in/jacquelinephichith/

    About the Show:
    Outside the Corporate Box is a Monday podcast co-hosted by JMan and Jeffrey Scott Stanton. Every episode explores what happens when ambitious professionals step beyond traditional titles and build something on their own terms. Real stories about reinvention, risk, and what it actually takes to bet on yourself.

    FOUNDING SPONSORS:
    1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

    2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

    3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% off

    SUBSCRIBE to Outside the Corporate Box for new episodes every Monday.

    Outside the Corporate Box is part of J Squared Podcast Productions — a premium media network built for professionals who want more than entertainment.

    Show More Show Less
    46 mins
  • Leaving Corporate to Build Relay Recruiting: Lauren Dunkle Dlugosh's Story
    Jun 1 2026

    Lauren Dunkle Dlugosh was one of the top billing recruiters at her firm in Rochester, regularly placing $550K to $650K in fees annually. She had great colleagues, a strong reputation, and no real reason to leave. And the night before she quit, she slept perfectly.

    That is what this conversation is really about. Not the business plan or the LinkedIn announcement. The moment before all of it, when everything felt right even though nothing was certain yet.

    What You Will Learn:
    1: What a non-solicitation agreement actually means and what it costs you when you walk away from a decade of client relationships
    2: Why Lauren named her first year of entrepreneurship grief, and how that honesty made her a better founder and recruiter
    3: How the golden handcuffs concept applies beyond recruiting and how to know when the cage is no longer worth it
    4: What Lauren's cross-country camper van trip has to do with landing a client after she went independent
    5: The one reframe that shifted everything: it was not about what she was running from, it was what she was running toward
    6: Why Lauren went from being a doer at her old firm to a creator building her own

    TIMESTAMPS:
    00:00 — Introduction & The Hook
    00:42 — Guest Introduction: Lauren Dunkle Dlugosh
    01:10 — Life Before Relay: The Rochester Firm
    04:22 — The Slow Burn: When Fine Stops Being Enough
    05:11 — AI in Recruiting: What Lauren Wanted to Build
    10:20 — Non-Solicitation Agreements Explained
    12:50 — Golden Handcuffs: The Cost of Comfort
    15:16 — Life With Intention: The Camper Van Trip
    17:03 — The Loneliness Nobody Talks About in Year One
    21:05 — Grieving a Life You Actually Loved
    24:43 — Stopping Waiting for Permission
    27:48 — Lightning Round
    33:25 — The Last Question: What Would You Tell Yourself on Day One?
    34:07 — Outro

    About Lauren Dunkle Dlugosh:
    Lauren Dunkle Dlugosh is the Founder and CEO of Relay Recruiting, an executive and professional search firm based in Rochester, New York. With nearly a decade of experience recruiting across nonprofit, higher education, manufacturing, energy, and the C-suite, she built her reputation as a top billing recruiter before launching independently. Her work combines deep relationship-based search with a forward-thinking approach to AI and workflow efficiency.

    Connect with Lauren Dunkle Dlugosh
    Guest LinkedIn: https://www.linkedin.com/in/laurendunkle/
    Website: https://www.relayrecruiting.com/

    FOUNDING SPONSORS:
    1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.

    2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.

    3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% off

    SUBSCRIBE to Outside the Corporate Box for new episodes every Monday.

    Outside the Corporate Box is part of J Squared Podcast Productions — a premium media network built for professionals who want more than entertainment.

    Show More Show Less
    36 mins
adbl_web_anon_alc_button_suppression_t1
No reviews yet