What A Prison Experience Taught Me About Entrepreneurial Freedom

What A Prison Experience Taught Me About Entrepreneurial Freedom

Yesterday I was at the Little Beach House in Malibu, overlooking the ocean, with an entrepreneur who told me her number one goal is freedom.

Freedom of time
Freedom of money
Freedom from pressure

She said:

“If I could just get free, everything would change.”

The next morning, I walked into California Correctional Institution (CCI) with Defy Ventures through the Entrepreneurs’ Organization (EO) Los Angeles Chapter.

Defy Ventures helps people in prison develop entrepreneurial skills, leadership, and accountability, giving them tools to change their lives and their communities.

Many of the people I met are serving life sentences, some for murder. It was heavy, real, and sobering.

And yet, the energy in that room was level 10:

High fives
Cheers
Fist bumps

It felt like a championship boxing match, complete with a Rocky theme playing in my imagination—every pitch like a round, every clap like a victory bell.

Defy Ventures asks participants to take personal responsibility:

No excuses
No blaming
Write leadership statements
Design logos
Print business cards
Build full business plans
Present to investors and judges

Five winners were selected.

First place in my cohort went to Kool Kenny and his business, Hats and Tatts, a mobile tattoo shop.

Clear repayment plan for investors
10% of profits donated to a breast cancer nonprofit because his grandmother, who he calls his everything, is battling the disease

Inside prison walls, he was thinking about impact, structure, and giving back.

We also did an exercise called Step to the Line:

If you finished high school
If you experienced violence at home
If you were abused
If you still have someone you need to forgive
If you have lost someone to violence

For a few minutes, labels disappeared. There was no volunteer and no inmate. Just humans recognizing shared pain, courage, and hope.

Quan Huynh, Executive Director of Defy, shared his story:

Once had a life sentence
Discovered meditation in prison and realized he could be free even in confinement
Later wrote Sparrow in the Razor Wire, sharing how inner freedom begins long before physical freedom

Key Takeaways for Entrepreneurs

As entrepreneurs, we have unfair advantages: mobility, networks, and access. Yet many of us feel trapped—by comparison, fear, or distraction.

We say we want freedom. But we already have it.

The real question:

Are we doom scrolling and binge watching?
Or building something meaningful?
Are we blaming external circumstances?
Or taking ownership?

Freedom begins with responsibility.

A Step-by-Step Guide to Practicing Real Freedom

Step 1: Own Your Results
Write down three areas where you’ve been blaming external circumstances. For each, list what is fully within your control.

Step 2: Bring Level 10 Energy
Show up with high energy. Ask: What energy am I bringing into my meetings, my team, my home this week?

Step 3: Write Your Leadership Statement
Who are you when things get hard? Describe your leadership choices and values in 1–2 paragraphs.

Step 4: Audit Your Time
Track a week. Identify time spent on distractions like social media or Netflix. Decide consciously where to redirect your time.

Step 5: Build with Purpose
Tie your work to something bigger than revenue. Contribution changes your focus and commitment.

Step 6: Practice Mental Freedom Daily
Meditation, journaling, or even five minutes of silence can strengthen awareness and free your mind.

Step 7: Celebrate Wins Like a Championship
Share small victories with your team, fist bump a colleague, or reflect quietly. Celebrating success reinforces energy and momentum.

If you want focused support in building your business and life with intention, schedule a discovery call: https://calendly.com/Kalika