65 episodes

We’ve been in the food delivery industry since 2005 and have bootstrapped the entire way. While we compete with VC backed behemoths, this podcast gives listeners an idea about day to day life as an entrepreneur behind closed doors.

Bootstrapped: In The Trenches Michael Lee Rolland

    • Business

We’ve been in the food delivery industry since 2005 and have bootstrapped the entire way. While we compete with VC backed behemoths, this podcast gives listeners an idea about day to day life as an entrepreneur behind closed doors.

    Greed isn’t good

    Greed isn’t good

    We review Evan Ratliff’s “The Mastermind” and break down our thoughts on the current role that greed plays in society.

    • 1 hr 11 min
    Brunch Boys and why working smart is more important than working hard

    Brunch Boys and why working smart is more important than working hard

    We have our first guest, Jeremy Jacobowitz from BrunchBoys. Jeremy dives into life in the food fast lane and what his day to day is like as a major food influencer in New York City. We also review “The 4-Hour Work Week” by Tim Ferriss and discuss how the 80/20 rule really allows works for everything in life!

    • 1 hr 20 min
    Bootstrapped in the Trenches- Our 14 year journey in the food delivery space!

    Bootstrapped in the Trenches- Our 14 year journey in the food delivery space!

    Listen to our first episode as we break down our 14 year bootstrapped journey in the food delivery industry!

    • 38 min
    Entrepreneurs are Problem Solvers

    Entrepreneurs are Problem Solvers

    In this episode we dive into how Entrepreneurs are trail blazers and problem solvers.   We relate this to our business and review Phil Knight's memoir, "Shoe Dog".   Knight founded Nike who probably has the most world renown slogan of all time "Just do it". 

    • 57 min
    Adventure, No Fear, and The Art of Storytelling

    Adventure, No Fear, and The Art of Storytelling

    We dive into stories from our business over the years. Highlight the tragic death of Kobe Bryant and the major impact he made on this world. You’ll also hear us break down Richard Branson’s: “Losing My Virginity”

    • 1 hr 35 min
    Creativity comes to fruition when our backs are against the wall

    Creativity comes to fruition when our backs are against the wall

    We review Shark Tank’s Daymond John- Power of Broke. How being backed against the wall allows creativity to come to fruition

    • 57 min

Customer Reviews

foodboy33 ,

Awesome!

Love this podcast, very entertaining and insightful

golfandfood ,

Awesome

This is dope! Love the book reviews

jacque foley ,

From life as entrepreneurs, to book reviews, this podcast covers it all!

Very impressed with bootstrapped in the trenches! Lots of amazing insight about life in the entrepreneurial fast lane and then some!

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