Stand Back Up with Steven Borrelli | Cuts Founder on Entrepreneurship & Resilience

Podcast: Kreatures Of Habit
Host: Michael Chernow
Guest: Steven Borrelli (Founder, Cuts Clothing)
Date: August 20, 2025

Overview

This deeply candid episode of the Kreatures Of Habit podcast centers around entrepreneurship, resilience, and the habits that sustain a founder through both success and adversity. Michael Chernow sits down with Steven Borrelli, founder of Cuts Clothing, who shares the inside story of building—and nearly losing—his business, lessons on leadership, the power of faith and taking risks, and actionable routines that anchor both his personal and professional life. With unfiltered insights, practical advice, and memorable anecdotes, this conversation is a masterclass in the gritty realities of building something meaningful.

Key Discussion Points & Insights

1. Navigating Crises & Near-Death Business Experiences

• Early Success and Sudden Challenges:

  • Cuts saw explosive growth from 2018–2022, but rapid scaling led to taking on risky debt and overextending resources.
  • A banking crisis and predatory lending practices left the company at the brink of bankruptcy.
  • Detailed story of how the company almost went under and how Steven led them back.

• Learning Financial Discipline the Hard Way:

  • "We lost the discipline of what got us here. When we started, the first $10 million was with no full-time employees. But then we got access to $20 million in credit, and spent too freely."
    — Steven Borrelli [04:39]

• Slow Down and Focus—The Walks:

  • Steven's coping technique:
    "I go on long walks... right foot, left foot, right foot, left foot. Just try to make big problems really small."
    — [00:00]; [11:50]
  • Repeating this as a mantra helps him decompress and regain clarity under pressure.

• Transparency and Trust in Leadership:

  • During crises, Steven stresses open communication and showing the business numbers to all employees:
    "Being as transparent as possible...especially when things aren't going well, because no one wants to be bullshit."
    — [14:03]

2. Resilience, Faith, and Surrendering Control

• Finding Meaning in Adversity:

  • "None of the books I read in entrepreneurship didn’t have near death experiences. This is just mine."
    — Steven Borrelli [00:00]
  • Experiences taught him perspective and the value of focusing on things within his control.

• Faith as a Source of Strength:

  • After another crisis—a 145% tariff leading to an effective business embargo—Steven fasted for 72 hours, deepened his faith, and penned a viral letter to President Trump.
  • "Sometimes in the biggest pain points you can find the biggest miracles... Through that experience, people saw my leadership in the moment... it just taught me, like, there's such a power in being able to surrender."
    — [15:07]

• On Taking Risk and Avoiding Regret:

  • Michael remarks:
    "Life is going to be uncomfortable no matter what. The decision you have to make is whether you want to take a risk or live with regret."
    — [24:20]

3. Team, Culture, and Leadership Evolution

• Learning from Culture Mistakes:

  • Hired rapidly without vetting for DNA fit or cultural values, leading to misalignment and poor decisions (e.g., overextending product line for inclusivity at the expense of the brand’s identity).
  • "A great culture knows who we are as a business, and they protect it... They didn’t know who we are, and so they couldn’t protect it."
    — Steven Borrelli [39:19]; [41:16]

• Being Unapologetic About Brand Identity:

  • "You cannot be for everyone. When you try to be for everyone, you lose your way."
    — Michael Chernow [41:16]
  • Shared example of Creatures of Habit raising prices to preserve brand value.

• Influencer and Ambassador Selection:

  • Steven personally manages outreach to ensure all reps fit the Cuts ethos: athletic, aspirational, community-oriented—work, work out, go out.

4. Health, Personal Habits, and Mental Resilience

• Daily Routines:

  • Steven’s current morning:
    • Lemon water with creatine
    • 1.5-mile faith walk (Christian music)
    • Gym session 6–7 am
    • Protein shake, work
    • Targets ~9 miles walking/20,000 steps per day ([32:18])
    • Uses walks not just for fitness but as creative and management time.

• Adapting Under Stress:

  • Under severe work stress, his health suffered (poor sleep, workouts, diet), but in facing later crises, he foregrounded health—proving its necessity for endurance.

• Sleep Challenges & Realizations:

  • Became obsessive about tracking sleep (Oura Ring), which worsened insomnia; the lesson:
    "Don’t think about sleep. Actually go to bed when you’re tired...I figured out what worked for me."
    — Steven Borrelli [53:44]

5. Growth, Mentorship, and Looking Ahead

• Retail Expansion and Aspirations:

  • Plans to scale to more retail stores, inspired by brands like Vuori.
  • Deep pride in launching stores and tangible community-building.

• Peer Mentorship and Founders’ Network:

  • Steven values both muses (older CEOs like Vuori’s CEO Joe Kudla) and peers (founders of Blenders, Truff Sauce, etc.), often taking trips and sharing battle stories together.

Notable Quotes & Memorable Moments

• On Perspective During Hard Times:
  "I’m lucky. It’s a privilege to be in this. I signed up for this. I don’t want anyone feeling sorry for me...I’m not a victim."
  — Steven Borrelli [00:00], repeated [11:50]

• The Audacity of Entrepreneurship:
  "Coming up with an idea in your head that you think is gonna move thousands, potentially millions of people...that takes balls."
  — Michael Chernow [24:20]

• Culture & Authenticity:
  "Be unapologetic. That’s what I love about watching your stuff. You’re very unapologetic."
  — Steven Borrelli [43:23]

• On Surrender and Faith:
  "Complete surrender, like, I’m going to bust my ass. But God, I need you. I need you to have my back...there’s such a power in being able to surrender as...And it doesn’t mean not work hard, but it just means you’re okay with what the outcome is and it allows you to have peace."
  — Steven Borrelli [17:22]

• On Building Winning Momentum:
  "If you can control these little [wins] in the beginning of your day, the chances of you being ready to rock and roll and in unison with the rest of your team are just far greater."
  — Michael Chernow [67:22]

Timestamps for Important Segments

• [00:00] Steven’s “right foot, left foot” mantra for coping with stress
• [04:39] Near-business-failure, predatory loans, and founder lessons
• [11:27] How it feels to go from dreaming CEO to nightmare scenario
• [13:13] Leading through adversity, the importance of team
• [15:05] Cutting $350k–$500k/month in expenses; massive budgeting discipline
• [15:40] Dealing with sudden tariffs and policy risks; viral letter to President Trump
• [32:18] Steven’s morning routine and the power of intentional walks
• [39:20] Company culture mistakes, and the lesson of “protecting the DNA”
• [41:16] Michael on the necessity of NOT being for everyone
• [53:44] Steven’s candid experience with sleep obsession and practical advice
• [67:22] Michael’s philosophy on “winning” and daily momentum
• [72:01] Final thoughts on founder intuition, responsibility, and leading by example

The Habits Question Segment (Rapid-Fire)

Steven Borrelli’s Three Most Transformative Habits:

1. Intentional Walking (movement for clarity and stress relief)
2. Radical Transparency (with team, daily business numbers)
3. Morning Faith Routine (lemon water + creatine + faith walk + gym)

One Habit Broken:

• Over-obsession with Sleep Tracking: Letting go of intense data obsession improved sleep and well-being.

Final Thoughts

This episode is a raw exploration of the heartbreaks and high points of entrepreneurship. Steven’s willingness to publicly take risks (from writing the president to being transparent with his team and audience), his emphasis on discipline and authenticity, and both speakers' belief in robust daily routines provide rich, practical lessons for anyone on the founder’s journey or seeking better habits and resilience.

Key takeaway:
No matter how high the stakes or how strong the setbacks, resilience is built on perspective, purposeful daily practices, and the courage to own your story and brand—unapologetically.