How to Money: "Bouncing Back from Bankruptcy & Business Failure w/ Phil Sanders"

Episode #1109 | iHeartPodcasts | March 4, 2026

Episode Overview

Host Joel sits down with Phil Sanders, a seasoned entrepreneur and founder of Multiply, to discuss the realities of business ownership—including hitting rock bottom after bankruptcy and rebounding to build a healthier, more intentional company. The conversation offers hard-fought wisdom on risk, failure, personal identity, and forging a sustainable path for both your business and your life. Sanders shares candid stories from his journey, offering grounded, empathetic advice for aspiring and current business owners.

Key Discussion Points & Insights

1. The Realities of Entrepreneurship

• Entrepreneurship is not one-size-fits-all
  Phil started his entrepreneurial journey at age 24, shifting from barista to self-employed photographer/designer. He emphasizes that while anyone can start a business, life circumstances (family, responsibilities) make it riskier as you get older.

  • "The longer we wait or the more complexities there might be in life, maybe can make it a tougher decision to make that jump." — Phil [07:06]

• Know thyself: Build a business around who you are
  Success comes from authenticity, not imitation. Avoid the trap of replicating someone else’s business or social media image.

  • "The opportunity is to be yourself in entrepreneurship. ...If we try to build something in a different way, it's just filled with these traps." — Phil [08:23]

• Profitability and Discipline Before Growth
  Early focus should be on maintaining profitability, not just chasing revenue or expansion.

  • "Your goal in the beginning just needs to be: how can we be profitable from day one and keep sustained profitability as a trait in this business?" — Phil [09:24]

2. Scaling and Knowing When to Pivot or Quit

• Patience & the Long Game
  Building a successful company is about time invested—a five-year vision is more powerful and sustainable than chasing quick wins.

  • "You can do less than you think in a year, but more than you can imagine in 10." — Phil [10:28]

• When is it time to quit?
  Review if your business structure can realistically achieve your personal and financial goals—or if it would be faster to start over. Candid customer feedback and market demand are critical signals.

  • "Market demand—if there aren't people wanting the thing that you sell, we've got to pull a lever. ...The number one thing we can do is just talk to customers." — Phil [14:28]

3. Risk, Debt, and the Dangers of Growing Too Fast

• Cautious Debt Usage
  New entrepreneurs must be especially careful with personal guarantees and predatory loans. Debt should not be a substitute for hard decisions or a shortcut for real growth.

  • "Entrepreneurs need to be able to sit with their money, sit with their numbers and just understand them. ...Many times when an entrepreneur takes on debt, it's a band aid that punts a decision that needs to be made now." — Phil [20:54]

• Expect Surprises: Stress-Test Your Plan
  Over-optimism is a liability. Assume headwinds, not just tailwinds.

  • "If your business plan...needs to go perfect to win, the chances are just very slim it's going to do that. Like, where's the margin for error here?" — Phil [24:32]

4. The "Valleys of Death" and Emotional Management

• Business growth = personal growth
  Each business phase requires new leadership skills and self-mastery; being a jack-of-all-trades at first, then learning to delegate as you grow.

  • "To master business, you have to master yourself. ...There’s a lot of self-mastery that has to go on." — Phil [32:50]
  • "The reason there’s real respect for people who’ve conquered the business side is it requires them to master themselves." — Phil [33:03]

• Identity Separation
  Your business is not your worth. Keep healthy boundaries to avoid taking setbacks or criticism personally.

5. Phil's Bankruptcy Story: Hitting Bottom, Losing It All

• What led to bankruptcy?
  Overexpansion: 12,000 sq ft lease, 35 employees, complex retail business. Personal tragedies (family loss, illness) forced a shift in priorities and bandwidth.

  • "That business was like a house of cards...There wasn't enough stability anywhere." — Phil [36:58]

  • COVID-19 devastation: Went from six-figure monthly revenue to $200 in April 2020.

  • Involvement of friends as investors/mentors made the decision even more painful.

• Processing the fallout
  The emotional toll is immense—dealing with creditors, firing staff, telling stakeholders. Phil stresses the importance of support and mentorship through this process.

6. Lessons and Mindset After Bankruptcy

• Fear as an Illusion
  Phil credits the experience with banishing emotional fear of financial ruin, clarifying his life’s real values.

  • "Once you realize that the thing you fear won't kill you...my kids do not care what I do for a living." — Phil [41:30]

• Taking Time to Rebuild—Intentionally
  Legal/financial constraints forced Phil to work below his previous earning potential for nearly two years. Ultimately, this pause gave him space for reflection, slowing down, rebuilding confidence, and preparing for future success.

  • "My attorneys were like, you cannot go out there and earn money. ...So I just had to sit for like two years. I think that forced me to do the things I needed to do but didn’t want to do." — Phil [44:09]

• Sustainable Pace and Lowered Expectations
  Going slower and being more methodical about growth would have increased his chance of long-term success.

  • "Speed is one of those things...If you move at too fast of a pace, the decisions you make when you don’t know something...you're gonna deal with those consequences later." — Phil [46:40]

7. Life After Bankruptcy: Rebuilding

• Family and Simplicity
  After losing everything (including health insurance, housing complications), Phil and his wife focused on daily rhythms and teamwork, slowly establishing stability.

  • "In the beginning it was: what has to get done today. ...Because I could not worry about how’s this thing actually going to play out in the future." — Phil [51:24]
  • "There was zero shame from her. ...We were just like a team, man." — Phil [51:53]

• Relationship-Focused Business Building
  The impact on staff and partners reinforced Phil’s commitment to stewardship and transparency in future ventures. Vulnerability and open communication are superpowers, not weaknesses.

  • "Entrepreneurs and people, in general, have a pretty good gut. ...but just ask questions." — Phil [55:49]

Notable Quotes & Memorable Moments

• "If you can give business, 'I want to have X result over five years,' at the end of five years, that's a whole different business than if you're saying, 'I need these things immediately.'" — Phil [10:28]
• "The profit and the financials of a company, a lot of time, are a lagging measure—the lead measure is where we're spending our time...what our attitude is in the business." — Phil [14:28]
• "If you can accept worst case, then it frees you to go do the damn thing." — Phil [17:15]
• "Debt should not be a shortcut for hard decisions." — Phil [20:54]
• "My business is what I do, not who I am." — Paraphrased from Phil's comments on identity separation [34:31]
• "There’s so much strength that comes from just having authority over the money... it doesn’t own you." — Phil [58:28]

Timestamps for Key Segments

• [03:03] – Phil's "splurge" post-bankruptcy: kids' activities and "living now"
• [06:35] – Who is cut out for entrepreneurship? Nature, nurture, and the trap of imitation
• [09:24] – Importance of profitability and discipline in entrepreneurship
• [13:02] – Knowing when to quit or pivot: reverse-engineering business viability
• [17:15] – Risk, expanding at the right pace, getting input from mentors and family
• [20:54] – The role and risks of debt in entrepreneurship
• [24:32] – Stress-testing your business plan; expect the unexpected
• [30:32] – What makes businesses fail? The "valleys of death" and self-mastery
• [36:33] – Phil's bankruptcy: what happened and how personal hardship played a role
• [41:30] – On overcoming fear and separation of business and self
• [51:24] – Life after bankruptcy: daily cadence, focusing on what matters
• [55:49] – Stewardship, transparency, and vulnerability as core business values
• [58:28] – Where to follow/connect with Phil Sanders

Final Takeaways

• Business success requires self-awareness, discipline, realistic planning, and a willingness to ask for help.
• Move at a pace that matches your season of life, factoring in family, risk tolerance, and capacity.
• Failure, while painful, is not fatal—it can be a profound catalyst for personal and professional growth.
• Transparency, stewardship, and strong relationships with employees, customers, and mentors are key to building something that lasts.
• Rebuilding after failure is possible—with humility, patience, and intentionality.

Where to Find Phil Sanders

• Multiply Website: MLTPLY.co
• LinkedIn: Phil Sanders

This episode is a goldmine for anyone starting out—or starting over—in business. It's also deeply relatable for anyone wrestling with uncertainty, striving for balance, or facing the aftermath of failure. Phil’s story is a testament that financial hardship and personal setbacks, while excruciating, can set the stage for transformation and better leadership.