Founders Podcast: My Conversation with Brad Jacobs

Host: David Senra
Guest: Brad Jacobs
Date: October 28, 2025

Episode Overview

In this episode, David Senra sits down for an in-depth conversation with Brad Jacobs, the rare serial entrepreneur who has founded eight separate billion-dollar companies. Together, they explore Jacobs' guiding philosophies, from the central importance of people and culture, to rigorous self-examination, time management, and the relentless pursuit of big opportunities. The conversation covers lessons from mentors like Ludwig Jesselson and Fred Smith, discusses the mechanics of building scalable teams, and dives into personal routines, mindset, and the emotional side of enduring business challenges. Jacobs also shares the thinking behind his celebrated book and offers advice for emerging founders based on decades of high-stakes, high-growth entrepreneurship.

Key Discussion Points & Insights

1. Energy, Enthusiasm, and First Principles

• David opens noting Brad’s infectious energy and curiosity, and asks about his early mentors, particularly Ludwig Jesselson, who ingrained in him the importance of “getting the major trend right.”

• Jacobs recalls Jesselson’s deep ethical core and his philosophy of focusing on long-term trends:

  "If you don't get the long-term trend right, you're kind of in trouble... You need context, you need to see what's happening, what did happen, what is happening and what will likely happen in the future." — Brad Jacobs (02:59)

2. Problems as Opportunities

• Brad learned early to embrace business problems. Both Jesselson and other mentors like Sam Zell taught him that “business is problems,” and reframing them is essential:

  "Problems are just opportunities in work clothes." — David Senra, quoting Henry Kaiser (04:05)

  "You make money, so the more problems you have, as long as you solve them… that's how you're creating value." — Brad Jacobs (04:31)

• Echoed in lessons from Bezos: The best founders get excited by challenges because solving them increases the value of their business (06:49).

3. Reputation, Relationships, and Long-Term Orientation

• Jacobs stresses the cumulative importance of personal and business reputations.
  Deals were done on trust alone, and the lesson—"Your brand is your most important asset"—is central:

  "Every day you're... either raising your brand or you're lowering your brand... Make sure your brand reflects integrity and honesty and dependability." — Brad Jacobs (09:44)

• Mentors like Buffett and Jesselson solidified the absolute priority of reputation over money.

4. Context, Meditation, and Perspective

• Brad describes using meditation for wider context and perspective: He visualizes himself in both cosmic and atomic scales to gain humility and clarity (11:08). This provides equanimity under pressure and a sense of insignificance and connectedness at the same time.

  "I'm just one little tiny jet. At the same time, I'm part of that. So I'm very uplifted. I'm very inspired. I'm very motivated. Like, wow. I'm part of, like, a real big deal here." — Brad Jacobs (12:14)

5. Motivation: Positivity vs. Negativity

• David notes many famous founders are driven by negative motivation or trauma. Brad is different:

  "I don't embrace negativity. I'm okay with it, but I don't make a big deal about negativity. I'd much rather enjoy the positivity. I'm a sunny side up guy." — Brad Jacobs (15:19)

• Brad’s approach: Problems aren’t to be run from but toward. “Run to the fire.” He cultivates a generally positive, accepting internal dialogue:

  "You can either dispute [negative thoughts]... or just witness it. And I vacillate between those two." — Brad Jacobs (17:52)

  Centering is his mental practice: Everyone should seek their own inner calm and center.

6. Overcoming Perfectionism and Dealing with Criticism

• Brad battled perfectionism in his youth; therapy gave him strategies:

  • First, validate automatic negative thoughts.
  • Then, dispute them with evidence (25:13).
  • Radical acceptance: "Don't fight with reality, because reality always wins." — Brad Jacobs, paraphrasing Jeff Bezos (25:13).
  • Criticism is inevitable; don’t obsess over universal approval.

7. Building Repeatable Success: The Jacobs "Toolkit"

• Why did he start so many companies?

  "Everybody's got their thing... This is what I'm good at. I'm good at figuring out what's the right industry to consolidate, and secondly, I have a toolkit..." — Brad Jacobs (27:28)

• The playbook:

  • Enter a big, growing, fragmented, low-tech industry.
  • Assemble a superlative team, even if "smarter than me" (28:05).
  • Structure compensation for alignment—heavy equity, with lockups to force long-term commitment.
  • Create a respectful but highly analytical, scientific, debate-heavy culture.
  • Focus on buying at reasonable prices and improving target companies operationally, aiming to double profits in 3-5 years.

8. Recruiting A+ Talent & People-First Culture

• Relentless focus on extraordinary talent:

  • "The CEO's most important job is recruiting superlative people." — Brad Jacobs & Steve Jobs (35:08)
  • Regular thought experiment: “If they walked in and quit, would I panic?” If yes, they are an A player (39:31).
  • Only build teams with those whose “star going up” uplifts the group.

• Culture is paramount:

  • "An organization is like a party. You only want to invite people who bring the vibe up." — Brad Jacobs (43:11)

9. Meetings, Decision Making, and Leadership Style

• His archetype is not the “dictator founder”:

  • Prefers a superorganism/brain model—not all-knowing, but facilitating, integrating, and leveraging all voices.
  • Monthly Operating Reviews: 25-person, all-hands, data-driven, with distributed pre-work and agenda-setting by everyone (52:52).
  • Assiduously models vulnerability, debate, and flexibility.

  "Be flexible in thinking, don't be rigid in thinking... That's okay to be proven wrong." — Brad Jacobs (56:12)

• His leadership: “Create a beehive or human body—not a command structure, but an organism.”

10. Feedback Loops and Direct Access to Truth

• Brad stresses relentless feedback at all levels:

  • Employee surveys, 360 reviews, anonymous questions.
  • “What’s the stupidest thing we’re doing? What’s the smartest?” (61:50).

• Learned from historical role models: Sam Walton and Jim Casey (UPS) always got unfiltered field input.

• Emphasizes sharing both good and bad news widely—transparency > fear of leaks.

11. Technology and Major Trends

• Every company is a tech company: Applies to Walmart, Zara, Michelin, and his own ventures.
  • Invest in technology relentlessly; the savings compound (95:28).
  • Watch the “main trend”: Humans outsourcing tasks/decision-making to technology (92:29).

12. Brutal Time Management

• Time, not just money, is the CEO’s greatest constraint.
  • “You have to be absolutely brutal in the management of your time.” — Quoting Fred Smith (101:27).
  • Leverages a chief of staff to protect his priorities; only spends time on high-leverage activities: “If it doesn’t move the top-line or margin needle, it’s ‘WOT WOTM’—waste of time, waste of money.” (113:05).

13. Incentives, Compensation, and Alignment

• Incentives are crucial:
  • "People are coming to work... to make money for themselves and more often to make money for others" (115:33).
  • “Show me the incentive, I will show you the outcome.” — Citing Charlie Munger (117:95).
  • Gives meaningful, long-vesting equity; reviews regularly: Does this incentive still create drive and alignment?

14. On Being Public, Pressure, and Scale

• Jacobs loves the public markets.
  • Pressure is motivating, and the market’s feedback is free intelligence: “I like the pressure. I enjoy that pressure. That motivates me, inspires me.” (81:24)
  • Being public allows faster brand-building and more credible equity incentives.
  • Take advice from everywhere, but ultimately, make your own call.

15. Passion, Going All-In, and the Meaning of a Business Life

• Work-life balance:

  • Jacobs owns being “imbalanced”—his work is his craft and calling (47:04).
  • But he’s also managed not to burn out: He still values meditation, music, and family.
  • Driving purpose isn’t simply money but building something important for employees, shareholders, and the greater good.

• Ultimate advice:

  "You can diddle daddle through life and just kind of sleepwalk and then die. Or you can live life. You can embrace life. You can have big dreams and go all in and find your passion..." — Brad Jacobs (123:05)

Notable Quotes & Memorable Moments (with Timestamps)

• On Problems:

  "You can do a thousand things right, but if you get the major trend wrong, you're not going to create alpha." — Brad Jacobs (02:59)

• On Reputation:

  "You lose money, that's fine, but you lose a shred of reputation—I'll be absolutely ruthless." — David Senra, referencing Buffett (09:08)

• On Context:

  “I accordion my mind… getting really big and then really, really small. Time and space juxtaposition… Gives me context. It gives me humility.” — Brad Jacobs (11:08)

• On Motivation:

  “I don't embrace negativity. I'm okay with it, but I don't make a big deal about negativity. I'd much rather enjoy the positivity. I'm a sunny side up guy.” — Brad Jacobs (15:19)

• On Self-Talk & Therapy:

  “First validate, then dispute [negative thoughts]... and then see, what does the evidence say here?” — Brad Jacobs (17:52, 25:13)

• On Team Building:

  “I'm good at figuring out what's the right industry to consolidate, and secondly, I have a toolkit… it's the same playbook, industry after industry.” — Brad Jacobs (28:05)

  “The CEO's most important job is recruiting superlative people.” (35:08)

• On A Players:

  “If when I visualize that person quitting, my reaction to that is pure terror and absolute panic... that's an A player.” — Brad Jacobs (39:31)

• On Meetings:

  “What I do is just the opposite [of dictatorship]... the agenda is group-sourced—now you've got the benefit of everybody's perspective.” — Brad Jacobs (52:52)

• On Feedback:

  “All the different constituents in an organization need to be talking to each other… If you're not asking your customers how you're doing, you may think you're doing a lot better than you really are.” — Brad Jacobs (75:17)

• On Time:

  “If it doesn't [grow organic revenue or margin], it's a waste of time, waste of money. WOT WOTM.” — Brad Jacobs (113:05)

• On Incentives:

  “People are coming to work not because they love me... [They're motivated by] what's in it for them... It's called theory of mind.” — Brad Jacobs (115:33)

• On Passion:

  “If I put my whole heart and soul into a project, I had it in me to create really cool stuff.” — Brad Jacobs (123:05)

Timestamps for Key Segments

• Jesselson and Major Trends: (01:50–03:35)
• Problems are Business: (04:31–06:02)
• Reputation and Long-term Thinking: (09:44–11:06)
• Meditation, Perspective, and Context: (11:08–12:38)
• Inner Monologue & Motivation: (14:38–17:52)
• On Perfectionism & Therapy: (22:50–25:13)
• Building the Playbook: (28:05–31:59)
• On Recruiting Superlative People: (35:08–45:39)
• Monthly Operating Review Process: (52:52–57:45)
• On Feedback Loops: (61:50–67:44)
• Embracing Technology: (92:29–100:23)
• Brutal Time Management: (101:27–113:05)
• Incentives and Alignment: (115:27–118:48)
• Public Markets and Pressure: (81:24–82:35)
• Advice on Going All-In: (123:05–123:48)

Final Takeaway

Brad Jacobs is the rare founder whose superpower is scaling enormous, complex organizations by focusing on timeless principles: guided by trend recognition, recruiting and incentivizing the best people, honest feedback, deliberate time management, and an unflagging, positive approach to problems and pressure. His advice for entrepreneurs: Find your center, embrace life's big challenges head-on, and build something that’s true to your unique talents, all while thinking on the biggest scale you can imagine.

“If I put my whole heart and soul into a project, I had it in me to create really cool stuff.” —Brad Jacobs (123:05)

For listeners eager to learn from the firsthand experiences of business titans, this episode is an advanced masterclass in how to think, build, and lead at the highest level.