Brad Jacobs on building eight billion-dollar companies

Executive overview

Brad Jacobs has started eight separate billion-dollar companies across garbage, construction, transportation, logistics, and now distribution — each using an identical playbook. The playbook works because the industries share the same characteristics, not because the industries are the same.

The repeatable edge: find a fragmented, tech-laggard industry; recruit superlative people; align them with locked-up equity; buy companies at disciplined prices; then double EBITDA in three to five years.

Getting the major trend right

• Mentor Ludwig Jesselson's core rule: if you get the long-term trend wrong, a thousand other correct decisions still lose.
• Map what did happen, is happening, and will likely happen — assign probabilities to each future state.
• The main trend for two million years: humans outsource tasks to tools. AI, robotics, and automation are the current wave.
• Screen industries for resistance to near-term AI disruption before committing capital.
• Jacobs ruled out online education (Chegg) early; the stock fell from $50 to single digits.

Selecting the right industry

• Must be large, growing, and fragmented.
• Acquisition targets must be available at reasonable — not cheap — prices.
• Technology adoption must be low enough that the toolkit adds visible uplift.
• AI and automation must not be able to disrupt it in the foreseeable future.

Recruiting and keeping A players

• The CEO's most important job is recruiting superlative people — more time goes here than anywhere else.
• Mental test: picture that person walking in to quit. Pure terror = A player. Mild inconvenience = B player. Relief = C player; remove them now.
• There is no substitute for raw intelligence; screen for it first, eliminating 90% of candidates.
• Pair IQ with honesty, work ethic, collegiality, and genuine commitment — technical skill alone is insufficient.
• Give senior people heavy equity locked for five years, most vesting in the final two years; it aligns everyone on the long horizon.
• Organization is like a party: only invite people who raise the energy.

Building a super-organism management team

• Target 20–25 people for the monthly operating review (MOR) — enough for diverse perspectives, small enough for vulnerability.
• Before the MOR, distribute all pre-reads; each person submits key takeaways and questions via app; the group ranks them 1–10.
• Only questions rated 8–10 become the agenda — crowd-sourced, not dictated from above.
• The CEO opens with ~one hour: balanced state-of-the-union covering wins and gaps. Then mostly listens.
• End-of-meeting human rounds: who disagrees with something said today; biggest single takeaway; MVP in the field; whose star rose and why; "I resolve to improve the company by…"
• Closing ritual: stand in a circle, silently project gratitude and good wishes for each person; declare the day a success.

Feedback loops and information flow

• Share information more widely than feels comfortable — the benefit of collective learning outweighs competitive risk.
• Read employee surveys personally; Jacobs asks two questions: best idea to improve the company and job satisfaction 1–10.
• Ask frontline employees: "What's the stupidest thing we're doing?" and "What's the smartest thing we're doing?"
• The person handling a process for eight hours a day knows something the CEO in the office does not.
• Bezos published his email and read customer replies; Jim Casey pulled over to talk to UPS drivers; Sam Walton left meetings early to visit stores. Unfiltered access is the pattern.

Buying companies and creating value

• Two non-negotiable levers: grow organic revenue faster than the market and expand margins. Everything else flows from these.
• Discipline on price: look at many candidates simultaneously so you never fall in love with any one deal.
• Over 500 acquisitions; thousands of candidates reviewed.
• Target: double EBITDA within three to five years by improving pricing (elasticity algorithms), procurement, compensation structures, HR systems, and technology stack.
• Being public provides free advice from the world's best capital allocators, accelerates talent attraction, and lets employees see the real-time value of their equity.

Managing time and energy

• Time and capital are the only two things a CEO controls; how they're deployed equals results.
• A CEO must be across all ~20 domains (people, tech, budgets, pricing, customers, sales, procurement, M&A, etc.) — not just the ones they like.
• Filter every request through WOTWOM: waste of time, waste of money. If it doesn't influence organic growth or margin, cut it.
• Use a chief of staff who deeply understands your two to three priority levers; let them gate the calendar accordingly.
• Warren Buffett's benchmark: a mostly empty calendar is proof of wealth — because time is the real scarce resource.

Mindset: problems, perfectionism, and going all in

• Problems are not threats to tolerate; they are the mechanism of value creation. Run toward them.
• Perfectionism — demanding that self, others, and the universe perform flawlessly — causes unnecessary stress and distorts reality. Reduce musts to preferences.
• Cognitive therapy helped Jacobs identify automatic negative thoughts, validate them, then dispute them against evidence.
• Context from meditation (expanding and contracting perspective across space and time) creates humility and proportion.
• The driven people Jacobs admires were not fuelled by trauma or insecurity — they were energised by the work itself.
• The exit strategy for people who love what they do is death. If you truly love it, they couldn't pay you to stop.