CHAPTERS
- 0:00 – 3:02
Raymond Plank’s memoir framing: “make a small difference” and choosing the riskier path
The episode opens with passages from Raymond Plank’s memoir that explain why he’s writing in his nineties and what he hopes readers take from his life. He ties his values to a lesson from his father about helping others and to a final message from his mother before her death, then connects those influences to his decision to be self-employed and take entrepreneurial risk.
- •The memoir’s purpose is to share lifetime learnings to help others pursue “worthy goals” beyond self.
- •A formative lesson from his father: try to make a very small difference for others.
- •A postcard from his mother before her death becomes a lifelong cornerstone.
- •Plank links these cornerstones to choosing self-employment and a smaller, riskier initiative.
- •The scale of what followed is previewed: Apache’s modest start grew enormously over decades.
- 3:02 – 3:33
Why the book stands out: a 60-year diary distilled into philosophy
David explains why he finds the book unusual and compelling: it reads like a diary because Plank kept a daily diary for decades. Rather than focusing only on Apache’s corporate history, David emphasizes the value of Plank’s accumulated maxims, beliefs, and entrepreneurial worldview across seven decades of experience.
- •The book’s diary-like feel comes from a daily diary habit maintained for 60 years.
- •David shifts focus from company chronology to Plank’s ideas, maxims, and philosophy.
- •Plank’s age and depth of experience shape the reflective tone of the book.
- •The episode will highlight patterns in Plank’s thinking more than operational details.
- •Entrepreneurial bent shows up early and persists throughout the narrative.
- 3:33 – 5:04
Early farm-rooted entrepreneurship: eggs, firewood, and syrup as training grounds
David recounts Plank’s childhood and teenage businesses, showing how work ethic and self-sufficiency formed early. Plank experiments with selling eggs, then expands into firewood and syrup after spotting an adjacent opportunity while sawing trees.
- •Farm responsibilities instill a work ethic where privileges are earned, not assumed.
- •Selling eggs provides early lessons in marketing and sales.
- •By high school he’s running a firewood operation alongside raising chickens.
- •He identifies a complementary business: collecting sap and producing syrup to sell.
- •He sells to local grocery stores and meat markets near Minneapolis.
- 5:04 – 7:35
Depression-era imprint and the loss of his mother: integrity, credibility, and grief
The episode highlights how the Great Depression shaped Plank’s financial conservatism and respect for credibility and paying bills. It then moves to the pivotal trauma of his mother’s sudden death after a routine procedure, including how that grief interrupted his diary writing.
- •Plank’s father loses his net worth in the Great Depression, reinforcing financial conservatism.
- •Despite losses, the family maintains basics like food and a mortgage-free home.
- •His father’s credit and credibility as an honest businessman are emphasized.
- •His mother dies suddenly from a blood clot following a routine appendectomy.
- •Plank describes being unable to write in his diary for six months afterward.
- 7:35 – 11:07
World War II and courage: combat experience reshapes risk tolerance
David describes Plank’s early-20s wartime role as a pilot and the exposure to death that intensified his zest for life. Plank reflects on courage as foundational, and David connects the extremity of wartime stakes to Plank’s later comfort with entrepreneurial risk.
- •Plank flies a four-engine bomber responsible for a 10-person crew.
- •He frames combat bluntly as killing enemies who sought to kill them.
- •He notes many missions were dangerous, with the squadron repeatedly shot up.
- •Plank records quotes about courage, including the idea that it underpins other virtues.
- •David links wartime hardship to why later business risks felt smaller by comparison.
- 11:07 – 13:09
Postwar clarity: rejecting big-company life and building a service business first
After discharge, Plank sees his future as self-directed for the first time and moves quickly toward entrepreneurship. David explains how Plank anticipates a postwar boom and starts a simple tax and accounting service aimed at small businesses, using professional groups to generate leads.
- •Plank describes feeling “in charge” of his personal destiny for the first time.
- •He seeks a career involved in starting businesses and rejects large-company work.
- •He predicts deferred demand and innovation will drive postwar job creation.
- •He co-founds a tax and accounting service for new businesses: Northwest Business Service.
- •A referral-focused professional club structure becomes a key distribution channel.
- 13:09 – 15:10
Stumbling into oil: spotting investor abuse and taking over despite inexperience
David traces how serving oil investors through accounting work exposes Plank to the oil and gas world and to misconduct. Plank investigates charges that seem inflated, uncovers kickbacks, and is pushed by investors to manage substantial assets—accepting even while admitting he lacks technical expertise.
- •Accounting work for Minneapolis oil investors becomes the unexpected gateway to energy.
- •Postwar conditions and incentives drive highly taxed individuals into oil investing.
- •Plank studies the market and checks costs directly with oil field service providers.
- •He uncovers kickback checks benefiting unscrupulous promoters and reports them.
- •Investors demand he take over management; Plank proceeds despite not feeling qualified.
- 15:10 – 17:10
Founding Apache and building a lean culture: “do more with less” and cost discipline
Apache is formed with modest capital and a small initial team, and David emphasizes two operating principles that endure: a belief they can outperform with fewer resources and an intense focus on cost control. Plank’s approach centers on avoiding redundancy and treating every dollar as important.
- •Apache is founded in 1954 with a small amount of initial capital and a handful of hires.
- •Early staffing includes key roles like geology and land/administrative support.
- •A cultural refrain reflects optimism about discoveries and internal standards.
- •Cost-consciousness is explicit: controlling spending and avoiding redundancy.
- •David frames Plank as seeing waste in the industry and using hustle as an advantage.
- 17:10 – 19:41
Apache’s first “product”: a tax-advantaged drilling program that solves financing
David explains that Apache initially isn’t just selling oil prospects—it’s offering a tax-efficient investment structure that appeals to wealthy, highly taxed investors. The generous deductions and treatment of future income reduce downside for investors and, crucially, make it easier for Apache to raise the money needed to lease and drill without relying on banks.
- •Apache positions drilling participation as both upside potential and immediate tax advantages.
- •Large upfront deductions make the effective investor out-of-pocket risk much smaller.
- •Special tax treatment of production income further improves after-tax outcomes.
- •These features attract wealthy investors and provide Apache with scalable capital.
- •David frames this as a financing solution for a young company with limited resources.
- 19:41 – 22:12
Edge through uncommon expertise—and the cofounder war that follows
Plank identifies his unique advantage: strong financial and tax knowledge paired with a willingness to learn the technical side by hiring experts and spending time in the field. The episode then turns to a destructive conflict with cofounder Truman Anderson, culminating in office bugging and a lesson about ego outstripping competence.
- •Plank says his technical oil-and-gas knowledge began near zero, but his finance/tax knowledge was rare in the industry.
- •He learns “by osmosis” through field visits with technical experts he hires.
- •A widening schism emerges: Plank is long-term oriented while Truman seeks fast status and wealth.
- •The conflict escalates into extreme behavior, including bugging offices and board rooms.
- •Plank’s takeaway: ego can exceed competence, and “fat heads get flattened.”
- 22:12 – 25:44
Earning trust through over-communication—and studying competitors obsessively
Following turmoil, Plank adopts a practice of writing daily activity reports to keep the board aligned and prevent surprises. David also highlights a vivid example of Plank’s competitive intensity: keeping competitors’ annual reports pinned behind his desk to study them constantly.
- •Plank writes daily reports for months to build confidence and maintain board support.
- •He treats the reporting habit as valuable even outside crisis periods.
- •The approach reflects a broader tendency toward discipline and accountability.
- •Competitor intelligence is constant: annual reports are kept on the wall for study.
- •David portrays Plank as relentless and unusually “hardcore” in execution.
- 25:44 – 26:15
Speed as strategy: buying a plane while staying protective of company costs
David describes Plank’s “get the plane” theme: owning a small aircraft enables rapid travel for deals and meetings on short notice. Even with that advantage, Plank structures reimbursement conservatively by charging Apache only the equivalent of commercial airfare.
- •Plank buys a plane and uses it to move quickly between opportunities.
- •Rapid response becomes a practical edge in negotiations and scheduling.
- •He calls the plane a life-changing event in terms of operating speed.
- •He remains cost-protective, billing the company at commercial airfare rates.
- •The plane fits the broader pattern of efficiency paired with urgency.
- 26:15 – 28:45
Becoming a mini-conglomerate to survive oil cycles—and a shocking deal interruption
Facing severe revenue pressure from industry downturns, Plank shifts Apache into a diversified acquirer using stock to buy entrepreneurial businesses and bridge cyclical gaps. David outlines how Apache manages acquisitions without smothering operators—and includes a startling episode where a key potential buyer’s CEO is killed in a car bombing.
- •A sharp downturn pushes Apache to seek non-oil revenue to offset cycles.
- •Apache acquires many businesses across widely different industries over about a decade.
- •Plank says they avoid a common conglomerate mistake: imposing heavy corporate overhead on acquired operators.
- •They centralize some decisions while letting operators run their businesses day to day.
- •A negotiated telephone-business sale is disrupted when the buyer’s CEO is killed in a car bomb.
- 28:45 – 31:46
Unwinding diversification and playing the long game: tech makes old assets valuable again
Plank later reverses course and refocuses Apache on being an independent oil and gas company, selling off diversified holdings when conditions shift. David emphasizes Plank’s lack of emotional attachment to prior decisions and illustrates the long-term payoff: decades later, new drilling techniques make older land and wells far more productive than expected.
- •Plank chooses to transition back from a conglomerate to a focused oil-and-gas company.
- •He sells off most non-core businesses rather than staying diversified indefinitely.
- •David underscores Plank’s willingness to change direction quickly when conditions change.
- •Decades later, a new report shows old land purchases producing strong results again.
- •The episode frames this as staying in the game long enough for outside innovation to increase asset value.
- 31:46 – 34:48
Late-life maxims and personal tradeoffs: learning, respect, persuasion, and family costs
David shifts to a series of Plank’s reflections and maxims, which he considers a core strength of the book. Alongside observations about learning, self-respect, and persuasion through analogies, Plank candidly acknowledges that his work focus came at a cost to his family—while also rejecting regret as a way of living.
- •Plank offers maxims about learning through achievement and continuing to learn even late in life.
- •He notes the link between self-respect and earning respect from others.
- •He describes using analogies and unscripted delivery to persuade and communicate effectively.
- •He observes that markets often don’t stabilize where “rationality” suggests they should.
- •He admits shortchanging family time, while emphasizing living, learning, and growth over regret.
- 34:48 – 37:55
“Pigs following cows through a cornfield”: making money in the majors’ scraps—and closing lessons
The episode closes on Apache’s counterpositioning: buying overlooked, older properties from major oil companies and improving them through “acquire-and-exploit” tactics. Plank explains why majors sell, shares his memorable “scraps” metaphor, reflects on the advantage of not being trapped by conventional practice, and ends with a son’s letter summarizing Plank’s values and the goal of making a small difference.
- •Apache shifts primary focus from drilling to acquiring operated assets with upside potential.
- •Plank explains majors sell to cut costs, redeploy cash, and chase larger reserve opportunities.
- •A reporter question prompts Plank’s metaphor about profiting from “scraps” others leave behind.
- •Plank says not knowing conventional practice helped Apache develop its own way; he repeats “beaten paths are for beaten men.”
- •A closing letter from his son highlights passion, integrity, respect for individuals, compassion, creating opportunity, and making a small difference.
