The Most Founder Mode CEO Working Today Isn’t the Founder: Opendoor’s Kaz Nejatian
In a Nutshell
Kaz Nejatian, ex-Shopify CTO now Opendoor CEO, embodies founder mode by refounding the company from scratch—overriding defaults like professional management, prioritizing stewardship over status, daily Bible reading for grounded reflection, and AI-native operations via companywide hackathons where even non-coders automate jobs. Successful companies thrive on first derivatives (e.g., Google's ads from search, Shopify's payments from SaaS), while Valley misunderstands churn-heavy SMB/consumer models; Kaz hires process experts to complement his outcome-focused leadership, starts trust at 75%, and aligns family life to mission for resilience amid turnarounds. Optimize for service over happiness or status, build careers not jobs by working extremes to master craft, and view marriage/kids as CEO superpowers—data shows they slash poverty/unhappiness risks and provide emotional anchors during crises like RIFs.
These notes were generated by AI and may contain inaccuracies.
Most successful companies are built on a first derivative of the core business. Union Pacific Railway made more money selling land and homes than building rail or carrying stuff. Google: search leads to ads as first derivative. First derivatives build enduring companies.
Kaz Nejatian was longtime CTO at Shopify, recently left, now CEO of Opendoor. Most founder mode CEO encountered: incredibly aggressive, not transforming the company but in a real refounding moment, rethinking everything from scratch. Will rewrite the refounding playbook. Discusses work-life balance, faith, marriage, ambition, immigrant experience. Lines whole family around job and company mission.
Grew up in Middle East, moved to Canada at age 12. Immigrants reconsider roots and beliefs deliberately, especially those who assimilate successfully.
Four core beliefs:
- Stewardship over status: Optimize for doing things rather than being things. People who optimize for happiness (a state) aren't happy; those optimizing for service are deeply happy.
- Defaults over everything else: Power of defaults underestimated in life and software. People accept defaults; rejecting them fires the software or current life. Override defaults deliberately with full force.
Professional examples of overriding defaults:
- Took job at Opendoor, not the default career choice; committed with full force.
- Went to business school for undergrad, got private equity job (default), lasted 11 days at Ephraim, resigned because it wasn't right.
Personal examples:
- Religious despite default not to be: reads Bible every day, goes to church every Sunday. Makes him better as a human (selfish reason). First time talking about it publicly; rare among tech CEOs.
- With wife, optimized life for different set of priorities.
These changes enabled his career.
People who optimize for happiness end up not being happy because happiness is a state. People who optimize for service end up actually being usually deeply happy.
Stewardship over status is one of the most important ones for me.
Grew up nerd, coding at age 6, aware of brain's power over life. Without care, depression sets in (common for founders/rich people). Lose control over core beliefs, life becomes rat race (e.g., Elon always richer). Need winnable races.
Found prayer powerful early (grew up Muslim): sit, reflect, admit lack of control. Meditation does similar job; most successful people meditate one way or another. He meditates "with someone else present."
Immigrants succeed as entrepreneurs not just from reset, but no safety net: e.g., Toby (Shopify CEO) couldn't get job, had to start Shopify; Kaz paid for college by hustling, building websites.
If I knew everything I know now, I would not have done it. [Common founder sentiment]
Entrepreneurship has highest risk-adjusted upside when options limited. Humans structurally misprice risk in entrepreneurs' favor: things going poorly not as painful as thought, recovery happens; more pains occur but each less bad.
Founder mode (Paul Graham essay ~1 year ago) now default; CEOs don't apologize for it.
Kaz uncomfortable as poster child; prefers Figma/product problems over talking about job. At 42-43, feels responsibility to world.
Past: Boss said he lacked "executive voice" (proved by reaction), painful. "Bring your whole self to work" excluded disagreeable detail-oriented people who reject 9-5.
Founder mode = CEO takes responsibility for outcomes, not processes. Delegates process design; holds self accountable for delivery. Listens to process person (e.g., "Cass, calm down") 4-5 times.
Professional managers care more about process than truth, appearances over reality (power from management). Kaz not seen as great manager despite managing thousands; people say good leader, would work for him again.
Hires around weaknesses: Doesn't make self well-rounded. Always had process person:
- Current: Jung, COO of Opendoor, from Shopify.
- At Facebook (as PM), unknown person kicked him under table in first meeting, later joined at Shopify.
Feedback trap: Manager feedback makes you think fix weakness, but ask if weakness enables strengths.
Published blueprint (user manual for working with Kaz) ~10 years old, minor word changes; used at Shopify. All quirky CEOs/founders should write one: strong attract, strong repel.
If you go to an Italian restaurant and complain the sushi is bad, that's your fault. ... My job is to tell you what kind of a person I am so you can opt in or opt out.
Top item: "I got your back and I trust you" (high starting trust to allocate risk early).
Trust battery (from Toby): Kaz starts at 75% (vs. Toby's 50%), depletes faster. Underwrites risk-taking.
Hire/fire: Not slow fire; since joining 2 quarters ago, 1 original exec left (strong repel). Assume new teammate good at job initially.
- Discount rate: Toby applies zero discount to future (cares about 10 years from now equally to now); hard in public companies.
- Useful timeframes: this week (validate/ship ideas) and 10 years. Quarters (12 weeks) useless: cohorts don't bake, not measurable.
- Build outside Silicon Valley: Shopify, HubSpot succeeded in SMB (Valley allergic); couldn't raise/start there. Same for real estate software, Opendoor. Valley understands enterprise sales (clear ICP), loves it; doesn't grasp churn, SMB/consumer cohorts (theoretical vs. deep understanding).
Valley doesn't genuinely understand churn. Valley doesn't understand first derivative businesses, which is odd. Toby asked Kaz to take over Shopify Shipping. Kaz read the US Postal Service Act from the 1700s to understand the system. He's deeply curious about the history of things.
Most successful companies are built on a first derivative of the core business. Union Pacific Railway made more money selling land and homes than from rail. Shopify started as SaaS, payments, became merchant services with payments, tax, billing, ads. Google: search leads to ads. First derivatives build enduring companies. Valley misunderstands them because CAC LTV is harder to calculate.
Shopify bet on buying warehouses and inventory for full e-commerce stack. Kaz took over as COO in September 2022, sold logistics publicly in May 2023 (decision ~3-4 weeks, sales take 3 months to negotiate). Don't hold past self guilty; make new decisions on new facts. Shopify needed to focus on core, not side quests. Toby agreed to main mission.
Facts changed: When Shopify entered logistics, no good options for small businesses (Amazon or bust). In four years, good companies emerged: Walmart, DHL. Alternatives improved, so customers didn't need Shopify. Not jealous of margins; people served didn't need it. Concrete annoying, prefer electrons.
No internal fight; easy alignment and execution. Shopify good at discovering what doesn't work and being honest. Truth commitment from Toby. Companies are exoskeletons of their leaders if good. Shopify is exoskeleton of Toby.
Worked closely with Toby, knew Mark. Both deeply product-focused, long-term focused, built companies the hard way. Mark lost entire executive team after turning down Yahoo acquisition. Mark more product manager, Toby engineer (discussions on API shape).
Opendoor cruising low market cap. In February, flying back from Dallas (hosting Shopify Top 100 event), for fun studied Opendoor history, modeled it four weekends, used product. Wife and he only talked Opendoor. Texted Keith in March: going all in, spend entire net worth, leverage to take private (company worth few hundred million). Keith (knew from boy adventures): "Yeah, let's talk." Then insane financing made takeover unprofitable. Plan was stay at Shopify, join board, yell about product.
Sunday call from recruiter Paul Diversa (previously pitched other CEO jobs, always declined). Kaz: "Unless it's Opendoor." Paul: "It is. How fast to New York?" There in 5 hours. From call to CEO announcement: 15-16 days. Keith and Eric (original founder/investor) decided to rescue, needed CEO. Fast process.
Mechanically: Met existing board in CEO search. They asked conditions. Wanted Keith/Eric on board, promise not to care about optics (not caretaker, build product). Easy conversation, everyone solving problem. Night before announcement, 3:30am pacing Central Park West on call (wife sleeping, public company).
Keith/Eric invested via PIPE. Board refreshed (few remained, few left); excellent board now.
Refounding. More public companies should. Professional managers good at managing decline. Exothermic power for extraordinary outcomes not in them. Leads to up then slow decline (e.g., General Electric). Microsoft refounded. Question: is founder seat occupied? Product companies need exothermic pressure (upsides/downsides), not decline management. Conglomerates hard.
Stock jumped 67x on joining (bullish long-term). Kaz doesn't think about stock price; correlated long-term. Talked stock twice: "Stock up 15% doesn't mean 15% smarter." Create value, solve user problems. Watching CNBC doesn't make good CEO (like ESPN doesn't make good QB). Duty to shareholders: long-term value, agnostic day-to-day.
Turnarounds rare in Silicon Valley. Most teams don't do it like this. Apple most successful (worse position than Opendoor). Management types: slow decline/climb, not big change.
VC-held companies sideways in death spiral (not one thing wrong, everything). Change everything. Managers incentivized to delay death. RSUs harmful (prefer ISOs); incentivize performance. Kaz compensation: $1 salary + options-like (PSUs with zero value below price, some high strikes). Aligns with shareholders. Wall Street has Harvard MBAs rich destroying companies.
Opendoor not AI-native, not product-oriented. Wants to be most aggressive software company. Companywide hackathon 10 days ago. HPM (home project managers who renovate homes): GC wrote software automating his job (never coded; used Cursor, Gumloop; coaching from them + OpenAI). Now manages software. Everyone at Opendoor uses AI daily. Hackathon tested 10 weeks of muscle-building.
Honest company conversation: Job descriptions start "default to AI." Performance management = whether you make team (like pro sports). First eval question: do you default to AI?
VP at public company (HubSpot, Facebook, Google) wanting this: No 10-year plan. Have career, not job. Job: do for someone else to get paid. Career: work on every day for yourself. Optimizes life around it (wife, kids know Opendoor; dinner talks product; family main mission). Care deeply, self-identify with work not ideas.
Young advice terrible. Work all hours if manager allows to master craft (like woodworker feeling wood, Tom Brady throws). Discover breaking points by working hard.
Do young people follow passion? Rich say follow passion but...
They dug in on something nasty and practical. Think: how can I be of service to the world? If you view yourself as a net addition to things around you, things work out okay. If you think what can I get, things work poorly. This applies to relationships as much as career.
I've never been married at 58. The average person doing what you're doing would be doing it wrong, but extremes don't follow averages. Wrote a book Get Married. Focuses on health, wealth, and happiness impacts of marriage on men. Data shows for certain cancers, being married is as good an indicator of survival as chemotherapy. In US or Canada, do these three things in order: graduate high school, get work experience, get married before 30—odds of being unhappy or poor are almost zero. Know yourself, but be honest: odds are you're not special; what worked historically for humanity will work for you. Some are different, like Brian and I.
Society undervalues marriage and especially kids. I'm a better CEO because I have kids. CEO job is deeply lonely. Kids know Opendoor's mission, ask about it, are proud. Conversations make hard days less hard.
RIF Story at Shopify
On RIF day at Shopify, insisted on most one-on-ones. Arrived at Palo Alto office at 3:45 a.m., finished around 7:00 p.m., burst out crying after last hangout. Walked to Airbnb; son ran and hugged me. Daddy mode kicked in, changed the day. Worst day of career, deep pain I may never recover from, but could do it because of son and family. Deeply grateful.
You've had good karma. Ben Horowitz says life is deeply unfair, get over it. Life isn't unfair. You are destined for something; job is to discover your destiny and mission, work on yourself until you do. The more good you do, the more good you get back. It may be difficult, not easy, but not unfair. My purpose: make average family able to afford good home, raise good family, reduce friction and cost of home ownership. Difficult and fulfilling are highly correlated.
Kaz is one of the most intentional people, overrides every default in leadership, family, success definition. Good podcast for existing CEOs: approach as if today is your first day as outside CEO, unencumbered by past decisions and baggage. Otherwise, board might do it for you. Conversation made me re-examine how I'm showing up everywhere and rethink defaults.
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