CEO/ founder @VertoEducation. Dedicated to transforming #HigherEd. Curious, always. Informed citizen. Lover of the outdoors.

San Francisco, CA
Joined May 2011
You’re not going to make everyone happy, and if you try too hard you’ll make yourself unhappy.
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G. K. Chesterton explains that reading gives a man more lives than he was born with: “A man who has read a thousand books is armed for life; a man who has read none is easy prey. The man who has read a thousand books has lived a thousand lives. He has seen cities he has never visited, spoken to men who died centuries ago, and walked in worlds that no longer exist. Reading does not merely inform him; it enlarges him. It stretches the boundaries of his own experience until he becomes something more than himself.”
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Mitch Gordon retweeted
Wow. I struggle to find time for enough podcasts Glad I made an exception for @bhalligan & @nejatian at recommendation of @rabois … so good
The most ‘Founder Mode’ CEO working today is not actually the founder. NEW EPISODE with Kaz @nejatian of @Opendoor is now live. This is a special one. Kaz left Shopify to pull off the refounding of a struggling public company in just 16 days. Incredible story. Here are just a few of my learnings from our conversation on the latest episode of Long Strange Trip: 1. First Derivative Businesses The most enduring companies are rarely built on their primary activity; they are built on the first derivative of that core business. Great founders identify and weaponize the secondary value stream. This is important. 2. Rejecting Defaults Success is a function of the defaults you choose to overwrite. Most operators accept the 'software' of their industry or life on autopilot; exceptional builders identify the one or two critical defaults and fight them with all their power to create a new trajectory. Kaz is a master at this, and he explains how. 3. Stewardship Over Status Optimize for doing things rather than being things. When a leader optimizes for a title or happiness, they create fragile organizations; when they optimize for stewardship and service, they build a mission-driven culture that can withstand the lonely and painful stretches of the journey. 4. Write a user manual for yourself "Strong attract, strong repel. My job is to tell you what kind of a person I am so you can opt in or opt out." I love this quote. If you're a founder, you owe this to everyone around you. 5. Founder mode = responsibility for outcomes Hold yourself responsible for truth and outcomes, not processes. Hire people to round you out. Don't try to be well-rounded yourself. And don't work on your weaknesses. "Is the fact that I'm bad at this the reason I'm good at everything else?" 6. Structural Risk Mispricing The one permanent advantage for entrepreneurs is that the rest of the world structurally misprices risk. While others see a 'lion bite' in every setback, the best CEOs recognizes that things going poorly is not as painful as you think,  allowing them to lean into volatility that scares off the incumbent. That's the difference. 7. Death Spiral Honesty When a company is in a death spiral, incrementalism is fatal; "what must change os everything." Professional managers are often incentivized by RSUs to delay the inevitable and manage a slow decline. You need zero incentive to manage a decline and a compensation structure aligned purely with performance. 8. AI as the New Performance Default Default to AI is not a suggestion; it is the first line of the job description. A company becomes AI-native not through top-down mandates, but by making AI proficiency a core pillar of the performance management system - effectively deciding who gets to play on the team based on their ability to automate their own craft. 9. The Career vs. Job Distinction "A job is something you do for someone else in order to get paid. A career is something you work on every day for yourself." Kaz's kids know what @Opendoor is. His family is all in. Exceptional companies are built by people who self-identify with their work and treat their professional mission as a family-integrated pursuit. 10. Two timeframes matter. Everything else is noise. This week and 10 years from now. "This quarter is a deeply useless measuring period." @tobi applies a discount rate of basically zero to the future. That's the model. My takeaway from this conversation: ask yourself what defaults you're living by that you haven't deliberately chosen. Kaz overrides every default, and he does it over and over again.
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Packed Alpha School info session in SF today. “If you’re hiring a tutor, we’re not doing our job.” “If a student isn’t learning, it’s our fault, not the student’s.” I don’t understand how one cannot be incredibly excited about this.
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Mitch Gordon retweeted
Jim Carrey got real about the chase: "The first half of life is all about adding—cool car, nice clothes, things people admire. It looks great… but it never fulfills you. Happiness doesn't live there." Then he flips it: After wrestling depression, he says he's free of it now. No depression at all. Just the full weather of being human—sadness, joy, elation, gratitude—all passing through like clouds. None of it sticks long enough to crush him. In this short, honest 59-sec clip [link to video], he reminds us: The stuff we stack up doesn't fill the hole. Real peace comes when you stop trying to own every feeling and just let them move through. Feels like he cracked the code most of us are still searching for. What's one thing you used to chase that you now see doesn't actually bring the peace you thought it would? No judgment—just curious what you've noticed lately.
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Mitch Gordon retweeted
If you want to scale as an exec, work yourself out of a job as fast as you can. Jeanne DeWitt Grosser, COO @vercel nailed this advice, "The best piece of advice I ever got that stuck with me is you need to work yourself out of a job. As you're scaling, you're comfortable doing the job you've become good at. But if you keep doing that job, that is no longer the job at $100 million versus $25 million. And so I think the minute you feel you have deeply mastered something is probably the point at which you should be figuring out how somebody else does that. Either you're teaching it to somebody below you who's going to be able to move in and take that off your plate, or you're starting to think about how do I hire for that — so I now have the bandwidth to go learn the next thing."
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At hypergrowth companies like Vercel, Harvey, and Cognition, executives face a brutal challenge: keeping pace with a company that might grow 5-10x in a year. That means hiring aggressively without lowering the bar, figuring out how to mature the org without slowing down, operating at different altitudes, solving novel problems, and much more. Their role changes quarter to quarter, and the margin for error is razor thin. I'm really excited to launch our newest podcast, Executive Function, which explores a simple question: what is the difference between a good and truly great scaleup executive? We learn what these exceptional execs are doing differently, how they approach their work, how they make decisions, and how they make a difference for their companies. The first episode drops later this week. Learn more at: review.firstround.com/execut…
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Mitch Gordon retweeted
Phones are corrupting children. Loved this book by @JonHaidt. His critique of the smartphone childhood is rigorous and credible. I don’t fault parents, they’re doing their best and are trapped in a system they didn’t create. I want a societal structure that grants people like Jonathan more power not because he gets it by being Machiavellian but because he’s fundamentally an adept advocate for human vibrance. Some really useful guidelines for parents and children outlined.
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Mitch Gordon retweeted
11 months after his release from the concentration camps, Viktor Frankl gave a set of lectures on moving beyond optimism and pessimism to find life's deepest source of meaning. They were lost for decades, never before published in English—and now they are: themarginalian.org/2020/05/1…
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Mitch Gordon retweeted
The ultimate long-term competitive advantage is having fun. You can never bet against the person who just seems to have fun doing the work.
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Sometime in my 20s my mom told me “you’re too old to blame your parents for anything you don’t like about yourself,” and I think that’s the most important thing she’s ever said to me. Agency will set you free.
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Mitch Gordon retweeted
Aldous Huxley, just leaving this here
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Ok politics aside (which I know will be tough for many, but) ... go apologize. Go fix a broken relationship. Just say you are sorry. It's the first Sunday of 2026. A time to do better. Even relationships that seem totally broken can sometimes be repaired. In business, at home, at work, with old friends. Sometimes at least. An honest, sincere, caveat-free apology can go a long way. If there's one relationship you broke in 2025 (or even before) that you regret breaking, just go apologize. Pick up the phone, or at least, the email. No caveats. No passive voice. Own it. Apologize. No one does this. It works. Not always. But often. Often enough.
Had a lovely dinner last night with @POTUS and @FLOTUS. 2026 is going to be amazing!
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This is incredibly well said.
$10M ARR is the FU MONEY of SaaS. At $10M ARR bootstrapped, you and your co-founder clear $1M+/year in salary and dividends easily. You can sell instantly for $30-40M. There are hundreds of EBITDA buyers at this level vs. a handful at $1B valuations. From here, you can do whatever you want. Hire a CEO and work 1 hour/week. Grind 100 hours if that's your thing. Raise $50M from a position of strength. Scale to $25M ARR with 25 people and pay yourself $10-15M/year. Most companies never get here because VCs show up early with decacorn dreams and money you don't need. That capital interferes with the one thing that makes you great: product-market fit. Bootstrapping to $10M ARR is easier and less risky than creating a VC-backed unicorn, with a far higher probability-weighted outcome. If you can find PMF and use customer money to get to $10M, you can do anything you want with your life.
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Mitch Gordon retweeted
Career advice: Stay long enough to have an impact I’m seeing many folks who exhibit the following pattern: - Do a role for 12-18 months - Change roles - Repeat They are “job optimizers”, constantly on the lookout for something better, almost from the moment they land in a new role. The purpose of their current role is to help them find their next role. If this is you, stop. Take a breath. Embrace your current role. In fact, fall in love with it. Throw yourself into learning, building and having impact. You need at least 3-4 years at a company to have real impact. Have impact with measurable outcomes, and the next role will take care of itself. If you do great work at a good company, word will get out and you will never need to look for a job again. Plus, the joy and satisfaction of having meaningful impact is reward in and of itself. Frank Slootman offers a few other reasons why employers see too many short-tenured jobs as a red flag.
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everyone should have two therapists, a man who tells you to grow up and get your shit together, and a woman who tells you to love yourself the way you are. Ideally they should be married to each other since at least 9 months before you were born
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Words to live by today—and every day.
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Serial entrepeneur is good Even better is putting in the 15-20 years it likely takes to build something iconic that lasts
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"If you want to accomplish something truly extraordinary, if you want to be in the 99th percentile in terms of outcomes, it's going to be really difficult. It's going to be really uncomfortable. You have to remind people of that that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. They have definitely screwed up somehow. It's supposed to be really fricking exhausting. On Friday night when you get hit with an escalation, when you get hit with a bunch of new bugs from someone in the engineering team that you've got a triage, those are the moments where great players and great teams are separated from good players and good teams." — Matt MacInnis (@stanine), CPO/COO at @Rippling
“Extraordinary results demand extraordinary effort” A powerful conversation with Matt MacInnis (@stanine), long-time COO and newly minted CPO at @Rippling We discuss: 🔸 Matt’s transition from COO to CPO and what surprised him about leading product 🔸 The “high alpha, low beta” framework for evaluating people, processes, and products 🔸 Why you should deliberately understaff projects 🔸 Why you should treat escalations as gifts 🔸 Why processes exist to reduce volatility—and why it will also suppress creativity 🔸 When founders should quit their startups (hint: much earlier than VCs want you to) 🔸 Much more Listen now 👇 • YouTube: youtu.be/O_W76LR77Vw • Spotify: open.spotify.com/episode/1Id… • Apple: podcasts.apple.com/us/podcas… Thank you to our wonderful sponsors for supporting the podcast: 🏆 @GeminiApp — Your everyday AI assistant: ai.dev/ 🏆 @datadoghq — Now home to Eppo, the leading experimentation and feature flagging platform: datadoghq.com/lenny 🏆 @gofundme Giving Funds — Make year-end giving easy: gofundme.com/lenny
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Surprise. Surprise.
If you *only* used SAT to admit to elite colleges, share of admits from top 1% income falls 15.8% → 9.9% and representation from <$200k rises by +8.8%, with no reduction in post-college outcomes. It's 'holistic review' and 'ban SAT' policy that allows the most wealthy and powerful to virtue signal while getting an edge.
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