Ray Hespen

@PennCoSheriff Amazing! Loved the updates... kept looking at your X account for the latest and greatest.

Coyote Flats Fire. Pending weather changes, all evacuation & road restrictions will be lifted at 10am. No homes were lost in this fire. 3 small outbuildings and a camper were burned. No animals were injured by fire. Prompt response by firefighters prevented a catastrophe!

@bhalligan starting to wonder if great CEOs are just great question askers... that translate to being great podcast hosts... Some bangers: - "Professional managers are intended to manage decline." - "It's not if the founder is there, but has someone occupied the founder's seat?" - Concept of discounting - Difference between job and career

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.

@jasonlk And boy... the increased pricing worked for NRR in the short term, but now seeing some operators really try and build some in house too. Seems compounding.

When B2B growth falls to < 20% YoY, you are in the Danger Zone. It’s likely mostly fueled by retaining existing customers, raising prices, and selling your base more and more products. You aren’t acquiring enough net new customers. When B2B growth falls to < 10% YoY, you are in the Dead Zone. You aren’t dead yet, but if you don’t make radical change, your business is likely terminal. You have truly fallen out of product market fit. You need to re-found the company. For real.

@bhalligan It's a flex... not sure if that's the goal.

I moved from 60 minute meetings to 30 minutes a couple of years ago. Can I move to 15 minutes or is that insulting?

It's the seat belt that fascinates me most...

@midwestern_ope You missed the question about corn.

@jasonlk @levie Awaiting reply here....

@levie Agreed 100% but serious question, because this is already happening IRL: When an agent signs up for Box but wasn’t authorized to do so, do you refund the customer?

As agents become the highest volume users of software in the future, a lot is going to become critical to support for them to be effective. Agents need to be able to signup for your tool on their own, have their own scoped access controls, be able to use your entire system through API/CLI, be able to be billed for their usage, need a computer and filesystem to use, and much more. We’re going to evolve from building primarily for the human user, with APIs as a means to get that data or tool in another platform, to a world where the API becomes the core source of truth actions. Any software that can’t support this basically won’t exist to agents.

@bhalligan @bhorowitz @a16z @HubSpot One of your best - I LOVE @bhorowitz just pure, raw, conflict that he even brings into this pod... you can tell it's just his M.O. Especially valued the culture section - tricky when words mean different things to different people.

New episode of Long Strange Trip with @bhorowitz of @a16z is now live. The first time I pitched Ben for @HubSpot, he passed on us. It stung. So naturally, it’s the first thing I brought up with him in this convo. He’s seen more founders up close over the last 20 years than most, so I wanted to ask him what separates good founders from great ones, what CEOs get wrong the most, and how they can fix it. He even names the best CEO he currently works with… Even at our Series D, when Ben passed, deep down I felt like I had no idea what I was doing. Turns out, that’s pretty common. The dangerous response is to start over-deferring to others to compensate, which is exactly when things go sideways. Here’s what else I got from this conversation: • On ‘Founder Mode’ going too far: The original insight from @bchesky is right: don't over-hire senior people and then over-defer to them. That creates fiefdoms and a political vacuum. But Ben thinks people have twisted it into "don't hire experienced people at all," which is dangerous. Founder mode means staying accountable to outcomes and having the confidence to manage people with more experience than you. • Decision debt: Ben calls decision debt "the worst debt" a company can carry because it paralyzes the entire organization. Founders who hesitate at 52/48 decisions, waiting for certainty that never comes, create a vacuum that breeds politics and dysfunction. The pile of decisions you're avoiding? A bad hire you are still trying to make work? A board member dynamic that's off and has been for awhile? A pricing model you know isn't scaling? I had this at HubSpot. Every 4-5 months I'd look up and realize everything had slowed down, and the only fix was to make a bunch of decisions I'd been dodging. The moment I made them, things started flowing again. • “Constructive confrontation”: Running away from the truth to spare feelings is dangerous. One of my bugs as CEO of HubSpot was that I’m pretty conflict averse. I think a lot of first-time founder CEOs are. But bad news has to travel fast inside fast growing companies, it’s a good thing if it reaches the CEO efficiently. And that only happens if people are willing to say the hard thing, and you’re willing to hear it. I probably should have leaned into that earlier. • Why founder-engineers suck at hiring salespeople: This is where most technical founders get wrecked. Engineers and salespeople are wired opposite: Ask an engineer a question, they try to find the correct answer. Ask a good salesperson the same question, their first instinct is: Why are you asking me that? If you're an engineer interviewing a sales candidate, their answers are going to feel evasive and it's going to annoy you: that's exactly why you'll reject the best ones and hire the worst ones. • His fix? Blind references. Call people who owe you a favor, not people who owe the candidate one. And ask who they can bring with them. Great sales leaders have a crew of followers. • What the best CEOs actually have in common: The greats can be introverts or extroverts, ivy-leaguers or dropouts. None of that stuff matters. The through-line he sees across Zuckerberg, Musk, Jensen Huang, Ali Ghodsi: they think for themselves (you can feel when someone's working from original thought vs. reading the room), they stay deeply curious, and they are blunt. This was a fun one. Enjoy.

@typesfast ... and reduce blood pressure medication consumption by 72.6%

Starlink coming to United flights will boost US GDP by at least 1%

@bhalligan Great advice. Needed this 5 years ago... but absolutely sage advice (even in hindsight). This stuff is gold.

First board meeting? Tips: 1. Send the board deck (or memo) 48 hours before. 2. Assume board members have read it, so you don't have go through everything they've already processed. 3. Bring your hardest problems and debates explicitly to the board meeting. Put in the deck/memo. 4. It should be more a collaboration meeting with the board than a readout. 5. You are always kinda in sell mode b/c you need things from the board, but you need to show your warts too. 6. Have your execs on for the meeting, but excuse them for a private session at the end. 7. Try to nail the right altitude -- not too in the weeds, but not too in the sky. Tricky. Good luck.

@ThePrimeagen the term is "the ick"

Just caught my co-founder using 5.2

U.S. existing home sales totaled 223K in January 2026 That's the lowest January existing sales volumes since 2009 Turnover remains strained in the existing-home market

2022 Tenant: toilets broken Me: I'll send a plumber over right away! Any other issues? Tenant: no 2023 Tenant: sink is backing up Me: I'll send a plumber over right away! Any other issues? Tenant: no 2024 Tenant: water in bath not draining fast Me: I'll send a plumber over right away! Any other issues? Tenant: No 2025-2026: Tenant: Dear Barry, I am writing to formally notify you of a serious mold problem in the bathroom my of unit at 1234 Figueroa St, which requires your immediate attention. The ongoing presence of mold has created unsafe and unhealthy living conditions for my family and me. Members of my family are currently experiencing health symptoms consistent with mold exposure. As you are aware, landlords are legally required to maintain rental units in habitable condition, and the current condition of the bathroom fails to meet basic habitability standards. I hope this matter can be resolved quickly and professionally. I expect your prompt response. Sincerely, Jimmy

@PennCoSheriff Pumped! Will be down this month!

It’s FREE February pistol permits at the @penncosheriff. There are some age and address restrictions. Come on down to the Public Safety Building and get your permit! 300 Kansas City Street (605) 394-6114

@OnlyCFO Feels like if you can make the case that AI unlocks massive ROI that human interaction limited - seems like a good first step. Secondarily adding that AI alone couldn't do (and actually have thoughtful conviction) is nearly equally important. Great write-up, as always.

New post: 5 things SaaS companies should be doing to survive SaaSocalypse -Not all SaaS will be equally disrupted (despite the market thinking it’s all a zero) -Not all companies are adapting (and following these 5 things👇) onlycfo.io/p/how-to-survi…

I remember the name of the customer, time of day, where they were, where I was, what phone I was using...

@karpathy Ive been trying to reach them for weeks. It seems they are so difficult to get ahold of anymore...

Anyone else approved for a loan every single day 20 times or so? Overcome with joy, really

@SpeerUnfiltered Impressive.

Our team has been at this for ~9 months. This past WEEK we grew our ARR by ~35% 🤯 profile.stripe.com/propertymanage…

Has anyone tried turning it off and then back on again...?

Try turning it off and then on again...