In 2023, I left Ramp to move to Israel. It's now worth $44B. My equity hadn't even vested yet. My friends joke that I made the most expensive move in the world. It was still the right call. Every time I've had to choose between the comfortable path and the harder one, the harder one paid off. 10 times out of 10. Since then, I've gotten married, started a company, and become a dad. I don't think the purpose of life is to live a comfortable life. I'm optimizing mine for meaning, not comfort.

"You have to give up everything for a few years" I hear this far too often. Here's how I did it: → Got married at 25 → Had a son at 27 → I watch Netflix with my wife every night → I take off 25 hours every single week for Shabbat. No phone, no Slack, no email. I also got fired on a Monday, started a company that week, and raised a pre-seed 42 days later. You don't need to sacrifice your entire life to start a company.

Underrated career hack: Do what you said you were going to do. Do the work before anyone asks for it. Send the Loom nobody requested. Reply to the DM. Say what you're building in public so people can find you. Leave when you said you'd leave. Do what you said you'd do and you'll be impossible to replace.

I'm convinced that anyone who isn't bothered by the idea of never starting a company shouldn't start one. The only thing that got me through a bad year is knowing I couldn't have done anything else.

Tale as old as time: 1. Founder discovers AI can write 2. Generates 30 posts in an hour 3. Posts them 4. Gets two likes 5. Says the algorithm is broken 6. Repeat

Biggest canon events for anyone posting online: - Your first post - Posting into the void - Getting ratio’d - Your mom leaving a comment - Deleting it 20 minutes later - Writing 11 hooks for one post - A coworker mentioning they saw it - Someone you admire following you back - The post you almost deleted doing 10x - Your family still not sure what you do - Your first person arguing in the replies - A stranger quoting your own line back to you - A customer saying they've read you for years

I tell every prospect this upfront: No one from the first day or the first week is going to write better than you. A prospect told me this week that his ghostwriter writes better than he does. Then told me that “nicer writing” isn't bringing in customers. Funny how that works 😅

For 7 months we struggled to win customers, and struggled even more to keep them happy. Then we switched from software as a service to service as software, 20x'd revenue in 3 months, and hit profitability. This summer, Lightbank and Verissimo led a round which closed in 36 hours. So why raise, right after you stop needing to? Because there's a massive opportunity to 100x what we're building, I'd rather move now than wish I had later.

Imagine paying $10k a month for posts you end up rewriting yourself 💀

Everyone I've hired did these before I hired them: - Read my stuff for months first - Came direct, not through a form - Sent a Loom nobody asked for - Referenced something specific I'd said - Told me what they'd do in the first 30 days - Had already done a version of the work beforehand

What posting online has actually gotten me: 1. a job at Ramp 2. a job at beehiiv 2. a pre-seed from a VC who read my posts and DM'd me first 3. every customer we have 4. a founding engineer 5. a head of content 6. a GTM engineer 7. 75+ engineers applying without a job post 8. 148 people applying to write for us 9. a call with a $2B company 10. Billion dollar CEOs in my DMs To everyone who read the first few posts when nobody else did, and stuck around from 0 to 1.6K followers, thank you. You're the reason this is still fun.

Wispr Flow is the most underrated content tool right now, and nobody uses it that way. - turn the notetaker on for every call with someone outside your company - search the transcripts for question marks - the question you got asked more than once is your post - write the answer you gave on the call, not the better one you thought of after - ship it before you talk yourself out of it Every exec I work with tells me they have nothing to say. Then they spend all week answering the same questions over and over. Literal goldmine.

My caffeine gummy company (ember) taught me why I love selling a service. The old way: - Every unit had a cost - Every order had shipping attached - No amount of volume fixed the margin We sold to the US and Ukrainian military and still lost money on every order. Selling a service is the opposite: - Nothing to manufacture - Nothing to ship - The work gets better the more we do it, and costs the same

I used to think posting publicly would cost me a career. 7 years ago a Goldman Sachs partner told me posting on LinkedIn would cost me a job. But I kept posting. I kept posting through years of zero engagement, while people asked why I was bothering. It got me the job at beehiiv. Then a pre-seed from a VC who read my posts and DM'd me first. Then every customer and every hire since. p.s. to that Goldman partner, wherever you are: I hope this post finds you well 😉

Nobody gets to decide how big their market is. You can't choose your competitors, you can't control the algorithm, and you don't get a vote on whether your category gets hot this year. But your own account and how you tell your story to the world… that's entirely yours. It's where the actual relationships happen. A VC read my posts for months, then DM'd me, and that's how I raised. A $2B company took my call because someone there had followed me since my last job. It’s compounded more than I give it credit for. Literally the most undervalued asset there is.

📂 RallyUp │ ├ 📂 1. Pick the people │ ├ Not the whole company │ ├ 2-10% of employees ever post │ ├ 2 or 3 customer facing execs people already trust │ └ CEO, CRO, CMO, VP Sales │ ├ 📂 2. Build context first │ ├ How they actually talk │ ├ The topics they know cold │ ├ The stories they've lived │ └ The lines they'd never cross │ ├ 📂 3. Find their moments │ ├ Not "3 thoughts on leadership" │ ├ One thing they went through │ └ A running bank, never a blank page │ └ 📂 4. Match exec to buyer ├ End users trust your head of product ├ Buyers trust your head of sales └ Founders buy from founders

Everyone says you have to be here every day, in the replies within the first hour. I put my phone away for 25 hours every week for Shabbat. Same day, every week, for 6+ years. So I can't reply fast and I can't ride a post while it's trending. Whatever I write has to work without me in the replies. It's the only rule I've never broken, but my account is still growing! Must be God.

I just connected Instinct to my bank account and saved 746$ Steal this if your phone is full of apps you never open: -> Text it instead of setting a reminder. Mine got flowers across the world while my phone was off for 25 hours -> Connect your Chase account and card statements. It found subscriptions I'd stopped using, canceled them, and disputed a charge -> Connect your smartwatch. Mine checks in on its own about sleep and workouts, unprompted -> Get ready for the brutal honesty, even when you would rather it wasn't ps, don't just download it and ask it questions. I haven't felt this kind of amazement since I first used Claude.

August 4, 2025: I was fired with half the marketing team. That same week: found out my wife was pregnant with our first. So I had two options, go get another job with Ramp and beehiiv on my resume, or start something with no product, no customers, and a kid on the way. I chose the latter and started building in public... Four days later people were paying me for beta access to a product that didn't exist. That’s the power of a personal brand.

When a client stops replying, they're either your best customer for years or they're gone in a month. There's no in-between.