Over the years, I have tried to share learnings from my startups and seed investing.
Decided to combine my startup tweets+tweetstorms into a tweethurricane.
Here are my learnings + advice, from pitching investors to getting through the journey:
What just happened?
The S&P 500 just erased nearly -$2 TRILLION of market cap just hours after 3rd strongest US jobs report in 18 months.
Meanwhile, Bitcoin is officially down over -50% from its record high in October 2025.
What's happening? Let us explain.
(a thread)
Karri’s new social media shtick is to take hyperbolic tech memes and just give a very sensible+reasonable take on it. Love it.
My experience with VCs is fairly similar to Karri’s.
imo, the most frustrating problem with VCs is that they share your deck + info with competitors.
I don’t really have many VC horror stories.
The worst ones are just meetings where there isn’t much interest. Everyone is still polite, but you can feel it’s not going anywhere. With my first company, I pitched a lot of VCs and got a lot of polite rejections.
With Linear, I approached fundraising differently. I tried to always be in a position where I didn’t need funding.
I also didn’t do pitch meetings unless there was real mutual interest. I would take casual meetings, but tried to avoid pitch meetings, until I thought the timing was right, I was in the process, and I was interested and I could see the VC interested too.
Early on, we raised a small amount from angels. We didn’t want to commit to a VC at the very beginning, and with three co-founders we knew we could build the first version without much money.
After we announced the company, investor interest started to pick up. I told most VCs no and said I was focused on building the product.
Then Sequoia reached out. I took a coffee meeting with one of the partners because, well, it was Sequoia.
The partner later pushed me to come in and “meet more people.” I assumed this might turn into more of a pitch meeting, so I came prepared with slides and some thinking. I was willing to do it, again because it was Sequoia.
Before committing to the meeting, I told them clearly that I wasn’t raising and didn’t want to waste their time. They still wanted me to come in.
After the pitch, someone asked how much we were raising, since it wasn’t in the deck.
I said what I had already told them: I’m not raising.
They asked, “Well, if you were raising, what would you raise?”
I said I hadn’t really thought about it, and we wrapped the meeting.
They didn’t invest in that moment, but a few weeks later, once we actually decided to raise, they fought against other term sheets and led our seed round.
About a year later, Linear became breakeven/profitable. Every round since has been more focused. I’ve mostly met casually with VCs, usually engaging with 3–5 firms per round, and only doing a pitch if I thought they were good and they really wanted it. I’ve still gotten plenty of passes too.
Each round has taken about 2-3 weeks, because I've built the relationships, then just completed the show, and closed within couple of weeks.
With every round, I’ve also given VCs some homework. I send them a memo and questions about the business, ask them to write answers, and then we discuss them live.
For our Series B, several people from Accel flew to where I live, booked a hotel space, and came with binders of research about our company. It wasn’t a formal pitch meeting. It was a discussion.
I share this because for every VC horror story, there are also stories where investors really go the extra mile.
There are many cases where the VC builds the case, defends and believes in the founder, and does everything they can to make the investment happen, even when the rest of the partnership isn’t fully there yet.
I’ve only raised in 2012 and from 2019 onward, so I do believe there were times when VCs had more power and could abuse it more. YC, in some ways, helped put a stop to that.
But my guess is that VCs more often do something extraordinary than treat someone badly. You just don’t hear about those extraordinary experiences as much.
I’ve seen VCs fly anywhere in the world on a moment’s notice to try to convince a founder. I’ve been called many times to help sell a founder on a firm. VCs will do everything, call in every favor, to impress the founder.
And I don’t envy the job. It seems grueling. You have to pass on a lot of people who are obviously passionate about their business, and people take it personally. At the same time, you have to work incredibly hard to get into the best deals.
Going public changes everything. Colin Angle (@colinangle) rang the Nasdaq bell, walked into his first interview as a public CEO, and got asked: "My wife says Roomba doesn't work." Full conversation with Colin on Founders in Arms. Link in bio.
Turns out @zackfox already runs his finances on Mercury. On June 25, he'll command a room with us.
An immersive live set. Spots open now → https://t.co/CBNTFBxxT6
We just raised $40M to solve America’s affordability crisis.
Groceries are the #1 financial stressor in America. Food prices are up 30% since the pandemic. For the 100 million Americans earning under $50K, the money runs out before the month does.
To fix it, Forage is building a network for affordability:
1. For families, we’re building a suite of products to expand financial access
2. For partners, we’re building a revenue growth engine by helping them win on affordability
Today, our technology is used in over 100,000 stores across all 50 states. Our payments volume is up 13x YoY. When grocers switch to Forage, they see a 15% lift in EBT revenue.
We also launched the Forage app, a free tool that helps cost-conscious families check their EBT balances, save on groceries, and earn rewards on every purchases.
US grocery is a $1.5T market. We're just getting started.
Onwards! 🚀
You can work 5 days a week and succeed as a startup.
Mercury has done that from day 0 and we are valued @ $5.2bn 7 years after launch.
I have been an entrepreneur for 20 years and raised 3 kids while doing it.
The point of success is to have a great life not just a startup 😊
"If you are not working 7 days per week, you are going to lose".
Corgi Insurance is the most intense workplace culture in startups.
- The company works 7 days per week.
- Founder (@nico_laqua) lives and sleeps in the office.
- He built a cafe in the office because there was no local cafe that was open 24/7.
- 2/3 of the first 30 team members have the Corgi logo as a tattoo.
Today I went behind the scenes with Nico, who has used this culture to scale the company to a $2.6BN valuation in just two years.
My condensed notes below:
1. If You Are Not Working 7 Days Per Week, You Are Going to Lose:
Whatever you can get done in 5 days, you'll get more done in 6 and 7. If you are trying to solve the world’s hardest problems, a standard 5-day workweek will not cut it.
2. Work Trials Repel the Mediocre:
Corgi forces candidates into mock work trials over the weekend. If seeing a full office on a Saturday scares them, they don't belong. True intensity acts as a natural filter to attract killers and repel clock-watchers.
3. Lead from the Front Lines
You can’t demand 7-day weeks while sitting on a yacht. Nico sleeps 3–4 hours a night on a mattress inside the office. If you want your troops to bleed, you have to be in the trenches with them.
4. Culture Only Means One Thing: Winning
Forget superficial jargon like "hackers" or "ex-founders." Strip away the corporate fluff. A great startup culture is aggressively optimized around one single word: Winning.
5. Lifespan vs. Victories
Building something world-historic requires radical sacrifice. When asked if he'd rather build a trillion-dollar company and die at 50, or fail and live to 80, the answer was easy. "I would rather measure my lifespan in victories."
6. Reject the Comfort of "Quiet Quitting."
If you are operating in a hyper-growth environment and your days off happen to be Saturday and Sunday every single week, you are quiet quitting. To win, you must deliberately bypass the off-ramps of personal comfort and low volatility.
Corgi isn't for everyone—and that’s exactly the point.
Hosting the first USVC event in SF next Tuesday (6/9) with @immad
Who wants to join?
Leave a comment if you wanna come by
(priority for friends + investors)
Every VC had a reason Vercel shouldn't exist.
Guillermo Rauch heard a different reason from every investor he spoke to when building Vercel, and he kept going anyway.
He joined us live at Mercury HQ in SF for Founders in Arms, and this was one of the sharpest moments in the conversation: the idea that consensus is a signal to walk away, not lean in.
Full conversation with Guillermo Rauch (CEO, Vercel) on the latest Founders in Arms episode. Link in bio.
California elections are next week (June 2), here’s my voting guide.
As usual, the ballot is way too long and asks voters to decide things no normal person should be expected to know. I did my best to figure it out.
My basic lens: competent government, housing abundance, public safety, fiscal discipline, better schools, and less performative politics.
TL;DR:
Governor: Matt Mahan
Lt. Governor: Josh Fryday
Secretary of State: Shirley Weber
Controller: Herb Morgan
Treasurer: Eleni Kounalakis
Attorney General: Rob Bonta
Insurance Commissioner: Patrick Wolff
Board of Equalization, D2: Sally Lieber
US Representative, D11: Scott Wiener
State Assembly, D17: Matt Haney
Superior Court Judge: Phoebe Maffei
State Superintendent: Josh Newman
Board of Education: Phil Kim
Props:
A: Yes
B: Yes
C: Yes
D: No
Statewide races
Governor: Matt Mahan
He’s the most pragmatic, execution-focused candidate in the race, and the only candidate (of 61) that I really like. California needs someone smart and pragmatic who has dealt with stuff that matters: homelessness, permitting, public safety, and budgets. Mahan has done a great job as Mayor of San Jose and is the governor California needs.
On the others:
Katie Porter is sharp, but insufferable and a bit performative... We have enough political theater. We need a governor who can run the state.
Tom Steyer is economically illiterate in the way rich progressives often are. He favors a wealth tax, which would be a disaster for California. We already have a narrow, volatile tax base that depends heavily on high earners, capital gains, and founder outcomes. A wealth tax would push more mobile capital, founders, and investors out of the state, potentially reduce tax revenue, and make the budget more fragile. It feels good to some people politically. It is terrible policy.
Xavier Becerra also worries me. He feels like an old-school machine politics candidate who has held jobs with no evidence that he can actually run things well. California has a serious insurance crisis, and I don’t trust him to handle it. When asked for his plan, he said he would "tell insurers they can’t raise rates." But if you treat insurers as villains that can simply be forced to write policies at politically convenient prices, you don’t get cheaper insurance. You get fewer insurers, more non-renewals, less availability, and more risk dumped onto the state. That is already part of the problem.
He also does not strike me as an effective executive. His time in the Biden administration was widely viewed as underwhelming, and California is too big and too broken to hand the job to a default partisan résumé candidate.
If the general election ends up as Becerra or Steyer vs. Steve Hilton, I would vote for Steve Hilton. I don’t like Hilton’s style, and if Trump endorses him, he’s probably toast in California. But Hilton has genuinely good ideas and is at least thinking about the right problems: housing, affordability, energy, schools, and government failure. He would be a better candidate than Becerra or Steyer.
Lieutenant Governor: Josh Fryday
The race for backup governor doesn't really matter much TBH. Fryday and Tubbs are both smart and pro-housing, I could vote for either of them. Fryday has the idea to build housing on the vast amount of developable land that universities and state agencies sit on top of. Let's do it!
Secretary of State: Shirley Weber
This office oversees elections, business filings, campaign and lobbying disclosures, and state archives. Weber is the incumbent and seems fine.
Controller: Herb Morgan
You could make a reasonable case for Malia Cohen. She seems to have done an okay job, and she will probably win. But I prefer Morgan because he seems more focused on audits, waste, and fiscal discipline.
The mark against Cohen for me: when she ran last time, she said she would audit state homelessness spending. That still hasn't happened.
Cohen is not bad, I just think Morgan is the better vote.
Treasurer: Eleni Kounalakis
She has private-sector experience and has actually built housing. The treasurer’s office touches debt, infrastructure finance, housing finance, and the state’s balance sheet.
Two things I especially like: she wants to hold California’s debt-service-to-General Fund ratio at or below 6%, and she wants to publish a public “California Balance Sheet” dashboard. Make the state’s finances more legible and harder to hide behind accounting fog.
Attorney General: Rob Bonta
He’s fine. I don’t love everything about him, but he is going to win, and I don’t see a better option here.
Insurance Commissioner: Patrick Wolff
This is sneakily one of the most important races on the ballot... California’s insurance market is in real trouble. Homeowners are losing coverage, premiums are rising, and wildfire risk is making the system harder to sustain. The next Insurance Commissioner needs to understand insurance as a market, not just as a political talking point.
Wolff is really smart, knows insurance well, and thinks about the problem from a market perspective. He is also a chess grandmaster, which is not a qualification by itself, but does suggest a certain kind of analytical mind.
Please vote for him.
District / local races
Board of Equalization, District 2: Sally J. Lieber
Honestly, I’m not even sure why this role still exists in this form. It has a weird, random set of responsibilities, and I don’t think voters should be electing people to this office.
That said, Lieber seems to have done a fine job, and I don’t see a strong reason to replace her.
US Representative, District 11: Scott Wiener
Listen, I don’t love everything about him. I disagreed with his AI regulation approach, and I think he sometimes has the standard Sacramento instinct to regulate first and ask questions later.
But this race is not close for me.
Saikat Chakrabarti is an economically destructive populist. He supports a wealth tax, backed Prop D with $500K of his own money, and seems far too comfortable with the idea that San Francisco can tax its way out of dysfunction. That is exactly the wrong lesson to take from the last decade. SF does not need more anti-business symbolism. It needs more housing, more jobs, cleaner streets, better schools, and a government that can execute.
Connie Chan is also not the answer. Her record is too NIMBY and too aligned with the old SF politics that got us into this mess. She has opposed or slowed housing, resisted streamlining, and was opposed to the recall of Chesa Boudin. She represents less housing, higher rents, and more veto power for neighborhood obstructionists.
Wiener is imperfect, but he has been genuinely pro-housing, pro-transit, and pro-abundance when those positions were politically hard. That matters. He is the best choice in this race.
State Assembly, District 17: Matt Haney
He’s good and unopposed.
Judge of the Superior Court: Phoebe Maffei
To be honest, both candidates seem fine. You could just as easily make the case for Alexandra Pray. They are both experienced.
State Superintendent of Public Instruction: Josh Newman
This is another important one. Newman has good ideas, including learning from the “Mississippi Miracle,” focusing on basic literacy, and being open to school choice.
I also strongly agree with him that we should not be electing this position at all. It should be appointed... voters do not have enough bandwidth or information to evaluate this role!
Board of Education: Phil Kim
His top goals are student outcomes and safety. He also voted to bring algebra back. It is insane that this was even controversial, and even more insane that it passed narrowly. He was on the right side of it.
SF Props
Prop A: Yes
This is the Earthquake Safety and Emergency Response Bond. It authorizes $535 million in bonds for seismic upgrades and emergency response infrastructure.
I hate spending money, and I especially hate when people pretend bonds are free - they are not! The city says this won’t raise tax rates, but that does not mean it has no cost. Taxpayers are still committing to repay principal plus interest. In this case, the estimated repayment is about $933 million over 26 years for a $535 million bond.
That said, bonds are probably the best way to fund long-lived emergency infrastructure. Earthquake safety, fire response, and emergency facilities are exactly the kind of things that can justify debt financing. I haven't been able to figure out if we REALLY need it but I'm going to say it's important enough that I'm ok paying for it.
Prop B: Yes
I don’t feel strongly about this, but it fixes a weird quirk in our law. San Francisco has a two-term limit for mayors and supervisors, but it is written as a limit on successive terms. So you can serve two terms, do something else for a while, and then come back.
Two terms should probably mean two terms.
Prop C: Yes
This is a very slight adjustment to San Francisco business taxes. It helps small businesses while raising rates on larger businesses to partially offset the cost.
The main reason I care is that Prop C is that it's a foil to Prop D. Both change the same tax code, so if Prop D passes but Prop C gets more votes, then Prop C gets enacted instead.
Stupid California politics, but here we are. Vote yes on C.
Prop D: No
Saikat and Bernie Sanders call this the “CEO tax,” but that’s misleading. It’s really a business tax, mostly through the gross receipts tax, with the rate tied to executive-to-worker pay ratios. It would raise some tax rates by roughly 800%.
This is emotionally satisfying to some, but would be economically destructive. It could cause companies to shift jobs, headquarters, or revenue out of SF. Companies that stay may hire less, pass costs to customers, or avoid expanding here.
The revenue may also get tied up in court, while businesses face years of uncertainty.
SF needs more companies choosing to be here, not another reason to leave. Vote No on D.
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It took me a long time to research all this. The fact that voters are expected to have an informed view on every race and measure is part of the problem. California has too many elected offices, too many ballot measures, and too little accountability... but here we are, so vote for the least crazy path toward a more functional state, please!
SpaceX drops the hypiest IPO filing and says "we believe we have identified the largest TAM in human history", and you're like, my interplanetary east India company, what delectable spice have you decided to ship across the stars, and it's like... 22 trillion dollars of b2b saas