Chad Jardine 🧘‍♂️

@adam__xyz And get big time hoodwinked by survivorship bias.

we never hear from losers. they never show up on podcasts. they don't get the hero treatment from Colossus or the New Yorker. thoughtbois don't write threads about their miraculous journey. who do I mean?the founder who couldn't find PMF and now works in mid-management sales at some Stagnant Series B. the junior VC who was let go after a year at a top-tier fund, and now coaches tennis in Hawaii and is a delightful hang. the CTO who had a toxic fallout with the founding team and never really got over it. i wish we made media about the people who didn't win. their stories have a different texture; their orientation to capitalism and tech isn't always so clear. when we just put the winners up on the pedestal, we lose sight of the beauty below.

@sarahdavis @austin_rief True em dashes were the province of we who loved English. And we're not happy that AI has stripped this secret sign of superiority, this badge of Cmd-Shift-Hyphen fluency from us. Not. One. Bit.

@austin_rief Were we all using em dashes or were we all using dashes? Cause I never really saw true em dashes used in mass before AI. Dashes, yes. The difference between this — and this - . The dash and double dash are still gtg.

You should never use an em dash in your writing anymore. You will 100% be accused of using AI, especially if its on social.

every founder has two companies: the one they’re building, and the one that's in their head

@jefielding So true. Any < Series B investor has to understand: 1. This is about uncertainty, not risk (no, you can't pick them—founder pattern-matching isn't it). 2. You can pick losers, but not winners. ALL your potential investments contain flaws that can metastasize and kill the co.

You will never hear a VC say to a limited partner…’WE are just excellent pickers’. But most VCs believe this to be true. Strange industry when you can’t pitch your true strength.

yc for shutting startups down do it as a batch so you’re not lonely and depressed meet your next cofounders share post mortems and lessons learned bootstrap your next startup with second time founders using the severance you pay yourselves

Amazon is currently selling the Dark Edition of my book with a 27% discount, which makes it less expensive than the regular paperback edition. If you've always wanted to read a dark mode textbook, it's the perfect moment to do that.

@jaltma Agree on “return-free risk” but the company comment is B.S. This is a symptom of viewing the universe as only low-hanging fruit. Most of the interesting opportunities aren’t even there.

This was an exceptionally cogent articulation from Roelof about the state of venture capital. "There's a lot more talent than really interesting companies to be built. And I think we're spreading a lot of that talent thin right now." "Venture is a return-free risk."

@TakoTreba Amen. Selling products > selling stock.

I’ve been on both sides. VC-funded. And now bootstrapped. Here’s what I learned: In the beginning, you don’t need to chase investors. You need to chase customers. You don’t validate an idea with a pitch deck. You validate it with MRR. Because MRR tells you one thing no investor ever will, whether people actually care. Once you have that, you can raise money, stay bootstrapped, or build a spaceship, doesn’t matter. You’ll have proof that it works. That’s what is happening with Chatbase. No funding. No safety net. Just product, community, and consistency. And now it’s quietly taking a piece of the market.

@jasonlk 🫶Vesting is a terrible way to do this. You're going to buy my stock, but then tell me how to get my own stock back? You don't sell 40% of your company to investors to gain adult supervision.

If all founders started off with 10-year vesting, I suspect this would reduce and minimize like 50% of co-founder issues * It forces you to have the tough conversation up front * It protects the ones that stay from the ones that quit * It better aligns expectations

@asmartbear Day 1 is even better.

The payback period for customer acquisition should be 4-6 months for a bootstrapped company. Funded companies might accept 12-24 months, but your cash flow won't allow that luxury. Annuals help, but this article explains why this limit makes sense: longform.asmartbear.com/bootstrapped-c…

@hthieblot I’m not opposed to selling ahead for urgency. Just make sure you can deliver!

1. Build the product 2. Sell/market the product Resist everything else, it doesn't move the needle.

Chart crimes are real.

@edsuh Amen. At least for the last 20 years that I’ve been paying attention, complaints of scant deals are completely bogus.

The same 10 VCs every week: “this is the frothiest market I’ve ever seen. Every round is preempted at insane valuations. I don’t know how anyone will make money in this environment. Nobody can compete with the big firms” The reality: they’re only being exposed to the most consensus deals. Like an iceberg, beneath the surface there are many reasonably valued, non competitive, non consensus investment opportunities in quality businesses with quality founders (albeit not from of central casting). You just have to know where to look, and have the fortitude to step out of the consensus bubble.

major life update: we are shutting down @useplumb after several years of hustling on agentic workflow automation, we have decided to hang it up what we got right: ✅ Agentic Workflows > Agents - determinism and the ability to debug still matter guys (even Open AI gets this with agent builder) ✅UX/UI - the hand feel of building in Plumb is what I’m going to miss the most, nothing else even comes close ✅Structured Output - exquisite JSON schema out of every step unlocks so many cool possibilities, agentic branching among them ✅HITL - being able to interact with agents/flows via SMS, email, and Slack is so important, and nodes like “collect input” (that inject responses downstream) are 🤌 what we got wrong: ❌ We invented workflow subscription (and a bunch of tech like MetaJSONSchema) BUT nobody asked us to, and nobody cared ❌ As a result of that decision ^ we couldn’t easily utilize MCP, iPaaS, webhooks, API triggers, etc. and that severely limited what you could build on Plumb ❌ We didn’t pick a vertical, function, or high value set of tasks to solve on day one - instead we spent way too long playing with “nice to have” flows that were technically interesting but not operationally valuable If we did it all again, we’d do it differently. More learnings in a future post. For now, we want to thank our investors, including @BenjLerer @asymmetric_vc @greenfield_cap @humanvc @galeforceVC @theready @scottbelsky @ericries and many many more - you won’t find a more supportive bunch out there. If you're raising, ask them. 🚨 Finally, we’re officially looking for a home for this team, so if you want to snap up an elite squad of applied AI nerds… my DMs are open Please RT this for reach bc this team hangs the moon 👉 @chaseadams @keyavadgama @petekp @tihalstead @abtweedy @sarashpit And now for what's next...

@lizwessel So right on. If you haven’t done it before it’s a wake up call to realize that the C-suite, especially the founder… has no peers in the company. Nobody who really gets the grind of what you’re responsible for.

As a founder, every 1-2 months Id meet up w 2 other founders who I trusted completely. The 3 of us would get dinner & vent, tell war stories + give each other advice. Complete transparency. It was the best + core to my staying sane. I recommend all founders find their equivalent.

@asmartbear VCs love to tell founders when the company is a bad fit for the VC model. They don’t like admitting it as much when the shoe is on the other foot.

The common wisdom in Silicon Valley is that if it’s not unique, it’s not worth doing. This is logical because: • The world doesn't need another copy of everything. AI further proves that. • You have no basis for competitive advantage, neither temporary nor permanent. But what that perspective leaves out is that “competitive advantage” or “shareholder value” or even “getting rich” isn’t always the goal of entrepreneurship. It’s interesting when it is, but often it isn’t. Indeed, 𝘶𝘴𝘶𝘢𝘭𝘭𝘺 it isn’t. Rather, the goal for small businesses -- software or restaurants or freelancers or car washes or landscapers or cleaners -- is ownership, pride, autonomy, fulfillment. Sure more money is better, and certainly low profits or shrinking businesses are bad. But they’re bad because the personal goal is slipping away, not because of “shareholder value.” This is why it makes sense for small business owners to work 11 hours a day for the same take-home money as the job they left. This is why it makes sense to make “yet another” design firm or restaurant or car wash or productivity app or time-tracking app or AI-whatever. Not because it results in a big company, but because it results in fulfilled people doing work they are proud of, and customers thrilled to receive that sort of experience. We should celebrate that too.

@MartinGTobias TAM is a vanity metric. Nobody actually understands with any precision a. How big it is b. How it might change as the product evolves or c. How their best guesses are impacted by macro conditions. Can we just ask founders their plan when they get back pressure?

Founder reminder: Be honest on your initial TAM. On a call today, pre-seed founder admitted that only 20% of his TAM was addressable by his product, contradicting the deck numbers. He instantly lost credibility with me. Please do not do this.

@PeterJ_Walker How did this anomaly become a trend? This type of BS will garner same contempt as 2+X liquidation preferences from 2010. It’s the definition of vulture capital. Show me any 2X founder who agrees vest their equity. Founders, you’re selling stock not indenturing yourself.

6 year vesting should be the new normal. Maybe 8 years? (but founders also need to get credit for any capital they themselves invest in the company. Probably preferred equity although this is tricky at very early stages)

@christianbusch @villi 1% is pretty close to the actual likelihood of any U.S. company getting funded. 😁

@villi Nice story but the likelihood of that happening is something like 1%. Good for him if he pulled it off but in 99% of cases USA VCS are simply not interested in International companies unless they already have significant traction.

A founder this week was telling me he had been raising in Europe for a month and said he had numerous conversations with a few VCs, all of which were slow and came back with $8-10M pre-money. He said "screw that", bought a ticket to SF, and raised at $20M in a week.

Nailed it. #pricing is a secret weapon many founders don’t invest in, yet it’s cheap to learn and the ROI is massive.