-
Brief the Analysts: You’re Aiming at the Pins Instead of the Arrows
The free channel every founder walks past on the way to buying more ads.
A textbook strike touches four pins. Four. The ball hits the 1, the 3, the 5 and the 9, and the other six go down because pins hit pins. Founders keep trying to hit all ten with the ball. That is not how the deck works, and it is not how AI-assisted buying works either. The assistant your buyer is talking to does not take your word for anything. It goes looking for someone else to say it first.
- Your website is the 5-pin, not the headpin. AirOps found roughly 85% of brand mentions live on third-party pages rather than your own domain, and Otterly’s State of AI Search puts the figure at 95% of all AI citations. One study of 233 ChatGPT software recommendations found the vendor’s own site cited just 11.6% of the time. You are being talked about, not read.
- Aim at the arrows. The lane is 60 feet long; the arrows sit about 15 feet out. Nobody decent stares at the pins, because you cannot control something 60 feet away, you can only control what the ball does at 15. Analysts and research sites are the arrows. Hit those and the pins take care of themselves.
- The whole invoice is one hour. Gartner vendor briefings run 45 minutes with one or two analysts, routed to a specialist within a business day and typically scheduled two to four weeks out. Forrester allots 30 or 60. Neither requires you to be a paying client, and most firms will take one or two briefings a year from a non-client. An hour. A deck. A calendar hole. That’s it.
- Do not throw it harder. Ball speed never fixed a bad line, and volume never fixed a bad pitch. Analysts have sat through hundreds of these. Give them the five-minute version: who you are, what problem you kill, who switched to you and what they left behind. Do not open with a demo, and never quote a rival firm’s market forecast in the deck.
- You are not leaving a split, you are not bowling. Quoleady’s 2026 research found 100% of tools that ChatGPT named in B2B answers had Capterra reviews and 99% had G2 reviews. Being absent from the sources isn’t a bad shot, it’s showing up without a ball. Meanwhile only about 30% of brands stay visible in back-to-back responses to the same question, so one appearance is not a position.
- Carry compounds, and so does staleness. Pin action is the whole game: an analyst mentions you, the trade press repeats it, the crawlers eat the trade press, and the model repeats it back to your buyer. But roughly 65% of AI crawl activity targets content from the past year, and pages refreshed within two months earn about 28% more citations. Coverage dries out like lane oil. Re-brief.
- Read your own lane. One Q2 2026 sample had the big aggregators at only 8.6% of citations; another had G2 as ChatGPT’s fourth most-cited source. Both are probably right for their category and wrong for yours. House shot or Sport pattern, you find out by throwing the ball and watching, not by trusting a stranger’s chart. Including mine.
The score. A 300 is twelve strikes, but it’s really one shot you trusted twelve times. The briefing is that shot: repeatable, free, and boring in the way profitable things usually are. Your competitor booked theirs in March.
-
When Rivals Raise Big: A Seven-Day Panic Playbook
What actually changes the week a competitor announces a monster round, what doesn’t, and why a funding headline is a receipt – not a scoreboard.
- Monday: Read it like an accountant, not a fan. A round is not revenue. Nobody earned $80 million; somebody sold a slice of their company and promised to grow into a number a stranger picked. The headline is a liability with a party attached. Paul Graham’s old test – “default alive or default dead” – still decides everything, and cash moves a company between those columns without improving the product by one pixel.
- Tuesday: Track the burn multiple, not the valuation. David Sacks’ metric – net burn divided by net new ARR – is the honest scoreboard. Under 1x is elite; 2x to 3x is “suspect”; north of 3x is a countdown clock with a logo on it. A monster round inflates the numerator and promises nothing about the denominator.
- Wednesday: Visit the graveyard. It is beautifully funded. Quibi raised $1.75 billion and lasted about six months. Jawbone burned roughly $930 million and liquidated while Fitbit just kept shipping. Fast raised $120 million on reportedly around $600,000 of annual revenue. Zume: $445 million, pizza robots, gone. Katerra: about $2 billion, bankrupt. CB Insights’ startup post-mortems put “ran out of cash” at 38% and “no market need” at 35% – and the first is usually just the second, wearing a nicer suit.
- Thursday: Call five customers – not to reassure them. They didn’t notice. Gartner found B2B buyers spend only about 17% of the purchase journey with all potential suppliers combined, and roughly 5% with any single vendor’s reps. Your buyer’s awareness of anyone’s Series C rounds to zero. They care about price, uptime, and whether support answers on Monday. Ask what would make them leave, then go fix that instead of refreshing TechCrunch.
- Friday: Price in the noise, because the money does buy three real things. Recruiters, ad inventory, and enterprise logos bought at a discount. Expect your CAC to drift up and expect two or three offers to land in your best engineer’s inbox by month’s end. Counter with ownership and meaning, not a salary-matching war you’ll lose. Reichheld’s Bain research pegs a 5% retention lift at 25–95% more profit – keeping people and accounts is dramatically cheaper than outbidding a balance sheet.
- What did not change, at all: your gross margin, your churn, your sales cycle, your renewal rate, your product roadmap. Not one of those numbers moved because a term sheet was signed in another building. Peter Thiel’s “competition is for losers” isn’t swagger – it’s a warning that obsession is the real tax. Roughly three in four venture-backed companies never return investor capital; a big round buys a longer at-bat, not a hit.
- The honest counterweight, and the receipts. Capital isn’t nothing. Marc Andreessen’s rule – raise when you can, not when you need to – exists because runway is optionality, and a funded rival can absorb losses through a price war longer than you can. So: if you sell an undifferentiated commodity in a land-grab market, take it seriously. Otherwise, note that Mailchimp took zero venture dollars and sold to Intuit for $12 billion, Atlassian bootstrapped for eight years before touching outside money, and Zoom reached its IPO on roughly $160 million while noisier, better-capitalized rivals faded.
- Send the one-page memo by Friday at 4pm. Three bullets: what we learned, what we’re changing (honest answer: probably nothing), what we’re doing instead. Leadership silence never stays empty – your team fills it with fan fiction, and fan fiction is how good engineers talk themselves into taking the recruiter’s call.
Funding news is a lagging indicator of a conversation that ended weeks ago between two parties, neither of whom is your customer. Win the Monday. Ship the thing.
-
Translate the Jargon
Why the person who explains it out-earns the person who knows it
Every industry has a word it says fifty times a day and has never once defined out loud. Ours is “social inflation.” Here is how to hand it to somebody who does not sell insurance for a living, and why that skill is worth more than being the smartest person in the room.
1. Nobody is confused. They are uncontexted.
When an American says soccer is boring, he is not stupid. He is watching without a frame. Tell him offside is just cherry-picking, that you cannot camp under the hoop waiting for the long pass, and he is arguing about it by halftime. One sentence. That is the entire job.
2. The curse of knowledge, measured.
In 1990, a Stanford researcher had people tap out famous songs on a tabletop. The tappers predicted listeners would name the tune about 50% of the time. Across 120 songs, listeners got 3 right. That is 2.5%. You hear the melody. Everyone else hears knocking.
3. Social inflation, in one breath.
The textbook version is “liability claim costs rising faster than economic inflation.” Nobody has ever repeated that sentence at a dinner table. The human version: your policy was priced for a 2010 jury and you are getting a 2026 jury. Same wreck, same injuries, different number.
4. Then hit them with the number.
The median nuclear verdict (anything over $10 million) ran about $21 million across 2013-2022, hit $44 million in 2023, and reached $51 million in 2024. That year brought 135 nuclear verdicts against corporate defendants, up 52%, totaling $31.3 billion, a 116% jump in twelve months. Verdicts above $100 million climbed 81.5%, to 49. Five of them cleared a billion dollars.
5. Stoppage time is reserve development.
Nothing enrages a new soccer fan like the fourth official holding up a board reading “4 minutes” and then playing six. The board is a minimum, not a promise. That is reserving. We post a number, the game keeps going, and the number moves; recent adverse casualty development has run around $15.8 billion. Every American who has ever screamed at a referee already understands our reserving problem.
6. Explain the engine, not the trivia.
Americans did not fall for the Premier League because someone explained the offside trap. They fell for it when someone said: imagine the three worst NFL teams get thrown out of the league. Relegation turned a meaningless February match into appointment television. So skip the actuarial triangles and explain the engine: third-party litigation funding, a business estimated near $18 billion worldwide, where investors buy a slice of a lawsuit the way they would buy a slice of a startup. That is who paid for the billboard.
7. Simple is not stupid, and that cuts both ways.
Study after study finds that denser, less readable academic abstracts collect more citations from other academics. Of course they do. They are written for people paid to decode them. You are not. Roughly 54% of American adults read below a sixth-grade level, and your smart, busy buyer is reading your email at 6:40 a.m. on a phone in a parking lot. He will forgive simple. He will never forgive confusing.
The expert gets deposed. The translator gets quoted.
Reporters, buyers, brokers and juries all repeat the person they actually understood. Say it in a sentence someone could hand to their spouse, and you have done what no white paper or acronym will ever do for you: made a stranger care.
-
Teach, Don’t Speak: Why your next conference slot should be a workshop
Why your next conference slot should be a workshop – and what NFL coaching staffs figured out decades ago
A talk ends in applause. A workshop ends in a deliverable. Only one of those changes the phone call you get on Tuesday.
1. A speech is the broadcast. A workshop is practice.
The Wall Street Journal once stopwatched an NFL game: 3 hours and 12 minutes of programming wrapped around roughly 11 minutes of live football. Nobody has ever won during the other three hours. Bill Walsh scripted his first 15 to 25 plays so that by Sunday they felt like a rerun of Wednesday. Your keynote is the broadcast. Be the practice.
2. The research is not a close call.
A 2014 PNAS meta-analysis pooled 225 studies. Failure rate under traditional lecture: 33.8%. Under active learning: 21.8%. Exam scores rose about 6%, and lecture students were roughly 1.5 times likelier to fail. (Note whose numbers those are. The “we remember 90% of what we do” pyramid on LinkedIn has never been traced to an actual study.)
3. A good workshop feels worse in the room. Run it anyway.
Harvard physicists tested this in 2019: students in active classrooms scored measurably higher and rated their own learning lower. Polish produces the feeling of learning; struggle produces the fact of it. Highlight reels feel fantastic. Walk-throughs feel like chores. December decides which one mattered.
4. Scarcity is what forces you to actually teach.
The CBA allows NFL teams just 14 padded practices all season, 11 of them in the first 11 weeks. Coaches who once ran three-hour hitting sessions now install concepts in walk-throughs and meeting rooms – and the constraint made them better teachers, not worse. Give yourself 45 minutes instead of 60. Cut content, keep reps.
5. Their numbers, not your demo file.
A demo on your clean sample data is a magic trick: impressive, entirely non-transferable. The same method run on their messy Q3 export is a skill they now own. That one swap rewrites the follow-up – instead of “interesting, send the deck,” you get “what do I do about row 14?” Players study their own film, not just the coordinator’s cut-ups.
6. If they can leave empty-handed, you gave a speech with the chairs moved.
Put the deliverable on slide one and work backwards, ruthlessly: one filled-in model, one finished template, one draft they would be annoyed to lose. Everything that doesn’t survive contact with that goal is a story you can tell at dinner instead.
The Bottom Line
Lombardi opened camp holding a football: “Gentlemen, this is a football.” That wasn’t a keynote. That was the first rep. Stop performing your expertise and start handing it over – someone who has already run your method on their own numbers, in front of you, is not an audience member anymore. They’re a user. Users call back.
-
500 fictional venture capitalists at an open bar
This morning I put 500 fictional venture capitalists in a building.
I broke them into 100 rooms, five people each, and had them argue about a client’s funding strategy. Standard stuff – I run persona work like this on most engagements, whether the question is fundraising, positioning, or go-to-market.
Then I added an open bar.
Tipsy VCs, it turns out, are more useful than sober ones. The sober rooms produced the answers you’d expect: raise a priced seed, here’s your comp table, here’s your dilution. The bar rooms started saying things like “You’re running a restaurant and you’ve never asked what the food costs.” Blunter. Less hedged. Occasionally wrong in interesting ways.
To be clear about what this is: I’m not simulating market feedback, and no fictional VC is going to tell me what a real one will do. What this does is widen the range of angles I have to consider before I am on the call. The unhedged version of an objection is easier to prepare for than the polite one.
The client got better funding options and a cleaner business structure out of it. I credit the bar.