Slack

The daily Slack happiness ping for managing people

As a 25-year-old CEO managing 20-plus people, Shaan had an engineer build a tool that pings each employee in Slack at the end of the workday asking for a 1-10 happiness score plus an optional note, giving him a dashboard to spot problems he'd never otherwise see.

“Can you just set up a thing so that at the end of every workday, so at 4:30 PM or whatever, it just pings everybody individually in Slack and it just says, 'Hey Sean, how you feeling today? 1 to 10.'”

Steal thisPing each report a 1-10 mood score daily with an optional 'why' note, and learn each person's normal range before reacting to a number.

Billboarding: your customers wear your logo for free

Julian defines 'billboarding,' a subtype of product-led growth anyone can use even without software. The OG examples are the Hotmail email signature and 'Sent from my iPhone'; every customer action quietly broadcasts your brand to others and keeps you top of mind for free.

“And billboarding is a subtype of product-led growth that is my favorite because anyone can do it. You don't have to be a software company. And I'll give you the OG example of billboarding. If I sign up for Hotmail and I send an email, and you know where I'm going with this, which is there's that Hotmail signature in the email, right? Or if I send with my iPhone, there's that sent from iPhone in the email signature, right?”

Steal thisEmbed your logo or a referral line into the artifact customers naturally share, so every use becomes a free impression.

Every big platform with an app store breeds winners

Shaan's broader thesis: any platform that reaches critical mass and opens an app store will spawn winners. Beyond Apple and Google, he points to HubSpot, Salesforce, and Slack as under-discussed platforms where frictionless, revenue-generating products can be built.

“Like, once these platforms reach a critical mass, somebody's going to build something that's frictionless on top of it, that is able to generate revenue. So I think there's, there's money to be made in the unconventional app platforms that you don't really think about first.”

Steal thisBuild on an under-served platform app store (HubSpot, Salesforce, Slack) before it's crowded.

San Quentin's coding program with a near-zero recidivism rate

Sam recounts visiting The Last Mile at San Quentin, founded by investor Chris Redlitz, which teaches inmates web skills (WordPress, front-end) so they can land jobs - some at companies like Slack - and over a decade had essentially zero recidivism among graduates.

“he was a god there because everyone knows if you get into his program, they have a 0% or they had a zero recidivism rate, meaning everyone over the last 10 years who went through their program, not one of them went back to prison.”

Once you see a '12' you can't unsee it: spotting and riding new-money patterns

Shaan argues that once you witness someone make money a new way (SPVs, ICOs, SPACs, new platforms like the App Store or Slack), you recognize the pattern and can jump in aggressively to become a first mover before the window closes.

“When you see the SPV thing, then you know that when the SPAC thing starts, you're like, oh, I see the pattern. This is kind of like that. Or when you see the ICO thing, you're like, oh, this is kind of like that. If you decide to jump in aggressively, you can rise to be like the top 1% early on.”

Steal thisWhen a new money-making vehicle or platform appears, recognize it as a repeat of a past pattern and move aggressively early to capture the first-mover window.

The Switchlog: timestamp every task switch in Slack to see where time went

Rahul Vohra's time-tracking system: every time he starts, ends, or switches a task he types 'ts:' plus the task name into a dedicated Slack channel, so he can later analyze exactly where his time actually went, unlike a calendar that only records intent.

“Every time I start a task, end a task, or switch a task, I simply go over to Slack, go to a channel I have specifically for this purpose, type in "ts:" and then the name of the task that I am switching to.. And this turns out to be remarkably effective, because then I can go back afterwards and analyze exactly where my time went. Your calendar, in theory, does this for you. But your calendar, at best, says what you wanted to do. And for most founders, it doesn't record what actually happened. The Switchlog does.”

Steal thisLog every task switch with a short tag into one Slack channel, then review weekly to see where your time truly went.

Semil Shah's breakout-company-of-the-year track record

Investor Semil Shah picks one breakout company each year. His list: Stripe (2012), Snapchat (2013), Slack (2014), Coinbase (2017), Airtable (2018), Superhuman (2019), and Hopin (2020) — a near-perfect hit rate of generational companies.

“So 2012, he picked Stripe. 2013, he picked Snapchat. 2014, he picked Slack. Um, didn't do 2015, didn't do 2016. 2017, he did Coinbase. Um, 2018, Airtable. 2019 was Superhuman. And for 2020, he picked Hoppin.”

Steal thisTrack who the best investors publicly call as breakout each year, and study what those companies have in common.

Forwarded-email sales tactic closed $500K in 2 days

Shaan says copying Brex's 'private forwarded email' sales technique let his team close about $500,000 for their investment fund in just two days.

“And we used this tactic to close about $500,000 for our fund in 2 days. We used it for fundraising, but you can pretty much use it for any sales process that happens over email.”

Find your retention 'magic moment' and force every new user to hit it

Facebook found that friending 10 people in 7 days predicted ~85% retention. The playbook: identify the single action that predicts a retained user, then re-engineer onboarding so every new user is pushed past that threshold fast. Slack's version was 1,000 messages sent.

“And I was like, well, at Facebook, like, I think if I remember correctly, it's like if you get 10 friends in 7 days or something, right? If you like friend 10 people, then like there's like an 85% chance, whatever the number is.”

Steal thisFind the single action that predicts retention, then re-engineer onboarding so new users can't avoid doing it fast.

Neil Patel's model: sell software, make the money on services

Sam explains Neil Patel's SEO consultancy playbook drawn from reading Slack's S-1: most revenue concentrated in a few hundred big companies, and maintenance/service margins beat the software itself. Patel keeps software on the backend but makes money on the service layer.

“his insight was he read Slack's S-1. So that's the document that they, that they publish when they go public. And his whole shtick was, he goes, man, Slack's S-1, the majority of revenue, it came from bigger companies. So the majority of revenue came from like 600 companies. That were huge and also the margins on maintenance and service revenue were significantly larger than the actual software.”

Steal thisSell cheap or commodity software, then layer high-margin service and maintenance fees on top.

We don't sell saddles here: sell the lifestyle, not the product

Shaan summarizes Stewart Butterfield's pre-Slack memo. A saddle company shouldn't sell saddles to existing riders; it should sell the joy of horseback riding so more people want to ride and then need a saddle. Lululemon used the same move by spreading the yoga lifestyle rather than pitching $100 pants.

“the reason he says we don't sell saddles here even though we're a saddle company— is that what we need to do is sell the joy of horseback riding. If we can make people want a horseback ride, we can tell them about how awesome it is to ride horses, how it's fun, how it's great exercise, how it feels great to have the wind blowing in your hair, then they'll want to do it. And when they do it, they'll be like, oh shit, I need a saddle.”

Steal thisIf your category is small, grow the category by selling the lifestyle, then sell your product to the newcomers you created.

Bottoms-up is sexy, but whales pay for billion-dollar companies

Kukoff pushes back on the bottoms-up adoption trend, pointing to public S-1s from Zoom, PagerDuty and Slack where revenue is wildly concentrated, in some cases around 5 customers driving roughly 30% of revenue. Bottoms-up works early, but big whales are needed for a billion-dollar outcome.

“Look at Zoom, which we're in. Look at PagerDuty. Look at Slack. And look at where their revenue comes from. I think it's like Slack, like 5 of their— or maybe it's another one, but like in many cases, 5 of their customers have like 30% of their revenue. It's super, super concentrated in just a few huge customers. And so the bottoms-up motion can— it actually can work in early days and it works for a little bit, but when you get big enough that you have a billion-dollar outcome, you need big whales to actually pay for the whole company.”

Direct listing = liquidity without raising capital

Shaan explains why Slack and Spotify chose direct listings over IPOs: a direct listing gives a company public liquidity without selling new shares to raise capital, and it's faster and cheaper than a traditional bank-underwritten IPO.

“So it's what a direct listing is, is it's the liquidity of being public without raising capital. So if you go public in an IPO, it's your initial public offering, you're selling shares in order to raise money.”

Selling to schools: enterprise sales cycle without the enterprise price tag

Sam shares the Mystery Science founders' warning about edtech: schools force you through a slow, bureaucratic enterprise sales cycle but won't pay enterprise prices. The mitigation is designing for teacher-led, bottom-up adoption (like Slack) rather than top-down CIO/district decisions.

“It's an enterprise sales cycle without the enterprise price tag. So you got to go through the slow bureaucracy, but you don't get to charge $100 grand or a million dollars a year.”

Pivoting was the highest-stress point — but Slack, Twitter, Instagram all pivoted

Iman calls the pivot to Incredible Health the highest-stress moment of her entrepreneurial journey, but argues pivoting should be acceptable since Slack, Twitter, Twitch, and Instagram were all pivots — you just have to be bold and take the leap.

“This was the highest stress point I've had in my entire entrepreneurial journey. Wow. Pivoting is hard, but the thing is, it should be, should be acceptable. A lot of massive companies today were pivots. Slack, Twitter, Twitch, Twitch, many, many, right? And so Instagram, Instagram, you just have to be bold. Like many things in entrepreneurship, you just have to be brave.”