Idea
Dharmesh offers Shaan a $5M check on-air to build a crypto LinkedIn
HubSpot co-founder Dharmesh Shah pitches a blockchain-based professional network to replace LinkedIn and offers to fund Shaan with up to $5 million as a seed round, plus a 7-figure domain name he already owns.
“Here's what I even have a 7-figure domain name picked out for you. I will write the $5 million check for you to go do it as far as a seed round, uh, or up to $5 million if you want to let other people in.”
Steal thisBuild a professional network on the blockchain where every member has a coin price, so endorsements cost real money and carry weighted authority.
Idea
A LinkedIn where you set a price to be spammed and get paid for attention
Shaan builds out the crypto-LinkedIn idea: because every person has a coin value, career hierarchy is baked into the network, and you can charge outsiders to reach you rather than letting LinkedIn capture all the InMail revenue.
“Now, if I go pay LinkedIn I can send you spam in mail. You do not receive any of the revenue from me paying LinkedIn for the right to spam you. In this case, I could say, hey, if you want to spam me, if you want me to read your thing and you want me to respond to it, here's my prices. So it becomes revenue ge”
Steal thisLet users price their own inbox so cold outreach pays the recipient, not the platform.
Framework
The orthogonal attack: beat an incumbent from a different angle
Shaan introduces 'orthogonal' as the way to beat LinkedIn — not by building a better LinkedIn, but by attacking from a different angle, like AngelList pulling startup jobs off LinkedIn or Dribbble/Behance/GitHub owning designers and developers.
“here's a company I invested in that I think has a cool chance of beating LinkedIn. I want to describe their strategy, but I don't want to use the Silicon Valley jargon. You know this word orthogonal? No. Have you heard people say this? It's like, yeah, you have to take an orthogonal angle, or it's an orthogonal—”
Steal thisDon't out-feature an incumbent; attack the job-to-be-done from an orthogonal angle they can't copy.
Idea
Decentralized LinkedIn: niche job boards living inside communities
Shaan's thesis for Pallet: nobody will rebuild LinkedIn's 500M-person network, so instead create a distributed version — thousands of niche job boards (e.g. a community of Angular developers) each living in its own community. Employers would rather post to a targeted Angular job board than to LinkedIn.
“So, so I think this is a distributed version of LinkedIn. It's basically saying nobody, nobody's going to build a 500 million person social network for professionals, professionals again, that's LinkedIn's advantage. But what if instead of 500 million people on one network, you had 500, you know, you have 50,000 people on whatever, 100 networks or whatever it is, do the math.”
Steal thisUnbundle a giant network into many niche community job boards employers will pay a premium to reach.
Story
Sam wanted WeWork or LinkedIn to buy The Hustle, then HubSpot cold-emailed
Sam recounts rejecting private-equity and legacy-media suitors because they felt like a culture mismatch, and how he'd long fantasized about a tech company (WeWork, LinkedIn, Salesforce) buying The Hustle. HubSpot reached out unsolicited last fall and the plan clicked.
“And so in my head, I always thought, you know who should buy us? WeWork. I thought WeWork should buy us, like when they— before we found out that they weren't that great. And then I thought, um, LinkedIn should buy us. And then I started thinking, oh, what about like a Salesforce or like companies like this? And then last fall, HubSpot reached out to me and I was like, oh my God, this is finally happening.”
Story
Rapportive sold to LinkedIn making only 15 cents of total revenue
Rahul Vohra reflects that selling Rapportive 20 months in was an efficient outcome, but admits the business was brittle: across its entire history it had figured out how to make only 15 cents of revenue.
“You have to remember that I sold the company only 20 months into its existence for a sum that even to this day remains undisclosed. Assuming it was a good amount of money, then it was a very efficient outcome for the amount of time we put in for what was actually a very brittle business. We'd only figured out how to make 15 cents of revenue in the entire history of the company.”
Framework
Reid Hoffman's GUR: Growth, then Usage, then Revenue
In his 2003 LinkedIn interview, Reid Hoffman explained how the company would win in three sequenced phases: first grow into the largest network using viral mechanics, then drive usage by making members better professionals daily, then layer in revenue by selling engagement and search to HR, sales, and recruiters.
“He called it growth, then usage, then revenue, which I then called GIR. He said, "First, we're going to grow and become the largest network. It's going to have utility for a few people. Then for most people, they'll just be latently there, but we're going to use all the viral mechanics to actually capture the network. Then we're going to focus on usage." which is we're going to figure out how to get you using your network to make you a better professional more every day. Then we're going to focus on revenue”
Steal thisSequence a network product: win growth first, then engineer usage, then monetize, in that order.
Framework
The audience-building playbook: answer questions, then climb the authority ladder
Altucher's playbook for building an audience from zero: answer every question on Quora, LinkedIn and Facebook groups to establish expertise, then graduate to higher-barrier outlets like Forbes and TechCrunch for authority, then launch a free newsletter, and only later a paid subscription.
“I would go on Quora and just answer every question I could. I would participate on LinkedIn groups, again, answering every question I could. I would go on groups like the Trends Group or other Facebook groups, and you know, a lot of people ask questions.”
Steal thisStart by answering every question in public forums to build expertise, then climb to authority outlets before monetizing.
Idea
Consumer Reports for workplaces: a curated, editorial job board
Sam pitches a curated job board (he ran a beta called Sam's Jobs / samsjobs.co) where a trusted editorial group profiles companies and roles honestly, sourcing truth beyond LinkedIn/Glassdoor's biased company-vs-disgruntled-employee framing, telling seekers exactly which culture fits them.
“why don't you have an editorial group of people give their opinions and what they can say is if you're young and hungry and want to work yourself to death but have huge opportunity, this place is an interesting.”
Steal thisBuild an editorial, opinionated job board that interviews real employees and matches seekers to culture (family-builder vs alpha hustle), charging the seeker so the truth stays unbiased.
Idea
Org-chart-as-a-service: the wiki that could become the next LinkedIn
Daniel Gross pitches a crowdsourced org-chart product for sales teams trying to map who's who at target companies; solve the employee incentive to update their profile and you may build the next big social network.
“It's industry-specific and it's like a weird Sneakernet-style thing. And like, I think, I think someone could really knock it out of the park here and build something that over time maybe even becomes the next LinkedIn. Just org chart as a service.”
Steal thisBuild a UGC org-chart wiki; crack the incentive for employees to self-update and you have a LinkedIn-scale network.
Story
LinkedIn's 'next play' culture funded his startup
LinkedIn told new sales hires that in two years none of them would be in the same role and to find a better replacement when they leave. Galanis left on his exact 2-year anniversary; his goodbye 'next play' letter reached sales boss Mike Gamson, who three months later led Cameo's first angel round.
“When I wrote my goodbye letter, they called it the next play letter at LinkedIn, I told that story. That got to Gamson. He saw it, he thanked me for the kind words, and then 3 months later he ended up calling me out of nowhere and leading our first angel round in the company.”
Billy
The LinkedIn ad targeting hack: minimum audience of 7 people
Jack reverse-engineered a new LinkedIn ad system by repeatedly shrinking the audience until it accepted an ad targeting just 7 people, then padded it with 6 irrelevant strangers so the one person he wanted would see it.
“And so I kept on doing that one after another and then basically found found out that it would let me submit an ad when I had an advertisement targeting only 7 people. I don't know why 7 was the number. Again, probably someone pushed the wrong— perhaps they meant it's 7,000 people and they only pressed 7 by mistake.”
Steal thisHunt for exploits on newly launched ad platforms before they harden — the rules aren't enforced yet.
Story
The bait-and-switch ad: approve a clean ad, then swap the creative
Because new LinkedIn ads were manually reviewed but editable after approval, Jack submitted an innocent ad, then swapped it for one showing the AngelPad founder's face urging connections to pass along an 'urgent message' linking to his pitch video.
“So basically I would create like an innocent looking ad, um, just targeting whatever, and then I'd change it after they approved it, um, because otherwise they wouldn't have approved it. So basically the and it said, it had a picture of the founder of AngelPad's face and it said, "Do you know Tomasz? We've got an urgent message we need to get to him. Click here."”
Billy
The LinkedIn ad targeted at a single person
Unable to get into AngelPad among 2,000 applicants for one spot, Jack discovered a loophole in LinkedIn's new ad system letting him target an ad down to essentially one specific person to reach the accelerator's founder.
“I'd found this kind of loophole hack on LinkedIn where I was able to create an advertisement and target it down to a specific person. So LinkedIn has its kind of own ad system like Google AdWords, but they— I think it was a software engineer, like, I think some software engineer had done this as a bug that I found I could set the targeting so specifically, say, like, job title AngelPad, job title CEO, that there's kind of only one person who that ad would show it to, you know.”
Framework
Nascent platforms hold the undiscovered hacks
Jack's thesis: the best exploitable opportunities live on brand-new platforms. Mature systems like Google AdWords have 15-20 years of optimization and armies of engineers, leaving no easy hacks, while a just-launched ad system is wide open.
“I think this is where the most opportunities are, is when it's like a nascent platform. Um, if you're trying to find hacks on Google AdWords, there's probably none left because, you know, people have like 15, 20 years experience with Google words, you know, and they've got loads of engineers working on it. LinkedIn, this ad system was new. They just launched it. And so I was just testing it out.”
Steal thisHunt for exploits on newly launched platforms, not mature ones where every edge is already taken.
Tactic
Describe the exact person you need and the network delivers them
Scudamore wrote a few-paragraph 'painted picture' describing his ideal leader, posted it to LinkedIn, and three unrelated people independently replied with the same name - Eric Church - who became his 'two-in-the-box' partner; revenue then quadrupled.
“I was so clear that I had 3 people unrelated in different parts of the country reach out and said, the person you describe is Eric Church. They didn't refer 5 names. Names of execs that they thought would fit the bill. These people said, you're describing Eric Church.”
Steal thisWrite a vivid description of the exact hire you want and broadcast it - specificity acts as a magnet for the right referral.