Pretty soon after leaving Globality, I wrote some thoughts on the next 10 years. One core bet was around authenticity:
Consumers are going to be awash in generated content. This will serve the purpose of private marketing (classic advertising or astroturfing campaigns) and more malicious state-actor attempts to sway public opinion. As a result, people are going to place a much higher emphasis on trust capital online. The value of real, provable, and authentic relationships are going to increase.
More than two years later, I think this holds up pretty well. Voice cloning and video generations have gotten shockingly good, shockingly quickly. And while we haven't yet seen mass market deepfakes used for nefarious purposes, I do find myself double checking twitter handles and the validation checkmark to make sure people are who I think they are.1
On some level, maybe it doesn't matter if you're arguing with an anon on Twitter. A good argument is a good argument regardless of who makes it. But a bit of authenticity makes it feel like you're not wasting your time debating a bot.
The state of verification is all over the place among the major social networks:
LinkedIn sits in an interesting place with its identity verification because it's so tied to professional identity. Either you - or someone in your network - is going to provide some independently verifiable information. If you're part of the leadership team, you'll also appear on the company's website. There are more datapoints to cross reference than a random account on IG.
Ethos is definitionally missing from conversation when you're unable to assess the legitimacy of the person you're talking to. The biggest knock on LI is they rely too much on ethos: "you should care about me because I'm successful." The content can also get pretty cringe.
I met Will through the larger Stanford network3. When we first met in March of 2024, he was researching government procurement ideas and thinking about posting more on LinkedIn. I gave him some takes on procurement software. On LinkedIn I couldn't even hazard a guess; I thought it was a funny side-quest and wished him well.
A month later we caught up again over a latte. He already had 85,000 followers. A few weeks later he had surged to 100,000.
Watching Will's growth got us thinking more seriously about social selling. Having prospects come to you instead of you coming to them is the dream of most sales organization. But easier said than done. Most enterprise companies are still heavily reliant on outbound sales. It's way easier for you to find companies you want to pursue than for those companies to hear about you.
Alas, our hands might be finally forced. Cold outbound is getting harder by the month. My inbox is littered with more AI generated bullshit than I can ever sift through. Hundreds of startups are coming to market with slightly-smarter cold outreach platforms. You input your list of sales prospects and the tool will crawl their sites and write something "personalized".
Most of this content is just straight bad - but even if they're good, they make you feel like someone didn't even care enough to reach out personally. As LLMs converge to better human speech patterns4, distinguishing between a person or a machine reaching out to you cold will literally be impossible. It's already feeling too fatiguing to try.
Based on my own experience selling enterprise software over the last few years, I'm willing to say that cold email outbound is pretty dead. I imagine the future looks a lot more like warm intros. People don't want to pick up the phone from someone they don't know. But they do - perhaps even do enthusiastically - for people that are in their broader circles.5 It's easier to get into that broader circle online by developing authority.
The sales playbook is shifting toward the pillars of founder brand, referrals, and in-person events.
You've seen consumer companies do this for some time but it's been missing from the small and mid stage B2B companies. The term social selling is starting to define these channels. Most succinctly:
Using social media algorithmic newsfeeds to reach a larger audience, at a lower CAC, than normal channels.
Social selling supports all three. Your content builds the founder brand that makes people want to meet you at conferences. Those conference connections turn into referrals. And the referrals come with built-in trust because they're coming from someone in the prospect's network who already believes in what you're building.
Social selling relies heavily on the persona behind the content. It's certainly possible to bootstrap a successful selling motion as a random BDE on an enterprise sales team, but it's hard. People in your industry are heuristically filtering for clout: they're looking for CEOs or VPs of Sales. So if you're at a bigger company, you're going to need exec buy-in. You need to focus on building up their personal brand as a way of building the company's brand.6
To be interesting online, you either have to position yourself as an expert or position yourself as seeing trends across industries that the industry experts are missing. Becoming an expert is pretty obvious if you can do it. The interdisciplinary play is the fallback if you can't.
Buyers themselves are probably already experts in their field. A bunch of insurance brokers aren't going to turn to a tech founder for insurance advice. That's a tough game to play. It's easier to admit that you won't ever out-insurance the insurance expert. You're the tech person who understands insurance well enough to spot inefficiencies they're blind to. Tech credibility can actually help you there because it's different.
The arbitrage opportunity seems to be in being the person who can bridge worlds.
The north star of growing a social profile is the amount of your impressions: how many people see your content & how many followers you're getting. It's easily trackable and there's a dopamine rush to it. You can cosplay at being famous. But for social selling it doesn't really affect your outcomes. You're trying to influence behavior not fight for likes.
Take Adam Robinson here. He has a healthy following but certainly not the most followers in the business-influencer crowd. But he doesn't need that. He already has significant trust with his audience from building a $20M+ ARR business & creating long-form video content through his weekly podcast.
In both trust comes from depth. A smaller audience that trusts your judgment is far more valuable than a massive audience that chuckles but keeps scrolling. The people who trust you are the ones who will take meetings, make introductions, and eventually buy.
As an aside, we can't seem to crack the trust game on TikTok the same way that we can on YouTube, Instagram, and LinkedIn. I'm sure some people manage to make this work, but the convention of following accounts seem less established there versus other platforms. My guess is because the algorithm is so good people just expect to see good content in their main feed. You don't have to curate the list of people yourself - which also means that you're not guaranteed to see content from the same people multiple times.
The only way for this trust capital to work is for someone to scroll through their feed, notice your avatar, and think "huh, Jeff always has interesting things to say I'm going to give this a read."
A creator, an influencer, and a thought leader walk into a bar. Ouch. Get me out of here. - Old English Proverb
When I first explain social selling to people, they usually think it's just a paid partnership. Companies have been doing this with influencers for as long as social networks have existed. You give them free products7 and they'll post a photo with your product. You get the exposure and perhaps the shine of the influencer. Think Alix Earle posing with a Poppi.
Personally, I think that shine is overblown. People understand how paid partnerships work now. Instagram and TikTok even label them explicitly. We've already built our mental model that influencers don't really care about the product - they just get something out of posing with it.8
Content about a company is far more interesting, and yields far more engagement, when it's the people who are actually running the company talking about it themselves. This is why founder brands have become increasingly powerful. Everyone wants to pick up the phone from the CEO of a startup, especially when they have some fame to go with it.
Founder brand works because it's inherently more authentic than traditional corporate marketing. When a CEO talks about their product, we like it because it's (1) aspirational to have a successful product and (2) often feels pretty genuine. But the way that successful founders (Elon Musk, Sam Altman, etc) leverage social is different from how a fledgling founder with no credibility needs to leverage it to sell a product. Musk can get earned media just by tweeting out a meme because the follower base is so large.9 Smaller founders need to play a different game.
Will optimizes his content more rigorously than most creators I know. I'd heard that Mr. Beast A/B tests every piece of content he publishes, but it turns out creators with smaller audiences do this too. Most people with ~10k followers run similar experiments. Each post is essentially a testable hypothesis. Is this content reaching future clients? And do those people like what you're saying? The best approach to actually succeeding is to treat it with the scientific rigor that you'd apply to a data science problem. Even if it feels like social media is fuzzy, the algorithms behind it are cold and calculating. Treat the creation of your content the same way.
Most people don't actually post regularly. Of all the people in my network from Stanford and SF (~1500), only about 10 are consistent posters. Standing out right now is pretty straightforward as long as you post consistently. There's literally novelty in just showing up.
I imagine this won't last forever. So there's a bit of a land-grab happening to build an audience before the opportunity window closes. But there's some cost to premature diversification.
Content will only help you if you're writing content and delivering authority in the space that you're eventually going to sell into. I find it much more helpful to focus on a vertical here (think: the insurance part of insurtech, the healthcare part of healtech, etc). Startup founders love seeing the content from other founders but they rarely convert into buyers. If you start writing non-sales content about a generic vertical, you have the ability to pivot it into a sales pitch later.
Some fields are more crowded than others. There's a lot of competition in the generic spaces: entrepreneurship fundamentals, writing advice, self-development. I'd stay out of these spaces. It fails the test of writing content that will stick to your name.10
Unfortunately for the B2C founders among us, I think your niches have already been arbitraged. Social selling there is pretty mature at this point. Beauty brands, fashion companies, and consumer products have been leveraging influencer partnerships and social commerce for years. The playbook is well-established. But B2B social selling is still very immature.
A lot of content on LinkedIn is genuinely cringe-inducing. "Here's what my honeymoon taught me about B2B sales..." or "My 7-year-old asked me why I work so hard. Here's what I told her..." There's a reason why Reddit has r/linkedinlunatics and doesn't have the same for Nextdoor.
Some of this comes from people trying to self-promote instead of focusing on giving away value first. But I have some bad news: there's a whole category of intentionally cringe content. It's cringe because unfortunately it works.
LinkedIn's algorithm rewards engagement above all else. Comments, reactions, shares, and dwell time are the main implicit signal to the platform that content is worth showing to more people. Get enough of these signals in the first 30 minutes and you'll have a successful post that receives algorithmic propagation. And what drives engagement better than content that makes people feel something? Even if that feeling is secondhand embarrassment.
There are a few cringe formulas:
The humble-brag (disguised as a lesson): "I just closed the biggest deal of my career, but here's what I learned about rejection along the way..."
The conversation (imaginary): "My Uber driver turned to me and said..." or "A junior employee pulled me aside..."
The controversy (manufactured): Taking a mild business opinion and presenting it as a contrarian hot take
The inspiration (success porn): Finding the most dramatic possible angle on a mundane business experience
The weird thing is that these posts often come from genuinely smart, accomplished people. They've A/B tested their way into discovering that authenticity doesn't always win on social platforms. A depressing insight for society but maybe worth accepting for the sake of your sales pipeline?
I find it funny here that even your audience knows it's performative. The comments are full of people calling out the obvious fabrications. Yet the posts still get thousands of likes and hundreds of shares.
The challenge for social selling is navigating this landscape without becoming part of the problem. You need engagement to build an audience but you don't want to sacrifice credibility for virality. I err on the credibility side of the fence (and I have an infinitesimally smaller following than Will). Will is the first one to admit he calls on the virality portion of things. Choose your calibration.
One bridging strategy is meta-commentary on the industry itself. Trends and tactical stories that actually happened will speak to the people that actually want to see them. People want to read this content and it's a bit easier to be objective. Feeding into infographics, anecdotes, and listacles is harder to churn out reliably. But regardless of what you do, the point of arbitrage is in being different from the masses.
We have a somewhat meta case in Saywhat because it's a platform for entrepreneurs. We're selling to the same people that want to post more on LinkedIn. So you can pretty safely assume they're more active on social networks than an average user.
It's also unique in the setup of social selling. For one thing, Will was already huge when he started the company. We went out of stealth and into private beta when he already had 150k followers. And most of these followers were already interested in personal branding and LinkedIn content creation - which is exactly why they were following him in the first place.
The alignment was fairly optimal. We had a large portion of our total addressable market already following the founder. When Will posted about launching Saywhat, we had hundreds of signups within hours. But there's no fundamental reason why that is only true for a content product. The same principle applies across industries and products, so long as you can calibrate for the algorithmic push.
I suspect we're in the early innings of this shift. As more people realize cold email is dead, social selling will become more competitive. The bar for content quality will rise. The window for easy growth will close.
But I don't think this necessarily ends with LinkedIn. Every professional community will likely develop its own version of this. Discord servers, Slack communities, niche forums. Really anywhere professionals gather and trust can be built. Hell, I still think Reddit is undervalued in this niche. You just have to broadcast your relationship to your company and a lot more people than you expect will listen.
In a world drowning in generated content, authentic relationships become the most valuable currency. Social selling is just one way to build that currency at scale. The challenge now is doing it before everyone else figures it out.
There are a ton of them in the Bitcoin-adjacent spaces, trying to use celebrity personas to get people to part with their dollars. ↩
They also have a partnership with Clear to do full ID verification, but given their data access I doubt they need it. ↩
He went to business school when I was AI/Systems. ↩
Which is exactly what we optimize for in pretraining, so it's a matter of time. ↩
This advice in general is nothing new. The Mom Test preaches going to conferences and building casual relationships with people in your trade group. But that's expensive in practice and only gives you a few touchpoints within a potentially huge region. Online might be easier and more effective. ↩
The value here is maybe more obvious if you're a entrepreneur or solopreneur. You control the brand: the brand is basically yourself anyway. ↩
And increasingly pay $15k per collaboration post. ↩
This is different only in cases where the sponsored content overlaps really squarely with the focus of the influencer, or if they seem to have a unique relationship with the company. If they go on for minutes talking about how they first got interested in the arena, did research to find the company, sampled the product by themselves, and only now are doing a paid promotion - that's one thing. A car sponsorship on a cooking channel going to the grocery store is something else. ↩
Owning X doesn't hurt either. ↩
The indie maker community on Twitter is super well known for this. Most of the famous examples like Pieter Levels (levelsio) or John Rush have 5+ projects that mostly target the same user persona. Even when they branch out to other spaces, they get amplification from their existing follower networks. ↩
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