10 Well-Intentioned Content Suggestions from a Startup-Loving 20VC Fanboy
Armchair Consulting is a series of articles where I make marketing suggestions for businesses I love. If anyone from 20VC actually reads this and wants to chat, drop me a line.
10 Well-Intentioned Content Suggestions from a Startup-Loving 20VC Fanboy
Armchair Consulting is a series of articles where I make marketing suggestions for businesses I love. If anyone from 20VC actually reads this and wants to chat, drop me a line.
Hi Harry.
You’re the only person I’m writing this for.
If others get something out of it, that’s fine, I guess.
But it’s really just meant to be a cozy chat between two Commonwealth lads (I’m Canadian), not dissimilar, I hope, to the warm, welcoming environment you create for your many interview guests, minus that one Jason Lemkin podcast where it looked so cold in the studio that you can practically see everyone’s nipples through their shirts. Seriously, put on some jackets.
Who cranked the air-con? It looks colder than the IPO climate.
Anyway. I like your content. A lot.
The brand you’re building is polished af, and the effort you’re putting into content is impressive. The sun may have set on the British Empire, but Stebbings’s is shining brightly.
What follows is unsolicited advice of what I would do if I were given the reins on content at 20VC. Take it with as many grains of salt or scoops of clotted cream and jam as you like.
Top 10 Content Recommendations for 20VC
1. Build a "20VC Vault" With A.I.
Agree or disagree: Dharmesh Shah knows a thing or two about content marketing.
On a recent episode of My First Million, he explained how creators are using A.I. agents to massively increase their output and make their resources more interactive.
The My First Million guys have already started doing it. See the MFM Vault.
That’s essentially what I’m proposing here. AKA a search engine meets LLM for 20VC, as it’s a bitch trying to find clips, quotes, and frameworks when you produce as much as you do.
Imagine a site where people can find frameworks and info from past episodes without having to dig through the show notes. You could even train an "A.I. Harry" for folks to engage with. We'll call it ChatGPTea&Crumpets.
There have been times when I want to know your thoughts on topics like win rates or outbound, but I can’t easily comb through the episodes and find what I want. This is the answer.
Dharmesh says you can even build it with AI.
He recommends 5 agents that do the following:
- Agent #1: The Listener >> Listens for new episode and passes them to the Transcriber.
- Agent #2: The Transcriber >> Transcribes new videos and passes them to the Extractor.
- Agent #3: The Extractor >> Extracts and highlights everything quote-worthy / tweet-worthy / remark-worthy, then passes them to the Clipper.
- Agent #4: The Clipper >> Creates platform-specific clips and posts, ready for review.
- Agent #5: The Summarizer >> Delivers all the media for approval and posting.
Hubba Hubba, Mr. Hubspot. You ain’t no billionaire CTO for nothing.
This system is great for two reasons.
First, it’s efficient. You’ll be able to test 10x the volume of clips and find more “greatest hits.”
Second, it’s valuable. People don’t just want show notes anymore. They want a way to query your back catalog and interact with it.
So that’s what we’re going to build and automate: The 20VC Vault. A site that’s not just a directory of episodes but an interactive resource that fans can engage with.
2. Run the Ryan Serhant Playbook
Ryan Serhant is the white-haired real estate Targaryean who’s building a media empire of his own. He’s got 3x NYT best-selling books, a sales training academy that prints money, and a breakout Netflix show called “Owning Manhattan” that’s already in production for season two.
If you haven't seen what Serhant is doing in luxury real estate, it's pretty much what I would recommend you do in venture. Go upmarket with content via streamers, traditional publishers, etc.
You could do all of that, but let’s zoom in on the Netflix piece for a second.
If you haven’t talked to any of the streamers yet, here are a few pitches you can use.
Pitch #1
Silicon Kingdom
In the heart of the UK, far from Silicon Valley, Harry Stebbings is rewriting the rules of venture capital. With sky-high stakes and unrelenting ambition, Silicon Kingdom takes viewers inside the high-speed world of founders, deals, and the quest to build the next decacorns from across the pond.
Pitch #2
Uncommonwealth
What does it take to go from a kid with no cash to conquering the world of venture capital? Harry Stebbings is on a mission to turn his vision into a VC empire. Uncommonwealth is a story of grit, bold bets, and the unshakable belief that innovation can thrive far from Silicon Valley, proving that greatness can come from anywhere.
Pitch #3
Owning the Future
Harry Stebbings is on the cutting edge of technology as he builds 20VC into one of the most influential venture firms in Europe. Owning the Future captures the drama, the deals, and the relentless drive to shape the next generation of innovation and push humanity forward.
Pardon my shitty Photoshop skills, but you get the picture.
This is about “going enterprise” with your content, which is exactly what Serhant is doing.
And here’s the thing: no A-list VCs have done this yet. But they will, so beat them to it. ASAP. I know you fucking hate losing, so don’t lose the race on this one.
3. Document, Don't Create
Let’s be honest, getting a Netflix show up and running will take 12-24 months or more.
In the meantime, let’s prep with Gary Vaynerchuk’s “Document, Don’t Create” strategy.
The idea is simple. Instead of scripting everything and doing pre-planned shoots, just hire a run-and-gun videographer to capture your daily life and turn it into a weekly vlog.
People would watch the shit out of a venture vlog that follows you around and shows behind the scenes
People would watch the shit out of a venture vlog that follows you around and shows behind the scenes
One well-produced 5-minute episode every week or two would crush it.
Sprinkle in some Q&A, some on-the-spot interviews, and you’re in business.
Even better, use it to double down on aspirational content. If you look at Gary’s most-viewed videos, that’s what gets the most attention.
All of Gary's top videos are inspirational clips or short films. These four alone have 17.2M views.
That’s what’s missing right now: more aspirational content and peeks behind the curtain.
Thing is, you’re already producing this type of content on LinkedIn.
These types of posts should be short videos & films too
Not only is this stuff valuable as long-form content on YouTube, but it can also be clipped to drive awareness without additional lift on your end.
4. Go Head-to-Head with All-In
The 20VC podcast is a one-man show.
Which is great.
But there’s a reason that All-In has become as popular as it is.
Because like The Beatles, The Stones, and the Spice Girls, people love a good group.
This is the only correct casting and you know it
If I were you, I’d pull a Calacanis and do both: a solo show and a group project.
Team up with Hoffman, Ackman, Rabois — whoever. Marvel has the Avengers, DC has the Justice League. Find your Batman, Wonder Woman, and Green Lantern and go for it.
And here’s the secret…
You’re going to make it even BETTER than All-In.
How? Follow these three steps.
1. Don’t Overindex on Politics. A lot of people peaced out on All-In when it got too political. You don’t have to stay in your lane exclusively, but focus on business.
2. Have Call-In Segments. The besties never take calls or Q&A, which is a missed opportunity. If you interact with listeners, you could build a much more engaging show.
3. Oprah the Shit Out of It. Never underestimate the power of good giveaways. Whether it’s time, money, or connections that can help founders or VCs, I’ll be damned if there isn’t a way to use contests and giveaways to create viral loops.
Don’t get me wrong. Your solo show kicks ass. Keep doing it.
But a group show would help you kick more ass. There’s something about the camaraderie and debates you get with a good group that cranks the entertainment value and keeps listeners coming back for more. It’s not about solo versus group. It’s about both if possible.
5. Barstool for Founders & VCs
Another playbook we’re going to borrow from is Dave Portnoy’s.
Now look. We’re not gonna go full Portnoy.
That would be insane.
40% Portnoy should be enough.
Dave is a content savante BUT he’s made even better by the characters around him, so let’s shine some light on your supporting cast and show people how the sausage gets made.
Barstool isn't just about Dave. It's about the people around him. Who are 20VC's equivalents?
I’m sure you interact with all sorts of characters every day.
Are there a bunch of McKinseyish kids running around finding startups? Who’s doing the diligence? Is your family active in the business?
Again, we’re not going full Barstool with the drama, but we’ll show behind the scenes and all the reasons why people should work with you. You could have your team share metrics they care about, examples of good pitches, favorite pivot stories, worst investor meetings, etc.
This is actually similar to the Office Hours content that YC puts out with their group partners.
YC's Office Hours series with group partners average 100k views. Don't let them have all the fun.
Except yours is going to be better.
It won’t just be people sitting around a table talking. It should show the ups and downs, the folks behind the business, and the activity in the office rather than just boring roundtables.
And if you have the cash to buy up a few shows and create a nice little media moat like Barstool, HubSpot, Morning Brew, and others have? Even better.
6. Get Physical
Everything you’re doing is digital. That’s what everyone else is doing, too.
It leaves a lot of room to stand out with something physical.
Here are three ideas that could extend 20VC’s brand into the real world.
1. Quarterly Magazine. It wouldn’t be hard to repurpose your content into a quarterly magazine that lands on the desks of all the founders and VCs you care about. People delete emails in seconds, but a sleek magazine would get more attention.
2. Performance Wear. Your active lifestyle makes a good match for anything but the typical startup hoodie. Get some high-end performance wear with cheeky phrases like “Don’t Sweat the Dilution” and “Seed Stage Energy.” Could look awful if done poorly or sick if done well. Work with a solid designer.
3. “Unmade Decisions” Coin. Did you know Ryan Holiday makes over $1M per year just from selling his Memento Mori medallion? That’s wild. Your favorite quote on the pod seems to be “The heaviest things in life aren’t iron or gold but unmade decisions.” Turn that into 20p-size coin. It’s not just a token — it’s a physical reminder to decide. Great for founders waffling on whether to raise that Series A, fire that VP, or ship that next product.
Create your own "Unmade Decisions" coin. If Hormozi wants to promote and split the profits, beautiful.
Create your own "Unmade Decisions" coin. If Hormozi wants to promote and split the profits, beautiful.
The world doesn’t need any more crap t-shirts, water bottles, or phone cases. Go for unique, premium ideas like the ones above and it’ll pay off.
7. VC: Venture Camp
The last thing you want to do is run a conference. I get it.
Here’s what you should do instead.
Invite 20-30 VIP guests to an exclusive annual retreat called Venture Camp.
Host it in a unique location (European vineyard, skiing lodge, etc.) and curate the guest list so it’s founders, VCs, and operators whom you want to hang out with. Bring in a chef, get some surprise custom swag, and organize unforgettable experiences like football training with Premier League players, kayaking dramatic coastlines, etc.
The MFM guys do this every year. They rent out a house and invite founders and celebrities like Mr. Beast and Hasan Minhaj to stay, play basketball, and learn from each other.
Founders and celebs like Mr. Beast get together every year for Camp MFM, an exclusive retreat where they spend two days doing adventures and learning from each other. Try your own version called Venture Camp.
Normally, meet-ups suck. You go out for dinner, you sit around for a few hours, and you leave.
With this experience, you’re under one roof for multiple days, so you get to know people on a deeper level. And while most of it would be private, unrecorded sessions, you could definitely leverage key moments for some of the best content and interview opportunities all year.
8. Create a Video Game
Stay with me, Stebbings.
We’re going to create a video game about trying to make it as a VC.
Picture that Uber game that went viral a few years ago, except for venture.
Remember the Uber game that went viral? Let's do something fun like that, but for venture.
Remember the Uber game that went viral? Let's do something fun like that, but for venture.
It’s perfect because you can use data from your interviews and reports from the venture world to craft the levels and promote your content further.
Plus, it would generate a good amount of earned media, backlinks, and buzz.
Not much more to say except find the developers who made the Uber one and hire them to do it again. Or, even better, partner with Replit, Cursor, etc. to show off their AI capabilities.
9. Build a Two-Sided Community
I’ve heard several advisors and VCs say communities are their #1 growth lever.
One guy I know runs a two-sided network for Fortune 500 executives and startup founders. It gives the Fortune 500 leaders access to new tech and deal flow, and the founders get a foot in the door with decision makers at enterprise orgs.
A two-sided community of founders and operators seems like a natural fit here.
BTW, I think I’ve heard you mention that you have a private Slack group for growth people or something like that? Is that true? Can we just scale that? Makes a ton of sense.
Alternately, there are a good number of founder and operator networks that already exist, which might make interesting acquisition targets. Vistage, YPO, Chief, Hampton, EO, Pavilion, etc.
Buy or build your own community that brings founders and operators together
A lot of them are already big businesses with revenue north of $100M. However, many of their brands are in decline. They have aging bases and problems attracting younger members.
You could build or buy one of these and use it to connect successful founders with the best operational talent in the world. Either way, I’d hire a beast to operate it and double down on providing founders value so they know where to go when it’s time to raise. Even if they don’t take your term sheet, it could be a big business on its own.
10. Sweat the Small Stuff
In your recent episode with Raman Malik, you asked how Perplexity balances iterative improvements with big swings.
Malik said that they take one concentrated bet per quarter and expect 1 in 4 to work out.
Beyond that, it’s about iterative, compounding improvements.
The previous nine ideas in this list are big swings, no question. They’d take at least a quarter to get off the ground — some more — so my final recommendation is to tackle one at a time while focusing on iterative improvements to your existing business.
Examples of iterative improvements I might consider include:
- Push harder for subs, but in a clever way. I don’t think I’ve ever heard you ask for subs, but the occasional ask makes a difference. A lot of channels have cheeky ways of doing it that don’t feel lame, like telling listeners that it’s part of your “gentleman’s agreement.”
- Run a review campaign. Reviews matter for both perception and rankings. Run a campaign for a month where you rack up more reviews across platforms.
- TikTok challenge. Offer a cash prize for whoever can clip your content and generate the most views on TikTok. Great way to get big boosts of engagement.
- Improve ad reads. Get more creative with ad reads (test formats like Smartless, Theo Von) and having them throughout episodes instead of just the beginning and end.
- Book higher-profile guests. Big names move needles. Focus on the middle of the Venn diagram between investors and celebs. Ashton Kutcher, Serena Williams, Richard Branson, Tyra Banks, A-Rod, Kevin Hart, etc. You’ll see bumps in listeners and then a steady rise in back catalog engagement as new fans dig through older content.
I’m sure you have a longer backlog than this, so continue working through it while leaving room for one big swing per quarter from the rest of this list.
Summary
20VC is doing a lot of things right.
You’re a helluva podcaster, a no-bullshit interviewer.
I guess what I’m trying to say is, “Yer a content wizard, ‘Arry,” and with a few of these big swings, 20VC will be, in Lemkin terms (to bring this full circle) not only unkillable, but invincible.
1. Build a 20VC Vault >> Create an interactive archive of episodes with AI.
2. Run the Ryan Serhant Playbook >> Pitch streamer-worthy shows and go upmarket.
3. Document, Don’t Create >> Hire a run-and-gun videographer for a venture vlog.
4. Go Head-to-Head with All-In >> Record a group pod with listener call-ins and giveaways.
5. Barstool for Venture >> Showcase characters behind 20VC, similar to YC’s Office Hours.
6. Get Physical >> Introduce sick branded products and high-end swag.
7. Start VC: Venture Camp >> Host an annual VIP retreat for founders and operators.
8. Create a Video Game >> Develop an online game to generate earned media.
9. Build a Two-Sided Community >> Buy or build a network for founders + operators.
10. Sweat the Small Stuff >> Run review campaigns, clip challenges, etc.
As a 20VC fanboy, I’d be excited to see even one or two of these take off.
Let me know if your team wants to jam on any of them. Ideas are great, but I realize execution is everything. Happy to help bring some of this to life.
Happy New Year, God save the King, and all that 🇬🇧 🫡
Devon
About the Author
Devon Hennig is a 20VC fanboy with 10+ years experience running marketing and growth teams at startups and public companies. If anyone from 20VC wants to hop on a call and nerd out about content marketing, don’t be shy. Like Charlie Puth, he’s only one call (or email) away.