You can write to almost anyone alive (billion-dollar CEOs, famous authors, etc) and the message actually lands in their inbox.

So it bugs me how badly most people use it.

A few months ago, a founder I was advising sent me his cold DMs and asked why he hadn’t received any replies. He runs a billion-dollar company with a great product, and he was messaging exactly the right people. Still… got nothing back.

It wasn’t his fault:

He paid an agency five figures, and they’d given him the same templated script they give everyone. The kind you (and me) ignore.

I fucking hate agencies. 🤬

The people who run them have never ONCE been on the other side of one of these messages. They’ve never opened LinkedIn as a CEO with 40 identical pitches waiting. So they hand every client the same “proven” script, a thousand other agencies hand out that exact script too, and every inbox fills up with the same cringeworthy slop.

Here’s the message the agency told him to send (I stripped the names):

Where do I even start…

• ❌ That first line, “figured I’d reach out directly”, is the bit that shows up in the notification preview before you even open the message. Most valuable real estate he’s got, and he spent it saying nothing.

• ❌ Then it’s him, him, him. His title, his company, the startups he built before. I don’t know this guy. Why would I read his CV before he’s given me one reason to care?

• ❌ After that comes four sentences of product I never asked about.

• ❌ And then he asks me, a total stranger, to sacrifice 30 minutes for a call. For WHAT, exactly?

[I’m not above this. My own first cold DMs looked exactly like that, and I cringe thinking about them now. But after tons of trial and error, I think I cracked the code. My DMs now actually get replies from strangers.]

So I told the founder to delete it, then wrote him a new one myself.

This is the re-written DM he sent that night:

The next day he texted me, saying he’d gotten 4 replies overnight!

And it wasn’t a one-off. ✅

I’ve been doing this for years for the CEOs and CMOs I advise, and it plays out the same way every time. I’m also on the receiving end of these messages all day, so I know exactly which ones get a reply and which get ignored 100% of the time.

My LinkedIn DM cheat sheet 📋

None of that was luck. I use the same set of tactics on every cold DM, starting with making the person feel chosen (which is why I wrote “We’re being picky about who sees it before launch”).

Below is the full set of tactics, and exactly what to write (copy & paste). I've never published any of it.

What you’re getting today:

1. 💎 10+ LinkedIn DM tactics, each with copy-paste lines to drop straight in.

2. 🧪 7 Ready-to-send templates for the awkward spots: warm leads, the wrong contact, a soft no, etc.

3. 💰 Follow-up sequences that revive people who’ve gone silent (there’s one line that always works).

4. ⚙️ Specific LinkedIn timing and mechanics, from the connection request to InMail, so you never make the big mistakes.

Read more

If you need to reach tech people, you should know this: they don’t see your ads. Ad blockers, LinkedIn fatigue, banner blindness - they’ve tuned it all out.

But they read TLDR. 7 million tech professionals subscribe to these daily newsletters because they actually want them. You can sponsor any of their 13 newsletters (including Tech, AI, Dev, DevOps, InfoSec, Product, Marketing) and reach people who are actually reading (including me).

Open rates average 42% and they write the ad copy for you.

Get TLDR’s media kit →

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🥇 How to become the “no-brainer” choice

I keep noticing the same pattern on every great homepage: there’s one word doing 90% of the positioning work.

Once you see it → you can’t unsee it.

I’ve been obsessed with this pattern recently. It’s the cheapest, fastest fix I know. And it’s the core lesson of the most-quoted marketing book of the last 30 years.

🧠 The law of mainstream

The book Crossing the Chasm, by Geoffrey Moore, came out in 1991.

The big idea of the book - how new products win a market:

The left side (your first 100 customers) loves cool features. The right side (the mainstream market) buys “whole” products. They want the complete, obvious answer to all their pains and problems in a given category.

The chasm is the gap between.

Most startups fall in because they can’t cross that chasm: they keep talking to enthusiasts when they should be talking to pragmatists on the right.

Your homepage hero is the first signal of which side you’re talking to. ↓

Subscribe now

✏️ The one word doing the work: “all”

Fin is solving this beautifully right now.

Their hero:

The word they highlighted with glow is “all”.

It tells every pragmatist on Earth: you don’t need to bolt Zendesk together with Claude Code and Slack. We’re the whole thing. That’s how you OWN a category.

I love it.

✂️ You can do it in reverse

I’m the Director of Growth at Wiz.

Our hero used to read:

We recently cut “in the Cloud”:

“In the Cloud” was the limiting phrase, especially in the AI era.

Thanks to this cut, the buyer’s question changed from “what cloud security tool should I get?” to “what will protect everything I build?” - that’s a pragmatist question.

🍣 Pick one problem → solve all of it

Every founder reading this has heard “niche down” a thousand times.

So when I tell you to own “ALL your customer service”, your gut reaction is probably wait, isn’t that the opposite of niching?

You’re conflating two different axes:

• ✅ Niching down on category is what makes you trustworthy. You pick one specific space and commit to it.

• ❌ Niching down on features (inside a category that’s already narrow) is what kills you. You pick one slice of one category and try to call it a company.

The whole-product move is the first kind of niching.

A pizza place that says “every style of pizza” picked the pizza category and went deep on every variation. They’re the king of pizza in town. A pizza-and-sushi place picked two categories at once. That’s the move people don’t trust.

⚙️ Your playbook

Pick one direction:

→ Add a word that owns the whole category. Fin’s “all” is the perfect example. “Everything” or “anywhere” do similar work depending on the business.

→ Delete a word that traps you in a niche. E.g. “In the Cloud”.

I know it sounds insane to add a word like “all” when your product technically can’t do everything yet. Or to delete the most accurate word in your hero. Trust me, category ownership is what closes deals.

Go own your category ✌️

Tom

P.S. This idea pairs with another positioning move worth stealing - how to look “big” before you actually are. I wrote the full playbook here: Look big → become big

Paid subscribers get a free year of Base44 (the AI app builder), a new premium tactic every week, the full back-catalog of 300+ ideas, live weekly Q&As, a community invite, and a PDF copy of my book.

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Being a guest on a podcast or newsletter is the #1 fastest way to borrow an audience that someone else spent years building.

The hard part is knowing which shows to pitch, and how to pitch them without sounding cringe (or self-promoting) ❌

I’ve spent years solving that for myself. I pay for every podcast database out there (like MillionPodcasts, Rephonic, ListenNotes, etc). To be 100% honest, I think their data sucks.

So I built my own database, and worked hard to keep it up to date.

Today, for the first time, I’m giving it away ✅

340+ podcasts and newsletters that take guests, sorted so you can find your fit in seconds and pitch yourself or your CEO.

What’s inside:

• Every podcast/newsletter sorted by category: marketing, engineering, security, data & AI, HR, ops, design, fintech, and more

• A validated contact for each one (email address or form)

• Tons of data like audience size, host’s socials, frequency, typical guest seniority, and more

• No-cringe email template that hosts say yes to + the exact pitch that worked for me (multiple times)

I put this together because I know how hard it can be to get in front of the right hosts and authors. Having direct access can make all the difference.

First things first, download the database using this secret link:

Read more

Along the way, I also stumble onto the worst ones.

I’ve been slowly collecting them for 10+ years.

Today I’m releasing the full list of “UMMM PLEASE DON’T DO THIS” ideas.

Note: The goal isn’t to defame anyone or dunk on the companies that I (sadly) spotlight below. The goal is to learn from their mistakes. Because you don’t want to be featured in the next PR-nightmare LinkedIn post:

If you do marketing for a living, this article is a must-read.

Buckle up for a ride… 🎢

Read more

I talk to a lot of marketers who obsess over subject lines and copy, but their emails are landing in spam (and they have no idea). It’s such a waste.

Warmy fixes email deliverability - it warms up your domain, monitors inbox placement, and keeps you out of spam folders. Most companies don’t realize their emails are getting filtered until their open rates tank.

Worth checking if you’re doing email marketing:

Try Warmy

(Click here to sponsor the Marketing Ideas newsletter)

What to do if your marketing budget is $0 🪫

If your marketing budget is $0, you already have everything you need.

I’ve run marketing for companies with $32 billion exits and side projects with literally zero dollars in spend. I also went through 50 of the fastest-growing companies to map exactly how they reach new customers. The pattern was identical every time: Every great $0 win came from inside the company before any external spend.

In today’s newsletter: the 7 internal resources every company already has, and how to turn each one into a $0 marketing channel. 🔋

Here we go ↓

1. Your product → free mini-tools 🧪

Take an existing feature from your product, strip it down, and ship it as a standalone free tool with its own URL (don’t ask for email or any other friction).

Examples:

• Grammarly built a $13B company on the back of its free Chrome extension and plagiarism checker.

• At Wiz I worked on shipping our free Cloud Threat Landscape. It’s the same internal threat intel database our researchers build daily, just opened up to the world.

• Shopify’s Name Generator ranks for a billion long-tail searches.

All examples I found were once part of a larger product. But they’re now their own SEO target and their own backlink magnet (and their own Product Hunt launch). You’re giving people a free solution to a small problem, so your main product becomes the obvious upgrade.

How to do it: walk through your product with your PM, and find a feature that solves a narrow problem on its own. Strip it out and launch it on its own URL.

2. Your product → brute-force demos 🥷

Use your product on a dream prospect’s behalf, then send them the result (with no pitch or strings attached).

I learned this works because somebody did it to me. When my Substack account got impersonated, the CEO of Charm Security ran his impersonator-hunting product on the fake account, caught it, and DM’d me the proof. I wrote a whole article about them because of that move (it was not sponsored).

Examples:

• Christina Cacioppo, co-founder of Vanta, heard the Segment team was struggling with SOC-2 compliance. She proactively sent them a personalized compliance spreadsheet, for free, and it worked.

• Goldcast built a hyper-personalized demo video for every dream account. They closed deals before sales calls even happened. (Full play here)

• Tomer Dean, founder of Lychee (AI podcast editor), manually clipped real episodes for real hosts, emailed them the result, and closed deals:

The exact copy you should send:

“I spent [X] hours analyzing [their thing] and created [this] for you. No strings attached… thought you might find it useful: [link/image]”

If they ignore you → make it public. Post on LinkedIn, tag them, praise their work, mention how your product “helped.” Worst case they ignore you again. Best case they share it. (Default.com’s CEO did this with Deel and went viral.)

How to do it: pick 5 dream customers, spend 30 minutes on each doing manually what your product does automatically, then send the result with the line above.

3. Your data → exclusive insights 📡

Mine your internal data for a surprising pattern → publish it → then journalists, customers, and even competitors share it for you.

Examples:

• Carta’s startup equity data reveals founder ownership rates at IPO and equity for early hires. Founders share it like wildfire. Every funding article on TechCrunch quotes it.

• Okta’s “Businesses at Work” ranks the fastest-growing SaaS apps using their own usage data. Every company featured shares it because it praises them. Startups are motivated to integrate with Okta just for a chance to be featured.

• Spotify Wrapped is the most copied marketing campaign of the last 5 years. It’s an SQL query.

• (Bonus: Spotify noticed 3,749 people streamed “It’s the End of the World As We Know It” on the day of the Brexit vote and made an ad about it. Genius real-time data play!)

• Asana’s “Anatomy of Work” Index revealed workers spend 58% of their time on “work about work”. Cited everywhere from HBR to Ali Abdaal.

• Stripe’s Online Economic Indicators publishes real-time payment data that gets cited as if Stripe were a research firm.

• Gong analyzed millions of sales calls and found that the opening line “How have you been?” outperforms “How are you?” because it implies an existing relationship. Super valuable for sales teams.

No interesting data? Run a survey. That’s how Asana built the Anatomy of Work from scratch.

How to do it: ask yourself: “what’s the most surprising number in our database?”

4. Your users → status symbols 🎟️

Give your users something worth showing off publicly. Certificates, badges, “Verified” tags, exclusive club memberships, etc. They promote for you because the badge makes THEM look good.

The trick (we learned this at Wiz): make the user’s NAME big, not your logo. When you flip those proportions, social shares jump → at Wiz they went up 300% almost overnight.

Examples:

• HubSpot Academy certifications get added to thousands of LinkedIn profiles every single month.

• AWS certifications are job requirements at half the cloud-engineering postings on LinkedIn. The badge is the resume.

• GitHub’s contribution graph and Stars program are like a professional currency for developers.

• Salesforce Trailblazer ranks end up in email signatures across every sales org on earth.

• Duolingo’s streak counter has people sharing their 1,000-day milestones on Instagram. The streak is the marketing.

• Goodreads’ annual reading challenge counter has millions of people posting their book counts in December.

How to do it: figure out the one status the top 10% of your users would brag about owning. Build the cheapest version of it possible (a PDF certificate or an SVG badge) and email your power users.

5. Your team → employee-led marketing 🎤

Personal profiles reach 2-3x more people than company pages. Get your founder, your team, your engineers posting from their own LinkedIn accounts.

At Wiz, the company page on LinkedIn has 400K followers. But our 2,000 employees, with an average 2,000 connections each, have a combined reach of 4 million people. The math isn’t close.

The Wiz playbook (now public):

• Spoon-feed everyone. Pre-write the posts, make personalized images, and send each one via Slack 1:1 with “copy/paste/post” instructions.

• Run internal contests with real money. Alex Lieberman at storyarb ran a 10-week “Own The Internet” competition with a $5,000 prize that pushed impressions up 87% and pipeline up $183K (22%).

• Build a private “Wizfluencers” club. A Slack channel for the social superstars in the company, with perks, early product access, shareable certificates, and a private leaderboard.

• 15-min LinkedIn workshops on demand. Any team that wants help books me, I show up to their weekly sync, walk through the playbook, then take posts for 1:1 feedback after.

The pattern repeats outside of Wiz. My favorite example is Cluely’s Roy Lee - he built the entire company through his own personal posting. Roy *is* the marketing channel.

And if your founder won’t write, hire a ghostwriter. A part-time ghostwriter costs wayyyyy less than a single month of paid ads, and the output compounds for years.

How to do it: start with the founder. Book a recurring 30-minute slot where a marketer or ghostwriter pulls 3 insights out of them, then publish 3 posts a week from the founder’s personal account.

6. Your design → “Word of Sight” 🖼️

Design your product so the act of using it spreads the brand. Either by making the logo extremely big in the UI, or by baking a public-by-default action into the core workflow.

I call it “Word of Sight” - an upgrade to word-of-mouth.

Examples:

• Apple is the best example. Every logo on every MacBook in every coffee shop is a $0 ad. Steve Jobs flipped the logo to face the audience (instead of the user) in 1999 for exactly this reason. Before 1999, it looked like this:

  

• Shazam puts a giant logo on the recording screen. People hold their phones up at concerts, and everyone around them sees Shazam.

• Slack’s interface (the sidebar, the super ugly purple, the channel list) shows up in every Zoom screenshare on earth and every viral screenshot of a team chat gone wrong. Super easy to recognize.

• Loom keeps videos on loom.com instead of letting people export an MP4 (on the free plan) → every shared link is brand exposure.

• Otter.ai auto-joins meetings as a participant. Everyone on the call sees “Otter.ai” in the participant list.

• Readwise makes users publicly tag @readwise in the comments to save a tweet. Every save becomes a public ad.

This one’s brilliant because it compounds. Every screenshot a user takes of your product is free marketing forever.

How to do it: find where your product gets seen by people who don’t use it (app icon, loading screen, email signature, exported file, public share link). Make the brand large and unmissable in that exact moment. Then find one private action you can make public-by-default (a save → tag, a share → branded URL, an export → watermarked logo, etc).

7. Your name → praise others 🏆

My favorite play in the entire $0 playbook.

Even if you don’t have an audience, your personal name and your brand name are still valuable resources (as long as they look “real”). Use them to celebrate the best people in your space. They’ll repay you in shares, intros, and reciprocal praise.

Remember: Your greatest existing resource is your ability to make other people feel good about themselves. And you can do it by leveraging your name.

• At Mine, I built a “Top 10 DPOs to Follow” page → emailed all 10 → all 10 said yes to interviews → all 10 shared it on their LinkedIn. Site traffic up 4,000% that month. $0 spent.

• Forbes 30 Under 30 is the most successful praise-led marketing engine in media.

• Ahrefs publishes “best SEO blogs to follow” and “top SEO experts” lists. Every person on those lists reposts them.

• Zapier celebrates top AI builders in a special ceremony.

• Glassdoor’s “Best Places to Work” is the same play at enterprise scale. Every CEO on the list brags about it from what I’ve seen.

The exact DM that worked for me at Mine:

“Hi [Name], we’re recognizing the top [role] in [industry] and you made the list. We’ll be writing an article about you and your role in [specific achievement]. Would you be open to a quick 15-min interview to make sure we get it right? Here’s the project: [link]”

The real hack is the phrase “we will be writing”. The decisive verb makes the recipient slightly nervous about how they’ll be portrayed, so they say yes immediately (to control the narrative).

If I had $0 and one week, I’d run this on day one.

How to do it: pick a tight, specific role inside your ICP. The narrower the better (”B2B SaaS marketers at Series B startups” is great; “marketers” alone is too broad). List the 10 best people in it. Build a tiny site with their photos and one quote each. Email them with the DM above. Wait.

Bonus: 7 more $0 plays I couldn’t fit above ↓

1. Optimize for “+ reddit” SEO 🟧

People add “reddit” to Google searches to skip marketing fluff. Reddit is now the #3 most visible domain on Google. Build a presence on relevant subreddits, answer real questions, build karma, and mention your product only when it’s actually the right answer. Full playbook here.

2. Get recommended by AI chatbots 💻

ChatGPT, Claude, and Perplexity recommend brands by name. If yours isn’t in their training data, you don’t exist. SEO lead at HiBob took their AI mention rate from 17% to 51% with one specific playbook. I broke the whole thing down here.

3. The “inspired by” trick 🪞

Build a project, tag the influencer who inspired it, credit them publicly. Strokes their ego → triggers reciprocity → gives them social proof to share. Dan Ariely shared my Viral Post Generator after one “inspired by you” email. Full story.

4. Launch on Product Hunt 🏆

A successful Product Hunt launch can drive thousands of visitors and years of passive traffic. I launched Marketing Ideas in Feb 2024 and still get dozens of subscribers every month from it 15+ months later. My #1-of-the-month playbook here.

5. Career page stunts 💼

Your careers page gets high-intent traffic with zero marketing leverage, unless you make the job posts shareable. Beehiiv’s “Remote Office Manager” went viral on LinkedIn. Fiverr created a job for a “GIF Picker” and traffic went up 91%. Templates and full breakdown.

6. Collect “love stories” instead of testimonials 💌

Generic “Best [industry] product!” reviews are useless. They sound fake and anyone can get those. The reviews that actually convert are what I call love letters: emotional, metaphor-heavy stories about your product. Full guide here.

7. Ambush “[competitor] discount” searches 😈

Build pages that rank for “[competitor] coupon” and “[competitor] discount.” Those searchers have credit cards in hand. This is the “evil genius” way to steal customers from competitors.

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See you next week ✌️

Tom

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That was enough to win:

1. Money to be seen. Attention, TV spots, billboards, magazines, conference booths, ads. The more you spent = the more “real” your brand felt.

2. Money to be first. R&D, product development, speed to market. Outspend competitors → own the category.

3. Money to look good. High-end design, photography, video, packaging. If your brand looked expensive, people assumed you were worth it.

4. Money to be good. The big one. Actual quality. Useful features. Building something worth buying.

Every “classic” moat (network effects, patents, scale) was a child of money. The whole VC model ran on it. You’re a young startup with nothing? Here’s $40 million. Go buy the talent, the visibility, the speed, the quality. Done.

Money was your moat.

But then winter came.

AI showed up. And turns out the “money moat” wasn’t that hard to cross. AI gave everyone a bridge long enough to walk right over it.

Suddenly everyone can look good, be seen, be first, and be good.

Which is a disaster if you’re a founder building something new. Because now you’re fighting a flood of AI-generated competitors who look exactly as legit as you.

You know what I mean:

Fake content by fake influencers with fake engagement from fake followers, launching fake products with fake testimonials. Temu for brands.

And when prospects can’t tell real from fake, they default to NO. They can’t help it. Every signal we used to rely on can be faked now, so skepticism is the only safe bet.

Now the silent question every prospect asks about your brand is:

“Can I actually trust these guys?”

Trust is the new moat.

It’s so damn big that AI can’t cross it.

How to build trust for your brand 🌱

I’ve built trust twice in my career:

Once for Wiz as the early Director of Growth (where trust IS the business → no CISO hands you cloud access because your website looks nice). Once for this newsletter (zero → 90K subscribers in under 3 years). I’ve learned what works.

And here’s the good news: you don’t need $40M to build trust. You don’t need 5-7 years. You just need to know what actually moves the needle.

For paid subscribers, I’ve put together everything you need 🔒

Below are the 13 specific plays you can steal to make people trust your brand, ranked by impact. Start with #1.

Once these 13 are running, your homepage starts converting strangers. Prospects DM you instead of you DMing them. The whole funnel flips.

Here’s exactly what to do:

Read more

People are calling Brew the “Claude Design for email marketing” - and I think that’s 100% true.

You describe what you want in plain English, and Brew builds the entire campaign: copy, design, automations, all on-brand. It learns your colors, fonts, voice, and imagery from your website, so every email looks like your team wrote it.

I’ve been playing with Brew and it’s honestly *wild* how fast you can go from idea to sent email. Works with any ESP you already use - Klaviyo, HubSpot, Mailchimp, etc. Give it a shot!

Try Brew

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Last week, Nikita Bier (Head of Product at X) tweeted this:

He’s right. People watch videos on mute. That’s why we need captions.

But there’s a HUGE gap between “I added captions” and “my captions are working.” If you do it right → you can 5x your chance of going viral.

🎬 Here’s exactly how to do it right

1. Lock the first subtitle on screen at second 0. People will keep on scrolling if they’re not sure the video is “optimized” for watching on mute. That’s why the first subtitle has to be there BEFORE the speaker’s mouth opens. Burn it into the video file in your editor (CapCut, Descript, Premiere). Auto-caption tools always lag 200-500ms behind the speaker. That tiny lag makes people scroll.

HubSpot does this perfectly:

2. First line under 6 words. Your reader has 1 second to decide if this video is worth their attention. They cannot read 15 words in 1 second. They CAN read 6. Treat the first subtitle like a headline. If the speaker says “Today I want to tell you about something I’ve been obsessed with for months,” then your subtitle should either rewrite it (“I’ve been obsessed with this.”) or split it across frames. Never dump the full sentence on screen at once.

3. Turn OFF the platform’s auto-captions on upload. This one drives me crazy. Literally 99% of marketers are doing it wrong. LinkedIn and X both stack their own auto-captions on top of yours, so you end up with two layers of text on screen. Turn off auto-captions in the upload modal before you publish.

4. Size up the part you want to emphasize. Pick the most important part of each section (a number or a punchline phrase) and bump its size 1.5-2x. This is a great way to keep people hooked.

5. Add a background for contrast. Another one most marketers skip. If your subtitle is white text and the speaker is standing in front of a white wall, the subtitle disappears. Fix: add a subtle drop shadow, a semi-transparent dark bar behind the text, or a thick outline.

6. Position subtitles in the SAFE ZONE. TikTok and Instagram overlay their own UI on top of your video. Usernames at the top, share buttons on the right, link previews, and text at the bottom. LinkedIn and X put video controls on the bottom 15%. Keep subtitles in the middle 60% of the frame vertically.

I spent way too long getting these wrong on my own ads. Saving you the trouble.

Have a great week ✌️

Tom

P.S. If you’re wondering what to actually put in the first few seconds of your video → the 3-second rule.

He’d ask one question → go quiet → let the prospect fill the silence.

On repeat.

He talked less than anyone, and closed 10x more than everyone. ✅

There are two ways to handle a prospect who goes quiet on you:

1. Path A: ask another question about what they need, then shut up.

2. Path B: ask something desperate like:

And if that doesn’t work:

Yikes.

Path A wins, every time.

(These are real texts Sam Altman sent his board while being fired, published in the Musk v. Altman lawsuit last week. Same energy as bad SDRs 😅)

Sales tactics every marketer should know 💰

I know, I know.

This is a marketing newsletter.

But I’m the Director of Growth at Wiz. We grew from zero to over $1B ARR faster than almost any company in history. For years, my desk was ten feet from the revenue team that made it happen.

I heard more calls, more post-mortems, more wins and losses than I can count. I’m convinced I’m a 10x marketer because of it. 💎

Here’s everything I know about sales ↓

Read more

Reaching developers and tech people isn’t easy. They ignore LinkedIn, skip past Google ads, and tune out most marketing.

TLDR works because 7 million tech professionals actually WANT to read it (including me). You can sponsor any of their 12 specialized newsletters (AI, DevOps, Product, Marketing, etc) and get in front of exactly who you need.

Companies like Threatspike use TLDR to reach tech audiences at scale (and they drive $75k+ in pipeline per campaign).

Get TLDR's media kit →

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Make customers feel like they won the lottery 💸

Last week, Photo AI told me I was “randomly selected” for free credits.

I’d bet money they sent that to every user. I still felt a tiny dopamine hit → logged in → and burned them.

Now look at this email I got from Canva:

Same situation: free credits for something I’m not using. But instead of “you just won 🎉”, Canva said “looks like you haven’t tried this 🥺”.

The marketing idea 💡

My greatest retention trick:

1. Take a bonus you were already going to give (free credits, a discount, a bonus month, free shipping)

2. Reframe the email so the customer feels like they randomly won a prize. Make them feel like only they won it, not other customers.

That’s it!

I discovered it by accident in 2014 ↓

People don’t want discounts. They want to win. 🎟️

In 2014, I ran my first ever marketing campaign at a translation startup called One Hour Translation. My boss gave me a 5% Halloween discount and wanted maximum redemption.

5% off… it’s not exactly life-changing. 😅

The obvious play was to send everyone “5% off for Halloween”. Instead, I made it look like a mystery prize with three possible outcomes: 3%, 4%, or 5% off.

To find out what you won, you had to paste the coupon code at checkout.

The secret: everyone got the same code, worth 5% (the best possible outcome).

Best campaign we’d ever run up to that point. That’s when I learned we should make our customers feel like winners.

Copy to steal:

• “Congrats! You’ve been randomly selected for [X].”

• “Your account was randomly picked for [X].”

• “You’re our daily winner.”

• “Mystery gift voucher”

• “Surprise! You just unlocked [X] for free.”

• “You just won…”

One more thing: Add a soft deadline. “Claim by Friday” works great even if nothing actually expires Friday.

See you next week ✌️

Tom

Here’s how they did it ↓

A few days before launch, they posted a sick teaser video on social. The video pointed everyone to a Luma event page where they could RSVP for the launch demo:

(Yes, a Luma event, like the kind people normally use for parties and meetups.)

Event location: YouTube.

1,000+ people RSVP’d. On launch day, the founder went live on YouTube, shared his screen, and walked through the whole product. Big audience, already hyped, reacting “woooooooooow” in the chat.

After the launch, the team cut a 25-second highlights video and posted it everywhere.

The old launch playbook is dead ☠️

99% of marketers launch by writing “we’re excited to announce 🎉” on LinkedIn (and nothing more).

I know that because I get the same question every week:

Then they always follow up with what they actually want:

I fucking hate the “list of channels” mentality.

They want an easy checklist they can run through and move on:

• 📋 Product Hunt → “let’s win #1 of the day”

• 📋 Hacker News → “front page here we come”

• 📋 Reddit → “r/SaaS will love it right?”

• 📋 LinkedIn → “viral post from the CEO”

• 📋 X → “thread will 100% blow up”

It’s lazy, it’s predictable, it’s the post-and-pray approach to launching, and it’s why your CEO will ask you on Monday: “wait did we even launch?”

A great launch is built on the TACTICS around it 🌈

Done right, you get tons of potential customers before you’ve even shown the product, a flood of LinkedIn posts about you from people you’ve never met, and a couple of journalists in your inbox asking for a chat. None of them require a budget. Almost no one is using them.

I’ve been collecting these powerful tactics for 5+ years.

Every time I launch something (e.g. my Viral Post Generator that hit 2 million users in 48 hours) → I run through the same internal cheat sheet.

So I cleaned it up and turned it into a Google Doc.

And today, I’m sharing it with you:

Note: anything you do counts as a “launch”. The same tactics work for going out of stealth, feature drops, hiring announcements, even your next big blog post. If you’ve ever shipped something that got crickets → this fixes it.

Here’s what you’re getting:

1. ✅ The full 30-page launch cheat sheet (keep it forever)

2. 🎟️ 16 launch tactics the bottom 99% never try

3. 🎯 Fill-in-the-blank sections that make everything super actionable

4. ⚙️ Copy & paste templates: 6-email waitlist sequence, founder + employee posts, ambassador rules, partner brief, live event structure, recap plan, relaunch calendar

And yes, you can drop the whole doc into Claude Code and it’ll plan your next successful launch for you. I highly recommend doing it.

First things first, download the cheat sheet using this secret link:

Read more

Here’s your dose of inspiration - 5 viral hits to know about today:

#1

Steal this gifting playbook (closed $60k+ deals)

Delve sells SOC 2 compliance software (SOC 2 = the security audit every enterprise customer makes startups pass before signing).

Instead of cold emails → Delve shipped 100+ custom doormats to other startup offices.

Each doormat had the recipient’s company logo + this clever pun:

“Your shoes look good. Do your SOCs 2?”

The numbers are insane ↓

• ✅ $6K total spend → $500K in new pipeline in a single day. ~83x ROI.

• ✅ $60K+ in closed enterprise deals (per StartupSpells’ breakdown).

• ✅ 850K impressions and 6,000+ likes on LinkedIn = ~$7 CPM (vs. typical LinkedIn ads at $100-$200 CPM).

• ✅ Bypasses every gatekeeper. No spam filter, no SDR triage, no inbox to delete from.

Manufacturing the doormat itself is the easy part.

But how do you find 100 founder addresses to ship to?

That’s where most marketers give up. ❌

I’ve actually done it many times: My team and I ship physical gifts to prospects every week (books, posters, toys). I’ve built lists of 500+ founder addresses using the exact $0 tactic below.

Below is the 3-step playbook + the address-scraping trick I use on every gifting campaign:

Read more

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3. We may run out of Base44 codes at any time. Your code is only secured once you claim it.

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Here are 5 new marketing moves I can’t stop thinking about:

#1

Hiring a “really bad photographer”

Iceland’s main airline just posted a real job opening looking for the WORST photographer alive.

They want to prove that bad photos of Iceland don’t exist.

The gig: Go to reallybadphotographer.com (cool domain), upload your worst photos, and if you’re bad enough → you win a 10-day trip to Iceland, $50K, and your “photos” in a global campaign. Applications open until April 30.

It went so viral on Instagram that they had to release an official statement clarifying it’s NOT a joke 😂

The marketing idea is genius:

That’s a brand awareness campaign AND a confidence flex in one post. It also ties into the hiring-to-go-viral playbook → every job post can be a free ad if you treat it like one.

My take: Pick the one thing your product does 10x better than anyone and build a public “prove us wrong” contest around it.

#2

The best “X is dead” campaign I’ve ever seen

The positioning playbook I keep recommending everyone: take a public stance AGAINST something everyone is already tired of (“X is dead”).

Anthropic did it in 2025 → AI hype marketing is dead.

Last week, a smaller company did a fantastic “X is dead” campaign for only $10,000. It generated 2 million views and thousands of comments.

I couldn’t agree more.

Here’s the ad + how to do it yourself:

Read more

Part of the tradition is being invited to a gala dinner with all the other honorees.

The room was crazy: every founder, scientist, artist, and investor you’ve read about. Dozens of people who’d built amazing things before 30.

I figured it was my only shot at that kind of exclusive access, so I spent the night running a tiny experiment. I’d find an opening in every conversation and ask each person the same thing:

I expected a mess of different answers. Hustle, network, timing, luck. The usual stuff.

But what I got was the most unanimous answer I’ve ever heard to anything:

Taste 💋

Their answer was humbling -- and impossible to argue with. After 10 years of doing marketing, I can’t think of a job where it’s more true.

Let me explain why.

Taste is the #1 unfair advantage in marketing 🧠

Since 2022, every marketing craft has been automated or commoditized. Copy, design, research, analytics, targeting. All of it is now available to anyone with a $20 subscription and good context.

The result is a sea of marketing slop that’s technically valid and emotionally sh*t. Taste is what cuts through it.

The clearest proof I have is from hiring:

I’ve interviewed hundreds of marketers at Wiz and given take-home assignments to dozens. Almost all of them use AI now. (Which is great! I do too.) The ones I end up hiring share one thing: better taste. Same prompts, same tools, but they got sharper judgment about which of the 10 AI drafts is actually worth shipping.

That’s the whole marketing job now.

The lie the marketing industry sells you ❌

The industry has been selling us the same lie for decades: “taste comes with experience”. Put in 10 or 20 years, ship enough campaigns, and eventually your gut gets sharp.

Wrong. Taste is trainable. ✅

In this playbook, you’ll get:

→ The 4 daily habits that build the taste muscle + how to start
→ 7 quick rules I’ve stolen from people who are 10x smarter than me
→ The 5-pattern framework I use to reverse-engineer great marketing
→ The Notes system I use to calibrate my taste against reality every week

Do it for 30 days and you’ll know whether a piece of marketing is going to work BEFORE it’s published.

Here’s the full playbook 👇

Read more

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Monday inspiration time!

Here are 5 genius marketing ideas I found last week ↓

#1

The 404 page that gives you an AirPods case

TestResults is a startup for automating software testing. They built the best error page on the internet:

Instead of apologizing for the broken link → they send you a gift with your name engraved on it 🎁

It’s a perfect flex for their audience. They sell a software testing product to people who love finding bugs. So when one of their users stumbles onto a broken link, that user basically IS their ideal customer. Might as well throw them a prize.

And the form’s final step is actually the smartest part:

You’ll get an extra gift if you tell them what brought you there! 🧠

It’s important because of AI hallucinations:

ChatGPT, Claude, Gemini all invent URLs. Your 404 is getting hit by AI-confused users wayyyyy more than by actual broken-link users now.

How to steal this: Turn your 404 into a gift. Match the gift to your audience (swag for developers, a free product month for SaaS users, etc). Add one bonus question asking where they came from. You’ll learn a ton about AI referral traffic.

#2

The rogue "z" that made Warmly $100K in pipeline

Speaking of mistakes:

Warmly sent an email to 83,000 marketers last week. But their cofounder Alan accidentally left a lowercase “z” floating in the top-left corner.

Marketers HATE typos.

9 of them wrote back → all of them asking about the z, none about the actual content of the email. So Warmly leaned into it. They replied with: “sorry about the z, book a demo and we’ll have more rogue letters for you 😉”. 4 took demos. 3 are in pipeline. $100K from one stray letter.

People love catching brands being slightly imperfect - it’s the strongest signal that there’s a real human on the other end.

How to still this: next time a tiny mistake sneaks into a live campaign, don’t apologize. Reply with humor, double down on the weirdness, and turn it into your CTA. In my experience, a typo will get you more replies than a perfect email ever will.

#3

Every sale needs a reason. Nostalgia is the best one.

I spotted this Pret A Manger sign on a NYC sidewalk last week:

A generic "20% OFF" is meh. But a discount with a REASON attached to it becomes a story people repeat. And nostalgia is one of the best “reasons” you can attach to anything right now.

Justin Bieber just did the same play on the biggest stage in the world, plugging his laptop into the Coachella screen to play "Baby" straight from YouTube, harmonizing with his 2009 self.

It was perfect.

The people yearn for nostalgia. I wrote about why here a while back. Y2K fashion is back and film cameras are selling out because we all want to feel 12 again.

How to steal this: Pick a year your customers loved and tie your product back to it. “Spring sale” → “The menu from the summer you met your girlfriend”

#4

The GitHub trick every product is copying now

Every developer has bragged about their GitHub contribution grid at some point. Each green square = a day they pushed code:

Now everyone is copying the format.

Habit Kit uses the same grid to help users build new habits.

Blackmagic shows it to creators for tracking their social posts.

Claude Code just added a contributions grid to their desktop app yesterday.

Why does this format keep getting stolen?

1. ✅ It’s a screenshot magnet (it gives users social currency).

2. ✅ It rewards consistency over intensity, which is the exact behavior you want in any sticky product.

3. ✅ It triggers completionism.

4. ✅ It’s instantly understood with zero onboarding, zero copy, zero explanation needed.

How to steal this: pick one behavior you want your users to do daily, and ship a contribution map for it. Works for a B2C app (daily usage), a B2B SaaS tool (active days), a newsletter platform (publishing cadence), a CRM (touchpoints logged), etc. Cheap to build, massive retention lever, and almost nobody outside dev tools is using it yet :)

#5

She turned a LinkedIn post into a $0 growth channel

Amanda Zhu took her best-performing LinkedIn post, printed it on a postcard, and mailed it to the home address of Tenali's CEO.

I love it.

The CEO probably got 200 emails that day, 40 LinkedIn DMs, a dozen retargeting ads… and one postcard. Guess which one he’s telling his team about.

And the only thing better than sending your own post printed → sending THEIRS.

How to steal this: print people their own creations and mail them. Their best LinkedIn post from last year, framed. Their top tweet on a magnet. Their most popular Substack issue printed on heavy cardstock. Services like Postpilot, Lob, and Handwrytten make this trivial to run.

See you Thursday ✌️

Tom

I don’t know your name. I don’t know your job title. I’ve never met you.

But I’m going to tell you exactly who you are in 13 sentences. And I’m willing to bet you’ll think I nailed it.

Ready? 🪄

1. You have a great need for other people to like and admire you.

2. You have a tendency to be critical of yourself.

3. You have a great deal of unused capacity which you have not turned to your advantage.

4. While you have some personality weaknesses, you are generally able to compensate for them.

5. Your sexual adjustment has presented problems for you.

6. Disciplined and self-controlled outside, you tend to be worrisome and insecure inside.

7. At times you have serious doubts as to whether you have made the right decision or done the right thing.

8. You prefer a certain amount of change and variety and become dissatisfied when hemmed in by restrictions and limitations.

9. You pride yourself as an independent thinker and do not accept others’ statements without satisfactory proof.

10. You have found it unwise to be too frank in revealing yourself to others.

11. At times you are extroverted, affable, sociable, while at other times you are introverted, wary, reserved.

12. Some of your aspirations tend to be pretty unrealistic.

13. Security is one of your major goals in life.

How many felt accurate?

If you’re like most people, at least 10.

I just gave you the exact same “personality reading” that a psychology professor gave his students in 1948. Every student got the same 13 sentences.

When he asked them to rate the accuracy from 0 to 5 → the class averaged 4.26.

Almost perfect… For a personality reading that was completely fake 🤯

This is called the “Barnum-Forer effect” 🧠

Psychics use it. Horoscopes use it. BuzzFeed quizzes use it.

The top 1% marketers in the world use it to write copy so “personal” that people actually convert, stick around, and share it with their friends.

I first noticed this at MineOS, when we added a “What is your role?” box to the signup form.

It wasn’t connected to anything in the product.

But people started replying to our onboarding emails and converted more because they felt the entire platform was personalized. I’m not going to pretend that one form field 10x’d our revenue. But it changed how I think about every piece of copy I write.

This is the power of “fake personalization” 🎭

Most people think the takeaway is “write vague stuff that applies to everyone”. That’s NOT how to do it. If that’s all it took, every horoscope would go viral.

There’s a *very specific* way to do fake personalization that makes it actually work, and it has nothing to do with how clever your copy is. Once I figured it out, I started seeing it everywhere, and using it on landing pages, onboarding flows, and ads.

Today, I’m sharing my “fake personalization” playbook:

• 🧪 How to “read someone’s mind” without knowing anything about them

• ✍️ 6 copywriting techniques (with fill-in-the-blank examples) that make readers feel like you wrote it just for them

• 🎁 3 formats that do the personalization for you, without actually personalizing anything

• ⚖️ How to use it without crossing the line into manipulation

Read more

If your budget is small but your ideas are big - this one's for you. Here are 5 marketing ideas worth stealing this week.

Let’s go ↓

#1

A $3,500 stunt filled a startup’s pipeline for 3 months

Lunos is an AI startup that automates accounting.

Their pitch to CFOs:

So they hired an actual cowboy, put him on a horse, and sent him to Wall Street.

How much did it cost?

$3,500.

They got thousands of site visits, hundreds of LinkedIn comments, and word-of-mouth spreading through CFO Slack groups. Alex Mann (head of growth) said every single prospect who entered their pipeline mentioned seeing them on LinkedIn.

It worked because it wasn’t random:

They took their own metaphor and acted it out. Literally.

I call this 📝 Literal Marketing 📝 → take a figure of speech from your industry and make it physical.

Like this dress code:

Ask yourself: If you had to physically act out your value proposition in a public place, what would that look like?

That’s your stunt.

P.S. When you send images of your stunts to the press (or social) → it’s best to use images where someone is taking a photo of your stunt.

Lunos did this perfectly in The Guardian:

#2

You don’t do the stunt for the stunt. You do it for the LinkedIn posts.

Speaking of cowboys.

At HubSpot Inbound last fall, Virio (tiny AI startup) hired cowboys to walk two horses around the conference.

The horses moved too fast. The crowd was thin. There was a 💩 situation.

By every normal event metric, it flopped.

But they still got 300+ qualified website visitors and some discovery calls.

Co-founder Emmett Chen-Ran said it directly: the goal was never the stunt. It was the social content the stunt would generate.

Eric Lay (co-founder) wrote a brutally honest post about the whole thing. Instead of a $40K booth, they spent it on horses. Got more eyeballs than any booth at the conference.

I love that.

The difference between a booth and a stunt is “shelf life”. A booth works for three days. Virio’s horses are still being talked about months later. You’re reading about them right now.

If you’re going to a conference this year, ask yourself: what would make someone stop and take a photo? 🤳

I wrote a whole playbook on this - 28 ways to generate buzz at events WITHOUT a booth or sponsorship.

Worth a read.

#3

Reddit just did something big. Most marketers missed it.

Reddit killed r/all last week. It means the universal feed is gone: Every user now gets a personalized feed.

I know, I know.

“Reddit did something” doesn’t sound like urgent news. But hear me out:

Your customers already use Reddit before they buy. Threads about your product rank high on Google and AI answers.

You just need to be there.

Most marketers have no idea how to show up on Reddit without getting banned. I found a proven way to be there. Readers who tried it said it works. What Reddit just changed makes it significantly easier.

Here’s exactly what changed and what to do about it 👇

Read more

I know that sounds like a hot take from a newsletter writer, but the trend speaks for itself. In 2-3 years this will be as obvious as “your company should have a website”.

Last week, OpenAI put a price tag on what that’s worth:

They acquired media company TBPN for “low hundreds of millions”.

For context, TBPN is a live show that two guys started just 17 (!) months ago 🤯

A week earlier, Plaid ($8B) bought This Week in Fintech, a newsletter with 200K subscribers.

Same story, over and over:

• HubSpot bought The Hustle (2.5M subs) + Starter Story (800k subs)

• Semrush bought Search Engine Land + Backlinko

• Zapier bought MakerPad

• Stripe bought Indie Hackers

• Ahrefs acquired Detailed.com

• a16z acquired Turpentine

10+ acquisitions, billions of dollars. All because a trusting audience is the most valuable asset a company can own.

But there’s a cheaper path:

You don’t have to buy a media empire - you can build one for $0 👇

I think building a media brand around your company is the biggest arbitrage in marketing right now. It makes your company look 10x bigger than it actually is. It makes people trust you before they ever talk to your sales team. And it costs almost nothing compared to what these acquirers paid.

I’ve actually done it twice before:

At Wiz, we built a podcast that became #1 in cloud security using a tactic that takes us maybe 2 hours a month. I built this newsletter to 82,000+ subscribers with no team. Both on the side, almost no budget.

What if your company was THE media brand in your industry?

(It’s easier than you think.)

My practical “media empire” playbook 🎁

Let’s build a media empire from scratch.

I put together the most comprehensive guide I’ve ever written on this:

50+ real examples to copy, trade secrets from Wiz and Hubspot, the exact tactics I personally used, and a step-by-step guide you can start executing today with a single person and ZERO resources.

Here’s what you’re getting:

• 📡 Database of 50+ examples: companies running media empires in 2026 (with exactly what each one built and how)

• 🧲 The Substack growth hack that your company blog will never have

• 🤝 How to get the biggest names in your industry to create content for your media brand, for free

• 📈 How to 10x your content output with one writer and zero AI (a tactic I accidentally discovered while working with HubSpot)

• 📘 A step-by-step playbook for launching and growing a media brand with one person

Read more

(I was home all week)

KitKat posted an “Official Statement” confirming the theft.

That post lit the whole internet on fire.

Within 48 hours, every major brand on social media was posting their own “Official Statement” ↓

Domino’s sent condolences (and announced their new Kit Kat pizza).

Dr. Squatch pitched chocolate-scented soap (”we have 12 TONS of ingredients btw”). Picsart confirmed their app “cannot hijack trucks”.

DoorDash, RØDE, Ryanair, KFC, McDonald’s... the list is still growing.

KitKat’s social team leaned in even harder and launched a “Stolen KitKat Tracker” where you can check if your bar is from the missing batch.

The truck is still missing.

Every “marketing guru” got this wrong ❌

I’ve seen dozens of posts about this in the last week. All saying the same recycled lessons:

• “Don’t be afraid to show vulnerability!”

• “Join the conversation!”

• “Position yourself!”

I hate this advice. Try walking into a Monday morning meeting and saying “our strategy this quarter is showing vulnerability”. Your boss will kick you out the door.

I’ve been doing marketing for 12 years. I think the reason Kitkat went viral is way more specific, and way more useful:

KitKat gave everyone a “job” to do 👏

Think about it:

1. 🍫 KitKat played the “victim”. Their tone was serious, which created space for everyone else to be funny.

2. 🪞 Other brands became “suspects”. The “Official Statement” format was so simple that any social media manager could copy it in 10 minutes and plug their own product.

3. 🔮 Regular people became “detectives”. Sharing screenshots, tagging brands, speculating who did it, etc. When the tracker launched, they also had a game to play.

Everyone on the planet had something to do!

That’s why it spread the way it did.

Same pattern every time something truly blows up. When Duolingo “killed” their owl, users had the “job” of figuring out what happened, other brands posted RIP, and Duolingo kept dripping cryptic updates over days.

When your audience has a “job” → they do your marketing for you.

How to copy this for your next launch 🧪

Ok enough theory. Here’s the actual playbook for your next big announcement:

1. 🍫 The 4 “jobs” your audience needs before anything spreads (with examples for all types of businesses)

2. 📱 A copy-paste social media sequence for staging a mystery launch from scratch, day by day

3. 🐣 The small brand version how to use this playbook with 400 followers and zero budget

4. 🚨 What happens when you DON’T give people a “job” how a $300M startup nearly killed itself last week by doing the exact opposite of KitKat

You’ll finish this article knowing exactly how to run a viral stunt -- what to post, when to post it, who to partner with, and what to avoid.

Read more

If you need to reach tech people, here’s the thing: they don’t see your ads. Ad blockers, LinkedIn fatigue, banner blindness - they’ve tuned it all out.

But they read TLDR. 6 million tech professionals subscribe to these daily newsletters because they actually want them. You can sponsor any of their 12 newsletters (AI, DevOps, Marketing) and reach people who are actually reading (including me).

Open rates are 40-48% and they write the ad copy for you.

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Every Thursday at 12PM ET, I run a live Q&A for paid subscribers.

They can ask me anything: Marketing, growth, careers, launches, strategy, weird stuff.

Some of the recent questions were too good to keep behind the paywall, so here are my favorites (lightly edited for clarity and brevity).

How can I make a boring B2B product interesting on social? 😴

You don’t make the product interesting. You make the person interesting.

I was marketing a privacy-tech startup. Privacy is, objectively, not exciting. So I stopped trying to make it exciting and built campaigns celebrating Data Protection Officers (the humans doing the work) instead of the product. It outperformed everything product-focused we’d tried. I wrote about this here.

Think about why it works: A General Counsel who gets publicly celebrated as the unsung hero keeping the company out of legal trouble? That person 100% shares it. Their whole network sees your brand.

Praise the person. They’ll do your distribution for you.

Should I use LinkedIn automation for lead gen? 🤖

No. It’s all spam and everyone can smell it. Do inbound instead.

Here’s the playbook:

1. Send connection requests to your target audience with no welcome message. About 100/week is the safe max. Post daily about your niche. Don’t mention your product. Just share what you know about the problem it solves.

2. When someone engages with your content, THEN message them. Personally. Thank them for the comment, mention your product briefly if it fits.

Outbound LinkedIn is chasing strangers. Inbound means warm people are coming to you. The conversion rates aren’t in the same universe.

What’s the #1 thing to look for when sponsoring podcasts or newsletters? 🎙️

Does this creator actually USE the products they promote?

Check their past sponsorships. If the ad reads are personal, with their own experiences and real opinions, that’s who you want. If it reads like a script they saw five minutes before recording, pass.

That’s my best filter.

How do I build hype while still in stealth? 🤫

Lean into the mystery. It’s more interesting than a product demo anyway :)

1. Countdown teasers. Post every day. “19 days...” Then 18. Then 17. Humans love countdowns.

2. Buy the launch date as a domain (like 01-19-2026.com). Put a countdown timer, email capture, and maybe a raffle on it. Point all social traffic there.

3. Send the website or launch video to 20 influencers early. Don’t ask them to share it. Ask “may I get your feedback?” They feel invested before you ask for anything. And some of them will share it anyway, because people love leaking things they got early access to.

4. Vibe-code a .rip website for the problem you’re solving (as if it’s about to die) - with a graveyard of previous solutions. Great example here.

5. Censored content. Take a selfie with your cofounder, their face blurred, caption like “Building something huge with this person. Can’t say who yet.”

   

How do I get bold marketing ideas past risk-averse leadership? 😤

Win small first. Then swing big.

80% of your energy should go to safe, visible wins. Hit your numbers. Make your boss look good. Stack a track record of being right about small things.

Then use the other 20% to push through the bold thing. When you’ve been right about the small stuff, people give you room. Lenny Rachitsky wrote a great piece about this that I keep coming back to.

Most marketers pitch the risky idea before they’ve earned any trust. In my experience, that’s exactly why it dies.

Trust is like a currency - earn it first, then spend.

I have to rename my brand. How do I relaunch? 🔄

Treat it like a second launch. You literally get a second first impression.

Add “[formerly X]” temporarily so existing customers don’t get lost.

Then squeeze the rebrand for everything it’s worth. Document the process publicly: why you’re changing, the logo options you considered, the decisions you made. People love behind-the-scenes content. This alone gives you weeks of organic posts and humanizes the brand more than any campaign could.

How do I grow a job board with no budget? 📋

Three tactics:

1. Pinned spots for shares. Offer hiring managers a pinned spot on the board if they share it on LinkedIn. A little tacky, but it works because it’s a fair trade.

2. Logo grid graphics. “These companies are hiring engineering leaders right now” with a grid of recognizable brand logos. Gets 10x the engagement of a standard job-post link. I’ve seen this pattern work over and over. The logos are social proof that does the selling for you.

3. Undercover Reddit stunts. Post a spicy story about someone starting a new engineering leadership role. Someone in comments asks how they found it. OP links to your board. Sounds guerrilla because it is. I wrote about it here.

How do we grow a screen time blocker app with zero budget? 📵

Show up where the conversation is already happening.

I actually looked this up while answering this question live. Found a tweet about doomscrolling from that same day with 37,000+ engagements and thousands of people publicly saying “I have this problem”.

Those are your customers.

Your team needs to be in these conversations from personal profiles. When a post about phone addiction goes viral (and they do, regularly), be in the comments. Don’t pitch. Be useful. Mention what you’re building only when it fits the conversation.

P.S. Here’s how to find those conversations in real-time.

What’s the biggest mistake marketers make when pivoting? 🎯

Staying vague on purpose.

When a company pivots, leadership tries to keep messaging broad so they can pivot again if needed. They hedge. They use words that could mean anything.

The problem: a pivot is already confusing for your market. Vague messaging on top means almost nobody understands what you actually do now.

Pick one promise and commit to it. If you’re wrong, you can pivot again. A clear wrong bet teaches you what doesn’t resonate. Vagueness teaches you nothing because you can’t measure a reaction to something no one understood.

Gated or ungated content for lead gen? 🔐

Simple filter:

If it’s deeply tactical and hard to find elsewhere: gate it. People will trade their email for something they can’t Google.

If sharing it would make someone look smart: ungate it. The reach and brand awareness is worth more than the email addresses. When someone shares your content to look smart, they’re doing your marketing for free.

How should I upgrade my CV for a Head of Brand role? 📄

Three things:

First, make your most recent title match the role as closely as possible. If “Digital Media Lead” can honestly be reframed closer to brand, change it. Hiring managers (including myself) pattern-match titles before they read anything else.

Second, don’t put too much focus on metrics. Attribution in brand work is messy and everyone knows it. List actual projects with hyperlinks instead.

Third, and this is the best move for brand roles specifically: redesign your CV in the company’s brand colors. Someone did this for Spotify and it went viral. It shows taste, effort, and the exact skill they’re hiring for, all in one.

How to come up with content ideas without getting stuck? 🧠

Lurk on Reddit 24/7. Seriously.

Find the subreddits where your audience hangs out, and see what they talk about, complain about, ask about, argue about. That’s an endless stream of content ideas because it’s what real people actually care about right now.

Every post that gets 500+ upvotes in your niche is a content idea someone already validated for you.

How to do marketing in an industry where hype destroys trust? 🏦

Ask questions instead of making statements.

“What would happen to your family’s lifestyle if you couldn’t work for 6 months?” is just a question. But the person reading it will probably think about disability insurance for the next 20 minutes without anyone telling them to.

That’s the whole game in trust-first industries (finance, legal, healthcare, consulting). You don’t manufacture urgency. You surface a concern they already have but haven’t put into words yet. Once someone answers that question in their own head → they’ve basically sold themselves.

Three things I’d build:

1. A calculator. “Are you on track for retirement?” They discover the gap themselves. You didn’t tell them anything. The data did the selling.

2. “A client asked me...” posts on LinkedIn. “A client inherited $500K last month and had no idea what to do first.”

3. Client stories with no moral. Share what happened. Don’t say “this could be you.” Just tell the story and stop. Let the reader draw their own conclusion.

Best advice for launching a first product? 🚢

Waitlist + manufactured exclusivity.

Start a waitlist. Promote it hard. Make the product invite-only at launch.

Once you have 1,000+ signups, DM creators in your space: “Over a thousand people are waiting for this, but I’d love to give you early access in exchange for feedback.”

You don’t really need their feedback. You need visible people using your product. Once they’re in, they feel like insiders. “I got early access to this thing everyone’s waiting for” is content they want to post. You turned your launch into their social currency.

How do I market a Voice AI widget for websites? 🤖

A few ideas for your product:

1. Record a split screen. Your widget vs. a traditional contact form. Same question. Widget answers in 8 seconds. Contact form: still waiting 3 days later. That’s your entire pitch in one video.

2. Find bad checkout experiences and fix them publicly. “We added our AI to [industry]’s worst checkout flow.” Before/after. Tag similar companies. This works because you’re giving them free value and calling out a problem they know they have.

3. Hire voice actors on Fiverr to create funny conversations with your AI. Ridiculous 2am requests. People share funny stuff.

4. If you’re bold: pick a customer’s website, install your agent, and stream a live dashboard on X showing every sale it closes over 24 hours.

And install it on your own site first. If you don’t trust it enough to put it front and center on your homepage, why would anyone else?

Should I create a new category or compete in existing ones? 🗂️

I’d say compete (99.9% of the time).

Category creation takes years, costs a fortune, and confuses your market. Most startups die before it pays off.

“It’s like X but for Y” or “It’s X without the annoying Z” works because people need somewhere in their brain to file you. Give them that familiar drawer to put you in. Once you win, the new category shows up on its own. Customers start describing you differently. Analysts pick it up. But that happens after traction. Always after.

Good example: white chocolate isn’t technically “chocolate”. It’s sweet cocoa butter. But when it launched in the 1950s, the makers didn’t try to create a new category.

They called it “chocolate” (familiar) and added “white” (different). That’s the perfect move: state what you ARE using language people already know. Then add what makes you DIFFERENT.

How do I get more value out of speaking at events? 🎤

The talk itself is maybe 10% of the value.

Get someone following you around with a camera. Have conversations with known people at the event. Being a speaker makes you the event’s superstar automatically so most people would agree to talk. After a minute of chat, ask for a photo.

Every photo can then become a LinkedIn post. Tag them → their audience sees you. One day at a conference can give you weeks of content. The ROI is in the networking documentation, never the keynote itself.

How do I repurpose old webinar recordings and eBooks? ♻️

Rename them.

• “Webinar recording” → “Mini-course” or “Masterclass”

• “eBook” → “Playbook”

Split the webinar into individual lessons. Now it’s a course.

How to get a good testimonial from a customer? 💌

Timing is everything.

Ask them for a testimonial when they’re at ✨ peak happiness ✨ with your product.

The best way to do this: set up an automation that captures a success moment inside your product (first big win, milestone hit, goal reached) and triggers an email celebrating them with a gentle ask for a review.

The email copy should celebrate their achievement first, then ask. “You just hit [milestone], that’s amazing. Would you mind sharing a quick review?” People are far more likely to write something genuine when they’re already feeling good. You can also offer a gift card if budget allows. I wrote more about this here.

What will startup marketing look like in 2026? 🔮

Here’s what I see:

1. AI makes content free to produce. So the market floods with average stuff. The companies that publish less but make it weirder and more personal will own attention.

2. Founders who show their face and tell the truth about building their company will get more attention than brand accounts. Your face is your best ad.

3. Your employees’ LinkedIn accounts are also worth more than your brand account. Give your team posts to share. Make graphics about them. Let them take the credit.

4. Physical marketing is coming back. Everyone’s in the same digital channels with the same AI content. A handwritten note to 50 prospects will probably outperform your paid social budget because it’s surprising.

5. The smartest positioning move right now: go against the AI wave. While everyone screams “do more faster” → say “think deeper, make better stuff.” That’s where the loyal audience is.

6. Mini-tools will replace free trials. Give away something tiny that solves one problem. Just like my favorite mantra: get the user before your competitor gets the email!

7. And the boring stuff still wins. Good emails. Referral programs. Fast landing pages.

These came from one hour of live Q&A. Paid subscribers get a seat every Thursday at 12PM ET. Bring your weird and personal questions to the next one:

Join the next Q&A

See you inside ✌️

Tom