You found the ideal buyer. Their company is the right size, they have the exact problem you solve, and their title matches your target perfectly. Then you check LinkedIn and find their messages are disabled. No InMail, no connection requests. The front door is locked, and most freelancers stop there.
Why the Side Door Works Better Than Persistence at the Front
Tony Hughes’ Combo Prospecting framework argues that modern buyers have trained themselves to filter out any channel that becomes too noisy. Email, LinkedIn DMs, and cold calls have all crossed the noise threshold for senior buyers. The solution isn’t to be louder on those channels, it’s to find the channels where the buyer is still reachable because not everyone has found them yet.
Side-door channels work for a specific reason: they require you to show up as an engaged member of the buyer’s professional community, not as a vendor seeking access. That positioning shift is not cosmetic, it changes what the buyer infers about your intent, your credibility, and the value of engaging with you.
Channel 1: Newsletter Reply
Many buyers who lock down LinkedIn maintain personal newsletters or write on Substack, Beehiiv, or company blogs. Newsletters invite replies by design, the reply-to address is usually the writer’s direct inbox.
The etiquette: your first reply must be purely substantive. Pick one specific point from the newsletter and extend it, question it, or add a data point they might not have seen. Do not mention your service, your company, or why you’re reaching out. Just engage with the ideas.
If they reply to your reply, which happens frequently, because newsletter writers love readers who actually engage, you’ve opened a real conversation. The second exchange is where you can briefly mention what you do if it’s genuinely relevant: “Interestingly, this connects to something I’ve been working on with [type of client]…” Not a pitch. A connection.
Three to four exchanges in, if there’s a natural fit, you can say: “This would actually be worth a proper conversation, would a 20-minute call make sense?”
The newsletter reply is the highest-trust side-door channel because it bypasses all spam filtering and delivers your message directly to the buyer’s personal inbox. The tradeoff is it requires the most patience, you can’t use it for a pitch in touch one, or you’ve burned the channel permanently. One genuine conversation is worth ten ignored cold emails.
Channel 2: Podcast Comment
When a buyer has appeared as a podcast guest, the episode lives on the show’s platform (Spotify, Apple Podcasts, or the show’s own site) and sometimes on YouTube. Many shows have community features, comments on YouTube, discussion threads on the show’s Substack, or dedicated Discord/Slack servers for listeners.
The entry: engage with the specific episode content. Reference a moment in the interview with a timestamp if the platform supports it (“At 18:40 when you talked about X, I think there’s a counterargument worth considering…”). This specificity proves you actually listened and gives the buyer something real to respond to.
YouTube comments work particularly well for technical or educational podcast episodes where the buyer appeared as an expert. A high-quality comment on their episode often gets a reply from the guest because they’re monitoring their own appearance. That reply opens a conversation you can move to email.
Channel 3: Conference DM
Industry conferences, in-person and virtual, create temporary community spaces where all attendees can message each other. The shared context of being at the same event makes outreach feel like networking rather than cold contact.
Before the conference: identify which buyers are speaking or attending. Most conferences publish speaker lists and some publish attendee lists or have official apps with attendee directories.
During or immediately after a session they participated in: DM them via the conference platform referencing the session. Keep it conversational: “Your point about [specific topic] during [session name], I see that differently from my work with [type of company]. Would be curious to hear more of your thinking.”
After the conference: the window for follow-up on conference connections is 5–7 days. Beyond that, the shared context fades and the message starts to feel like a belated cold outreach rather than a follow-up from an event.
Channel 4: GitHub Message (Technical Buyers Only)
For CTOs, VPs of Engineering, Staff Engineers, and technical founders at developer-focused companies, GitHub is a genuine professional presence. Many maintain public profiles, contribute to open-source projects, and have public email addresses or GitHub Sponsors profiles.
The appropriate use: if the buyer has open-source projects or contributions relevant to a technical problem you solve, you can engage via repository issues, discussions, or, if they’ve published their email publicly on GitHub, direct email referencing their GitHub work.
The etiquette here is strict: never message a developer on GitHub about a business problem that has nothing to do with their technical work. The channel only earns its place if you genuinely understand their technical context and have something specific to contribute. A developer buyer who receives a pitch on GitHub from someone who clearly hasn’t read their code will find it more intrusive than a LinkedIn message, not less.
The Unified Rule Across All Four Channels
Every side-door channel shares one requirement: the first touch cannot be a pitch. The side doors exist because the buyer has withdrawn from channels that have become pitch-saturated. Walking through the side door and immediately pitching confirms their instinct was correct to lock the front door.
The universal structure: (1) engage genuinely with something they’ve created or said, (2) add value to that specific conversation, (3) establish familiarity across two to three exchanges, (4) only then introduce the professional context of who you are and what you work on. That sequence takes longer than a cold email, but it produces a conversation partner rather than a skeptical recipient, and conversation partners become clients.
