How do you do LinkedIn outreach to local business owners?

A founder running a local business directory told me his whole playbook in two sentences.

"Hey, we just launched a business directory. You can add yourself to it for free. Let me know if you want to be added to it. That's it."

He sends about 10 a day. Two out of 10 say yes. That's roughly two new listings a day. His upsell is a $20 a month highlighted listing.

What should I fix before I send a single request?

Your profile. Your LinkedIn is a sales page. Posting is secondary.

• A quality banner.
• A quality headshot.
• A clear title that states the offer, something like "[State] media brand owner, three media brands covering all corners of the state."
• A description of what you do.

Here's why. When a decision maker sees your request, they think, who is this? They click, see a media brand owner with tens of thousands of local readers, and think, I want to market to those people. Why would I not add this guy? Make accepting a no-brainer.

Then add people. I try to add 20 or 25 people almost every day in the space I'm going after. About five big, legit people a day add me back. Once we're connected, I can message them about things later.

It compounds. Mutual connections make every new request look better: he knows this guy and this guy.

Watch the titles. With franchise brands, people list themselves as owner or founder when they own one franchise location. If you want corporate, check before you message.

What's your version?

1. Build a prospect sheet. Sourced and deduplicated. Owner or founder first. I prefer $1M+ companies, but local relevance and a reachable decision maker matter more than a revenue guess you can't back up.
2. Send personal connection requests under 200 characters.
3. Offer two free things: claim your WilCo Guide business page, and a free owner interview.
4. Track it: the evidence link, status and next follow-up date for each person.

Who is actually on LinkedIn?

Not most small businesses. The bigger players and their marketing teams are. That's where $1,000 or $2,000 a month partnerships come from, because to a regional player that's nothing.

I think real success on the advertiser side comes from getting in front of the big players, not the coffee shop or the insurance agent with two employees. My split: Twitter is for entrepreneurs, LinkedIn is for corporate people. If you're selling ads or services like running someone's Meta ads, that's LinkedIn.

What if nobody answers?

It happens to me. I've friended and messaged so many owners of local media companies, my consulting prospects, and nobody responds. I suspect they don't even see it. I think the close rate would be shockingly high once they understand the offer. The problem is getting in front of them.

My answer is to mix channels:

• In person. An industry conference with 100 to 150 people from that world should be a gold mine of warm leads.
• Instagram DMs. A salesperson I work with gets way more local ad sales from Instagram DMs than from cold email.
• A named list. A peer suggested building a list of 50 to 100 named companies with a tool like Apollo, and asking each new client for warm intros.

Can I automate it?

Not the LinkedIn part. No bulk scraping and no automated LinkedIn messaging; LinkedIn's terms forbid those. We send personally from our own accounts. Software can help build and track the list.

How do you get featured people to share your content?

Put them on a list. A peer of mine picked 50 people himself and emailed each one: I'm adding you to the top 50 most connected people in Austin list. What do you want me to write up about you?

He published the full article and one post per person. Each person shared the group article, then their own post. Two shares per person, and it can all be done digitally as one extra step on top of interviews.

Custom outreach beats templates, in my experience. I build custom videos and even websites for influencers and prospects. People respect that you took the time.

What about cold email?

An operator I talked to sells a $6,000 a month service almost entirely through cold email, and his emails are long on purpose.

"Everybody sees short emails and they just assume it's junk and they delete it. If you do a long one, it stands out."

That goes against the standard short-email advice. I'm not sure it transfers to every offer, but it's worth testing an angle like that.

The simple cold email setup another publisher uses: pull emails with a tool like Outscraper for the industries you want (dentists, insurance agents, med spas), then send through SmartLead. Cold email generally has a low response rate, so it's not my ideal.

What I'm working on instead, early days, is hitting the same person everywhere. Find out who owns the med spa. DM them personally on Instagram, DM the business, and friend-request them on LinkedIn. My rules for cold email itself are in whether cold email works for local ad sales.