Should I hire someone to sell newsletter ads before selling them myself?

Hiring help before you've done the process yourself costs real money for nothing. I have the $16,000 receipt. That's roughly what I paid a cold-calling contractor to sell ads for my insurance newsletter, and I got nothing.

Why sell the ads yourself first?

Doing the hard selling personally is what makes you a good manager of salespeople later. You learn the objections, the price that closes, and which businesses say yes.

My advice to a young operator was to pick one new newsletter and do every step himself, all in: the Meta ads, the calls, the objections. Don't hire anybody until you've done it. Then you can question them better, because you'll know.

A guest on my podcast put it well: you have to be comfortable doing sales yourself, because it's a completely different skill set, and it's what separates local outlets that sell well from the ones that don't. Primarily we've got to be making money, and most people in local media aren't good at it, including me.

Is my problem really sales?

Probably. It's mine. I cannot stress enough that sales is why we don't have more advertisers. The audience is there. Content is a bigger-picture issue, but short term, sales is what makes or breaks this.

"Literally everything could change with one right sales hire."

In August 2026 I put it bluntly to my team: nobody is proactively doing sales. We were passively hoping advertisers would come to us. That works later, when you're bigger and have been around longer. It doesn't work in the next three months.

The big print magazine franchisors run the same basic model I do, and my version costs about 90% less with better engagement. The one thing they have that I don't is a killer sales system, because they come from direct-sales backgrounds. Their messaging, positioning and sales are dialed in.

Does hiring a salesperson actually move revenue?

Once you know the motion, yes. On my show, the best-documented hire that moved money was a salesperson, not a writer.

• One operator hired a commission rep and got to $25,000 a month.
• Another made very little for four and a half years, hired a salesperson around 22 years old, and hit $25,000 in a month.
• A guest made about $30,000 in the first half of a year, hired a salesperson, and finished the year around $100,000. That one is third-hand and approximate.
• A publisher I know had a big audience and little revenue for about two years. She's a writer, not a salesperson. Someone told her to find a relentless salesperson who'd do what she wasn't willing to do. About six months after hiring one, she went from a few thousand dollars a month to roughly $40,000.

Those are other operators' results, as they told them. Her offer wasn't special, either: newsletter ads, directory ads, Instagram story activations. Nothing I couldn't sell. The difference was one good, full-time salesperson. Another operator at that level just does all the selling himself and goes after it.

Revenue tends to snowball after that. Once you get to around $100,000 in sales, you know where the baseline is, you feel more confident, and you push harder.

Who should my first hire be?

I frame staffing a market three ways: AI only (which most people don't think will work), a paid editor in the town, or an entrepreneur who lives there and for whom that market is their own business. Anything that needs local taste, presence or a face at an event goes to a local human. The rest goes to agents. If you've already sold and sales is the bottleneck, the evidence points to the salesperson before the writer.

At bigger scale, the right hire opens bigger buyers. Someone with national or enterprise sales experience could pitch national realtor brands or custom home builders, not just small local shops.

Can a VA cold-call for me?

In theory it makes the most sense on cost, since they could smile and dial. I'm skeptical. In insurance or mortgages, maybe one in a hundred people is already thinking about buying, and you can convert them. Nobody wakes up thinking they want to advertise in a local newsletter. It's not an obvious purchase.

That leaves two problems: cost, and finding somebody who'd do it for that cost and be good.

Where do I find a salesperson?

Post the job to your own newsletter list and Instagram first. One operator on my show posted to her own list and hired for fit. Another drew about 50 applicants and sorted on attitude.

Job boards haven't worked for me. I posted on Indeed asking applicants to send a Loom or do something to stand out, and nobody did. About seven people have told me they want to do this, and not one followed up. My best lead came the other way: a retired newspaper ad salesman messaged me on Facebook because he was bored and wanted to sell for commission. Winners like that come from networking and relationships.

Have an offer ready. On my established Williamson County brands, I'd give a seller 50% of every ad they sell. I estimate somebody good could sell $200,000 there, which is $100,000 for them, quickly, because the brand already exists.

Not Upwork, for a committed role. Freelancers there are gig workers who don't want one employer, and nobody strong on my team came from Upwork. More in Upwork or a managed VA firm and paying a commission salesperson.

What's the one sales habit that matters most?

Follow-up. I come from insurance, where sales is everything, and it's all about follow-up.

I don't always follow my own advice here. I once forgot to follow up with an agency that showed interest. Whoever does the selling, you or a rep, has to build relationships with businesses and partners and keep following up.