How do I sell newsletter sponsorships to banks, hospitals and big regional brands?

"For bigger companies, you lose deals because your price is too low. For small companies, you lose deals because your price is too high."

This is the most counterintuitive thing in local ad sales. A bank or a hospital won't run a contract through legal for $500. $1,000 a month is unremarkable to them.

Why do big companies turn down cheap sponsorships?

Because a small contract isn't worth the internal work. If the check is $600 or $700 a month, that effort isn't worth it to a big enough client and they pass. For a big company, the only way you'll get someone there to work the contract with you is if it's $1,500 to $2,000.

Most of us walk in with a limiting mindset: "If I ask for $700, will they freak out?" With a large prospect, if they hesitate, check whether your price is too low before you assume it's too high. A commission rep I work with heard my rule for big brands: don't offer $500 a month, they'll turn you down. It needs to be two grand.

The buyer is different, too. A small business owner paying you is spending money they could have used to fix their car. A marketing person's job is to spend the budget. It's not their money, they can justify you to their boss if you have their ideal audience, and they need fresh ways to spend $30,000 a month to justify why they exist. Finding you actually helps them.

Which big organizations should I target?

"Don't go target the dry cleaner lady and her husband. Target the hospital chain, the college, the city, the visitors bureau, all the bigger industries where paying you a thousand bucks a month is not a big deal."

• Hospital systems and children's hospitals
• Banks and credit unions
• Colleges and university alumni associations
• The city, the economic development department, the visitors bureau
• The power company, water company or electric co-op
• Stadiums and minor-league teams
• Big regional retailers like a furniture destination store, or IKEA if there's one near you
• Insurance companies, including statewide insurers' regional marketing teams
• Custom home builders, big pool builders, estate planners and attorneys
• Restaurant groups with several concepts and locations, and large franchises

Regulated industries like banks and insurance are especially good. They have the money and a hard time making content people care about. You solve that. Local commercial banks check every box: they have a ton of money, want influence in the community, want to promote their clients and want to win new ones.

Attorneys could be huge. A $2,000-plus package is maybe 3% of what the heaviest legal advertisers already spend on marketing, and they'd get an owned audience instead of a rented one. An operator on one of my calls said a local lawyer spends $40,000 to $50,000 a month on billboards.

The target is businesses with a marketing department, not the owner. Truly tiny local businesses aren't ideal for postcards, magazines or newsletters. I had a handmade-soap maker sign up at $1,000 a month. Three emails a day, complaints, and more complaints after I lowered her price. I voided the contract. When a marketing department is paying, that money isn't coming out of anyone's rent.

What do big sponsors actually pay?

Deal	Price
What six-figure local operators I know sell banks and estate planners	$1,000 to $2,000 a month packages
Big-brand annual package	$10,000 to $20,000 a year
What I think a bank would pay without hesitating	About $15,000 a year
A community bank, one ad and one social post a month (second-hand, via a podcast guest)	$5,000 a month

On that $5,000 bank deal, the operator was nervous saying the number. The bank's marketing person said okay, just send it over. A bank probably spends 10 times that a month or more. I'm not saying you have to sell for $5,000, but $2,500 isn't crazy.

Mike Richardson of Kid Friendly Seattle told me on my podcast he planned to pitch the top 20 big brands for the next year with packages around $10,000.

How do I reach them?

They won't come to you. I get inbound every week, but it's usually small companies, and they don't recur. The better an advertiser is, the less likely they are to find you on their own. The people crushing this model track down the head of marketing at the power company and the university alumni association, the big spenders for whom a thousand bucks is a rounding error.

• LinkedIn. Their marketing teams are there, and that's where you get $1,000 and $2,000 a month partnerships, because to them that's nothing. A small ad form on your site brings in $100 to $200 ads. Different door, different buyer.
• Their marketing agency. The power company, the university and the 20-unit franchise often don't do their own marketing. Get in with the agency, and one person there can bring you five clients at $1,000 each. For attorneys, find the agencies that serve law firms and offer a referral reward, like a flat fee or 25% ongoing for as long as the client pays.
• Introductions. That $5,000 bank deal came through a friend's connection. The operator offered the friend 20% of whatever he got out of it.
• Networking. Go to the chamber and meet more people so you find out how to get in front of the right person.
• Plain hustle. Cold call, DM, and reply to the lead forms on their websites.

I'll admit I don't know how to get in front of a hospital system's marketing director myself. A go-getter salesperson could figure it out.

What do I pitch them?

Awareness and coverage. Bigger brands are often less fixated on conversions. A children's hospital isn't saying "if we give you $10,000 we expect 27 sales." They want to get the word out. Regional players also want regional coverage, so two or three newsletters across a region beat one small market.

For banks, exclusivity is a strong angle: only one bank gets the spot, so do they want to leave it open for a competitor? More in how category exclusivity works.

Go above and beyond on deliverables. Big partners get more than an ad: stories, social and video. One caution: you can't make a ton of videos about banks before people get annoyed. Save the heavy video for fun brands.

These partners will happily sign for a year and pay good money. They become your primary advertisers. Keep secondary slots, Instagram and in-person spots for smaller companies on top. The big ones are what keep you from needing another job.

When should I start pitching them?

Once you have the audience to back it up. Start with readers and small businesses, because you can call or DM them and they'll answer. Nobody DMs a hospital marketing director on Instagram. Around 20,000 subscribers, with real website traffic and 10,000 to 20,000 social followers, start hitting up the hospital and the big companies.

Don't jump the price too early. An operator I heard about had about 900 subscribers and planned to sell annual exclusive spots to banks at $30,000 each. The logic holds for some companies, since banks want local business owners and $30,000 is nothing to them over a year. But he also runs a lot of in-person events. I wouldn't try that price on a small audience.

My own plan in Williamson County is the opposite case. I have about 33,000 upper-middle-class, family-type readers, over 50% opens and 6 to 7% clicks. I should be making six figures in ads there. The play is annual partnerships with the bank, a big resort, the minor-league baseball team, a children's hospital and the electric co-op, at $1,000 to $1,500 a month. I still need a salesperson to prove it.

Treat big partners as a supplement, not the only plan. Get the $1,000 a month checks, and keep doing everything else too.