If you’re selling local advertising and you expect to walk into a business, give your pitch, and hear “Where do I sign?” every time, you’re going to have a pretty miserable week. That’s not how local advertising sales usually works. A lot of perfectly good prospects are going to say things like: “Let me think about it.” “Send me some information.” “I need to talk to my partner.” “Maybe next month.” “We already spend a lot on advertising.” Or my personal favorite: “Yeah, I’m definitely interested. Call me next week.” Then next week comes. You call. Voicemail. Welcome to sales. Here’s the mistake a lot of people make. They assume silence means no. It doesn’t. Most of the time, silence means the business owner is running a business. The roofer you talked to might have three crews calling him because somebody ordered the wrong shingles. The restaurant owner might have an employee who didn’t show up. The chiropractor might have patients stacked up all afternoon. The HVAC guy might be standing in somebody’s basement when your text comes through. Your postcard is important to you. It is probably somewhere around #37 on their list of things they’re thinking about today. That is why follow-up matters so much. The Fortune Is Literally in the Follow-Up Let’s say you’re selling a 9x12 postcard going to 2,500 homes. You walk into a local landscaping company and show them the card. They like the idea. The owner asks a few questions. You explain that they can lock up the landscaping category so another landscaper isn’t sitting right next to them. The spot is $200. He says: “Looks interesting. Leave this with me and I’ll think about it.” A beginner hears: “No.” An experienced salesperson hears: “Not yet.” So you follow up two days later. “Hey Mike, just checking back on that neighborhood postcard I showed you. I still have the landscaping category open.” Maybe he doesn’t respond. You follow up again. “Mike, I’m finalizing the card this week. Wanted to give you first shot at landscaping before I offer it to somebody else.”

I’m looking for a handful of entrepreneurial people who want to launch City Games in their own market this fall, and we’re building a pretty compelling way to get started. The launch strategy is built around football season and local bars. Instead of trying to introduce City Games to an entire city all at once, a publisher can start by building a network of participating sports bars, breweries and restaurants and running a season-long football promotion that gives people reasons to visit those locations, play local games, complete challenges and compete for prizes. That creates three things every new City Games market needs immediately: Players. Participating venues. Recurring advertisers. The bars get something much more interesting than another social media ad. They become part of an interactive local promotion running throughout football season. The publisher gets a natural reason to walk into bars and say, “We’re launching this across the city for football season. Want your bar to be one of the locations?” And once those businesses are inside City Games, the opportunity extends far beyond football. They can become ongoing Venue Partners while you expand into restaurants, retailers, suburban Side Quests, seasonal promotions and other local experiences. You don’t need to launch with 100 businesses. Start with 6 to 10 great bars. Build something people want to play. Then grow the market from there. City Games provides the platform, game concepts and business model. You build the local relationships and own the opportunity in your territory. If you’ve been looking for a local business you can actually build, this football season gives us a very natural starting line. Interested in becoming one of the first City Games publishers? Comment “CITY” below or message me.

Hey @Toby Shaver do you know where I could make/order some mockup samples of a 9x12 with my branding?

One of the biggest mistakes new Town Publishers make is thinking they’re selling postcards, newsletters, or games. They’re not. They’re selling something most local businesses have almost never been offered. Exclusivity. Think about the average local business owner. They run a Facebook ad. So does the competitor down the street. They boost an Instagram post. Their competitor does too. They both show up in Google search results, fighting over the same customer at the same moment. Every platform makes more money when multiple businesses compete for the same attention. The business owner pays more, the platform wins, and nobody owns the market. As a Town Publisher, you have the opportunity to offer something completely different. Instead of selling another advertising spot, you’re selling category ownership. One roofer. One chiropractor. One real estate agent. One HVAC company. One pizza place. When a household opens your Play My Town postcard, there isn’t a page full of competing roofers. There isn’t a sidebar with five other realtors. That business owns the category on that card. The same principle can extend across your entire local media ecosystem. Your newsletter. Your directory. Your City Games sponsorships. Your live events. Instead of selling endless inventory, you’re building long-term partnerships with businesses that want to own a position in the minds of local residents. That’s a fundamentally different conversation. You’re no longer asking, “Would you like to buy an ad?” You’re asking, “Would you like to become the exclusive roofer for East Grand Rapids before someone else does?” Scarcity changes everything. Business owners understand that if there’s only one available position, waiting has consequences. Once it’s filled, it’s gone until that partner leaves. That’s one of the reasons this model creates stronger relationships than traditional advertising. You’re not constantly replacing advertisers. You’re helping businesses defend a position they’ve earned.

One of the biggest prospecting mistakes is treating every local business as an equally good opportunity. They are not. Before you begin calling, emailing, or walking into businesses, spend an hour learning the territory. Define a specific area you can realistically own, such as one small town, downtown district, suburb, or cluster of nearby neighborhoods. Then identify the places where residents already eat, shop, gather, and spend money. Start by building a list of 50 strong prospects across several categories: - Restaurants, bars, coffee shops, and breweries - Home service companies - Health, beauty, and wellness businesses - Realtors, insurance agents, and financial professionals - Retail stores and family entertainment businesses - Community organizations and event venues Do not build the list entirely from Google. Drive through the territory. Visit the downtown district. Look at local Facebook groups, chamber directories, community event sponsors, and the businesses already advertising in local publications. Businesses that sponsor festivals, sports teams, fundraisers, and community events have already demonstrated that they understand local marketing. Next, rank each prospect based on three simple questions: 1. Is this business locally owned or locally managed? 2. Does it need customers from this specific territory? 3. Does it have a clear reason to participate in your first product? Your strongest prospects will usually be businesses that answer yes to all three. Those should receive your personal attention first. Finally, look for clusters. If three popular businesses on the same street participate, the fourth becomes easier to sell. If one respected business owner joins, ask who else they believe should be involved. Local business communities run on relationships, and one trusted introduction can outperform dozens of cold emails. The goal is not to contact every business in town. The goal is to identify the right businesses, understand how they fit into your local ad ecosystem, and approach them with an offer that makes sense for their market.