Running the business

Every answer 23 answers

• Do bigger customers push back less on price than small ones?

  Usually, yes. Selling upmarket feels harder but is often easier. Small customers fight a $40 increase; bigger ones shrug at $500 as long as it works. Solve a big enough problem and you can charge real money. Small clients are fine early, to learn, and at low prices I'd require quarterly payment.

• How do I cut newsletter production time without hurting quality?

  Ask what readers would do differently if an input were merely good instead of the best, and default to the fast version. Design the template once, skip per-issue polish until it's automated, and price every manual task across all your newsletters. My issues went from about three hours to around 10 minutes once software did the first 90%.

• How do I decide which business idea to pursue?

  I run every idea through three questions: can this 10x, does the math work, and can AI handle 80% of it? Then I compare time burden, custom work and whether it concentrates momentum. Short term, I pick whatever has the shortest path to income. Most effort goes to one main bet, and ideas that don't win get parked, not deleted.

• How do you run many brands without losing focus?

  Group them into a few real priorities and sell to one customer. I have five main brands but call it two priorities: the local media brands are one thing, Texas AI Lab is the other. Run one shared system across brands, hand each one to a person instead of learning it all yourself, and admit where you're spread too thin.

• How many hours a week does it take to run a local newsletter business?

  More than people think at the start. My wife and I put in probably 60 hours a week combined for the first five months with nothing to show financially. Once it's set up, a focused person can run one weekly newsletter in two to three hours a week. Setup, learning and selling are where the real hours go.

• How much equity should I give up or ask for in a newsletter partnership?

  Don't sell a big stake early in something you already know how to do. I'd rather self-fund until the list hits 5,000 to 10,000 subscribers, then give up 5% instead of 20%. When I'm the one bringing Meta ads, setup and know-how to someone else's money and effort, I ask for 30 to 40%.

• How much time should I spend on a business decision?

  Match the time to how hard it is to undo. Foundational, hard-to-reverse choices, like how your team's shared drive and naming system are set up, get real thought. Reversible ones, like where the logo goes, get decided on the spot. For a big new idea, cap the test at about a month so the downside is small and the upside can run for years.

• How should I set up QA between newsletter writers and the final editor?

  Put a QA step between the writers and the editor. An ops person checks each newsletter for mechanical errors like broken links, wrong locations and factual slips, so the editor gets work that's 99% right and only reads for context and voice. Give every issue its own task and checklist, and re-check automations after launch.

• How should a company with many brands set up shared email inboxes?

  Use Google Groups. Give each brand a shared inbox on its own domain that the whole team, and your AI agents, can read and reply from while logged into their own accounts. Assign access by role, not by person. Keep internal mail on the company domain and everything external on a brand domain. Don't share one fake login.

• How should an employee bring a plan to their boss so the boss only has to say yes or no?

  State the problem, state your plan, and ask for a yes: "The video is 40 seconds and too long. My plan is to cut it to 15. If you're good with it, just say yes." That takes the thinking off the owner. When the goal is clear, team members should be ready to do 90% of the work on incomplete information.

• Should I buy domains for future newsletter markets now, and where should I buy them?

  Buy them now. A domain costs about $11, and if someone else takes it you pay whatever they ask. I buy every domain on Cloudflare: it sells at cost and AI agents can manage it, so I change sites without logging in. Use the city plus a brand word. A .co is fine, and long names are fine because nobody types domains.

• Should I hire a virtual assistant from Upwork or a managed VA firm?

  For a committed role, skip Upwork. I found most of my good VAs on OnlineJobs.ph for about $1,000 a month, after weeding through a lot of spam. Managed firms do the same sifting for a big markup. Hire full time, know the job before you hire, and for content that needs local taste or presence, hire someone local.

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

  No. Sell it yourself first. I paid a cold-calling contractor about $16,000 to sell ads for my insurance newsletter and got nothing. Doing the selling yourself teaches you the objections, the price that closes and who says yes. Once you know the motion, one good salesperson is often the hire that changes the revenue most.

• Should I launch a product or event before I have a full plan?

  Yes. Always launch things before you make the full plans. Build the part that creates the decision, like a signup page with real pricing, leave costly commitments open, and spend real money only after people respond. A small test costs a few hundred to $1,000. It only works if you already have a way to get the launch in front of people.

• Should I pay someone to set up my first local newsletter, or just get advice and do it myself?

  For a first newsletter, pay someone to build the base layer right: the signup survey and Meta ads. Have them run it for the first couple of months, then take it over. A survey that takes me an hour or two would take a newcomer about eight hours, and it would probably be wrong.

• Should a newsletter team have separate writers and social media people, or one owner per brand?

  One owner per brand. Each person writes, edits and runs social for their newsletter, and maybe, eventually, handles local advertiser outreach. Split writing from social and nobody owns the brand's growth. It's doable because social templates exist and AI writes most of the content. Selling is the exception.

• What does "Who Not How" mean for a small business owner?

  When you hit a problem, stop asking how you'll fix it and ask who can do it for you or with you. The idea comes from the book Who Not How. For most local media owners the biggest "who" is sales: if you don't want to sell or don't have time, find someone who will, or partner with an agency and split the money.

• What kind of person should I hire for a small newsletter business?

  Hire for growth mindset and speed of learning, not specialized skill or a degree. The work is learnable. Look for people who push back, bring ideas and work AI-first. Test them on real tasks: show a faster way, then retest the next day. Slow at first is fine. Slow after being taught is the red flag.

• What tools do you use to run a multi-brand newsletter company?

  Beehiiv on an enterprise plan, so each extra newsletter costs about $10. Notion for the CRM and ideas, with cold prospects kept apart from warm relationships. One shared mailbox for reader replies. Templates built in one brand and copied to the rest, and one shared system for every site. Hard costs are small and scale well.

• When should I sell my newsletter business instead of holding it?

  Set your exit rules before an offer shows up. My goal is an eight-figure exit in about two years, not holding forever, because email, AI and media can change fast. Build a matrix of offer size against time elapsed and revenue. If an offer clears it, take the money. And brand the business neutrally so it can be sold.

• Why do business partners fail to follow through on sales, and how do I pick better ones?

  Busy, successful people say yes to the idea, then give it two hours a week, and the idea needs someone to actually sell. I've been bitten twice. Now I make sales an explicit priority before we start, pitch things that already work, check what each side gets out of it, and approach many partners expecting only one or two to deliver.

• Why do founders get stuck fixing bugs instead of growing revenue?

  Because when you build your own software, the clients who already pay you need constant fixes, and that crowds out selling. My fix: prioritize sales to fund help, protect one day a week for content, and consolidate overlapping systems so you're not fixing the same thing in two places.

• Why is my VA team underdelivering, and how do I fix it?

  Usually it's the system, not the people. Give every recurring task a time budget, put a manager in place before adding headcount, document and streamline the work before enforcing accountability, and skip monitoring software. Then keep one more person than the workload needs and cross-train everyone.