Running the business

Every answer 12 answers

• 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. Price each manual task across every newsletter you run, cut low-value recurring sections, and automate the rest. Writing 20 newsletters at two to three hours each is why I built my own software.

• 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 burden and whether it concentrates or fragments momentum. I favor fewer, larger, recurring customers. 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. I have five main brands but call it two priorities: the four local media brands are one thing, Texas AI Lab is the other, and my AI workforce sits under both. Attention isn't importance, exploring isn't deciding, and one shared system beats a custom setup per brand.

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

  More than people think. In the first five months my wife and I put in probably 60 hours a week combined and had nothing to show financially. The fantasy is three hours a week for $75,000 a year. It's a real business. If you're not willing to go all in, I'd tell you not to bother.

• 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 only reads for context and voice. Give every newsletter its own task with a linked doc, a checklist and source links so nobody works from memory.

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

  For a committed role, skip Upwork. Freelancers there are gig workers who don't want one employer, and nobody strong on my team came from there. Hire from places where people want one full-time job, or use a structured VA firm. For content that needs local taste or on-the-ground 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 hard selling yourself teaches you the objections, the price that closes and who says yes. Once you know the motion, a salesperson is often the hire that moves money 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 polished signup page with real pricing, leave costly commitments like the venue open, and spend money only after people sign up. It only works if you already have a way to get the launch in front of people.

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

  Notion for the CRM and business ideas, with cold prospects kept separate from warm relationships and clients. One shared mailbox for reader replies instead of aliases to the founder. Task templates with subtasks, built in one brand and copied to the rest. Spoken reviews in a meeting-note tool instead of written reports.

• 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.