Michael Ashley

AI pricing tools promise the one thing every business owner wants: optimized margins on autopilot. Here's what most people adopting them don't realize. The same tool quietly setting your prices may be coordinating them — with your competitors. Algorithmic collusion is becoming the new antitrust frontier. When multiple businesses feed their pricing decisions to the same AI, the algorithm can converge on prices no one explicitly agreed to. You never shook hands in a back room. But regulators increasingly aren't convinced that distinction protects you. For a small business owner, that's two kinds of risk wrapped into one tool. Legal risk — you may be participating in coordinated pricing without ever intending to. Reputational risk — and this is the one founders underestimate. "We let the algorithm decide" is not a story your customers, your press, or your board will forgive. Your brand is your promise. Outsourcing pricing to a black box you can't explain is a promise you can't keep. I'm not anti-AI. I build with it every day. But I've watched founders adopt powerful tools the same way for 25 years: fast, blindly, and without asking who's accountable when it goes wrong. The strategic move isn't to avoid AI. It's to stay the decision-maker. Three questions worth asking before you turn any pricing tool on: - Can I explain, in plain language, how this sets my prices? - Does it rely on competitor data I shouldn't have a window into? - If a regulator or a reporter asked me about it tomorrow, would my answer hold up? AI should amplify your judgment, not replace your accountability. The leaders who win the next decade won't be the ones who automated the most. They'll be the ones who stayed responsible for the decisions that actually mattered. For those of you leading high-stakes initiatives: where are you drawing the line between what AI gets to decide and what you stay accountable for? …more

Founders spend weeks building campaigns. Then discover the message doesn't resonate. I've learned to do the opposite. Test the message first. 5 conversations will teach you more than 50 hours of campaign planning. …more

When a public engagement gets scrutinized, everyone assumes it's about the price. It rarely is. I've watched this play out across organizations for 25 years. A consultant can be delivering enormous value — and still lose the room. Not because the work is bad, but because the people footing the bill can't see how the work connects to the mission. That's the gap that erodes trust. And it's especially dangerous in public initiatives like Measure M, where the audience is already hurting from job losses and watching every dollar. Here's the part leaders miss: consulting at this level is genuinely an art. You can't compare a complex transformation engagement to a landscaping contract with a fixed scope and a visible result. The value is real, but it's harder to see — which makes communication part of the work, not an afterthought. Value delivered in private isn't the same as value understood in public. So the lesson isn't "charge less" or "do more." It's this: When stakeholders can't see progress toward the goal, they fill the silence with doubt. The fix is rarely cheaper. It's clearer: - Tie the work back to the stated mission, every time. - Show progress in terms the public actually cares about, not internal milestones. - Treat transparency as a deliverable, not a courtesy. Trust isn't built by being the lowest bidder. It's built by letting people see how the work moves the mission forward. For those of you leading high-visibility, publicly-funded initiatives: how do you make progress legible to people who only see the invoice? …more

Most founders are more compelling in conversation than they are in writing. Why? Because when they write, they try to sound professional. When they talk, they sound human. Your audience wants the second version. …more

I've worked with hundreds of founders through my accelerator and peer groups. And when I look at why their marketing isn't converting, it almost always comes down to the same thing. They built the campaign before they validated the message. Here's what that looks like in practice: they spend two or three weeks building out a content calendar, designing assets, writing emails, setting up scheduling. Then they launch. And then they find out — through low engagement, no clicks, no replies — that the message doesn't resonate. All of that work, wasted. Not because the campaign was bad. Because the message was untested. The fix is simpler than most people think. Before you build a campaign, send 5 DMs or have 3 sales conversations using your core message. Pay attention to the responses. Do people light up? Do they ask follow-up questions? Do they forward it to someone else? Or do they politely change the subject? What you learn in those conversations is worth more than any A/B test you'll run later. Real humans responding to a real message in real time will tell you everything you need to know about whether your campaign is worth building. Build the conversation first. Build the campaign second. Book a free audit with me — I'll look at your current messaging and tell you exactly where I'd focus first. …more

What's the most expensive assumption you've ever made about your customers? Not the biggest mistake. The assumption you believed for months that turned out to be completely wrong. Mine cost me nearly a year. Curious what yours was. …more

I've been running founder peer groups for years. One thing I see constantly: founders who've done customer interviews but still don't know if their idea is viable. It's not because they skipped the research. It's because they asked the wrong questions. There's a difference between asking "Would you pay for this?" and asking "Walk me through the last time you dealt with this problem. What did you do?" The first question gets a guess. The second gets a story. Stories are what you can actually build on. This is the whole premise of The Mom Test — a book I recommend to every founder I work with. But even founders who've read it revert to opinion-seeking questions the moment they're in a real conversation. So I built MomTestQuestions.com. You put in your product and your target customer. It generates a set of behavior-based interview questions you can use in your next discovery call. Free. No account needed. If you're still trying to figure out whether you're building something people actually need — this is a good place to start. DM me if you want to talk through what you're hearing in your interviews. Happy to help you make sense of it. …more

AI made expertise abundant. It did not make trust abundant. For years, expertise was a competitive advantage. If you knew something others didn't, you could build a business around it. Today, anyone can ask Chat and get a decent answer in seconds. That changes the game. The question is no longer: 'What do you know?' The question is: 'Why should I trust you?' Trust comes from consistency. Experience. Judgment. Reputation. People don't hire advisors, consultants, founders, and experts because they have information. They hire them because they trust how they think. That's why I believe trust is becoming one of the most valuable assets in the age of AI. Expertise may be abundant. Trust is still scarce. …more

In every founder peer group I run, someone says some version of this: "I know I need to be posting more, but I don't want to sound like I'm just selling all the time." I hear this constantly. And I understand it. Nobody wants to be that person. Here's what I tell them. Salesy content isn't caused by selling. It's caused by skipping the value step. Look at your last 10 posts. How many of them taught something, shared a hard-won lesson, or gave your audience something they could use today? How many were asking for something — a click, a follow, a demo? The ratio matters more than the message. When your feed is mostly valuable, your promotional posts don't feel like interruptions. They feel like a natural next step from someone your audience already trusts. The rule I follow: for every post that promotes something, publish two that teach or share something genuinely useful. Not rephrased common knowledge. Something specific to your experience. It's not about being less promotional. It's about earning the right to promote. What's your biggest challenge when it comes to showing up consistently? Comment or DM me — I'm genuinely curious. …more

One audience. One message. One channel. One CTA. Run it for 30 days. Most startup marketing problems aren't caused by too little effort. They're caused by too many simultaneous experiments. …more

The revolution of independence is starting. For most of my career, building a successful business required assembling a company. Employees. Departments. Agencies. Specialists. Today, AI is changing that equation. One founder with expertise, good judgment, and the right tools can now create leverage that used to require an entire team. That's a massive shift. But it creates a new challenge. If expertise is no longer scarce, what is? Trust. Visibility. Reputation. The ability to consistently show up and demonstrate how you think. I believe we're entering an era where reputation becomes one of the most valuable business assets a person can own. Not because everyone needs to become a creator. Because everyone who sells expertise needs to become discoverable. Consultants. Advisors. Founders. Coaches. Fractional executives. The future belongs to people who can turn what they know into trust. That's the shift I'm watching most closely. …more

Tomorrow I'm doing a live Claude Code demo for the Inspiring Founders community — building a real app from scratch, no hand-waving. Latest newsletter has the full story: https://mashiam.substack.com/p/building-something-worth-showing …more