Michael Ashley

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

A lot of founders ask me how I use Claude and Radi8 together. Here's the honest answer: I don't really "use Claude" anymore. Not the way most people think. I don't write prompts. I don't paste in context. I don't explain my audience or my voice or my offers every time I sit down to create content. Radi8 handles all of that. My brand context, my strategy, my campaign plan, my voice, my proof points — it's all stored in Radi8. When Claude works inside Radi8, it already knows everything it needs to know. It's not starting from scratch. It's starting from me. The workflow: 1. Open Radi8 and pull up my campaign plan for the month 2. Pick the piece of content I'm working on — the brief is already there 3. Generate — Claude writes from my brief, my brand, my voice 4. One quick edit pass, maybe 5 minutes 5. Schedule That's it. No prompt engineering. No re-explaining yourself every session. No output that sounds like it could have come from anyone. The insight most people miss about AI content tools: the problem was never the AI. It was the setup. When the AI knows your business as well as you do, it stops feeling like a tool and starts feeling like a collaborator. That's what I built Radi8 to do. DM me "workflow" and I'll show you how it works. …more

Most founders I work with avoid customer discovery. Not because they don't understand the theory. Because it surfaces uncomfortable truths. When you sit down with a potential customer and ask the right questions, you're not just testing assumptions. You're inviting reality to challenge the story you've been telling yourself about your product, your positioning, and your market. That's hard. It's easier to keep building. Easier to refine the pitch. Easier to convince yourself that more features, better messaging, or a bigger launch will solve the problem. But avoidance has a cost. You burn months building something nobody wants. You misread demand signals. You position yourself in a crowded space because you never learned what makes you different in the eyes of the people who matter. I've seen this across four startups and dozens of advisory engagements. The founders who get traction fastest are not the ones with the best ideas. They're the ones willing to hear that their assumptions are wrong and adjust accordingly. Customer discovery is not a validation exercise. It's a correction mechanism. The goal is not to hear what you want to hear. The goal is to learn what you need to know before you make expensive decisions. That means asking questions that expose gaps in your thinking. It means listening to what customers are actually trying to solve, not what you hope they need. It means being willing to abandon ideas you were excited about yesterday. The discomfort is the signal. If the conversation doesn't make you rethink something, you're probably asking the wrong questions. After 25 years of building and advising startups, the pattern is clear. The founders who embrace this discomfort early save themselves time, money, and wasted opportunity. The ones who avoid it pay for it later in slower growth, misaligned product decisions, and go-to-market strategies that never gain traction. What assumption did customer discovery force you to abandon? …more

On June 11 at 10:00 AM, I'm hosting a free live workshop where we'll use Claude Code to build and deploy real applications — not talk about it, actually do it. We'll build a website, a full-stack web app with authentication, a backend server, a database, and a working front end. All live, all with Claude Code. If you've been curious about what's possible with AI-assisted development, this is a great place to see it in action. Founders, builders, students — everyone welcome. Free to join. 👇 https://www.skool.com/inspiring-founders-5861 …more

Why Founders Keep Asking the Wrong Questions in Customer Interviews I've been mentoring early-stage founders for a long time. One of the first books I put in front of all of them is The Mom Test by Rob Fitzpatrick. The core lesson: most founders ask questions that get polite answers, not honest ones. "Would you use this?" tells you nothing. People don't want to hurt your feelings. The book teaches you to ask about real behaviors instead — past experiences, actual workarounds, real decisions. Questions that can't be answered with a comfortable lie. The problem is, founders read it, get it, and then walk into their next interview and ask: "So does this solve a real pain point for you?" Every. Single. Time. Knowing what a good question looks like isn't the same as being able to generate one on the spot about your specific product and customer. So I built a free tool to close that gap: MomTestQuestions.com You describe your product and your target customer. It generates a set of high-quality interview questions built on Mom Test principles — questions about behavior, not opinions. Ready to use in your next customer conversation. No signup. No cost. Just better questions. If you're in customer discovery mode right now, try it before your next interview. Then come back and tell me what you learned. …more

I'm putting on a workshop for small business owners on May 28th in San Jose at the MLK Library. It's hosted by the Silicon Valley Small Business Development Center, and the focus is simple: how to use AI and social media without living on it all day. Most small business owners I work with tell me the same thing. They know they need to post. They know they need to stay active. But they hate the time it takes, and they never know what to say. That's the problem I solve. Not with another content calendar template. Not with another AI tool that spits out generic posts. But with one repeatable workflow that takes 15 minutes a day and fits your business. I've launched three startups. One ended in an acquisition. I've spent years building go-to-market strategies and helping founders run their own marketing without burning out. The truth is you don't need a marketing team. You need one habit that works. At this workshop, I'll walk you through the practical workflows and time-saving templates you can start using the next day. No fluff. No theory. Just the systems I use with clients who need to stay visible without adding another full-time job. If you can't make it to San Jose but you want help building your own 15-minute marketing habit, I'm offering free 15–20 minute marketing audits. I'll review what you're doing now, give you one or two quick wins, and build your first week of content with you. Book the audit: https://www.radi8.com/free-audit?utm_source=linkedin&utm_campaign=free_audit&utm_content=post_id Or if you're in the Bay Area on May 28th, I'd love to see you at the workshop. …more

Here's a workflow you can steal. One core message → five LinkedIn posts in 30 minutes. Step 1 (5 min): Pick one thing you believe about your industry. Not a tip. A point of view. Example: "Most marketing advice for small business owners is wrong because it assumes you have a marketing team." Step 2 (5 min): Write it as a single declarative sentence. That's your core message. Step 3 (10 min): Generate five angles on it with AI. Story angle (a moment this was true). Contrarian angle (what people get wrong). Tactical angle (one thing to do differently). Mistake angle (what you used to do). Persona angle (who specifically this hurts). Step 4 (10 min): For each angle, write the first two lines yourself — that's the hook. Let AI fill in the middle. Edit the ending so the CTA sounds like you. That's it. Five posts. Same core idea, five different doors into it. Your audience won't feel repetition because each post leads with a different shape of thought. I'm walking through this workflow plus two more — competitor research in 10 minutes, and an editorial system that runs in 15 minutes a day — at my workshop on May 28th in San Jose at the MLK Library, hosted by the Silicon Valley Small Business Development Center. If you can't make it, book a free 15 to 20 minute marketing audit and I'll run this workflow with you on your business. https://www.radi8.com/free-audit?utm_source=linkedin&utm_campaign=free_audit&utm_content=post_id DM me if you want the workshop link. …more