I’ve spent the better part of 25 years trying to understand two things: which problems are worth solving, and what is the simplest way to solve them. That pursuit has led me to start companies, build products, teach entrepreneurship, coach hundreds of founders, and participate in four startup exits—one as a founder and three as an advisor.
Along the way, I noticed a pattern. Founders are usually very good at solving problems. The trouble is that we’re often solving the wrong ones. What looks like a sales problem might really be positioning. A marketing problem might begin with not understanding the customer. An execution problem might simply be too many priorities competing for attention.
I came to think of this as finding the problem under the problem. When you find it, complicated decisions get simpler, teams align, and a surprising amount of work disappears.
Today I coach founders and startup teams around the world to do exactly that. Sometimes it’s a team scaling a company worth billions. Sometimes it’s one person turning what they know into a consulting business. The scale changes, but the work is remarkably similar.
Find the problem worth solving. Find the simplest way through it. Then get on with the work that matters.
After working with hundreds of founders, one pattern keeps repeating.
The ones who make faster progress are not the ones reading more blog posts or watching more tutorials. They are the ones sitting in a room with other founders who have already solved the same problem.
You skip the trial and error. You see what actually works. You adapt it to your business and move forward.
That is exactly why I created the Inspiring Founders Peer Group.
It is built for founders who want to build a valuable business without burning cash on marketing or headcount. We meet once a month in person in San Jose or Santa Cruz. The focus is on practical problems, real workflows, and honest feedback from people who understand the tradeoffs you are making.
You do not need to have everything dialed in. You just need to be willing to show up, ask good questions, and apply what you learn.
If this sounds like your next step, apply to join the next meeting at inspiringfounders.com.
https://www.inspiringfounders.com/#Founders#PeerGroup#BayArea…more
51,501 LinkedIn impressions in the last 90 days. Up 185% from the 90 days before.
Here's what actually changed: I started posting consistently. That's it. No growth hack, no algorithm trick.
The hard part isn't writing one good post. It's writing one this week, and next week, and the week after — while running a business.
That's the problem Radi8 is built to solve. Stay visible without living on social media.
Try it free → radi8.com …more
Santa Cruz Works Rooftop New Tech is back on May 6, and I'll be there.
If you're a founder working on something in tech, this is one of the best nights to show up. Six startups will present on the rooftop at Anton Pacific. Solid food and drinks. Great views. Real conversations with other builders.
I've advised and invested in startups for years. Three of those companies had billion-dollar exits. I've also launched three of my own, with one major acquisition. The early stages are hard when you're doing everything yourself—go-to-market, messaging, content—all while trying to build product.
The best part of events like this isn't the presentations. It's the conversations between them. The founder who's stuck on messaging and finally gets clarity. The team that's been guessing at go-to-market and walks away with a plan.
I'll be there between presentations. If you want to talk through your go-to-market strategy, your messaging, or how to build a content system that doesn't eat your week, come find me. I'm happy to walk through what's working and where you can get a quick win.
https://www.santacruzworks.org/news/santa-cruz-works-rooftop-new-tech-may-6…more
We just released Radi8 with Claude.
If you already use Claude for writing or research, you can now run your entire social media workflow without leaving the chat.
Create posts. Generate images. Schedule. Publish. All through Claude Code.
Most small business owners I talk to don't want to spend hours switching between tools or staring at social platforms. You know you need to stay visible with prospects and customers, but the process takes time you don't have.
Radi8 with Claude let's you run your entire social media workflow without leaving the chat.
Connect Radi8 to your own Claude instance. From there, ask Claude to draft a post, create supporting visuals, and schedule it to go live. The entire workflow happens in one conversation.
No separate design tool. No separate scheduler. No context-switching your way through content creation.
If you're already paying for Claude and handling your own marketing, this is the simplest way to stay consistent without living on social media.
Radi8 with Claude is live now. Want to see how it fits into your workflow? Send me a message and I'll walk you through it. …more
Just shipped something I'm really excited about.
The Radi8 MCP Connector is now live for Claude users. 🎉
What that means for you:
→ Connect Radi8 to Claude once
→ Claude gets access to your brand, strategy, content plan, and image generation tools
→ Ask Claude to write and schedule a post — it handles it, in your voice, aligned to your strategy
No more jumping between tools. No more losing your brand voice in AI-generated content.
Want to get set up? DM me or book a free audit at radi8.com/free-audit and I'll walk you through everything.
Three tools. One chat. Zero tabs.
Here's what I just did in Claude in about 3 minutes:
→ Asked Claude to design a LinkedIn graphic in Canva
→ Picked my favorite option
→ Had Claude write the copy using my brand voice from Radi8
→ Scheduled the post to LinkedIn — all in one conversation
This is the post you're reading right now.
If you're a small business owner or founder doing your own marketing, this is the kind of workflow that actually saves you hours a week. No switching between tools. No "I'll finish it tomorrow."
Comment "workflow" and I'll send you the setup.
Most small business owners don't have time to figure out AI tools — let alone connect them to their marketing stack.
That's exactly why we built Radi8-with-Claude AI.
Here's what it means practically: instead of jumping between tools, writing from scratch, or staring at a blank content calendar, you can now work with Radi8 directly inside ChatGPT or Claude AI — pulling your brand context, your content plan, and your strategy into every post you create.
No prompt engineering. No copy-pasting. Just a faster, more consistent way to create content that actually sounds like you.
If you're a founder or small business owner doing your own marketing and you want to see how this works for your business — DM me and I'll walk you through it.
I'm doing a live demo right now — and the demo *is* the post.
Inside a Claude chat, I pulled my Radi8 brand context (voice, audience, pillars), drafted this post in my tone, and spun up a Canva graphic to match. All in one window. No tab-switching. No copy-paste relay race.
This is what "handle your own marketing without living on social media" actually looks like in 2026:
→ Radi8 knows your brand, audience, and strategy
→ Claude drafts in your voice using that context
→ Canva designs the visual without leaving the chat
→ You review, tweak, publish
The whole thing — idea to scheduled post — in the time it used to take to find the right stock photo.
Small business owners and founders: this is the unlock. You don't need a marketing team. You need the right stack talking to each other.
Want to see it run on your brand? Book a free 15-minute audit — link in comments. Or just DM me and I'll walk you through it.
I'm doing a live demo right now — and the demo *is* the post.
Inside a Claude chat, I pulled my Radi8 brand context (voice, audience, pillars), drafted this post in my tone, and spun up a Canva graphic to match. All in one window. No tab-switching. No copy-paste relay race.
This is what "handle your own marketing without living on social media" actually looks like in 2026:
→ Radi8 knows your brand, audience, and strategy
→ Claude drafts in your voice using that context
→ Canva designs the visual without leaving the chat
→ You review, tweak, publish
The whole thing — idea to scheduled post — in the time it used to take to find the right stock photo.
Small business owners and founders: this is the unlock. You don't need a marketing team. You need the right stack talking to each other.
Want to see it run on your brand? Book a free 15-minute audit — link in comments. Or just DM me and I'll walk you through it.
Brian Solis argued at SXSW that augmentation is the new productivity: most people use AI to do what they already know. For founders this matters because the biggest gains come from changing how decisions are made, not just automating tasks.
Three practical steps I use with startups:
1) Map core decisions and the inputs that drive them.
2) Prototype one augmented workflow in two weeks and measure decision speed and quality.
3) Standardize prompts, tests, and handoffs so the capability scales.
If you want templates or pilot intros, send me a message. #AIhttps://briansolis.com/2026/03/worth-magazine-covers-brian-solis-keynote-at-sxsw-2026-augmentation-is-the-new-productivity/…more
Spent today in a workshop with Kent Kaufman, Manoj, and their Silicon Valley AI team. Farooq walked us through Spec Driven Development with AI Agents and how it produces stronger, more reliable code.
The session reinforced something I've been thinking about: the best tools don't just automate tasks. They change how we approach the work itself.
For founders building products while also trying to stay visible and engaged with customers, that shift matters. You need systems that help you think clearly, not just move faster.
If you're wrestling with how to stay consistent with marketing without it consuming all your time, send me a message.
Silicon Valley’s new frontier isn’t writing every line of code. It’s deciding what AI agents should do and how to evaluate them. From building startups and running accelerator programs, I’ve learned three practical rules for being agentic:
1) Define the objective, success metrics, and hard constraints up front.
2) Decompose work into discrete agent tasks with clear inputs and outputs.
3) Instrument feedback loops and human checkpoints to catch drift and control cost.
If you’re rethinking roles or workflows for agents, send me a message. #AIhttps://www.wired.com/story/silicon-valley-agentic-individuals-future-of-work/…more
How do you automate marketing with AI?
AI will handle repeatable execution: content variants, email follow-ups, ad creative tests, and performance monitoring. The real constraint is strategy. Without a clear go-to-market hypothesis and prioritized early growth channels, automation amplifies noise, not traction.
Practical path: pick one channel, design simple experiments, automate the repeatable steps, measure lift, and iterate.
With 20 years building and scaling startups, I help founders convert unclear go-to-market strategies into operational growth systems at Radi8. Send me a message to schedule a free marketing audit. #startup
My point of view on content marketing is simple.
Founders often treat content as a brand or traffic play. It delivers fastest when built as a repeatable acquisition engine: a defined buyer, a single, measurable offer, formats mapped to that buyer, and a small channel pilot to validate economics.
With 20 years of building and scaling startups, I use that framework at Radi8 to remove guesswork in early growth. If your go-to-market feels unclear, start with a testable acquisition hypothesis. Send me a message for a free marketing audit.
Are You ‘Agentic’ Enough for the AI Era?
Wired reports AI agents are taking on much of the grunt work. The most valuable skill today is deciding what those agents should do. I agree. For early-stage founders that means shifting from pure execution to designing clear agent workflows: name the outcome, define the success metric, and build a fast feedback loop. Start by automating one repeatable task—content drafts, user outreach, or ad copy—and specify the outcome, the KPI you’ll watch, and how often the agent reports back. Without that structure, automation increases overhead instead of removing it.
Send me a message to schedule a free marketing audit.
Michael Ashley, Founder & CEO, Radi8 | Startup advisor, investor, mentor
https://www.wired.com/story/silicon-valley-agentic-individuals-future-of-work/
The objection I keep hearing about automating marketing with AI, and why I still disagree
Objection: We can’t automate because our go-to-market is unclear and early channels are unproven. That mistakes automation for strategy. With 20 years of building and scaling startups, I use AI to accelerate learning, not replace decision making. In early GTM tests I use AI to run rapid channel experiments, generate audience hypotheses, automate creative and reporting, and keep validated channels running without heavy oversight. The result is shorter feedback loops so founders can make faster, better decisions.
If you are an early-stage founder testing GTM, send me a message to schedule a free marketing audit.
As founder of my own Santa Cruz Startup, @Radi8, I encourage Santa Cruz small business owners to complete the Santa Cruz Works Work-Life survey. Your responses will help shape local programs, events and benefits. All participants are entered to win gifts from UpperCrust, Merge4, Laili, Pleasure Pizza, Big Basin Vineyards, Humble Sea and Chaminade Resort and Spa. Winners announced May 7. Take the survey: https://www.santacruzworks.org/news/2026worklivesurvey
If you're a local business owner, comment and I’ll reach out to discuss simple marketing steps based on the results. #SantaCruz…more
What does it take to build, grow, and exit multiple companies? For serial entrepreneur Tom Shen, the secret isn't a high IQ or a perfect business plan—it’s humility.
In this episode of Inspiring Founders, host Mash sits down with Tom Shen and Bob Ashley to discuss the "heart" of entrepreneurship. They move past the spreadsheets and exit strategies to talk about what actually builds a legacy: servant leadership, creating a culture where people want to stay for 20+ years, and why the "smartest person in the room" is usually the one who loses.
Key Takeaways:
The Humility Edge: Why being the "dumbest person in the room" is your greatest competitive advantage.
Culture over Strategy: How Tom and Bob built a 23-year partnership based on trust and a "can-do" spirit.
EQ vs. IQ: Why emotional intelligence is the most critical skill for the future of leadership.
Leading with Heart: Lessons from the basketball court to the boardroom.
https://www.youtube.com/watch?v=Vl0VydscpGo…more
AI isn’t killing SaaS. It’s rewriting buyer budgets.
Founders I talk to say their product is better and still relied on, yet deals slow, expansions stall, and seats disappear. The gap is buyer priorities, not product.
Three quick moves:
1. Reframe messaging to quantify time and cost savings versus AI alternatives.
2. Offer short, low-friction pilots or outcome-based trials.
3. Publish 30-day ROI case studies to shorten evaluation cycles.
Radi8 helps founders create these assets faster and at lower cost than hiring consultants. Send me a message and I’ll reach out.
https://www.santacruzworks.org/news/ai-isnt-killing-saas-its-rewriting-the-budget#SaaS…more
AI isn’t killing SaaS. It’s rewriting buyer budgets.
Founders I talk to say their product is better and still relied on, yet deals slow, expansions stall, and seats disappear. The gap is buyer priorities, not product.
Three quick moves:
1. Reframe messaging to quantify time and cost savings versus AI alternatives.
2. Offer short, low-friction pilots or outcome-based trials.
3. Publish 30-day ROI case studies to shorten evaluation cycles.
Radi8 helps founders create these assets faster and at lower cost than hiring consultants. Send me a message and I’ll reach out.
https://www.santacruzworks.org/news/ai-isnt-killing-saas-its-rewriting-the-budget#SaaS
AI isn’t killing SaaS. It’s rewriting buyer budgets.
Founders I talk to say their product is better and still relied on, yet deals slow, expansions stall, and seats disappear. The gap is buyer priorities, not product.
Three quick moves:
1. Reframe messaging to quantify time and cost savings versus AI alternatives.
2. Offer short, low-friction pilots or outcome-based trials.
3. Publish 30-day ROI case studies to shorten evaluation cycles.
Radi8 helps founders create these assets faster and at lower cost than hiring consultants. Send me a message and I’ll reach out.
https://www.santacruzworks.org/news/ai-isnt-killing-saas-its-rewriting-the-budget#SaaS
Accelerators once extended runway with cloud credits. That logic still applies, but the center of gravity has shifted. Many early-stage products now spend more on AI tokens than on traditional infrastructure. If your financial plan still assumes free cloud credits, update it and protect your runway.
If marketing is eating your time and budget, Radi8 helps founders run marketing faster and cheaper than hiring consultants. Comment and I’ll reach out. #startupshttps://www.santacruzworks.org/news/startups-need-ai-tokens-more-than-cloud-credits…more
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