TLDR:
Andrew Ackerman shows how modern founders win by merging AI, voice, and storytelling into a single workflow. He wrote most of The Entrepreneur’s Odyssey by speaking it aloud, proving voice-to-text is a real multiplier. He warns against the “golden retriever problem,” where AI eagerly fetches tasks it can’t really do, and argues founders need multi-model fluency: ChatGPT for architecture, Perplexity for research, Claude for logic and legal, Gemini for deep analysis. His $6 index-card MVP method saves tens of thousands in wasted dev time, and AI video and legal tools now deliver pro-grade output for a fraction of the cost. His philosophy is simple: speed comes from removing friction, experimentation is a discipline, and every startup is a story the founder is trying to make real. This episode is a blueprint for building fast, smart, and AI-native.
Founders obsess over speed — usually the wrong kind. More tasks, more apps, more tabs, more chaos. But the real speed comes from collapsing friction, not adding horsepower. That’s what Andrew Ackerman figured out when he wrote eighty percent of his book *The Entrepreneur’s Odyssey* while commuting on the New York subway, talking his ideas into existence while the train rattled beneath him.
That’s the through-line of our conversation on the AI Main Streets Podcast: the next decade of entrepreneurship won’t be defined by who works harder, but by who works *with* AI in a way the rest of the world still hasn’t figured out.
Ackerman isn’t interested in hype cycles. He’s a venture capitalist who’s seen hundreds of founders flame out because they were afraid to test reality early. He’s also an educator, a bestselling author, and one of the few people who genuinely understands how to merge storytelling with startup execution. That’s why this conversation matters. It’s not theoretical. It’s not motivational. It’s tactical.
You’ll see why below.
AI literacy is no longer optional
Ackerman frames AI fluency like language immersion. If you want to think in it, you have to live in it. You don’t “learn ChatGPT.” You *develop intuition* for it.
His rule:
Ask ChatGPT first. Ask Google second.
It rewires your brain. It forces clarity. It speeds up pattern recognition. It trains you to think in the compressed logic AI understands.
Founders who still behave like 2020 — manually searching, manually drafting, manually parsing PDFs like medieval scribes — simply won’t keep up. Not because they’re dumber, but because they’re slower. Velocity compounds.
Ackerman’s line hits especially hard:
“To master AI, speak to it as often as you think.”
Voice-to-text is the real multiplier nobody’s talking about
There’s a moment every AI-heavy founder hits: typing becomes the bottleneck. Your ideas move too fast. Your hands can’t keep up.
For Andrew, the breakthrough came when Android’s voice recognition started making fewer mistakes than he made while typing. For me, it was Whisper. Now, most of my strategic thinking, content, and planning happen through dictation. The speed increase is absurd. You think better because you move faster. It forces clarity and eliminates the friction that kills creativity.
It’s why Andrew’s entire book feels alive. Spoken ideas translate differently. They carry momentum.
Once you switch, you don’t go back. You start punctuating your voice memos. You dictate entire plans while walking. You draft chapters while driving. You storyboard products while pacing around your kitchen.
The future founder doesn’t type — they narrate.
A textbook disguised as a novel
The Entrepreneur’s Odyssey isn’t a typical startup book. It’s fiction that smuggles in education. It’s the story of Marcus Williams, a founder navigating chaos under the guidance of his mentor Jason Murath, but it’s also a complete manual for customer discovery, validation, product iteration, fundraising, and survival.
It’s what every startup textbook tried to be but never pulled off: something you actually want to read.
And here’s the part that matters:
He wrote 80 percent of it by talking out loud!
The characters, the pacing, the rhythm — born from voice.
This isn’t just about writing. It’s about founders learning to externalize their thinking at the speed required to compete.
The “golden retriever problem”
The funniest — and truest — moment in our conversation:
ChatGPT will fetch any stick you throw, even when it can’t.”
If you ask it to edit video, it will try. If you ask it to build firmware, it will try. If you ask it to audit a contract, it might hallucinate a clause that never existed.
Founders waste hours forcing AI into tasks it’s simply not built for. Ackerman calls it what it is:
"The golden retriever problem.”
The fix is simple but rare:
Before diving in, ask whether the AI is capable *in this domain.*
One sentence. Two seconds. Saves days.
Discipline beats enthusiasm.
The multi-AI workflow is the new competitive edge
Ackerman’s brain works like mine: use the right AI for the right job. One model can’t be your entire stack — that’s how you get mediocre output and hallucinated logic.
His setup mirrors the NinjaAI visibility stack:
• ChatGPT — your architect, strategist, technical problem-solver
• Perplexity — your real-time research layer
• Claude — your empathetic writing, contracts, and logic model
• Gemini — your Google-native reasoning and data-heavy analysis
The founder who knows which engine to drive wins.
The founder who uses one AI for everything loses quietly.
The index card MVP: $6 prototypes that save $60,000
This was my favorite part. Ackerman teaches founders to ditch Figma, ditch engineering, ditch the illusion that an idea needs pixels to be valid.
He uses index cards — literally drawings of screens — and has users tap, swipe, scroll, and react.
If they hesitate, you learn. If they get confused, you fix it. If they love it, you know why.
Then he photographs the cards, feeds them into AI, and gets digital mockups automatically.
It’s scrappy brilliance. It’s 2025 craftsmanship. It’s how real founders think:
Validate the story before you build the product.
AI video is the creative director you can suddenly afford
Andrew’s book trailer looks like a $20,000 agency production. It cost his team less than $125 a month using AI Video.
You can remix scenes, test concepts, adjust pacing, and visualize brand stories without touching Premiere or hiring a team. This is the part most founders haven’t internalized yet:
AI video isn’t about “creating videos.”
It’s about exploring ideas visually at the speed of thought.
Once brands realize they can produce narratives weekly, then daily, then per-audience, the world changes. The only thing that will cut through?
Story.
The same thing that has always cut through.
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# **Experimentation is a discipline, not a hobby**
Ackerman blocks time every week for AI testing. No skipping. No excuses. He treats experimentation like gym training. Every failed prompt is a datapoint. Every misfire is a calibration. The discipline compounds.
This part matters:
**AI doesn’t reward dabblers. It rewards technicians.**
The founder who iterates daily accelerates beyond the founder who “occasionally uses ChatGPT for ideas.”
Iteration beats perfection. Every single time.
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# **The quotable core of the episode**
A few lines that capture the philosophy:
“ChatGPT is a brilliant but socially inept intern. You must check its work.”
“I wrote a book about a fictional startup on a real startup using speech-to-text.”
“Every startup is a new work of fiction trying to turn its story into reality.”
If you understand those three lines, you understand how to build in 2025.
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# **Takeaways for founders ready to move faster**
• Adopt an AI-first mindset.
• Use voice — it multiplies your speed.
• Prototype with paper — truth shows up early.
• Use multi-model workflows — stop expecting one AI to do it all.
• Document your wins — every prompt becomes leverage.
• Treat experimentation like training — consistent reps create durable intuition.
This is the new literacy. The new edge. The new competitive landscape.
And founders who embrace it early will make everyone else look slow.
Andrew's book: https://www.amazon.com/Entrepreneurs-Odyssey-Approach-Startup-Success/dp/1032883545/ref=tmm_pap_swatch_0
More about Andrew: https://www.andrewbackerman.com
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Jason Wade — AI Visibility Architect & Founder of NinjaAiOS
Jason Wade is the architect behind NinjaAiOS, a multi-layered AI visibility operating system built to redefine how small and mid-sized businesses are discovered in the AI era. He doesn’t build websites, agencies, or campaigns — he builds
visibility infrastructure: content engines, GEO/AEO discovery frameworks, automated audits, local knowledge systems, dashboards, and certification layers that didn’t exist before he created them.
In a landscape where most agencies still sell tactics, Jason is building the category itself. He’s the
founder of AI Visibility for Main Street, designing the discovery architecture that future businesses will depend on to appear inside ChatGPT, Perplexity, Gemini, Apple Intelligence, and every emerging AI search surface.
NinjaAiOS is the culmination of his approach — an orchestrated system that blends generative content automation, entity optimization, AI-driven mapping, dynamic dashboards, and real-time visibility intelligence into one unified platform. Instead of chasing algorithms, Jason builds the structures that algorithms reward.
Over seven months, he’s advanced from traditional SEO into a genuine new discipline: architecting end-to-end AI discovery systems that compress years of strategy into hours of automated output. His work fuses technical engineering instincts with small-town entrepreneurial grit, giving local businesses access to the kind of machine-intelligence frameworks previously reserved for global brands.
Jason’s mission is simple and ambitious:
Rebuild Main Street’s competitive edge using AI-powered discovery architecture that changes how America finds local businesses.
His OS.
His category.
His movement.
And he’s just getting started.
More:
https://jason-wade-0qhw5qv.gamma.site
