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Misfit Entrepreneur 15: Kelly Roach

Dave Lukas Chats with Mo Ahmed

442: Unleashing AI, Entrepreneurship, and Resilience with Mo Ahmed
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This week’s Misfit Entrepreneur is Mo Ahmed.  Mo is a serial entrepreneur with over 20 years in AI and Cloud Computing experience.  He has built and sold multiple successful companies for multiples of 10x plus and has helped founders secure over $30M in funding. 

Mo is also the author of Inside-Out Entrepreneurship which goes deep into the mental resilience and endurance of the entrepreneur journey.

With AI moving incredible fast and opportunities everywhere, I thought it would be great to have Mo on to get his take and have him share the best lessons from his journey.

https://boundlessfounder.co/
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Show Notes

Mo’s entrepreneurial journey started by chance while pursuing his PhD in computer science. One day, his class was moved to the business school, where he stumbled upon an advertisement for an Innovation Accelerator program at the University of Connecticut. The ad caught his eye because the program paid well, and at the time, his only goal was to buy a car.

Mo applied and got accepted, working with real-world entrepreneurs to help refine their go-to-market strategies. One day, a professor supervising the program asked him: “Why work at a big company when you could build one?”
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That question stuck with him. While he went on to work for Microsoft and Amazon, he eventually took the leap into founding and scaling multiple startups, learning hard lessons about pivoting, resilience, and AI-driven business growth along the way.

​What was the first business you created, and what happened along the way?
  • Mo’s first taste of business was at 17, selling burned software and music CDs in the 90s when CD-writers were rare.
  • During his PhD, he paused entrepreneurship but the spark never left.
  • In 2016, he launched his first high-growth startup, solving a problem he encountered while working at a company.
  • The business pivoted from cloud optimization to cybersecurity, highlighting the reality that many startups start with one focus but find success elsewhere.
  • Success in entrepreneurship often comes from pivoting when new opportunities reveal themselves.

What were some of the lessons you took away from working at Microsoft and Amazon that helped make you a better entrepreneur?
  • Big tech companies help you master problem-solution fit.
    • You learn to define problems clearly and anticipate customer needs beyond just an immediate solution.
  • The downside of big companies? Slow decision-making.
    • Unlike startups, where speed is king, large organizations require consensus, bureaucracy, and meetings, which slow down progress.
  • Startups must move fast and make decisions with incomplete information.
    • If you wait for perfect data before acting, it’s already too late.

You mentioned the speed of AI and how fast things are evolving. How can entrepreneurs keep up and maintain an edge?
  • Don’t confuse speed with working harder or longer hours.
    • Moving fast is about learning faster and making quick, informed decisions.
  • Maximize learning speed:
    • Entrepreneurs must learn faster than competitors—AI can compress weeks of research into 20 minutes.
  • Use AI to eliminate cognitive overload:
    • AI removes the mental friction of planning and allows you to focus on high-value execution.
  • AI agents are the future.
    • Rather than being tools you prompt, AI will soon act like proactive assistants, making independent business decisions.

What’s your take on AI agents and how they will impact businesses?
  • LLMs today are like smart high schoolers—they follow instructions but don’t yet innovate.
  • The quality of AI output depends on the quality of input.
    • “Garbage in, garbage out” applies to AI—entrepreneurs need to provide structured, detailed input for the best results.
  • AI agents are already replacing human labor in many areas.
    • Example: A business owner automated furniture flipping by using AI to scan Facebook Marketplace, negotiate deals, and create a resale business.
  • Within a few years, AI will run entire business functions autonomously.

How close do you think we are to AGI (Artificial General Intelligence)?
  • AGI is hard to define because humans vary in intelligence.
    • If AGI means “on par with the average human,” we are closer than ever.
  • DeepSeek’s recent breakthroughs show AI efficiency is increasing exponentially.
    • AI compute costs have dropped significantly, allowing for faster, cheaper model training.
  • Expect major AGI-like capabilities within the next 1-2 years.

What are the universal principles needed to build a great business?
  • You must build a business, not just a product.
    • Many founders focus too much on their technology and not enough on revenue.
    • If you rely on VC money without a real revenue model, you don’t have a business—you have a gamble.
  • Your startup does not define who you are.
    • Entrepreneurs often attach their identity to their business, making failure feel personal.
    • Success or failure, your business is just one chapter in your life.
  • The most important pivot is within yourself.
    • If you’re stuck, your biggest roadblock is likely your mindset.
    • Re-examine your decision-making process to break through growth plateaus.

You wrote Inside Out Entrepreneurship, which focuses on mental resilience. Can you explain why mindset is more important than funding?
  • Mental resilience is an entrepreneur’s biggest asset.
  • Your response to failure determines your success.
    • Early in his career, a surprise AWS bill of $65,000 nearly wiped Mo out—it took weeks to recover mentally.
    • Years later, when a major acquisition deal fell apart at the last minute, he rebounded in hours and secured new buyers immediately.
  • Entrepreneurs must train their minds like athletes train their bodies.
    • Resilience is the difference between those who succeed and those who quit.

Best Quote

  • The greatest startup pivot is the one you make within yourself.
Misfit Three

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 True entrepreneurial strength comes from the inside out.

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  Entrepreneurship requires conditioning—like training for a marathon.

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The best pivot you can make is within yourself.


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