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From Product Manager to Entrepreneur: The Grit, Grind, and Growth Behind the Title
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Leaving a steady role at a company like American Express to start your own AI consulting firm sounds glamorous… until you realize just how much grit it takes to turn that vision into revenue.
In a recent episode of Productside Stories, I sat down with Cooper Craig, a former product manager who traded enterprise decks for small-business deals and built a thriving AI agency from the ground up. His story (and his scars) reveal what it really takes to go from product manager to entrepreneur in 2025’s AI-charged economy.
Why So Many PMs Are Going from Product Manager to Entrepreneur
The timing isn’t accidental. 2025 has seen a wave of experienced product managers exploring entrepreneurship. Some are leaving big tech; others are launching AI automation consultancies, productized services, or indie SaaS tools.
What’s driving the shift?
- AI lowered the barrier to entry. Building, testing, and shipping now costs a fraction of what it did even two years ago.
- PM skills translate directly. Product managers already live at the intersection of business, tech, and customer insight (the same triad that defines a successful founder).
- Layoffs and role uncertainty. The past 24 months forced many PMs to rethink career safety and autonomy.
Cooper’s journey from product manager to entrepreneur captures all three forces colliding at once. After being laid off from Amex in 2024, he found himself doing gig work to stay afloat — until he decided to build something of his own: Smartify AI, a consulting agency helping small and mid-sized businesses automate workflows and customer engagement with AI tools.
Product Skills Are Founder Superpowers
What surprised Cooper most wasn’t the leap into entrepreneurship. It was how prepared he already was.
“My product background is definitely my secret sauce,” he explained. “When a client comes to me saying, ‘I want AI to do this, this, and that,’ I can see through the noise. I know how to frame a problem, validate it, and build iteratively instead of over-engineering.”
Every skill that makes PMs effective in organizations (discovery, prioritization, customer empathy, hypothesis testing) becomes an unfair advantage when building your own business.
- Discovery keeps you focused on problems worth solving, not shiny ideas.
- Agile iteration helps you ship fast, get feedback, and improve.
- Stakeholder management becomes client management: setting expectations, building trust, and delivering outcomes.
That combination is exactly what makes going from product manager to entrepreneur not just possible, but powerful.
The Grit: What the Transition Really Feels Like
Cooper’s story isn’t a LinkedIn success reel. It’s a crash course in humility.
When he was first laid off, he admits, “I felt like a failure. I’d been a PM for nearly 10 years and suddenly I was driving Uber to make ends meet.”
That raw honesty resonated with product leaders everywhere. The truth is, the from product manager to entrepreneur journey almost always starts with uncertainty, not funding. Many PMs are wired for systems and predictability; entrepreneurship is the opposite.
Cooper leaned on what PMs do best: structured learning. He spent a month immersing himself in no-code tools like Make.com and n8n, experimenting with automation workflows, voice agents, and AI assistants. Then, he landed his first client, a startup building the “GolfNow of pickleball.” From there, referrals snowballed.
His key lesson? Momentum compounds faster than confidence. Build something small, ship it, and let outcomes rebuild belief.
The Grind: Managing Growth Without Burning Out
Ask any founder and they’ll tell you, getting clients is one thing, keeping up with them is another.
Even after Smartify AI crossed $30K MRR, Cooper found himself trapped in the classic founder paradox:
“I needed to hire help to grow, but I couldn’t hire until I grew.”
The grind of going from product manager to entrepreneur often comes down to managing three overlapping systems:
- Pipeline: Replace “roadmap” thinking with “revenue runway.” Build consistent lead flow through referrals, case studies, or paid channels.
- Productized delivery: Turn repeatable projects into playbooks. Package your expertise so every engagement improves your process.
- Retention: Move from one-off gigs to retainers. As Cooper put it, “AI keeps changing, so clients need someone keeping them current.”
This is where experienced PMs have an edge. We know how to systematize, prioritize, and measure what matters. But make no mistake: founder life replaces Jira tickets with invoices, and stakeholder meetings with late-night problem-solving.
The Growth: Where PM Thinking Meets Founder Vision
Once you’ve survived the first year, something shifts. The same frameworks PMs use to guide product growth now guide business growth.
Cooper uses his own version of a product roadmap to track his company’s milestones. Weekly sprints? Still there. Retrospectives? Absolutely. Only now, the “users” are clients, the “features” are services, and the “product” is the business itself.
As AI consulting matures, he’s turning Smartify AI’s internal playbooks (like his VoiceMail Pro voice agent) into standalone products. That’s where the from product manager to entrepreneur evolution comes full circle: from managing someone else’s roadmap to owning your own.
And for product leaders reading this, that’s the deeper takeaway: you already have the mindset, frameworks, and rigor of a founder. What you might lack is permission to start.
Lessons for Product Leaders Considering the Leap
If you’ve ever wondered what it takes to go from product manager to entrepreneur, Cooper’s advice is deceptively simple:
- Build before you quit. Use AI tools and no-code platforms to test ideas cheaply and quickly.
- Treat your startup like a product. Hypothesize, test, measure, and iterate, not just on your offer, but on your own time and energy.
- Find your community. Surround yourself with other PMs and solopreneurs who understand the ambiguity and can offer tactical feedback.
- Prioritize learning velocity over perfection. The best founders aren’t fearless. They’re fast learners.
From Product Manager to Entrepreneur and Beyond
- Listen to the full conversation with Cooper Craig and Rina Alexin on Productside Stories — available now on Spotify, Apple Podcasts, and Amazon Music. You can also watch it on YouTube for the complete interview.
- Want to turn your own product management skills into entrepreneurial leverage? Explore our Optimal Product Management Certification: designed to help PMs move from tactical execution to strategic leadership, whether inside an organization or building one of your own.
- Now it’s your turn. Have you ever thought about making the leap from product manager to entrepreneur? What skills, frameworks, or lessons have shaped your path? Share your story and tag @Productside on LinkedIn. We’d love to hear how you’re turning product insight into independent impact.
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