In This Article
Most product managers seem content to climb the corporate ladder by following established rules, checking the right boxes, and staying in their lanes. But the ones who truly break out? From what I've seen, it's the ones who have stepped outside the safety net and built something from scratch who bring what it takes to get to the next level.
Having co-founded multiple companies and worked in both startups and Fortune 500 enterprises, I've found that entrepreneurial experience creates product leaders who think differently, act faster, and deliver results that seem impossible to their corporate-grown counterparts.
The Credibility Gap That Changed Everything
Early in my corporate career, I sat in countless meetings where development teams wouldn't let me near live environments, designers redid everything I sketched, and copywriters rewrote my content. It wasn't because I wasn't capable. It was corporate politics. Everyone had their lane, and crossing it was threatening and generally discouraged.
But I was fascinated by all of it. I wanted to understand code, design thinking, customer psychology, and how all the pieces fit together. So I started building my own projects on the side.
Of course, one quickly learns that it's not healthy or productive to do everything yourself. Once you're able, you have to bring in help. So I hired my own teams to help me bring my own projects to life.
The first time I had to pay for development, design, and hosting out of my own pocket, everything changed. When I was at the big companies, I let people do their jobs. But when it was my own project, I found myself giving incredibly detailed specifications. I learned to harness developers' creativity while keeping them focused on deliverables (and not wasting time and money).
This startup experience didn't just teach me skills. It transformed how I approached every corporate role afterward. It infused in me an ownership mindset that helped me launch 2-3x the features and experiments compared to my peers.
What Startups Teach That Corporate Roles Can't
Full-Stack Ownership Experience
In corporate environments, product managers often become skilled at writing requirements and managing stakeholders. But when you build your own startup, you can't delegate responsibility for results. You learn to:
Think in Systems: Understand how product, marketing, operations, and finance interconnect. It becomes second nature when you're responsible for all of them. You start seeing the ripple effects of product decisions across the entire business.
Optimize for Constraints: Make strategic trade-offs when resources are limited. This forces you to prioritize ruthlessly. Every dollar spent on development means less money for marketing or customer support.
Execute Across Disciplines: When you've personally written code, created wireframes, run sales calls, provided customer service, and managed accounting spreadsheets, you speak the language of every team member.
Direct Customer Connection
Corporate product managers often work through layers of customer research and user experience teams. Startup founders live with direct customer feedback daily. During my entrepreneurial ventures, I personally made sales calls and answered customer support emails. Those direct conversations taught me more about product-market fit than years of formal market research.
Unfiltered Market Reality: When a customer calls your product "useless" or cancels their subscription, you feel it personally. This emotional connection to customer pain drives better product decisions than any sanitized user research report.
Speed of Learning: You can launch a feature on Monday, get customer feedback by Wednesday, and iterate by Friday. This rapid feedback loop trains your intuition about what customers actually want versus what they say they want.
Rapid Iteration Under Pressure
Startups fail fast because they have to. Entrepreneurial experience teaches:
Hypothesis-Driven Thinking: Every feature becomes an experiment with clear success metrics. You can't afford to build anything without a testable hypothesis about customer behavior or business impact.
Pivot Decision Making: Knowing when to persevere versus when to change direction requires reading weak signals from customer behavior and market trends. When every month of runway matters, you eliminate unnecessary process and focus on learning that drives business outcomes.
Real-World Application Examples
Here's a few real world examples of what I'm talking about. You'll see how the corporate approach differs from the entrepreneurial.
The Feature Factory Problem
Corporate Approach: PM receives requirements from sales team, spends months gathering stakeholder input, ships feature that gets minimal adoption because it solved the problem the sales team thought customers had.
Entrepreneurial Approach: PM treats the request as a hypothesis, builds a minimal version to test with 5 target customers, discovers the underlying need is different, pivots to solve the actual problem, resulting in high adoption.
Customer Research Paralysis
Traditional Process: PM conducts extensive market research and user interviews for 3-6 months while customer needs evolve and competitors gain market share.
Entrepreneurial Process: PM launches a minimal landing page to gauge customer interest within 2 weeks, uses real customer behavior to inform product direction, starts building only after confirming demand with actual purchasing behavior.
Your Entrepreneurial Development Plan
Ready to get your feet wet on your own startup project. Here are some suggestions to get you started.
Immediate Actions (Week 1-2)
Start a Side Project: Identify a problem you personally experience and build a minimal solution. Even if it's just a landing page with an email signup, you'll learn about customer acquisition and validation.
Direct Customer Contact: Schedule 30-minute conversations with 3 actual customers this week. Skip the research team filters. Ask open-ended questions about their biggest challenges.
Implement Startup Speed: Choose one upcoming feature decision and commit to getting customer feedback within 2 weeks instead of 2 months.
Medium-Term Development (Month 1-3)
Learn Adjacent Skills: Pick one area outside product management (basic coding, design principles, or marketing fundamentals) and spend 30 minutes daily learning.
Practice Ownership Thinking: For your next project, calculate the actual business impact. What revenue could this generate? What costs would it reduce? Start thinking like a business owner, not just a feature manager.
Long-Term Investment (Month 3-12)
Build Something Real: Commit to building something that real customers will pay for. The experience of charging money changes how you think about value creation. It doesn't need to be your full-time job, but it needs to be real enough that success or failure matters.
Transform Your Product Management Career
The most successful product managers don't just manage products. Instead, they think like business owners. They've experienced the full weight of customer rejection, the thrill of product-market fit, and the challenge of building something from nothing.
You don't need to quit your job or raise venture capital. Start small, think like an owner, and build something that matters for real customers. The lessons you learn will transform how you approach every corporate project afterward.
Ready to develop your entrepreneurial product thinking? Whether you need strategic product leadership, want to develop your team's capabilities, or are ready to scale your own venture:
- Product Leadership Consulting: Transform your organization through Collective Nexus strategic consulting and interim leadership services
- Product Management Training: Master adaptable frameworks at Adaptable Product with proven methodologies for any environment
- AI-Powered Business Building: Develop your startup ideas with guided planning and community support at Subrize
What's your side project going to be?
Nathan Rohm has led product initiatives across startups and Fortune 500 companies, co-founding multiple ventures including CoachPlace.com, scaling products from $5M to $150M in revenue, and managing product strategy for 125+ person global teams.