The startup world celebrates pioneers, but a YouTube video featuring Rebecca Lynn reveals that first-mover advantage is often a myth. The real winners learn from others’ mistakes and execute better.
As someone who has witnessed numerous startup journeys, both successful and failed, I’ve seen how being first to market can actually be a significant disadvantage. The costs of educating the market, building infrastructure from scratch, and accumulating technical debt often outweigh the benefits of being first.
The Second-Mover Strategy: A Path to Success
Looking at the current landscape of successful public companies, you’ll find surprisingly few true first movers among them. Take Lending Club, for example. While Prosper blazed the trail in peer-to-peer lending, Lending Club learned from their predecessor’s experiences and ultimately became the largest US tech IPO in 2014.
The ideal position for a startup is to let another company validate the market, then swoop in with a superior product, better marketing, and clean technical architecture. This approach allows companies to avoid the costly mistakes of their predecessors while benefiting from an educated market.

The CEO’s Most Critical Skill: Salesmanship
In my evaluation of startups, I’ve found that the most successful CEOs share one crucial characteristic: exceptional salesmanship. The role of a CEO is fundamentally about selling – to customers, employees, investors, and partners.
A CEO who can sell you on their vision through genuine excitement while maintaining complete honesty and transparency is invaluable.
Consider the example of Jeff Tagnay at Doximity. His approach to product development involved creating a customer advisory committee from day one. This committee participated in strategy sessions and wireframing discussions, directly influencing the product roadmap. This customer-centric approach exemplifies the kind of leadership that builds trust and drives success.
The Product-Market Fit Trap
One of the most common pitfalls in startups is premature scaling based on a false sense of product-market fit. Here’s what typically happens:
- Founders believe they’ve achieved product-market fit too early
- They hire expensive sales executives and build out teams
- Cash burn increases dramatically
- Reality sets in, forcing layoffs and restructuring
- The company must return to basics and rebuild
CaseText’s experience illustrates this perfectly. Despite early optimism, they had to make the difficult decision to let go of their sales team when they realized their product wasn’t ready for scale. While painful, this decisive action allowed them to refocus and eventually achieve a successful exit to Thomson Reuters for $650 million.
The GenAI Challenge: Beyond the Demo
The current wave of generative AI startups presents a unique challenge. Creating impressive demos is easier than ever, but transitioning from demo to scalable production is where many fail. We’ve already seen well-funded companies collapse because they couldn’t bridge this gap.
When evaluating GenAI startups, I look beyond the flashy demonstrations. The key questions are:
- Do they have actual customers using the product in production?
- How are customers using the product?
- What unexpected learnings have emerged from real-world usage?
- How has the product evolved based on user feedback?
The Power of Self-Belief
Success in the startup world requires more than just technical skills or market understanding. It demands unwavering self-confidence. If you don’t believe you’re the best person for the job, why should anyone invest in you or your vision?
This lesson hit home for me when a friend from business school confidently rated herself as the top performer in every category during a leadership exercise. Her reasoning was simple: in the competitive world of business, you must first believe in yourself if you expect others to believe in you.
Frequently Asked Questions
Q: Why is being a first mover often disadvantageous for startups?
First movers typically face higher costs in market education, infrastructure development, and accumulate significant technical debt. They also make mistakes that later entrants can learn from and avoid.
Q: What should startups look for when hiring their first sales leader?
Instead of immediately hiring an expensive senior sales executive, consider starting with a director-level salesperson or chief of staff who can help develop the sales process gradually while you confirm product-market fit.
Q: How can founders know when they’ve truly achieved product-market fit?
True product-market fit is evidenced by consistent customer adoption, strong retention rates, and organic growth. Multiple checkpoints and validation from paying customers should be established before scaling the sales team.
Q: What makes a successful CEO in today’s startup environment?
A successful CEO combines strong salesmanship with the ability to listen to customers, adapt to feedback, and maintain transparency with all stakeholders. They should also have a compelling personal motivation that will sustain them through difficult times.
Q: How should GenAI startups approach the transition from demo to production?
Focus on getting real customers using the product in production before scaling. Collect extensive feedback, iterate based on actual usage patterns, and ensure the technology can perform reliably at scale before seeking significant investment.