Ted and I have been working on GameChanger for nearly 8 years now. Like most startups, we started off meeting at lunches, weekends, evenings, and slowly chipping away at a itch. We talked to customers, we raised money, we shipped things, we hired people. We had many successes and many failures and have done our best to take it all in and just keep learning and doing it better. Scaling the company itself has been full of surprises. At many of the crucial junctures along the way, I didn’t know going in what was happening or whether we’d get to the other side, or indeed what it would look like when we did. With the extreme benefit of hindsight (and the privilege of having lived to tell the story), I can now see a clear progression of eras. None of these were as clean or distinct as they come across here, but I wish someone had been able to give me a heads up on what was coming before I lived it. The Founder Era Ok, you’ve gotten enough chutzpah together to start building something that doesn’t exist. It’s an awesome feeling, full of optimism. : 1–3 founders with curiosity and drive Staff : learning your market, understanding your customers, proving your concept solves a real problem for someone, trying lots of shit Focus : being too obsessed with your own vision and not open enough to iterating toward the emerging reality Pitfall : bootstrapped, friends & family money, side gigs Economics The Scrappy Era Having created something of value to someone, you are now trying to reach some bar of quality or completeness to sell it. It feels like the hard part is behind you, and it’s all about execution now. : 4–10 mostly individual contributors, culture of passion & flexibility Staff : initiative, delivering on your promise to your customers, honing in on key areas of value, and moving fast Focus : stretching yourself too thin, not delivering at sufficient quality Pitfall : some outside funding, maybe some early drips of revenue Economics The Heroic Era Having slapped together a fully functioning product, you’re actually getting real usage by real customers and facing lots of new reality. : 10–25 of the smartest and hardest-working generalists out there Staff : productizing your prototype, hardening your infrastructure, formalizing your architecture, investing in user experience Focus : key players burn out if reinforcements aren’t fast enough, and your organization isn’t deep enough to take much turnover yet Pitfall : professional investors put in 7-digits, meaningful revenues Economics The Team Era Having stopped most of the bleeding, the company is evolving past reliance on individuals and developing into an organization that can sustain and focus. : 25–50 with a layer of domain experts and experienced management and clear areas of responsibility Staff : standardizing operations, creating clear goals and metrics, clarifying roles and responsibilities Focus : it’s easy to lose focus and drive as layers of management and indirection are new necessities, and failure to get strong leaders in place can overwhelm you Pitfall : institutional capital, maturing revenue model Economics The Enterprise Era It’s hard to keep calling yourself a , because you have established revenue streams and do grown-up things like make somewhat reliable annual projections and plans, but you need to expand. startup : 50–100+ with professional and great HR Staff management : optimally managing investment of resources and maintaining organizational alignment toward growth as the internal complexity grows Focus : it’s easy to get mediocre as your heroes ride off into the sunset Pitfall : growth capital, private equity, profitability Economics After that you’re not a startup anyway. Good luck.