In the early days, we set HubSpot's pricing at $250 a month, which remained unchanged for the first six years as we figured out our model.

We realized we needed to charge businesses a few hundred dollars a month instead of just $20-$30 to make our business model viable.

We decided to become a one-stop shop for accounting, taxes, and payroll, charging a few hundred dollars a month for our services.

During a call with a former colleague, I pitched Optimizely, and he immediately saw its value, suggesting a price of $1,000 a month, which was significantly more than we made with our previous ventures.

We decided to offer our product as a fully functional free beta for 30 days, with a commercial price of $299 for companies and $99 for hobbyists, trusting users to pay based on their usage.

We had our first paying customer for Optimizely before writing any code, demonstrating the demand for our product.

When I left the company, we grew from zero revenues to about $150 million in recurring revenue, leading to a sale to Microsoft for around $800 million.

To ensure cash flow, we asked our merchants to pay $500 per month, requiring six months' payment upfront, which made my company cash flow positive from the second month of service.

We started with a freemium model, but realized it distracted us; we shifted to a paid model and consistently increased prices over time, which helped us focus on serious customers.