Free trials may seem appealing, but they don't provide the commitment, validation, or revenue that startups need. It's better to seek a commitment from customers instead. We only do annual agreements, but if you're not satisfied in the first 30 days, you can opt out without penalty. This approach protects the customer while also showing our commitment to them.

Offering long free trials or pilots can be counterproductive, as customers may not fully commit to using the product. Keep trials short with clear success criteria.

If you're confident in your product, encourage customers to sign up for an annual contract with a 30 or 60-day money-back guarantee, making it a recurring revenue stream from the start.

Charging customers is essential for validating your product's value. Offering free trials can be tempting, but if customers aren't paying, they aren't truly customers. Resist the fear of rejection based on price.

It's better to have the default be that customers are signed up rather than needing to renegotiate after a short period. This way, you avoid the free trial trap and create a more stable relationship with customers.

In the early days, we avoided free trials to ensure we received feedback only from customers who truly valued our product, which helped us stay focused on delivering real value.

Consider offering a discount for commitment, such as 10-20% off for annual subscriptions, to encourage adoption and ensure revenue predictability.

New features are a great way to upsell; I often offer a 30-day trial of a new feature and ask if users would be willing to double their price if they find it valuable.

Understanding when users experience their 'aha moment' can guide improvements in the conversion process and increase signups. Addressing user concerns about starting a free trial by stating 'no credit card required' reduces perceived risk and encourages clicks.