Story of Early Experience with Calendly

Initial Engagement

• Early User: The speaker was an early user of Calendly and appreciated the product.
• Cold Email: Reached out to Taupe (likely a key person or founder) via a cold email.
• 500 Startups Accelerator: At the time, the speaker was running the 500 Startups Accelerator program.

Business Proposal

• Initial Offer: Made an offer to Taupe, which was declined due to valuation disagreements.
• Re-engagement: Attempted to negotiate at a higher price after consulting with mentors who were interested.

Outcome

• Final Response: Taupe declined further investment, stating sufficient revenue generation and lack of need for additional funding.
• Gifts: Received a t-shirt and a cat from Taupe.

Financial Journey of Calendly

• Bootstrap Success: Calendly was bootstrapped initially, raising less than half a million dollars.
• Significant Growth: Recent funding round valued at billions, signifying substantial growth without initial heavy investment.