Calendly Startups

Mentor Cruise is a marketplace connecting people in tech with mentors for long-term mentorship, typically priced at $0-$50 per week. Founded by Dominic Mon as a side project, the platform now has 160 mentors and generates $700/month MRR through a 15% commission on mentor fees. Growth has been driven primarily through SEO for mentor searches and word-of-mouth from early mentor referrals.

Mastermind Talks is an exclusive invite-only event for entrepreneurs founded by Jason Gaynard, building on his experience hosting mastermind dinners in Toronto. Starting with 4,200 applicants for 150 spots at $995, the event grew to $6,000 per ticket by maintaining intimacy and quality, with recent events generating approximately $800K-$900K in revenue from attendees alone. The business was built entirely through relationship-based networking and strategic speaker partnerships, with no paid marketing.

Shari Alexander runs Observe Connect Influence, a persuasiveness coaching and speaking business generating $150,000 in annual revenue ($15,000 monthly in January 2016). Her revenue comes from three main streams: one-on-one coaching packages ($5,000-$35,000), speaking engagements ($5,000-$7,500), and online courses. She grew her business primarily through personal referrals and direct outreach to her target market, maintaining a highly engaged 3,500-person email list rather than chasing scale.

Wing Assistant is a platform connecting SMBs with remote talent, positioning itself as a software-driven alternative to traditional virtual assistant services. They grew from ~$1M to $10M in GSV by mastering Google Ads with sophisticated conversion tracking and analytics, using techniques like tracking 'inconspicuous words' in chat to identify high-quality leads while filtering out job seekers and fraudulent traffic. Their data-driven approach led to a $41,000 refund from Google after detecting and proving malicious click fraud.