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Tope Awotona, founder of Calendly, started three very different companies for three completely different communities before eventually building the scheduling software business in 2013. In 2020, Calendly posted nearly $70 million in annual recurring revenue, more than double its 2019 figure. But Awotona’s first company was a dating app that never really got off the ground. The second was projectorspot.com, which sold (obviously) projectors, but sales were poor and margins small. He tried again with a third startup, selling grills, but as he says, “I didn’t know anything about grills and I didn’t want to! I lived in an apartment, and never even grilled.” Not only was he not part of the grilling community, but he didn’t even want to be! He took a different approach to building Calendly. He had been a sales rep earlier in his career, and he knew the hassle of sending multiple emails to schedule meetings. He had even run into the scheduling problem while trying to sell his own products as an entrepreneur. As time went on and his other ideas failed to gain traction, he saw a gap in the marketplace and resolved to address it for the community of sales reps he cared about and understood. He says that “the journey to creating something that’s impactful, something that serves people, something that you know people are willing to open up their wallets and pay for—is not something that you can do just for money.” While lots of people have scheduling fatigue, Awotona focused on problems specific to sales reps, which helped him define a problem he could both solve and monetize. What does that mean for you? First, get involved in those communities wherever they are, offline and online. Then, contribute, teach, and, most important, listen. Finally, use the filters above to make sure you are picking the right community to serve. Then, your problem becomes: Which problem should I pick?
Sahil Lavingia (The Minimalist Entrepreneur: How Great Founders Do More with Less)