What do you do when a friend asks for help with her wedding? If you’re veteran Microsoft engineer Vishal Joshi, you hack an app. And before you know it, you’re CEO and co-founder of a burgeoning startup disrupting a $90 billion industry.

In this edition of Series A-The Podcast, Joshi details the improbable rise of San Francisco-based Joy.

You could call it a happy accident. Joshi was a rising star at Microsoft on the fast track to senior leadership. But as word got out about the app that combines all of the disparate services needed to put together the perfect wedding, the pull to focus full-time on Joy with his co-founder Michael became too strong. His co-workers began leaving Post-It notes on his computer with their wedding dates, telling him to make sure the app was done before then. “It was just going to be a project. But at some point in time it just got to a state where it was just not ignorable anymore,” Joshi tells host Jim Brisimitzis.

Joshi offers a number of valuable insights for any founder with a rare honesty and sense of humor. He details the learning curve for forming a new venture, starting with the creation of a legal entity. There were no high-powered lawyers. Just a visit to Legal Zoom to create the company and a basic site license. “By using Joy, you agree to not sue us,” he recalls the initial license read with a laugh. “I mean really, the entire gobbly-goo that’s written is for that. We said we are making this for friends and family, it’s for a happy occasion. Just don’t sue us! We are working really hard to make this thing work.”

Did it ever. The first wedding was a success, and traffic to the site quickly grew as people discovered a one-stop shop for everything from invitations to catering to photography. Joshi tells of the unique way they chose their first employee, an under-employed physicist who was working odd handyman jobs to make ends meet. “We were foolish. That foolishness was necessary for us to get started,” he says. Joshi talks about the need to hire initially from what he calls the “missionary bucket” in building an early team. “You have to eventually hire from the mercenary bucket because you need people who are like hired guns, who are extremely good at stuff. But the initial 15-20 people you have to have those people you can really count on,” he says.

Joshi describes the serendipitous meetings and circumstances that led to Joy’s acceptance in a cohort of Y Combinator, and the lessons learned thanks to his tenure there. The insights are extremely valuable as one of only 100 chosen from about 7,000 applicants.

Most notably, the keys to successfully pitching potential investors. “It’s just crazy that your entire life’s work boils down to these three minutes,” he says of the YC pitchfest before hundreds of the most influential VC’s in the world.

Joshi’s secret? Refining his pitch with waiters, bartenders or anyone else who would listen. “I think that helped a lot,” Joshi says. “Talking to a real normal individual who’s not invested in investing, who’s not judging you, who’s just listening to your story. And if it resonates with them, I think it will resonate with investors too. They are also humans, you know?

“What I learned is you can raise when you really need money, second is when people really want to give you money…It is easier said, but I think that you should probably put 10x more effort to get into the second bucket,” he adds.

The story of Joy has been a rousing success so far. The site has tens of thousands of users, significant seed funding, and a bright future making the biggest day of couples’ lives go smoothly. And it offers a font of insights thanks to Joshi’s candor in this revealing edition of Series A – The Podcast.

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