IN-DEPTH Q&A: The cofounder of GroupMe — a text-messaging platform that sold for $85 million a year after launch — has raised $107 million for a startup that's revolutionizing how music gets made. Here are his lessons for pitching, leading, and building a company.

and an angel investor. He's also honing his leadership abilities under the tutelage of his coach Dick Costolo, former CEO of Twitter.

A founder who sold his first startup for $85 million explains why tons of VCs rejected his second startup idea despite his successDo you feel like you have that CEO bug, and you would go on and run another company? Or do you feel like your passion still lies with creating and engineering?I don't ever see myself as a good employee or working for someone else's business.

And so the timing was: We had a problem, we solved it. I think if you have a direct problem, that's a real problem that's real right now. And there are easy ways you can prove that. You can run ads about your idea and see if people click on it before you even build it. You can test if there's demand for things. There are ways to step outside what you actually have to build in order to figure out if the demand is there.[which lets users store their work and collaborate with others] with Splice. In the first two years, it didn't get the growth curve that we needed to out of it.

I was 27 when we sold [GroupMe]. So it's not like I have a ton of company-scaling experience underneath my belt. That was a lot of friends building an app. So I'd say continuing to try to be a great people leader is the hardest part. I think a lot of negativity people have when they meet with venture capitalists can be valid. They're not actually pitching them a venture company. The first thing you need to do is make sure the market [and] your marketing team are in place. Market size is the quickest thing that will hurt you in a venture conversation.

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