Meet Win: Building with Hulu, MasterClass, and Now Founders

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Win Chevapravatdumrong is not your typical lawyer. With a career spanning leadership roles across the early days of Hulu, Vessel (a short-form video platform), and MasterClass, Win has watched the streaming industry grow from nascent ideas to household names. He brings this unique blend of early-stage operator experience and level-headed business strategy to his role as General Counsel at M13. 

As a member of M13’s Propulsion engine, Win advises early-stage portfolio companies navigating the sometimes daunting waters of law, regulation, and operations. His approach is about demystifying (and defanging) the legal process, empowering startups to take calculated risks, and helping founders find actionable, efficient solutions. 

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Whether negotiating high-stakes contracts, innovating new partnerships, or guiding founders through uncharted territories, Win remains deeply attuned to the human side of business—empathic, creative, and grounded.

We sat down with Win to talk about how a lawyer works with portfolio companies, fundraising at different stages, Michigan football blogs, and more.

Win’s recent publications 

• 25 Predictions for 2025

Laying down the law 

As M13’s Head of Legal, how do you work with founders? 

I first meet founders pre-investment, then after the investment is made, I work with them as part of Propulsion. 

I like to tell our founders, call me before you call your outside counsel. First, because outside counsel can be very expensive. (Sorry; love you guys!) But second, because I know firsthand that navigating legal issues in early-stage land can be really scary. My job is to defang that and help founders understand the things they should actually be worried about and the things they shouldn’t. Some daunting problems can be fixed in half an hour—and I’d much rather have founders know that than to feel the weight of the world on their shoulders and do something unnecessary for their company because they’re scared. 

Thinking back to my days working at early-stage companies, I got in my own head a lot about legal and regulatory concerns. I want to help founders avoid that trepidation and focus on what really does matter.  

What kinds of legal topics do you consult on? 

For early-stage companies, common questions might be around intellectual property, data privacy, and regulatory compliance. 

What is a common misconception about your job? 

My biggest gripe is probably with the idea that lawyers get in the way. A good lawyer is a business-minded person who helps drive growth and finds ways to get things done, as opposed to just saying no and shutting ideas down. 

I think people don’t completely understand what in-house lawyers do. They picture something like Ally McBeal or procedural crime dramas. In reality, most in-house lawyers are generalists who make and de-risk business decisions. 

What makes a founder stand out to you? 

The ability to articulate a vision and get people motivated is so important. But even more fundamental than getting other people to believe is having deep conviction yourself. I’ve sat in a lot of investor meetings, on both sides of the table, where people are skeptical or point out a lot of ways something could go wrong. A founder who stays optimistic and visionary can go really far. And it’s so exciting to see someone accomplish something that other people thought couldn’t be done. 

{{appearances}}

Lessons from work and life  

What was it like being at Hulu in its early days? 

People thought the idea of putting TV on the internet was ridiculous. In the early days, reporters were calling Hulu the “clown company.” Netflix was not yet doing streaming at scale, and so we were doing something entirely new. Now, it’s amazing to look back and see that “Hulu” has become a household word. To be part of a nascent industry like that, and then see it become such a big part of everyone’s lives today, was really cool. 

You’ve said before that you’ve basically raised “every letter of the alphabet” over your career. What have you learned from working with companies at different stages? 

That’s a little bit of an exaggeration, but I have worked at companies at a range of stages. After serving as Senior Counsel at Hulu, I moved on to a short-form video platform called Vessel. I was essentially there from day one, which is a little unusual for a lawyer. At that stage—pre-product, pre-external funding—storytelling is crucial. You’re selling the vision to investors, and storytelling is what helped us raise our Series A and B. 

I joined MasterClass when the company was at Series C. Your fundraising focus eventually starts to shift from VCs to more institutional pre-IPO investors. There’s a real product now, and the hard metrics become more important than the vision. 

MasterClass’s founders had incredible stories about family and commitment to education—but at later stages, investors were less interested in that. The sense is “Cool, but tell me about your growth trajectory and CAC and margins.” It’s about financials and strategy. 

As a lawyer, what drew you to the world of tech startups? 

I studied engineering at MIT and started working at the tail end of the dot com boom, so my world was technology. I was a hardware engineer at a large company, and I struggled with not getting to see the bigger vision behind my day-to-day work. I’m wired to want to understand why I’m doing what I’m doing and how it connects holistically to the larger business. 

That desire to see a bigger picture is what drew me to the world of startups and entrepreneurship. With startups, especially early-stage ones, every single person knows what their mission is and why. I wanted to be part of a team with a shared mission. 

What’s a daily habit of yours? 

I try to take a walk every day to reset my mind. It helps me decompress from work and get un-stuck when I need to. (I also FaceTime my parents and sister every day.) 

Lightning round

What’s something most people don’t know about you? 

I was captain of the ultimate frisbee team at MIT. …and I tore my Achilles tendon playing. 

First job?

My parents ran a jewelry store that I worked in as a kid. 

Hidden talent? 

I have perfect pitch. Although as I’ve gotten older, it’s weirdly shifted by one whole step. Not sure what’s up with that.

Guilty pleasure? 

Michigan football blogs. 

Music rec? 

Raye

Musical rec? 

Guys and Dolls

Movie rec?

Is it ridiculous for a lawyer to say A Few Good Men? Because A Few Good Men. 

Favorite MasterClass class? 

Former FBI hostage negotiator Chris Voss’s class on negotiation.