Becki DeGraw on spinouts, IP licensing & clean exits | Wilson Sonsini Startup Legal Basics

This Week In Startups is made possible by: Wilson Sonsini Today's show: Spinouts are everywhere right now, and most founders get the cap table wrong. Jason sits down with Becki DeGraw, partner at Wilson Sonsini, to break down how to do it right, starting with his 80/20 rule for splitting the new cap table and why letting the old company keep too much of it kills your ability to raise. Becki also covers the legal side: who owns the IP, non-competes between the two companies, and the trap founders fall into when they're still on the old board. PLUS, the one question every Series A investor will ask. Guests: Becki DeGraw on LinkedIn: https://www.linkedin.com/in/rebecca-degraw-639bbb62/ Wilson Sonsini: https://www.wsgr.com/en/ Relevant Links: Wilson Sonsini Goodrich & Rosati (WSGR) — **https://www.wsgr.com/** Becki DeGraw — https://www.wsgr.com/en/people/becki-degraw.html Waymo — Jason's headline example of a big-company spinout — https://waymo.com/ Expedia's 1999 Microsoft spinout — https://www.britannica.com/topic/Expedia-com-American-company Nvidia's ~$20B deal for Groq's asset— https://www.cnbc.com/2025/12/24/nvidia-buying-ai-chip-startup-groq-for-about-20-billion-biggest-deal.html Timestamps: 0:00 What a spinout actually is 0:50 Becki: the real "why" behind spinouts 2:24 IP licenses and the "acquihire" workaround 3:09 University spinouts 4:41 Google/Waymo and Microsoft/Expedia: spinouts at scale 5:03 Jason's 80/20 rule and the unicorn test 6:06 The broken cap table problem 6:36 Licensing deals as an M&A workaround 8:44 Exclusive licenses, full assignments, and license-backs 11:07 "What if Google spun out YouTube" 12:31 Groq–Nvidia, capital gains vs. income 13:23 Confidentiality, customer lists, and fiduciary duty traps 15:16 Get the paper done BEFORE you start the new thing 15:56 "It's a divorce," — and the employees are the kids Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Check out all our partner offers: https://partners.launch.co/ Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason's suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com

• 0:06Speaker 00

  Welcome back to This Week in Startups. We're doing our Startup Basic Series. What is it? All the basics you need to know to run your company. Legal, accounting, marketing, you know, you name it, we go over it here. AI, a new one. thisweekinstartups.com/basics to see the entire library. I'm so lucky to have Becky deGraw from Wilson Sonsini, WSGR, on my team. She's my attorney and she helps me explain the basics to you. Welcome back to the program, Becky deGraw.

• 0:35Speaker 01

  Thank you so much. It's always good to be back. Always fun time to be here.

• 0:38Speaker 00

  We always have a good time. I wanted to talk to you. I came up with today's topic. Spinouts. Spinouts, spinouts, spinouts. Every week, every two weeks, some founders leaving a company, they built something inside the company, the CEO says, wow, that's a very interesting project. They let them work on it for six months, 12 months, and it has an absolute interesting success, but not breakout and it doesn't belong inside the first company. But the founder, the co-founder or, you know, an executive wants to go pursue it. So they say, sure, you can spin it out. You can spin it out. Second case, hey, we

• 1:18Speaker 00

  want to get hired, but maybe Washington DC doesn't exactly want us to sell a company and the shares in it. So we're going to do an IP license and we're going to spin it out that way. Two different situations, very different. Let's start with the first one, which keeps happening to me. I literally have three of these on my plate this month. And every time I've got a, you know, the one co-founder who's leaving, it doesn't, you know, there's too much equity, the holding company took too much equity. And then every CEO is just saying, why can't I leave and get 80% of this new company? This isn't fair. We should own 90% of the company and the co-founder leaving should get 10%. Tell us a little bit about spinouts, why they happen, and then what's the best practice?

• 2:02Speaker 01

  Yeah, I mean, you laid the groundwork perfectly. That is what the situation where we see the spinouts most often. Why, the why behind it might be, right, it's faster to start with that technology that has already been built and tested and validated. And like you said, may not just fit within that existing entity. It may not, it may be distracting to what the goal is there. From an existing entity's perspective, if they're not going to use that technology or that asset going forward, and they don't really want to put the funds to it or the resources toward it to, to, to scale and grow because it's maybe not in the direction of their strategic vision where they want that company to go,

• 2:45Speaker 01

  it may be more valuable to them to say, all right, well, you're interested in this. If I spin it out and I agree, I'll, I'll, I'll transfer X, Y, and Z over to you. You go grow it, or maybe I'll get some benefit from that. So that's, that's really the why behind it. You know, these things take all kinds of shapes and, and sizes. Oh, another example is that we see all the time is university, right? So you've got,

• 3:14Speaker 00

  Yes.

• 3:15Speaker 01

  You've got folks working at the university to do R and D. And then I'm like, whoa, we're on to something. That is also a, a spinout type situation where instead of negotiating with an, you know, like the, a company, you're negotiating with the university in terms of what are the terms going to look like of how am I going to get that, that IP into a new co and be able to start a new venture. But there's, there's a lot of considerations that go into how we would think about these and how we would structure them. They are so fast specific. So first thing I'll say is like, this is, this is going to be, you know, pretty high level and a lot more of, you should think about this and you should

• 3:56Speaker 01

  think about that. And here's a few different ways to, to go about it rather than, oh, well, when you do this, you should do this and you should do that. There's, I don't know, I don't know what it should look like. Because there are just so many different sizes and how these things take form.

• 4:12Speaker 00

  When this happens, sometimes it's at a big company. Google has famously spun out Waymo, very famous. Microsoft, back in the day, this little site, Expedia, that was internal. Now, that can be for economic reasons or the thing's getting so big and the existing management team is getting distracted by it. And Waymo needs to be out there on its own, raising capital to validate its, from what I understand, the back channel I got was, hey, we need to validate this valuation. And in order to get AI talent to work on a self-driving company, they, you know, we're up against Anthropic or SpaceX, Xi, or OpenAI. We need a currency where people can say, oh, this is going to be a

• 4:54Speaker 00

  trillion dollar company. So there's a real reason to spin it out. I like to run a little test when I talk to the two founders. I say to them, what's an amount where if this thing spun out and it became a unicorn, you would feel great about the terms that, you know, we got to. And typically I tell people, have the existing company keep 20%, let the new team keep 80. They want to go 51, 40, whatever. And sometimes it's 25, 75, 30, 70. It is specific because maybe the thing's making $0 and losing money. Sometimes it's making some money. So there's all kinds of provisions you can do. But when you look at that, almost universally, if it becomes a billion dollar outcome, the company that

• 5:38Speaker 00

  spun it out, getting 20% of a billion dollar company, you feel pretty, pretty smart, pretty savvy for having done that. But if you take 50, 60% and it goes to zero, well, you're like, well, that was dumb. And then for the co-founder, if he were to spin it out, they got 60, 70, 80% of the company, were able to build a team, raise more funding. That wouldn't feel so bad paying that 20%. Hey, we chose to do that. We could have left and just built it ourselves. Yeah. So there's, sometimes you have to take people through, well, here's the possible outcomes. Do you do that where you say, here are scenarios? And people ask their attorneys, like, can you play out some scenarios for me? So I understand, like, what's at the other side of the rainbow, practically speaking?

• 6:18Speaker 01

  The consideration often takes the form of equity. It can also be cash. Sometimes it's a combination of cash and equity. You know, if you start getting the more complex structures, you might see earnouts based on milestones or royalties. We'll often see those in connection with IP being spun out of universities. But when it is equity, because that is where oftentimes where the, either all or a big chunk of the consideration is going to be, there's negotiations definitely around the percentage, but also around what class of stock are you going to get? Are you getting common? Are you getting preferred? What rights go with that stock? Are you getting information rights? Are you getting

• 6:59Speaker 01

  pro rata rights? Whether you want a board seat or a board observer? We talked about that on another one of these. All of those things, kind of that, that's the package of things. Everybody does focus in on that percentage. The other stuff is like, kind of like, okay, well, we'll deal with that. But the percentage really matters. And I will say there's not a market range. It varies, varies a ton. But I will say, if it gets to be too large, that's where you are going to have potential problems going forward in new co. Investors, it'd be like, I imagine, the reason you're spinning this out is, it's going to get spun out. Whatever group of employees are going over there,

• 7:43Speaker 01

  they're going to grow it. They're going to go ask investors to make an investment over there and hopefully it becomes that unicorn. In order for investors to get excited about new co and making an investment in new co, they want to know the founders are motivated. The founders are invested here. If the old company, I'll call it parent or existing company, has an 80% stake or 50% stake in the company and the founders have smaller stakes, they're probably less motivated. I mean, that's the same in any, even if you're not doing a spin now, that's the same of any, you know, investment analysis at the early days is by an investor. And that's like, I want you to grow this company. I want you to drive long-term growth. I want you to be excited about that. If you have

• 8:28Speaker 01

  a small stake, it may not be.

• 8:29Speaker 00

  Don't break the cap table, is I think. We see it coming into, we will have sometimes somebody comes into the accelerator and they gave 25% of the company to the people who built the app, the first version, fully vested. And we have to tell them, you're never going to clear market with investors. We can't have you in the accelerator. If you don't have a chance of pulling through, why don't you go to them, say you'll give them $50,000 and two points in common shares. You know, so if it was going to cost them 100,000 to build the app, you're giving them 50,000 in cash and two points in common. And you have the right to buy those back at a $10 million valuation. So they can make 250 and they, you know, wow, you guys are suckers for, you know, spending 250 building the first version of the app. And, and you know, I'd say, when we give them the right...

• 9:13Speaker 00

  Language, it works more than half the time, maybe 60% of the time, but doesn't work 100% of the time. That's why it's important to like have a great attorney and think these things through before and understand the basics. What's happening with all these licensing deals? That seemed to me to be something that under a previous administration where M&A was being stifled and they weren't as in favor of it as opposed to maybe the world we're living in today, no politics here, but just the game on the field. People got creative. They said, hey, you want to, you want this team on your team and you want them there tomorrow? You want them working there Monday? It's Thursday. They'll be onsite Monday. We'll just give you a global license

• 9:55Speaker 00

  to this technology and the shell company remains. And then the licensed and the team goes to the company, creates all kinds of tax issues. We'll put that aside for the startup basics and accounting. But talk to me about that weird moment in time over the last couple of years. We had that. And is it still happening? And is that still part of the playbook? Or was that a moment in time? What's your take?

• 10:16Speaker 01

  Probably less so, because it does create a lot of other problems. So only in the situations where it's like, this is the only way I can get the deal done. Would you kind of resort to that? I think because there are some negative pieces that go along with it. But yeah, I mean, you can, there's a variety of ways to, to transfer assets. And if that's what you're looking for is, are I want this IP along with some other, you know, list of assets. How do I get that out of one entity and into another? You know, certainly a license arrangement works. You know, it can be an exclusive

• 10:59Speaker 01

  license even if it is a situation where like this is really going to kind of be a shell company. Maybe you don't care a whole lot. And it is like, yeah, sure. Exclusive license. Here you go forever. In the situation that we were talking about kind of originally of a founder wants to take some IP out of a company and start a new co with it, but that existing entity is, it's in full force, it's staying, it's doing its thing. Just this new co is going to be something different. In that situation, you know, we are thinking a lot about, and this is where, you know, getting your lawyer involved from day one is so important is understanding that IP, right? And who is going

• 11:42Speaker 01

  to own that IP going forward? Is it going to be that your existing entity, I don't care. I don't need this IP at all. It's going to be a full assignment. And I'm just, here you go. It's all yours now. Following this transaction, you give me equity, it's yours. That may be, maybe, maybe perfectly fine, but it really kind of depends on whether the existing entity needs to continue to use that in that. It may be intertwined with other things that they're doing. And maybe like, I'll assign it to you, but I need you to give me a license back because I still need to use it.

• 12:16Speaker 00

  The example would be there, to make it practical for people, if Google wanted to spin out YouTube, but YouTube might use the infrastructure and the video serving infrastructure of, you know, Google's cloud. Okay, well, we can't give you our infrastructure. So we'll give you a license to it and we'll let you use the infrastructure for two years. And then after that, if you want to be a customer of Google Cloud, you can. But if you want to go use Amazon, you can. I had this happen. We were investors in Grok bought by Nvidia. It was a large purchase price. And I suppose, you know, when these distributions happen, the distance between capital gains, tax treatment,

• 12:58Speaker 00

  which is generally lower than income, we'll have to deal with. But the buyer, if they really want, it can just raise the price a bit, some number of percentage to, you know, find that compromise, etc. So IP licensing, that's got to be tight. And then the cost structure has to be tight as well, because sometimes costs are being paid for by the previous or services are being rendered by the previous company. And then you also have clients, right? Like maybe some clients are shared between the two entities. How does that split up? And that can get a little dicey. And then there's competition. I think you have to put in these, hey, for the next five years, spin out company is not going to go to the parent company's business lines or seven years or 10 years. And that seems fair to me. Yep.

• 13:42Speaker 01

  All of those things are part of that package of things that gets negotiated as you're moving out, right? Like if you're a founder or an employee or part of a group that is even thinking about doing one of these, it's so important to, to really think from day one and think about like, what is your separation look like as well? Right? Like that IP that you want was developed while you were at this existing entity. That means confidentiality restrictions apply with respect to it, customer, any customer list, right? All of those things are owned by the existing entity. So when we do these spin outs, it's not just like, oh, well, this part of the business. How do you, how

• 14:27Speaker 01

  do you just circle just like very neatly part of the business? There's so much more that goes to it, but you have to get very granular about that. And there are, there's the IP ownership issues, the confidentiality issues. If you were a founder, director of existing entity, there may be fiduciary duty issues that you want to make sure really clear where those come into play in terms of your separation from, from the company. So

• 14:52Speaker 00

  That's interesting. Yeah. Because you could have been a board member and then you would have to exclude yourself as an interested party, I guess, or conflicted party might be the, the legal term.

• 15:02Speaker 01

  Interest, yeah, conflict of interest, interested. But also just, you know, in terms of before you go off and start like, okay, you know, I've kind of talked about this. I'm just gonna start doing my own thing. Get that papered before you just start go doing your own thing. Because that could actually be breach of fiduciary duty. It could be breach of your confidentiality provisions. Like just have the clean separation before you start on the new venture. Like, and it's going to take a little time. It's not going to be one of those things where, hey, I want to take 100K on a safe finance thing. Cool. We'll get it done this afternoon. This is much more in depth. Like it's going to involve like a corporate

• 15:45Speaker 00

  It's a divorce. It's a separation. Let's be honest. You know, we keep going back to these relationships, but in a separation, in a divorce, hey, what about the kids? Those are the employees. You're going to have them for one week. I'm going to have them one week. Doesn't work that way. You're going to have to basically give me some of the children. You're going to keep some of the children in this analogy, which is dark, but true. And that could be a blocker. And I always tell the people who are leaving, hey, if you really do want to spin this out, you're going to have to have a real heart to heart and say, heart to heart with yourself and with the other person. Is it actually worth going through all this? This sounds like a lot of paperwork. This sounds like a lot of negotiation, a lot of bad feelings. Maybe I'll just leave. I'll take a six months to 12

• 16:26Speaker 00

  months and go ski in Japan. And then I'll start my next company. And who knows what area it will be in, but you can be sure I will not be taking any of the confidential information from this company or any of the IP I developed while here. And I will start with a fresh sheet of paper and a brand new MacBook Pro. Do not keep your MacBook Pro. I keep telling developers this. I'm like, where'd you have that MacBook? Oh, I had it for my last company. No, no. Do not keep your MacBook Pro. Just give it back. Wipe it. Let them wipe it. Do not bring anything that you bring with you is what is in your big, beautiful brain. That's it.

• 17:04Speaker 01

  Yeah. And if you go through one of these exercises and you get to the other side and you've got new co set up and you're ready, you've got an investor who says, I want to invest $20 million. Guess what? The number one diligence exercise is going to be.

• 17:20Speaker 00

  Yeah.

• 17:20Speaker 01

  They want to know, they want to see a clean chain of title to that IP. And they are going to diligence the heck out of, how did this get spun out? It's totally fine.

• 17:31Speaker 00

  Yes.

• 17:32Speaker 01

  As long as it's done right. But that is going to be diligence exercise number one.

• 17:35Speaker 00

  100%. All right. Another amazing startup basics. Becky, thank you so much. Wilson and Ciney, my attorneys, they do a great job. Startup basics, thisweekinstartups.com/basics. You get the whole library. Take the time, watch it with your team, share it with your team, and we'll see you next time, everybody. Bye bye.