Creative Structures w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics

4 Sep 2025 · 23 min

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Podcast Summary: Creative Structures w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics

Episode Overview In this episode of *This Week in Startups*, host Jason Calacanis welcomes back Becki DeGraw, a partner at Wilson Sonsini, to discuss innovative legal structures emerging in the startup landscape, particularly among successful startups—termed “have” companies. The conversation highlights unique financing approaches, competitive investment terms, and the importance of legal counsel in navigating these complexities.

Key Concepts

  1. The “Haves” vs. “Have-Nots”
  2. Definition: The “haves” are successful startups with multiple attractive financing options, while “have-nots” face challenges in securing funding.
  3. Current Market Trends: There has been a resurgence of competitive valuations and favorable terms for the “haves,” reminiscent of the 2021 startup boom.
  1. Creative Legal Structures
  2. Off-Menu Financing Terms: Startups are now negotiating terms that are unconventional and not typically seen in standard financing agreements.
  3. Examples of Creative Terms:
  4. Founder Voting Proxies: Investors may grant a voting proxy over their shares to founders in exchange for participation in secondary sales.
  5. Mandatory Follow-On Investment Clauses: New investors may be required to invest in subsequent funding rounds at predetermined valuations.
  1. The Rise of Secondaries
  2. Secondary Sales: There is an increasing trend of secondary share sales, allowing employees and early investors to realize liquidity while still participating in the startup's growth.
  3. Implications: This trend can complicate governance structures and investor dynamics.
  1. Governance and Board Structures
  2. Lack of Preferred Directors: Some startups that have raised significant capital lack preferred directors on their boards, raising concerns about governance.
  3. Investor Viewpoints: The host and guest argue that having reputable board members is crucial for startups, as these individuals offer valuable connections and guidance.
  1. Diligence in Hot Deals
  2. Declining Due Diligence Standards: There is concern about a decline in thorough diligence practices among investors eager to participate in hot deals.
  3. Advice for Investors: Investors are advised to be strategic about their diligence processes to avoid being sidelined as funds chase after high-demand opportunities.
  1. Crypto's Resurgence
  2. Legal Implications: The resurgence of interest in crypto, along with regulatory developments, has led to increased activity in legal firms specializing in this area.
  3. Investor Caution: Investors need to be cautious about the speculative nature of crypto investments and ensure proper legal frameworks are in place.

Episode Highlights

  • Founder's Perspective: Becki shares insights on how the legal landscape is shifting and how founders can leverage current market conditions to negotiate favorable terms.
  • Challenges for Investors: Jason discusses the balancing act investors face between thorough due diligence and the risk of losing out on investment opportunities.
  • Personal Anecdotes: Both Jason and Becki share personal experiences that illustrate the complexities and unpredictabilities of the startup investment landscape.

Conclusion This episode provides actionable insights for both founders and investors navigating the current startup ecosystem. It underscores the importance of understanding new legal frameworks and being prepared for the dynamic nature of startup financing. Whether dealing with “have” companies or investing in the crypto space, the discussions offer valuable takeaways for anyone involved in the startup world.

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Useful Links

  • [Wilson Sonsini](https://www.wsgr.com)
  • [Startup Basics Episodes](https://thisweekinstartups.com/basics)
  • Follow Becki DeGraw on [LinkedIn](https://www.linkedin.com/in/rebecca-degraw-639bbb62/)
  • Follow Jason Calacanis on [Twitter](https://twitter.com/Jason) and [LinkedIn](https://www.linkedin.com/in/jasoncalacanis)
  • Follow *This Week in Startups* on [Twitter](https://twitter.com/TWiStartups) and [YouTube](https://www.youtube.com/thisweekin)

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Transcript

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0:03All right, everybody. Welcome back to Startup Basics. This is the program where I get the people who are my partners who help me run my businesses to basically help you, founders out there, angel investors, understand the game on the field. And you get some free advice, some free mentoring. And legal is where, gosh, there's so much going on. And I'm so lucky to have Becky DeGraw as my attorney. She's a partner at Wilson Sincini, and she's been helping me do these startup basic shows for years. God, we've done so many of these. And we talked on our last episode about the have-nots and protective provisions, cram down rounds, all this hand-wringing that's going on.

0:39But for every two or three have-nots, we're starting to see a have and have a lot. So when you're on a heater, you got a great team. You've got cash in the bank. You got revenue. You don't need to raise. What's the playbook now for that seed stage company that's breaking out and broke a million, two million in revenue, that series A company that has five term sheets they have to negotiate and you're picking between a lot of great options. Maybe even you got some overtures to be purchased, right? Yeah. Well, thanks for having me. It's always great to be here and do these with you. Legal oftentimes is, okay, yeah, we've got our playbook.

1:16We're going to do the same thing. It's the plain vanilla preferred stock financing. Not in this category. This is some fun stuff. I've been doing this for 18 years and there's some things that I'm seeing that I've never seen before. So do tell, do tell. I want to know where all the off menu items are. I know the standard documents. I got them all. And standard documents, you know, you go to your chat CPT and pull up a standard non-disclosure agreement. Now, all of that, what I would call chores for y 'all in the legal community. Like those chores are boiler plated. It's getting easier to get those out.

1:49But man, the complexity and the importance of your first round of financing, your first board of directors, maybe taking loans, doing a secondary sale, taking some money off the table. These are things that are the high order bits. These are the decisions you make that my friend Ruloff from Sequoia calls the crucible moments for your startup. So let's talk about those hard decisions founders have to make when they're the bell of the ball. Yeah. So it feels like we're back in 2021 all over again. You will look at, wow, all this that we've went through in 2022 when things started slowing down and 23 when it was crickets and wow everybody's a lot of uncertainty well guess what like in this category of the have companies it is 2021 all over again it's heyday it's super competitive multiple term shades like you said super company friendly terms founder friendly terms reduced diligence companies can really kind of pick which investor will provide the easiest path to funding because they have multiple investors lined up who are willing to write checks.

2:57And right, like that kind of relates to one of the things that we talked about on another episode, which is there is a lot of supply out there. There's a lot of dry powder. So when you do have one of these hot companies, everybody wants to write a check. Everybody wants to get in. And the company can't do a little picking and choosing on folks. I would say I represent companies about half the time and investors half the time. Investors are throwing their playbook out the window when it comes to these types of companies. And you kind of have to in order to get in. It's that same FOMO that was happening in 2021.

3:31How fast can we do this? Yep, I've never done this before, but I'm willing to accept it. So what are some of the things we're seeing? This is the off the menu. I like it. A la carte? Yeah. Or what you like. Let's go. I'm more costed. You surprised me. Give me some terms here. So it's not necessarily good things for the investor though. No, no. Yeah, for sure. So founder proxies. The way it works is if we let you, investor, buy my shares in a secondary or participate in a tender offer where you're going to buy lots of employee shares in a secondary, you have to give me, the founder, a voting proxy over your shares.

4:12Yeah. I like it. If you're on the company side. Yeah. Well, interestingly, some number of years into the cab company, my friend who was running at Travis was having a little bit of chippiness on his board, you may have read. And I was a shareholder with a significant number of shares, not anything close to a founder, but every vote counts. And I wanted a little liquidity because the Uber valuation had gotten so high that the percentage of my net worth was getting seriously out of balance. And people were predicting the end of that company since the day it was born. Putting that aside, I was like, maybe take a little chips off the table at an incredible price.

4:54I think I sold some shares early at like$32 a share long before Masa bought his. And I was talking to my friend And he said, you know, I could use a favor. It's up to you. But can I vote those shares so I have a little extra protection? You know, every little point here and there matters. And I said, sure. Yeah, you're my guy. You got me into this. You're responsible for 90 % plus of my net worth. I am more than happy to give you my shares to vote. And a number of us did that to try to help him. It didn't work. But we were right there. And I guess for an angel, it's much different than a fund.

5:27Because with a fund, if you were to do that, you had a board seat. they could vote you off or, you know. So that's where the devil's in the details. Yeah. And what exactly can that founder vote for? So oftentimes we carve out the director seat. We may carve out specific protective provisions, but it's not even all. So right, if you buy in a secondary, a lot of those secondary shares are getting exchanged for preferred shares. So I buy common from employee, but then the company doesn't exchange. So I now have preferred shares, but in return for this gift that you gave me to participate, I'm now going to give you a proxy over my preferred shares.

6:12And then we carve out one or two things, but it's kind of crazy world out there that big funds are saying, yep, I'll write big checks to do that and you can vote my shares. And this is because of the power law. And we all serve at the altar of the power law. If a company is breaking out and you own preferred shares in it and it's Robinhood, it's Uber, it's Coinbase, and you're lucky enough to get on those cap tables or SpaceX, the common thinking amongst investors with a lot of experience is you just need to own a piece of that company because they're so rare that if you have a chance to get on that rocket ship, in SpaceX's case, quite literally, you just take it.

6:55You take your seat and you shut up. Now, asking for those things early on before you've proven anything, I'm assuming we don't see too much of that. Yeah. I would say we're not seeing this like in the seed A, but we are seeing it as early as B. It's not waiting until your crossover, until your pre-IPO round. This is coming in much earlier than we would have. And so are secondaries, right? We're seeing a huge uptick in secondaries right now. for the category of the haves. Because remember, there is that whole other category that we're not talking about in this connection. But when you are in that category, it is.

7:34It's high-flying, great terms for the primary, and I'm throwing secondary on as well. Some of the other stuff we're seeing, we're seeing companies that have raised over a billion dollars, and there are no preferred directors on the board. I know. This is crazy. Governance is a good thing. Somehow we got into this very weird... A little bit of Paul Graham, I think, had a bad experience before Y Combinator. He always talks about it public. I'm not speaking at school here, where he felt like the VCs had too much power. And certainly during that era, that was true. And then this idea that somebody got in their heads that the investors are the enemies or a board of directors is adversarial is the opposite of, I think the game on the field today, the board of directors shows that that individual is giving you their most precious resource, which is their reputation and their time.

8:32Whereas anybody can buy some shares in your company and then go on vacation, go ski in Japan or whatever. These people do. That's me. But you having John Doerr on your board or Michael Moritz or Ruloff or any of these like high flutin individuals with big track records, Mary Meeker, like that's an incredible gift. It really is. Something's getting lost here. I think you're absolutely right. I sit in on a lot of board meetings when I'm representing companies, we always attend. Oftentimes, counsel is quiet in the corner, but we get to hear and see and observe it all. And man, when you have a good board member, particularly those that are the greats of the industry, you are getting one-on-one time with them to where they're paying nothing but attention to your business and how can I help you improve it?

9:23Who can I introduce you to? Where do I see holes? I mean, that's just like, that's amazing. The dream, it's the dream. It literally was the dream for Gen Xers and millennials. And then I think this weird thing occurred and gosh, I see some of these rudderless companies. And one of the ways we decide if we're going to do follow-on funding is, okay, the number of people who are competing for the next round, that's a really good signal for us as an early-stage investor. But we always want to see a priced round at some point, and we want to see somebody of quality join the board and governance to arrive.

9:58And we say, hey, if we own over 5 % or 10 % of the company, we would like the option of a board observer seat or a board seat. A little flexible on the margins there. And when I have that conversation with founders, I'm like, I know you've heard from the industry, oh, you don't want to have great board members, you don't want to have board members, you don't want to have board meetings. When you have those board meetings and something goes wrong and you need advice or you need money or you need an M &A landing, if there's no board, then there's nobody to go to who can tell your story to Sergey at Google or Elon at SpaceX or Zoc at Meta.

10:34Those people have those connections where they could send an email and say, hey, I'm on the board of this company. Now Zuck looks at that or Elon looks at it and goes, okay, you wouldn't waste your time. You're a quality person. And this might be an interesting thing for you to look at for an acquisition. Just like you got to think in a decade long period here of all the things that could go wrong. Oh, God. But I think a lot of our, a lot of the founders are not me, up and to the right, high valuation. I have no problems in my future. But for those of us that have been around for a long time, we know there will be.

11:08We talked about it on the last episode, like the half-nots. Those were the people who were the high flyers who stumbled. And then their boards are the ones who are going to eventually help them work these things out. So, gosh, incredible. I've got one more for you that I want to share because I also want to see if you've come across this or you've had to deal with this. So, this one goes like this. Okay. And I saw this in a series seed. Okay. So, series seed financing. Okay. So$5,$10 million finance thing. It's a two-year-old company. This was an AI company. Okay, so maybe it was 10, 20, a little higher.

11:46But it's a two or three-year-old company with 20 people in all likelihood as a footprint. But okay. And it says, if you invest now, and I let you come into my seed round, you have to also invest in my next immediately following round at a predetermined step up in valuation. What? And yeah, yeah. I've literally seen this to where it's like, if you want in, if you want to be in my seed round, you got to agree to participate in my A round essentially. And I'm going to tell you what the price of that A round is. And we're going to agree today that this is the big step up. I've had one, I've had one.

12:25Most of them have like a range or have a predetermined. I've had one where there was a range at the company's discretion of what the valuation would be at the next round. but you already signed in your series seed that you're going to invest, that you're committed. Dangerous for all parties to do these kinds of things because if you haven't hit the milestones and the money's not in your bank account, the VC has to send the money. Now, let's say you haven't performed. Now the VC could say, the reason we're not sending the money, even though we agree to it, is we believe that this startup has not been run properly.

12:59They could find some pretext to say, we're not funding for these reasons. say you guys didn't perform and they could, you know, then all of a sudden you're in a lawsuit with your venture capitalist to get them to compel them to put the next money in. It's very dysfunctional. And then what if your startup breaks out and it's worth more than the valuation and you get a billion dollar valuation and you, you pinned it at 200. Now what happens? Yeah. You just gave them a better look. Yeah. It's, it's, it's, but it's, it's really interesting. The stock that investors are willing to agree to out of fear.

13:33Don't leave me out. I want in on this one, right? Well, it all goes back to what we discussed on the previous episode was the game on the field is there's so much dry powder. If there's too much supply and not enough demand, you could see weird things happen in the market or it's too much demand and not enough supply. In this case, it would be too much demand for investment dollars and not enough supply of startups. So there's too much demand in a small number of startups. You have people competing on a small number of hotel rooms during F1 and the price of the hotel room is going to go up. That's it.

14:06There's just not that many of these rooms and you want to stay at the best place near the track. Sorry, this is the way it's going to go. Crypto seems to have been, my friend David's working there in the White House and they're trying to make some regulations. Are you seeing more activity come to your firm with regard to crypto? because I know in the past, I had maybe three or four companies that pivoted into crypto and never really tried to get into crypto too much because I was worried about regulations, specifically law. I'm wanting to break it. But some of them did anyway, but they all used, you may not say this, but I'll say Fugazi, Fugazi, law firms in the BVI and Panama, et cetera.

14:49But it does seem like with onshoring, does that mean people are starting to go to the legit venture firm, legit legal firms to get advice and counsel now? We've had a big uptick, so much so that we have hired a few folks specifically to help on the crypto side of things. Crypto a few years ago, I was like, okay, I'll become first in it and try to understand it because a lot of mainstream investors were starting to be like, well, maybe we'll go and then FTX happened. And then I decided, okay, that's a lot of wild, wild west. I'm going to leave that for our other colleagues at the firm to handle, but they are very, very busy right now.

15:29And it definitely is a crypto boom happening. I think there is a lot of uncertainty still in terms of where is that going to go? You know, we had a crypto boom and then who did it fall far? I think that, you know, I wouldn't be surprised if when it happens that there is kind of more dramatic shift in that industry. Well, you know, if you're doing something super speculative and you have a lot of participants who are momentum investors who don't have, we talked about protective provisions on both of these episodes, the episode with the have-nots and the haves. the reason protective provisions, boards, governance, Delaware law, all of this stuff became codified, refined, and the rule of law is so important is so that people feel comfortable investing.

16:20Now you look at the crypto space, if the people participating don't care about those things and they're just trying to see who has the most guts to hold on in this game of chicken and longer, you know, that's kind of anarchy. And you have to wonder if those people like to play a game that's based on anarchy and, you know, a big game of chicken. Some people might call them Ponzi. In some cases, they might have been. That attracts a certain element, I find. It is not for the faint of heart. It's like when I played poker games, Becky. That was my counsel here. I got invited to some poker games that were not fully legitimate in their construction.

17:05I went once or twice, and then I said to myself, this seems like a dangerous environment where at any minute the feds could come in or the police could come in or a rival gang or something could come in. How did I wind up with this game? Somebody who's a friend from the home game invited me to another game, and they're taking a rake. And then sure enough, in the press, I hear about this high-profile NBA guy who I knew through friends was playing these high-stakes games in LA in that circuit. They were doing all kinds of fugazi stuff and they all got pinched. I just decided I'll play in the regulated game.

17:38I'm totally fine playing in a casino or a regulated game with rules of the road. I don't know. It's not for me. If I can't understand how you make money and I can't understand the structure of the cap table, that's another thing that's weird. We'll end on this is due diligence. Does anybody besides me do due diligence anymore? You brought up FTX. A bunch of my friends YOLO'd money into that. And it turned out none of them, I mean, these are blue chip, like best of the best investors who all relied on each other's diligence. And a founder who was like mercurial and didn't want to do diligence apparently.

18:13and they were all like, well, we got to get in. Therefore, we'll not do diligence. What's your advice there? What are you seeing in terms of people doing proper diligence? I think in the early stages, we're still seeing diligence. So your seed A companies, absolutely. Maybe here or there, there's one that gets through with a lighter touch. But I would say that tends to be fairly normal. Where I am seeing some differences, and this is on the investor side I can speak to, is that those like super hot companies that we are all watching for the next wave of companies that might go IPO. And those companies have a line of investors out the door that are willing to invest.

18:59And when they decide, when they decide, it's not the investors, but when the company decides, okay, I'm ready to sell some shares, they know they have the line to go to. And they want to do it fast. they want to do it painless. And if that means if you're the investor at the front of the line and you say, okay, here's my laundry list of diligence that I want to do and I want to have these calls and it's going to take me two weeks to get through it, they're going to say, next, not you. So what we're having to do on the investor side of participating in these transactions is instead of just, you know, throwing across the bow kind of a full laundry list It's like, okay, let's be very specific about the things we care most about because we don't want to upset them and get kicked out of the room.

19:49I mean, it is a little different mentality for those types of companies. It's a negotiation. It's a dance. We try to prepare our startups in year zero, one, and two of like, here's what a proper Series A diligence is going to look like. Let's try doing it at the seed round. And okay, these 20 don't apply, but these 10 do. Like, are you incorporated? Where are you incorporated? You know, show us your bank account. Show us the money in the bank account. Show us the cap table. Man, I would say half the time, there is a significant thing that needs to be cleaned up in diligence in order for it to just be passable.

20:28Like, you didn't do IP assignments. You don't have documented the equity structure. There's literally no cap table. You just have an oral agreement about this. Okay, there's no vesting schedule for you. Okay, we're seed investors. We're pre-seed investors, really, in this world. And we just try to prepare people for what's going to come next. You have to get these things done. And if you have a great lawyer like Becky, he's going to tell you, hey, I know this is your first time at the rodeo, but you need to wear a saddle and you may want to put a helmet on. That Bronco can buck. You may want to put some elbow pads on, maybe a pair of gloves.

21:06I don't know, just thinking here out loud, You might need an IP assignment, investing schedule, or basic stuff. Yeah. It's just really interesting to watch the market go through boom-bust cycles, and just people suspend disbelief, and then people are incredibly pessimistic, and they become more diligent, and they become less diligent, they become more thoughtful, less thoughtful. during all of this, these weather patterns, these increasingly chaotic startup weather patterns. You need to have a great attorney. That's why I got Becky. Thanks, Jason. Another great one, a good banger, and WSGR.com.

21:47That's it. They're the best in the business. Larry Censini. That was a character right there. He still shows up to work. He still comes to work. I met him. He said, yeah, I was talking to uh steve and i was like jobs yeah hey mr smith yes sir yeah you know this i was talking to larry number one and larry number two and i was talking to larry and i was like larry page larry yeah i mean he was like literally i don't know if he still is but at that time he was literally those three people's attorneys. Yeah. Yeah. It's pretty amazing. Oh, it's really fun when we have like our partner retreat and he will share some of the more lively stories.

22:37It's going back in a time machine. It's awesome. It is. It is. And what a legend. I said, hi. I haven't seen him for 20 years. I literally met him when I was in my 30s in New York. I was running one of my magazines and I interviewed him. Wilson Sincene had opened their first office in New York, if you can imagine that, like 25 years ago. They're like, I think the Silicon Alley thing's going to be big. And I had Silicon Alley Reporter. We did an interview with him when he opened the office. Awesome. All right. Startup Basics. Find it at thisweekandstartups.com slash basics. You got to get your basics right.

23:08Have a great partner, yada, yada. See you next time. Bye-bye.

From the publisher

Today’s show:Wilson Sonsini Partner Becki DeGraw returns to Startup Legal Basics with Jason. This time, they dive into the “have” companies — the breakout startups with multiple term sheets, competitive valuations, and unusual deal terms.

From founder voting proxies to mandatory follow-on investment clauses, Becki breaks down the creative “off-menu” structures showing up in today’s financings, and what founders and investors need to watch for.

Whether you’re a founder navigating investor FOMO or a VC competing to get on the best cap tables, this conversation will give you insight into the new rules of the game.

*

Timestamps:

(0:00) Jason welcomes Becki back to Startup Legal Basics

(0:32) The “haves” vs. “have-nots” in today’s startup market

(1:28) Creative legal structures: the “off-menu” items

(4:19) Travis’ Uber favor & modern founder asks

(7:05) Rise of secondaries & unusual board structures

(11:22) Mandatory follow-on investment clauses in seed rounds?

(14:13) Crypto’s resurgence and legal implications

(15:55) The decline of proper diligence in hot deals

*

Check Out Wilson Sonsini: https://www.wsgr.com

Check out all of the Startup Basics episodes here: https://thisweekinstartups.com/basics

*

Follow Becki:LinkedIn: https://www.linkedin.com/in/rebecca-degraw-639bbb62/

*

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

*

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Twitter: https://twitter.com/TWiStartups

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