4.4 • 1.3K Ratings
🗓️ 4 September 2025
⏱️ 23 minutes
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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.
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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
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Check Out Wilson Sonsini: https://www.wsgr.com
Check out all of the Startup Basics episodes here: https://thisweekinstartups.com/basics
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Follow Becki:LinkedIn: https://www.linkedin.com/in/rebecca-degraw-639bbb62/
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Follow Jason:
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
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| 0:00.0 | All right, everybody, welcome back to Startup Basics. This is the program where I get the people |
| 0:08.6 | who are my partners who help me run my businesses to basically help you. Founders out there, |
| 0:14.6 | angel investors, understand the game on the field. And you get some free advice, some free mentoring. |
| 0:20.2 | And legal is where, gosh, there's so much going on, and I'm so lucky to have Becky DeGra as my attorney. She's a partner at Wilson Sucini, 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, |
| 0:38.0 | all this hand-wringing that's going on. But for every two or three have-nots, we're starting to |
| 0:43.1 | see a have and have a lot. So when you're on a heater, you've got a great team. You've got |
| 0:48.8 | cash in the bank. You got revenue. You don't need to raise. What's the playbook now for that |
| 0:53.8 | seed stage company that's |
| 0:55.3 | breaking out and broke a million, two million in revenue, that series A company that has five |
| 0:59.9 | term sheets that have to negotiate and you're picking between a lot of great options. Maybe even |
| 1:05.2 | you got some overtures to be purchased, right? Yeah. Well, thanks for having me. It's always great |
| 1:10.0 | to be here and do these with you. Legal oftentimes is, okay, yeah, we've got our playbook. We're going to do the same thing. It's the plain vanilla for Ferdstock 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. Do tell. Do tell. I want to know where all the off-menu items are. I know the standard |
| 1:34.0 | documents. I got them all. And standard documents, you know, you go to your chat cheapy team, |
| 1:39.3 | pull up a standard non-disclosure agreement now, all of that, what I would call chores for y'all in the legal |
| 1:45.1 | community. Like, those chores are boilerplated. It's getting easier to get those out. But, man, |
| 1:50.8 | the complexity and the importance of your first round of financing, your first board of directors, |
| 1:57.0 | maybe taking loans, doing a secondary sale, taking some money off the table. These are things |
| 2:01.7 | that are the high order bits. These are the decisions you make that my friend Ruloff from Sequoia calls |
| 2:07.7 | the crucible moments for your startup. So let's talk about those hard decisions founders have to make |
| 2:13.1 | when, you know, they're the bell of the ball. Yeah. So, you know, it feels like we're back in 2021 all over again. |
| 2:21.2 | 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. |
| 2:31.0 | Well, guess what? |
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