When it comes to startup journeys, few are as dynamic and wide-ranging as Anthony Rose’s. From shaping the future of digital media with BBC iPlayer to transforming how founders raise capital through SeedLegals, Anthony’s career is marked by spotting inefficiencies and building scalable solutions.
In our latest Ignite podcast episode, Anthony takes us behind the scenes of his entrepreneurial path, the lessons he’s learned, and how he’s helping founders and investors navigate the complex world of fundraising.
From Electronics to Media Disruption
Anthony’s entrepreneurial streak began early in South Africa, where he ran an electronics manufacturing business long before angel investing and venture capital were widely accessible. After a stint with the team behind Kazaa, he joined the BBC to lead the development of what became iPlayer, a platform that revolutionized on-demand TV and changed how millions consume media.
The experience cemented his belief in customer-driven development. Famously, he introduced the “chocolate box test,” bribing colleagues with chocolates to test products quickly and cheaply, highlighting the importance of real-world feedback in shaping technology.
The Birth of SeedLegals
After exiting multiple startups, Anthony grew frustrated with the cost, inefficiency, and slowness of traditional lawyers when raising capital. Alongside co-founder Laurent Laffy, he launched SeedLegals seven years ago to fix this.
Today, half of all UK startups use SeedLegals for fundraising, agreements, and cap table management. Unlike traditional firms, SeedLegals combines technology with human expertise, offering founders both automated legal documents and access to experts when they need advice.
What’s Broken in Fundraising
Anthony argues that founders don’t actually want legal documents—they want investment. Traditional systems, however, bury them in paperwork, costs, and delays.
SeedLegals reframed the process by asking:
What do founders ultimately need?
How can technology streamline the process?
Where do human conversations still matter?
The result is a platform that makes fundraising faster, cheaper, and far more transparent.
SAFEs vs. Priced Rounds: The Hidden Founder Trap
One of Anthony’s strongest views is around the use of SAFEs (Simple Agreements for Future Equity). While popular in the US, he warns that they can quietly erode founder equity.
Why? Each SAFE agreement stacks up, often leaving founders far more diluted than they expect once conversions occur. Priced rounds, while seen as more complex, often protect founders’ ownership in the long run.
SeedLegals’ mission is to make priced rounds as easy as SAFEs—what Anthony calls a “Safer” approach.
Untapped Investor Benefits
Beyond helping founders, SeedLegals also educates investors about overlooked advantages. For example:
QSBS (Qualified Small Business Stock) can eliminate federal capital gains tax after five years.
Section 1244 allows early investors to write off losses against ordinary income.
Yet many investors don’t leverage these opportunities because traditional systems don’t make them easy. SeedLegals sees a role in productizing these benefits so investors can reduce risk and stay engaged.
Expanding to the US
Having achieved dominance in the UK, SeedLegals is now expanding into the US. Anthony notes the cultural differences:
UK founders often raise smaller, tax-incentivized rounds.
US founders tend to go bigger, earlier, with more ambition and larger capital commitments.
Still, the frustrations are universal: high legal costs, slow processes, and confusion over deal terms. SeedLegals aims to bring the same efficiency and empowerment to US founders that it brought to the UK.
The Role of AI in Legal Tech
Anthony is cautious about AI hype in law. While many startups tout “AI-generated legal documents,” he believes founders need to understand the decisions they’re making, not just accept whatever an algorithm produces.
Instead, SeedLegals uses AI to analyze, summarize, and support decision-making, while ensuring a “lawyer-in-the-loop” approach when stakes are high. The future, he says, is platforms that balance automation with human expertise.
Lessons for Founders
Throughout the conversation, Anthony shares practical advice for entrepreneurs:
Talk to users early and often. Don’t build in isolation.
Be wary of SAFEs. They may cost you more equity than you realize.
Plan for founder fallouts. Reverse vesting and clear agreements prevent disasters.
Efficiency matters. Fewer employees with higher output is increasingly the badge of honor.
Adopt the right tools. From fundraising platforms to productivity software like Whisper Flow, leverage technology to reclaim your time.
Looking Ahead
Anthony envisions a future where fundraising is as fast and seamless as sending a safe link—but without the dilution risks. He believes startups will continue to push legal tech forward, just as streaming disrupted music and media.
As he puts it, “A funding round is like a bus trip—you want everyone on board. But technology can make that bus leave faster, smoother, and with far less friction.”
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Chapters:
00:00 From BBC iPlayer to SeedLegals: Anthony’s journey
02:30 The “chocolate box test” and lessons in user-driven development
05:40 What was broken in fundraising and how SeedLegals fixes it
07:30 Combining technology with human expertise
08:40 Expansion to the US and key market differences
11:16 Why priced rounds matter more than safes
13:58 The hidden dilution trap founders face with safes
16:50 Tax benefits (QSBS & Section 1244) that investors overlook
19:27 The concept of a “Safer” – making priced rounds as easy as safes
22:19 Helping investors recover losses with “Seedback”
24:41 Cultural and fundraising differences between UK and US founders
29:29 Post-money vs. pre-money safes explained
31:22 Why UK safes always convert in six months
33:20 Protecting founder control in priced rounds
35:36 Founder fallouts and why reverse vesting is critical
37:52 Trends in cap tables and funding behavior
39:27 The myth of the one-person unicorn company
42:22 Productivity tools that change founder workflows (Whisper Flow)
47:12 The future of AI in legal docs and contracts
53:57 How AI will disrupt (or fail to disrupt) law firms
56:19 Lessons from past disruptions: music, TV, and now law
58:20 Rapid-fire questions and bold predictions for 2030
Transcript
Brian Bell (00:00:51): Hey everyone, welcome back to the Ignite Podcast. Today we're thrilled to have Anthony Rose. He's the serial entrepreneur who took BBC iPlayer from skunkworks to national pastime and now helps 60,000 founders raise capital faster as co-founder and CEO of SeedLegals. Thanks for coming on, Anthony.
Anthony Rose (00:01:06): Thank you so much for having me on the show.
Brian Bell (00:01:08): Yeah, so you know back in 2008 one out of every five UK internet clicks pointed to a new tool called iPlayer, the architect. Ten years later, you asked, why is fundraising still stuck in dial-up and you built SeedLegals to fix it? Let's unpack that leap and maybe get the origin story.
Anthony Rose (00:01:23): My background's actually electronics. When I was a kid at school, I had a robot pick and place machine and a hot belt surface mount machine at home. And I built an electronics manufacturing business in the days before angel investments and VC. I was living in South Africa. And I learned that you actually had to like make money to build your business. You know, if you didn't get more money coming in at the end of the month than you were spending, you're out of business. But then things changed, of course, in the invention of VC and investment, which was great. But then left South Africa, moved to Australia, got hired by the folks who then became Kazan. They got involved in music file sharing, building a licensed music store. And then one day the BBC called and said, how would you like to join the BBC? And I went, sorry, where are the stock options? Because it's a public service broadcaster in the UK. But I was persuaded to leave Australia and move to the UK, which is where I am, as we talk today. And when I joined the BBC, iPlayer had been something they'd been working on for ages. For those who don't know iPlayer, it's like the Hulu or Netflix of the BBC. It's used by millions of UK viewers every day. A good fraction of TV viewing in the UK is now, of course, online and on your phone. And the BBC had been noodling over this for a while, not doing a great job on it. I think it was more like an ority, as you said, beautifully as skunkworks. And it needs really to be productized. And that's really where I guess I learned the set of things that are now commonplace. And you buy endless numbers of startup books on agile fundraising and customer-driven development and so on. And actually, I didn't know any of that stuff at the time and made it up as I went along. And one of the things I did was what I call Anthony's chocolate box test. So when I joined, the product didn't work very well. And pretty much everything you tried had some problems. And I went to the dev team, and they kept telling me, dude, it's just you. You're the only one who's using Microsoft Explorer with this combination of graphic card and this program. And I realized there were like 100 things didn't work. And if any one person experienced this only one time in 100, for most people, it's never going to work. So they didn't believe me, and so I needed to do user testing. So I went to the BBC's testing department. I hunted them down and said, I need to do some user testing. And they said, yes, we can do that. It costs £20,000, takes six weeks. Where do you want to start? And I went, there's no way I'm spending £20,000. And I don't have six weeks because my product launches in three months. It's not going to work. So instead, I went to the local supermarket and bought some big boxes of Lindt chocolates, those deluxe editions. And then I went to non-technical folks at the BBC, i.e. the legal department, and said, if I give you this big box of Lindt chocolate, will you come down and test my products? And they said, yes. So I got all the developers in a room, big screen TV, and then got this person to go and do some user testing. And the first time it was a disaster. Nothing worked. Like everyone's faces were like on the floor. I went, okay, what we're going to do, we're going to pick the top three things that were broken and we're going to fix it in like 24 or 48 hours. And then we're going to repeat. And actually by the third time or so we repeated, it worked. It was great. So then we could go and launch. And for me, this experience of customer driven development has changed and drives everything, which is I think a big problem founders make is they talk to their team and they sit in their office and they build stuff and they don't talk to real world users. So you want to bring those users as close to you as possible. But I completely digressed from your question. And after I left, then it was time when iPlayer was delivered and growing. Left the BBC, built a startup, sold it. Built another startup, sold it. Invested in a few. Got tired of paying lawyers. Met my co-founder, Laurent, who's a genius ex-VC and serial angel investor. We met at a fabulous party in Rome held by an investor in my previous startup. He was saying, those fundraising legals, you know, going to lawyers, it's broken. Lawyers take forever. They make mistakes. They charge a fortune. We should change it. And having built and sold a couple of companies and looking for my next gig, we thought, let's get together and do it, which we did. So that was like seven years ago. And now a good fraction of all UK startups are on SeedLegals as the platform that you know, to get investment ready to all those founder agreements, table funding rounds and beyond.
Brian Bell (00:05:49): Amazing. So in your opinion, when you look back, you know, seven years ago, what was most broken about the fundraising process and what did SeedLegals solve with its platform?
Anthony Rose (00:06:00): Great question. And I think at the time, I thought my goal was to build legal documents faster. But I realized, retrospectively, no one actually wants legal documents. What they want is fine investment or fine investors or a general empowerment that, as a founder, you've got many, many things to do. So on a rainy Sunday night, is there a platform you can log in and it will do the stuff you want? Yeah. If, you know, what I joke to my team about is think about what a law firm does and we're going to do completely the opposite. So the product is not a legal document. It's a video on the things you probably want to know about. It's data to show you what the common deal terms are so you're not the sucker in the room. It's an always-on platform. There's no billable hours. It's a fixed price and always-on SaaS platform. And oh, by the way, it's a legal document as well. So my goal is think what a founder, or putting this more widely, think about what your customer ultimately is looking for, and then have the website going, this is a problem you've got. This is the solution to that problem. And then figure out what's called, I guess, a man and machine or people and platform interface. So you can use technology, but often people want to talk to a human. So the platform will build all the legal docs that you want. People go, well, my investor, they want preference shares and this valuation. Do you think that's a good idea or not? So, of course, you might have a video on it, but they still want to talk to a human. So, you know, we have team and platform. And I think that's what the formula that I think our customers really love.
Brian Bell (00:07:38): Interesting. So it's not just, okay, here's your, you know, name your favorite platform, like AngelList or Carta, like here's all the stuff to do all this, you know, all the software to do all this legal stuff. But really, you have, you know, agents that you can talk to and actually get advice.
Anthony Rose (00:07:54): Exactly, because the reality is the creation of a safe or a cap table is a trivially easy, right? What you really want to find out is, my investor says my 10 mil valuation is crazy. Is it just them or is it me? And you can have data, but often people want to talk to you. Stuff goes wrong in a startup. My co-founder and I are just not getting along. Well, okay, great. There are WhatsApp groups for that. Maybe you need to get a couch. But where do you start? So we like to be there when things go right and when things don't go wrong and be generally helpful for the set of things that people want. But be able to do it, of course, in a scalable way because I have a business to run and want to be a platform business, not a law firm as well.
Brian Bell (00:08:37): So it sounds like, do you guys compete with kind of the angel-less sidecars, cartas of the world? If so, like how do you differentiate? And if not, like what's different?
Anthony Rose (00:08:45): Sure. So in the UK, we don't bump into them because they're really not in the UK. And essentially in the UK, it's SeedLegals, which is great. But now we're in the US as well. And I spend half my time in New York and half the time in London. You know, if half the UK startups are on our platform, that's great. But if we want to expand, we need to go further. So we've looked at, you know, what's the gap in the US market? I think people have kind of described one way is to say it's Carta with legals, which I think is not a bad description. So my goal is the all-in-one platform with people you can talk to. So, you know, what we discovered quite quickly in the US, you know, is that cap table and safes are highly commoditized. I mean, you can get them anywhere. You can incorporate a company that comes, you know, cap table and safes. So there's nothing special about that. But after that, you're stuck, right? So there's agreements that you need to grow your business. When you want to do a price round, there's no one that is a productized price round. There's no one really educating you on finding investors, the tax benefits, which I'm sure we'll get to in a minute, what happens when things go wrong. And so as we are now expanding in the US, we're covering the things that you need as you grow your company. But also actually, really interestingly, finding the gaps that others have left on the table. Is that the right metaphor? So, for example, about a third of companies we see are LLCs, and no one has productized the LLC to C-Corp. So investors aren't going to invest in an LLC because it's a pass-through tax structure. They don't want those problems. They don't get QSBS and other tax benefits. So you need to make it a C Corp. But where are you going to go? And half the lawyers you meet are going to go, well, you see, we know Delaware, but we don't know Wyoming or whatever. And the other half say, we know Wyoming, but not Delaware. So if only there was a low-cost, easy, productized way of flipping an LLC into a C Corp. And so that's the very next feature that we're building.
Brian Bell (00:10:44): Yeah. Why do you think the productization of price rounds does not happen?
Brian Bell (00:10:44): Yeah. Why do you think the productization of price rounds does not happen?
Anthony Rose (00:10:48): So I think the answer is that historically, you know, like Series A, Series B are like these sacred cows. And investors like, hey, our lawyers will send you the terms. And then the founder takes it to their lawyer. And the lawyers will do the dance for three months. And everyone ends up paying hundreds of thousands in legal fees. And so it's just the way it is. And people go, okay, that's the way it is. But we saw that the Series A can completely be productized. You know, when you think about it, a Series A is just a slightly more complicated seed round. So we figured, let's just extend what we've got. So our goal is to take the Series A, which is like three months, and do it in two weeks. And indeed, we've done that.
Brian Bell (00:11:30): Wow. So how do you actually compress that timeline? Like what happens differently on SeedLegals than when I just call up my lawyer and say, hey, I’m raising?
Anthony Rose (00:11:40): The big difference is product thinking. When you talk to a lawyer, they go, give me the information. I'll think about it. I'll draft some documents. I'll send it back to you. You tell me what you think. I'll change it. And that cycle repeats. And then the other side has their lawyer doing the same thing. So it's like this ping-pong of documents, right? But when you productize it, you create a workflow. So when you do a Series A on SeedLegals, the platform goes, okay, what's your valuation? How much are you raising? What are your investor rights? And then it automatically generates a term sheet and the associated docs. And then you send it to investors, and they can negotiate in the platform. So instead of being a ping-pong between lawyers, it's a collaborative workflow between founder and investors. And that cuts out like 80% of the nonsense.
Brian Bell (00:12:26): So basically instead of these legal ping-pong matches, it's structured inside the software and people just fill it out like TurboTax for fundraising.
Anthony Rose (00:12:35): Exactly. And then, of course, there’s always going to be something unusual. But 90% of it is always the same. Like liquidation preferences, drag along, tag along, voting rights — they’re always the same. So once you’ve seen it a few hundred times, you realize you don’t need to reinvent it every time. So we just built it into the product.
Brian Bell (00:12:56): That makes sense. And I guess you can see data at scale too — like what terms are trending across markets, what founders are actually agreeing to.
Anthony Rose (00:13:05): Right, and that’s huge. Because one of the worst things for founders is information asymmetry. The investor has done this 50 times, the founder maybe once. So the founder’s like, is this normal? Am I being taken for a ride? And if you don’t know, you might accept something crazy. But with data, we can show you: 80% of rounds last quarter had no participating preference, or the median discount on a safe was 20%. So now the founder has power. You can go back and say, hey, that’s not market.
Brian Bell (00:13:38): Yeah, that’s a huge equalizer. How much of your product today is the tooling versus the advisory and education layer?
Anthony Rose (00:13:47): It’s probably 70% product, 30% people. The tooling does the heavy lifting — create the docs, structure the round, manage signatures. But the people side is essential. Because no matter how much video or content you give, when it’s your business, your money, your co-founder, you want to ask a human being, “What do you think?” And so our model is to give you the platform that does 90% automatically, but also the human team who can sanity-check, explain, and handhold.
Brian Bell (00:14:21): So when you think about scaling SeedLegals globally, does that people piece become the bottleneck?
Anthony Rose (00:14:29): It could, but we’ve built the model so that each jurisdiction we enter, we hire a small team that knows the local market, and then we productize around their knowledge. So you don’t need 10,000 lawyers. You need a few experts who help you set the rules, and then the platform scales it. That’s how we’ve done it in the UK, France, Ireland, Hong Kong, and now the US.
Brian Bell (00:14:53): That’s interesting. So what’s been the hardest part of entering the US market so far?
Anthony Rose (00:14:59): The US is both the biggest opportunity and the biggest challenge. Biggest opportunity because obviously it’s the world’s largest startup ecosystem. But the challenge is fragmentation. In the UK, there’s basically one way of doing things — you incorporate in England, you raise under SEIS/EIS, you do a seed round. In the US, you’ve got Delaware, Wyoming, California, safes, convertible notes, series seed, preferred, QSBS, tax, LLCs. It’s a mess. So productizing that is harder, but that’s also the value. If we can simplify that, we’ve got a real advantage.
Brian Bell (00:15:40): Yeah, that makes sense. Do you think US founders are more or less savvy than their UK counterparts when it comes to fundraising?
Anthony Rose (00:15:49): Interesting question. I’d say US founders are more aggressive. They’ll go out and raise earlier, on bigger valuations, with more confidence. UK founders are more conservative — they’ll bootstrap longer, raise smaller amounts, and be more cautious. But in both cases, the lack of transparency and the legal friction is the same. And that’s where we come in.
Brian Bell (00:16:15): Got it. Let’s go a little deeper on safes versus priced rounds. In your experience, when should a founder choose one versus the other?
Anthony Rose (00:16:25): So safes are great for speed. If you’re raising a few hundred K and you don’t want to spend three months negotiating, a safe is perfect. You can close investors one by one, rolling, without aligning them all. But safes are also dangerous if you don’t know what you’re doing. Because you might stack up multiple safes with discounts and MFN clauses, and when you finally do a priced round, suddenly you’ve given away way more equity than you realized. So I’d say safes are fine up to maybe $1 million, but beyond that, do a priced round. It’s cleaner, everyone knows where they stand, and you avoid nasty surprises.
Brian Bell (00:17:05): And with SeedLegals, are you seeing that play out in the data? Like most early rounds safe, then transition to priced?
Anthony Rose (00:17:12): Exactly. In the UK, most early rounds used to be convertible notes. Then Y Combinator came with safes, and everyone started using safes. But now we’re seeing a shift back to priced rounds earlier, because investors want clarity. So the data shows maybe 60% safe at pre-seed, but by seed, most are priced.
Brian Bell (00:17:34): So for founders listening, if they’re thinking of raising right now, what’s your advice?
Anthony Rose (00:17:39): First, don’t overcomplicate. Pick a simple structure that matches your stage. If you need speed, go with a safe. If you’re raising a bigger amount and want investor alignment, go priced. Second, get investor readiness sorted before you raise — founder agreements, IP assignment, cap table clean. Nothing kills a deal faster than due diligence revealing a mess. And third, understand what’s market. Don’t just accept whatever terms investors give you. Use data, ask around, use platforms like SeedLegals.
Brian Bell (00:18:15): I love that. You mentioned founder agreements. What’s the most common mistake you see founders make there?
Anthony Rose (00:18:22): The biggest mistake is not having reverse vesting. Two founders start a company, split 50/50. A year later one leaves, and now they still own 50%. No investor is going to touch that company. So you need vesting — typically four years, one-year cliff. That way if someone leaves early, they don’t walk away with half the company.
Brian Bell (00:18:45): And you said earlier like 20% of the time founders fall out?
Anthony Rose (00:18:50): Yeah, that’s right. And it’s heartbreaking, because the idea might be great, the market’s there, but if the founder team implodes and the equity’s stuck with someone who’s not contributing, the business is basically uninvestable. That’s why we hammer on founder agreements so much.
Brian Bell (00:19:12): So if you were advising a brand new founder tomorrow, what’s the checklist of legal stuff they should do on day one?
Anthony Rose (00:19:20): Number one, incorporate properly. Number two, founder agreement with vesting. Number three, assign all IP to the company. Number four, set up a clean cap table — don’t randomly issue shares. Number five, document any money going in — even if it’s a loan from your uncle, put it in writing. Get those five right, and you’re investor-ready.
Brian Bell (00:19:47): And then from there it’s about raising at the right time?
Anthony Rose (00:19:50): Exactly. Raise when you have a story to tell — product, traction, market. Don’t raise just because you’re running out of cash, because that’s the worst negotiating position.
Brian Bell (00:20:05): That’s gold. Okay, shifting gears a bit: how do you see AI changing the fundraising and legal space in the next five years?
Anthony Rose (00:20:14): Huge impact. Already we’re using AI to help founders understand terms, draft docs, and answer common questions. But more interesting is predictive. With enough data, we can tell you: companies like yours raised at this valuation, with these terms, from these investors. Imagine a world where fundraising is as data-driven as programmatic ad buying. That’s where we’re going.
Brian Bell (00:20:41): That’s exciting.
Brian Bell (00:20:41): That’s exciting. So when you think about predictive fundraising, do you imagine SeedLegals one day saying, here are the top five investors most likely to back you based on your stage and sector?
Anthony Rose (00:20:53): Exactly. Because right now fundraising is like spray and pray — founders pitch to 100 investors, 90 say no, 10 say maybe, one says yes. It’s hugely inefficient. But if you’ve got data on what investors have backed in the past — stage, geography, ticket size, sector — you can start matching intelligently. So instead of 100 cold emails, you focus on the 10 most likely. That saves everyone time.
Brian Bell (00:21:22): Makes total sense. Do you see resistance from investors to that kind of transparency?
Anthony Rose (00:21:28): Some, because investors like the information asymmetry. But ultimately, the best investors want the best deals, and efficiency helps both sides. I think it’s inevitable. Ten years ago people thought pricing flights online would destroy travel agents, but now it’s normal. Same will happen here.
Brian Bell (00:21:50): Love that analogy. Switching gears a little, what’s been the most surprising thing you’ve learned about founders since starting SeedLegals?
Anthony Rose (00:21:59): The most surprising thing is how many founders are afraid of legals. They think it’s complicated, scary, expensive, and so they avoid it until the last minute. But the reality is 80% of it is simple once explained. So our job is education as much as product. When we demystify it, you see the relief on founders’ faces.
Brian Bell (00:22:24): Yeah, I can imagine. I’ve had those moments too. So in your opinion, what’s the biggest mindset shift founders need to make around fundraising?
Anthony Rose (00:22:34): That fundraising is not a distraction from building your business — it is part of building your business. Too many founders think, “I’ll build, build, build, and then one day I’ll fundraise.” But fundraising is storytelling, positioning, strategy. It should be integrated into your company narrative from day one.
Brian Bell (00:22:57): That’s powerful. So let’s say a founder is gearing up for their first raise. How should they actually prepare the story?
Anthony Rose (00:23:06): Three things: problem, solution, traction. Investors want to know: what’s the pain point, how do you solve it, and why should we believe you can scale? The deck doesn’t need to be 40 slides. Ten slides that tell a clear story beat 100 pages of fluff. And back it up with data — even if it’s small numbers, show the trend.
Brian Bell (00:23:31): Do you think founders overthink the deck?
Anthony Rose (00:23:34): Absolutely. Founders spend months agonizing over fonts and colors. Investors don’t care. They care about vision, market, team, traction. I always say: don’t spend three months on your deck, spend three months talking to customers and building traction. That’s what will raise the money.
Brian Bell (00:23:55): Love that. Okay, let’s talk about valuation. Founders always ask: how do I know what my company is worth? What’s your advice?
Anthony Rose (00:24:05): Valuation at early stage is more art than science. There’s no EBITDA multiple. It’s really: what will investors pay? So my advice is, ask yourself: how much money do I need to get to the next milestone? Divide that by how much equity you’re willing to give. That’s your target valuation. And then sense-check with market data. If everyone else is raising at $5–10M and you’re asking $50M, good luck.
Brian Bell (00:24:35): So it’s more about working backwards from the raise than some formula?
Anthony Rose (00:24:39): Exactly. The mistake founders make is anchoring too high. They raise at a crazy valuation, then can’t grow into it, and the next round is a down round. Much better to raise slightly lower, hit milestones, and have an up round. Investors love momentum.
Brian Bell (00:24:59): That’s interesting, because founders always feel pressure to push valuation higher.
Anthony Rose (00:25:05): True, but the best founders play the long game. If you’re going to raise multiple rounds, you want each one to be a step up. So be strategic. Don’t optimize for today, optimize for your journey.
Brian Bell (00:25:22): That’s a great insight. What about the current market — are valuations down compared to a couple years ago?
Anthony Rose (00:25:29): Definitely. In 2021, everything was crazy. Pre-seeds at $20M, seeds at $50M. That’s corrected. Now investors are more cautious, and valuations are back to earth. But honestly, that’s healthier. Founders who raised at insane valuations are struggling. Those who raised sensibly are doing fine.
Brian Bell (00:25:55): Do you see differences between US and UK valuations?
Anthony Rose (00:26:00): Yes, US valuations are typically higher. A company raising at $5M in the UK might raise at $10–15M in the US. Partly because of the size of the market, partly because of investor appetite. But again, higher valuation isn’t always better. It can be a trap.
Brian Bell (00:26:21): So for a UK founder thinking of expanding to the US, what’s your advice?
Anthony Rose (00:26:27): First, make sure you have a real reason. Don’t just go because it sounds cool. The US is expensive, competitive, and noisy. If your product fits the market, great. But don’t assume US investors will line up just because you have a UK accent. You need traction, local presence, and a clear story.
Brian Bell (00:26:51): Yeah, makes sense. So when you think about SeedLegals five years from now, what’s the vision?
Anthony Rose (00:26:58): The vision is to be the default operating system for startups globally. From day one — incorporate, founder agreements, IP, fundraising, hiring, ESOPs, compliance — all in one platform. Wherever you are, you log in, and it’s there. And powered by data and AI, so it gets smarter every day.
Brian Bell (00:27:22): That’s ambitious. Do you think you’ll need to raise more capital yourselves to get there?
Anthony Rose (00:27:28): We’ve raised so far, but we’ve been quite capital efficient. Because our model is SaaS, we generate revenue quickly. So we haven’t needed to raise the crazy rounds you see in Silicon Valley. That gives us more control and lets us build sustainably.
Brian Bell (00:27:48): Do you think founders should always raise VC, or are there cases where they shouldn’t?
Anthony Rose (00:27:54): Great question. Not every business should raise VC. If you’re building a lifestyle business or something that doesn’t scale exponentially, VC will push you to grow faster than makes sense. You’ll end up miserable. So ask yourself: do I want to build a unicorn, or a profitable company I own? Both are valid. Just be honest.
Brian Bell (00:28:20): That’s refreshing to hear. Because a lot of founders feel like if they’re not raising VC, they’re failing.
Anthony Rose (00:28:27): Exactly. There’s this myth that the only path is VC. But there are many paths: bootstrapping, revenue-based financing, angels, crowdfunding. The key is matching funding to your vision.
Brian Bell (00:28:45): Have you seen crowdfunding work well?
Anthony Rose (00:28:49): Yes, especially in the UK where it’s more established. Platforms like Crowdcube and Seedrs let you raise from hundreds of small investors. It’s great for consumer businesses, because your investors become your customers and advocates. But it also adds complexity — managing lots of investors, communications, admin. So it’s not for everyone.
Brian Bell (00:29:16): Right. And I guess SeedLegals supports crowdfunding rounds too?
Anthony Rose (00:29:20): Absolutely. We power many of them behind the scenes. We handle the legal structure, nominee arrangements, cap table management. So it’s seamless for founders.
Brian Bell (00:29:33): Amazing. Okay, last one in this segment: what’s the most counterintuitive lesson you’ve learned building SeedLegals?
Anthony Rose (00:29:42): That speed beats perfection. I used to obsess over making everything perfect before launch. But in startups, speed matters more. Launch, get feedback, iterate. Perfection is the enemy of progress.
Brian Bell (00:29:59): That’s a perfect place to pause.
Brian Bell (00:30:00): What are your thoughts, post-money SAFEs versus pre-money SAFEs? Because my problem with pre-money SAFEs — and I’ve actually backed out of deals because of this — is founders say, “I’m only raising a pre-money SAFE.” And I explain to them, that’s fine, but then I don’t know what I’m actually getting. You can keep raising money and diluting me forever before you convert. How do you advise VCs like me and founders on post-money versus pre-money SAFEs?
Anthony Rose (00:30:25): Let’s answer that by looking at the UK versus the US. Completely different patterns. In the UK, we’ve got these fantastic government tax benefits for angel investors. They say: keep your stock for three years, pay no capital gains tax. If the company goes out of business, you can write it off. Even better, you can immediately deduct 50% of your investment from income tax. Invest £50K, deduct £25K. It’s awesome.
Anthony Rose (00:30:56): But there’s a catch. If you invest with a SAFE or the UK equivalent, you must get your stock within six months — the SAFE has to convert. So UK fundraising is SAFEs with what’s called a “long stop date.” If the company raises a round in six months, great, you convert then. If not, you convert anyway at an agreed cap or valuation.
Brian Bell (00:31:19): So it lets you get the money right away but forces conversion within six months?
Anthony Rose (00:31:23): Exactly. In the UK, SAFEs are just a bridge to the next round. In the US, they are the next round — sometimes for years. That’s why the US version created post-money caps. If you don’t convert for five years, you don’t want to be the schmuck investing today at the valuation of five years later. Post-money caps promise you a fixed equity percent, whenever conversion happens.
Anthony Rose (00:31:51): But the truth is, that’s just one possible formula. In the UK, it’s often just a discount, because conversion happens soon anyway. You get your shares in six months, so you’re happy with 20% off the price. Both patterns are coherent, just solving different problems.
Brian Bell (00:32:12): Makes sense. So the US investor is protecting themselves from endless delays, whereas in the UK it’s short-term.
Anthony Rose (00:32:19): Exactly. And that’s why I think there’s an opportunity for a new pattern. If you make priced rounds as easy as SAFEs, suddenly founders can raise quickly, investors get stock right away, everyone gets tax benefits, and founders don’t get crushed by stacked non-diluting SAFEs.
Brian Bell (00:32:41): Right, because founders always worry investors will take control of the board or push them out.
Anthony Rose (00:32:46): Exactly. But that’s often just a negotiation point. The NVCA docs are parameterized — you choose how many board seats, what consents investors need. The key is educating founders on what they’re signing. Too often they get 200 pages of legalese and don’t realize they’ve lost control until later. That’s what I want to fix: lightweight, transparent rounds where founders know exactly what they’re giving away.
Brian Bell (00:33:14): That’s huge. And you’re not even a lawyer, right?
Anthony Rose (00:33:17): Nope. I used to be embarrassed about that. Now I love it. Being a product guy lets me see things differently. Lawyers focus on legalese. I focus on what founders really need: a simple, clear process that gets them funded and back to building.
Brian Bell (00:33:35): That’s a great mindset. So what advice do you give founders who worry too much about legal complexity?
Anthony Rose (00:33:42): Think of legal docs as the manual in your car. You don’t buy the car for the manual, but when something breaks down, you need it. Same with startups. Most problems founders face aren’t investor lawsuits — they’re co-founder fallouts. At least 20% of early-stage startups have them. If you don’t have reverse vesting, you’re in trouble. The departed founder walks away with half the company, and it’s uninvestable.
Anthony Rose (00:34:10): That’s why we push founders to have good leaver/bad leaver clauses, vesting schedules, founder agreements. If you’ve got those, when fights happen, you open the glove box and the manual tells you the answer. If you don’t, it’s pistols at dawn.
Brian Bell (00:34:28): So you’re almost saying founders should plan for breakups from day one.
Anthony Rose (00:34:32): Absolutely. It’s not about mistrust — it’s about protecting the company. And it actually makes relationships stronger because everyone knows the rules upfront.
Brian Bell (00:34:42): That’s a gem. Okay, shifting gears — SeedLegals manages thousands of cap tables. What trends are you seeing lately?
Anthony Rose (00:34:50): Three big ones. First, in the UK more founders are raising through SAFEs instead of full rounds, just converting after six months because it’s easier. Second, we’re seeing lots of top-ups and bridges instead of big new rounds — because valuations are tough right now. Third, efficiency is the new bragging rights. A few years ago, founders bragged about headcount. Now bragging rights are revenue per employee. Fewer people, more output.
Brian Bell (00:35:21): Yeah, I’m seeing that too. Do you think AI is accelerating that trend?
Anthony Rose (00:35:25): Definitely. Founders are asking: how lean can I go? Can I run a $10M business with 10 people, powered by AI? There’s even this narrative about the one-person unicorn. Personally, I think that’s a fun thought experiment, but not a great goal. Running a serious business needs people. If you’re at $100M revenue, paying $20M in salaries for 100 people is nothing. Optimize for revenue, not headcount.
Brian Bell (00:35:56): So what’s realistic — 5 to 10 people plus AI “agents”?
Anthony Rose (00:36:00): Exactly. You’ll still need functional heads — a head of marketing, a head of product, etc. They’ll manage swarms of AI tools. So maybe you run with 10x fewer people than before, but not zero. One-person unicorns are fun tweets, not reality.
Brian Bell (00:36:19): Fair. Out of curiosity, what AI tools are you personally loving right now?
Anthony Rose (00:36:24): My favorite is Whisperflow. I type a lot — emails, Slack, WhatsApp. I hate typing. Whisperflow lets me just speak at 140 words per minute, and it transcribes near perfectly. In the last 19 weeks I’ve dictated over 500,000 words. It’s life-changing.
Brian Bell (00:36:45): Wow. That’s like four or five books.
Anthony Rose (00:36:48): Exactly. And it’s fun — you feel like you’re conversing with your computer. My wife thinks it’s weird because she hears me having these mini conversations with the screen, but it makes me way more productive.
Brian Bell (00:37:01): How’s it better than just using ChatGPT dictation or Apple’s voice-to-text?
Anthony Rose (00:37:07): Accuracy and formatting. If I say “$100,” it writes “$100.” It removes ums and ahs, corrects backtracks. It’s smart but not too smart. My only worry is they’ll overdo the AI and start rewriting my words instead of just cleaning them. For legal and business use, precision matters.
Brian Bell (00:37:29): That makes sense. And I assume they just raised a big round, right?
Anthony Rose (00:37:33): Yes, $30M recently. Which is good — they can add humans for support. Because even in AI-first products, people matter. I message them feedback, they log it, ship updates weekly. That human-AI mix is gold.
Brian Bell (00:37:51): Love it. And it ties back to our earlier conversation — you’ve got to balance automation with human touch.
Anthony Rose (00:37:57): Exactly. Pure AI is not enough. Founders want to talk to a human sometimes. The future is people plus platform, not just one or the other.
Brian Bell (00:38:10): That’s a great point.
Brian Bell (00:40:00): So tying this back to fundraising, you mentioned SAFEs are an artifact of a bygone time. Now we’ve got AI-generated docs and AI reviews. Do you see a world where founders can just spin up a priced round with a click?
Anthony Rose (00:40:15): Absolutely. Imagine a founder saying: “I’m raising $500K at $5M valuation, priced round.” The platform auto-generates all the docs — subscription agreements, shareholder agreements, stock purchase agreements. It summarizes the terms in plain English. And it’s done. That’s where we’re heading.
Anthony Rose (00:40:34): But here’s the nuance: most legal tech startups are built by disaffected lawyers. They make AI tools to help law firms bill faster. But the law firm still charges you $20K, they just spent less time on it. At SeedLegals, we flipped it. We don’t make lawyers faster — we make lawyers irrelevant for most early-stage funding.
Brian Bell (00:40:56): Right — you’re focused on the founder, not the lawyer.
Anthony Rose (00:41:00): Exactly. Founders don’t want documents. They want investment. They want a platform that helps them go from meeting an investor to money in the bank. The docs are just a byproduct.
Brian Bell (00:41:12): So where does AI fit into your roadmap?
Anthony Rose (00:41:15): We’re launching AI in two ways. First, “AI for your company.” All your docs are on SeedLegals. You can ask: “When does this SAFE convert?” or “How much equity does Brian have?” The AI pulls that instantly. Second, pitch decks. Upload your deck, we auto-extract the key data, and give you insights.
Anthony Rose (00:41:36): The big picture? AI will accelerate document generation. But we’ll always keep the founder in the loop, making explicit choices. Otherwise, you end up with a car manual you’ve never read — and only when you break down do you discover you agreed to terms you didn’t understand.
Brian Bell (00:41:54): That’s a huge risk. So you see AI more as augmentation than replacement.
Anthony Rose (00:41:59): Exactly. Founders still need to know: how many board seats? What investor consents? How does dilution work? You don’t want AI quietly deciding those for you.
Brian Bell (00:42:12): Makes sense. But what about commercial contracts — licensing, partnerships? That feels ripe for AI disruption.
Anthony Rose (00:42:20): Totally. That’s where “lawyer in the loop” comes in. You use ChatGPT to draft 90% of a licensing agreement. Then you give it to a lawyer for final tweaks. That’s two hours of review, not 20 hours of drafting. Huge savings.
Brian Bell (00:42:37): So law firms might hate that, right?
Anthony Rose (00:42:40): Of course. Their business model is billable hours. If your software cuts hours in half, they’re not thanking you. That’s why I think true disruption won’t come from inside law firms — it’ll come from platforms like us.
Brian Bell (00:42:53): Do you think law firms eventually adapt, or do they go the way of record labels with Napster?
Anthony Rose (00:42:59): Great analogy. I was with Kazaa in the early days of music file sharing. The record labels defined success as selling CDs. They sued Napster instead of embracing streaming. Only when Apple, Spotify, and YouTube forced their hand did they adapt. Same with broadcasters and YouTube.
Anthony Rose (00:43:20): Law firms are in the same place. They’ll adopt AI internally, but only so far as it doesn’t break their business model. True change will come from outside — platforms offering $29/month contracts instead of $20K.
Brian Bell (00:43:35): So law firms will retreat into areas where humans are still needed, like litigation?
Anthony Rose (00:43:40): Exactly. Litigation, adversarial disputes, high-stakes custom negotiations — those won’t be automated soon. But fundraising, incorporations, cap tables, commercial agreements? Those are going to be platformized.
Brian Bell (00:43:56): And that’s where SeedLegals lives.
Anthony Rose (00:43:58): Exactly. We define success differently. For us, success is: did the founder raise capital quickly and keep control of their company? Not: did we bill 200 hours.
Brian Bell (00:44:11): Love it. Let’s zoom out. How do you see AI reshaping the entire legal industry over the next 5 years?
Anthony Rose (00:44:20): I think three waves. First, discovery and analysis — AI is already there. Tens of thousands of emails sorted in hours. Second, contract generation — fast, cheap, standardized. Third, vertical platforms. Divorce platforms. Probate platforms. Startup platforms like ours. People will stop going to lawyers for 80% of their legal needs.
Brian Bell (00:44:45): And the incumbents?
Anthony Rose (00:44:47): They won’t change until they’re forced. Same story, every industry. That’s the opportunity for startups.
Brian Bell (00:44:55): So you’re betting on the outside players.
Anthony Rose (00:44:58): Every time. That’s where innovation always wins.
Brian Bell (00:50:00): So let’s talk about law firms again. You’re not a lawyer, but you employ many. Five years out, do they adapt? Or do they just do more law, faster, thanks to AI?
Anthony Rose (00:50:12): Great question. I don’t have the crystal ball, but I see two forces. First, law is broad — litigation, wills, probates, commercial contracts. Some areas will change fast, others slower. Second, the billable hour model is broken. If AI makes you twice as fast, you either halve your revenue or you change your business model. Most incumbents won’t change until forced.
Anthony Rose (00:50:36): Look at music. I was with Kazaa — labels thought success meant selling CDs. They sued Napster instead of embracing streaming. Same with broadcasters thinking YouTube was “for kids.” Now TikTok eats their lunch. Law firms will be the same. They’ll tinker with AI internally, but disruption will come from platforms offering $29/month services instead of $20K contracts.
Brian Bell (00:51:00): So they’ll retreat into niches like litigation.
Anthony Rose (00:51:03): Exactly. Adversarial, high-stakes cases will stay with humans. But incorporations, funding rounds, divorces, probate? Platforms will take that over.
Brian Bell (00:51:15): Fascinating. Okay — let’s do a quick rapid fire. First line of code you ever wrote?
Anthony Rose (00:51:21): 6502 assembly language on an Apple II. Machine code. That definitely dates me.
Brian Bell (00:51:28): Hardest negotiation clause founders still underrate in 2025?
Anthony Rose (00:51:32): Vesting and leaver clauses. Founder fallouts kill more startups than investors do. If you don’t have reverse vesting, you’re in trouble.
Brian Bell (00:51:42): One UK regulation you wish America would copy tomorrow.
Anthony Rose (00:51:45): The angel investor tax breaks. In the UK, investors can immediately deduct 50% of their investment from income tax. That’s fueled the entire startup ecosystem.
Brian Bell (00:51:58): One U.S. incentive you wish the UK had.
Anthony Rose (00:52:02): Privacy. In the UK, shareholder lists are public on Companies House. The government even wanted to make profit-and-loss public. It drives companies to Delaware. The UK needs to learn from U.S. privacy protections.
Brian Bell (00:52:17): Bold prediction — by 2030, how long will the average seed round take from start to cash?
Anthony Rose (00:52:23): No change. Finding investors is still the bottleneck. But if you’ve got commitments lined up? On SeedLegals, we’ve seen priced rounds close in 2–3 days. That’s the future — fast execution once the money’s ready.
Brian Bell (00:52:40): Which is why Americans love SAFEs — it’s like driving your own car instead of waiting for the bus.
Anthony Rose (00:52:45): Exactly. A priced round is a bus trip — everyone on board before departure. A SAFE is an Uber — investors hop in one by one. At SeedLegals, we’ve built “instant investment” to bridge the two: investors get shares immediately, founders avoid the SAFE stacking problem.
Brian Bell (00:53:04): Amazing. Well, this has been a fascinating conversation. I’ve learned a ton. For folks listening, where can they find you online?
Anthony Rose (00:53:12): Thanks, Brian, this has been fun. You can find me on LinkedIn — Anthony Rose. Or email me at anthony@seedlegals.com. Or just head to SeedLegals.com, open the chat, and one of my colleagues can connect you with me.
Brian Bell (00:53:28): Perfect. Thanks so much for joining.
Anthony Rose (00:53:30): Thank you for having me.
