20VC: Why OpenAI Will Become an Infrastructure Play, Why Apple Will Win in an AI World, Why Google is the Most Vulnerable Incumbent, Will LLMs Be Commoditised, Which Startups Are Thin vs Thick Wrappers on Top of LLMs with Jeff Seibert, Founder @ Digits

22 Nov 2023 · 59 min

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Podcast Notes: The Twenty Minute VC (20VC) Episode with Jeff Seibert

Episode Summary In this episode of *The Twenty Minute VC*, host Harry Stebbings interviews Jeff Seibert, the Founder and CEO of Digits, an AI-powered accounting platform. The conversation covers a wide array of topics including the evolution of OpenAI, the competitive landscape in AI, the challenges faced by startups, and insights into effective management and product development.

Key Topics Discussed

  1. The Art of the Pivot
  2. Advice for Founders:
  3. Understand when enough data is available to pivot.
  4. Acknowledge common mistakes made during pivots.
  5. Key Questions:
  6. What are the signs indicating the need to pivot?
  7. How do you gauge the conviction and data needed to make a pivot?
  1. AI Landscape: Winners and Losers
  2. OpenAI's Future:
  3. Belief that OpenAI will transition into an infrastructure play similar to AWS.
  4. Challenges OpenAI may face ahead.
  5. Apple's Position:
  6. Considered best positioned to thrive in an AI-dominated world due to control of hardware and silicon.
  7. Google's Vulnerability:
  8. Viewed as the most vulnerable incumbent due to reliance on search for revenue.
  9. If AI replaces search, Google's business model is at risk.
  1. Understanding LLMs (Large Language Models)
  2. Commoditization Concerns:
  3. Discussion on whether LLMs will be commoditized and the implications of open-source models.
  4. Thick vs Thin Wrappers:
  5. Differentiating between substantial applications built on top of LLMs versus superficial implementations.
  1. Angel Portfolio Insights
  2. Investment Insights:
  3. Review of Seibert's angel investment portfolio, including successes and failures.
  4. Discussion on the sustainability of company valuations and market conditions.
  5. Advice for Angel Investors:
  6. Importance of discipline in investment and understanding market dynamics.

Key Takeaways

  • Execution is Critical: Successful companies require intentional and decisive execution, rather than relying solely on data-driven decisions.
  • Customer Focus: Founders should prioritize understanding and solving customer problems over competing directly with rivals.
  • Quick Decision Making: Emphasizing the need for fast and decisive action within startups to maintain momentum and reduce uncertainty.
  • Market Timing: Understanding market trends and timing is crucial for successful investment and product launch.

Concluding Remarks Jeff Seibert's insights highlight the rapidly evolving AI landscape and the critical role of adaptability in startups. The emphasis on understanding customer needs and the importance of decisive leadership resonate throughout the discussion, providing valuable lessons for entrepreneurs and investors alike.

Next Episode Teaser The next episode promises to explore the future of LLMs, pricing models for AI, and an analysis of incumbent companies in the rapidly changing technology landscape.

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Transcript

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0:00I view OpenAI probably evolving more into an infrastructure company like AWS. The road ahead for OpenAI is not easy. Google, if they need to go all in on it, I don't think they have a choice. Very few people I think are paying attention to is Apple. Because again, they control the Silicon. Imagine they're able to pioneer small models that run on device, and then they do custom Silicon to make them run. The performance could be outlandish compared to any other platform. Welcome to 20VC with me, Harry Stebings. Now they sure is an immensely special one for me. I first met this guest nine years ago when he was head of consumer product at Twitter.

0:33He then became a friend and Mark Suster says invest in lines and not dots. That friendship with today's guest then turned into an angel investment from me, into his company, and today, 20VC is one of today's guests and his company's largest investors. I'm thrilled to welcome Jeff Sybert, founder of Digis, reimagining the world of accounting, with backing from the lights of Peter Fountain and Benchmark who had an early round at the company. Before DigiS, Jeff Co founded Crashlytics, which now runs on almost every mobile device on the planet, they ultimately sold to Twitter. But before we dive into the show today, there is no shortage of helpful AI tools out there, but using the mean switching back and forth between yet another digital tool, what was supposed to simplify your workflow, just made it way more complicated, and less of course, you're in notion.

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3:30Jeff, I am so excited for this, what people don't know is I will always remember, I remember being 18, maybe 19 and being in your office at Twitter in San Francisco, I was so nervous. I was like, this is so cool. Anyway, that was a while ago. So first, thank you so much for joining me, stage F. Harry, no, it is so great to be here. Thanks for having me on. You know, the whole world only makes sense going backwards because like, who would have guessed from that needing? You'd become one of my largest investors like five years later. Just incredible what you've done. I mean, yeah, definitely not me to be on it.

4:03Everyone always thinks that things are so strategic and you're like, well, you know, sometimes you have to go to the party to meet cool people. So I always say, but I want to start. I find that she, like, one's childhood aspirations, quite revealing. What did you want to be when you're a child when you picture yourself growing up? Oh, man. So I loved building things since I was little and I was completely obsessed with Legos. And so my dream was honestly, literally, to be a Lego master builder until my mom did some research. And she found out that actually, like, it's not that great of a career.

4:33They're paid something like minimum wage. And that was in middle school. And so I forget if it was that Christmas or the next year, but she gave me a programming book for Christmas And I was and that was the end of the story. I was like, okay computers are next. Okay, so when I met you you were at Twitter And it is a incredibly Formative experience I think being a Twitter especially in the role that you are how did that period at Twitter shape your mindset and approach to operating Do you think yeah the biggest lesson I learned was empathy honestly So when you're in consumer software, you can't possibly begin to understand how many different people, personas, use cases, mindsets, the human experience all comes to bear on your product.

5:12And what I saw was actually a trap. So the product managers who were super data driven started designing and building features for the average user, because that's what the data told them. And they actually believe that there was something such as an average Twitter user. It's such a huge mistake, right? Like you're conflating all of these different populations. You have sports fans who want a live, like chronological timeline during the game. You have celebrities who want to maximize their reach. You have Japanese users who buy and large want to remain anonymous. None of them is average. And so what I really learned is you have to deeply understand each population and design and build a feature for them.

5:48Don't let the data lie to you. Can I ask you a bit of a weird one? but often we're told, you know, solve a problem that you personally know and experience and care about. But then, like, so you fully understand and have that empathy, but then other people have said to me before, don't, because you can be too emotionally attached to it, that you don't almost think rationally. Would you agree with that? Which side are you on? I'm definitely on the side of building it for yourself. Like, you deeply understand the problem, that gives you superpowers in terms of solving it the right way. You definitely need to understand are you repeated by many other people around the world?

6:24Do they share your problem? Do they share how you think it should be solved? But I think it's so much easier to build something that you personally feel than have to sort of try to interpret other people's Thoughts and beliefs about it. Um, so no, I would not be worried about getting too emotionally involved I think that's a superpower. Another thing is I speed which what is product kind of cadence now? regardless what one thinks of Elon and we won't get into that. But like, the cadence of release is very impressive in terms of what they're pushing out. How important is speed when it comes to product cadence?

6:56Do you think? I think it is critical. And it is too easy for companies to fall into like, oh, we don't know, we need more data, we need to run a survey for that, particularly at Twitter. We need to get Statsig data, which always took two to three weeks. And then you would have to analyze that and then see what happened. It's honestly a disaster and so agree or disagree with some of Elon's decisions But he is moving quickly in a direction that is way better than sort of standing still You know when we think about non -orvious things we mentioned that two commonly said tropes obviously speed and then solve for Problem that you know deeply.

7:30I think there's a lot of things that aren't well known about entrepreneurship Given the fact that you've done crash studies you've now been in Twitter. You've now founded digits What do you think is the most like misunderstood or non -orvious element of entrepreneurship? This sounds silly, but honestly pure execution. People know the vast majority of managers are terrible managers, right? The vast majority of founders are simply bad at running companies. And I'm sorry, but it's true. And so what I mean by that is like most founders aren't intentional about how they go through and operate the business, intentional with their time, with their decisions, with who they hire, with what they say no to.

8:06And so if you don't have conviction, you're really going to struggle as a founder, because you need this like deep -seated obsession of what's right and what's wrong and what you believe in and how that informs every decision you make and your decisions may still be right or wrong they're not gonna be perfect but if you are intentional about them at least you can trace that back and learn from it versus I see too many founders just sort of going on a random walk and then when it turns out they were wrong what do they have to learn there's not there's nothing to trace it back to I'm packing that you just gave me like Gold does that.

8:36Why am most manages bad do you think? Peter principle, they get promoted into management because they were good at a former job. They're passion, right? Their experience isn't managing. The feedback cycle is slow, they're the boss, so they don't get the raw feedback. I think there's a ton of challenges and it's even worse for CEOs because who in your company is going to give you really crisp blunt feedback on what you did right and wrong? And your investors aren't involved enough in the day to day to really know, so they can give strategy advice that they don't know how you're behaving in meetings.

9:06Okay, so how may aren't here? We're both CEOs as well. How do you think about promoting people then who are great ICs? Do you not promote them to managers? What's the right way to do that? Challenge them. That is a great question. So actually every time I've promoted an IC to a manager in a startup, this was not a Twitter. We've done it as sort of a trial period. And so it's like, hey, so and so, we have this opening for this new role, the team's growing, we need some structure. We are going to have zones of take on the role as a trial over the next two months. And let's see how they do. And honestly, there's been both outcomes in some circumstances.

9:38It's been great and everyone's rallied around them. It's like, great, okay, now they're the manager for that team. And I've had circumstances where they haven't. And it was sort of widely recognized that they weren't excelling in that role. And we decided to move them back to an IC. And that was okay as well. I think there's a really bad perception that being a manager is better than being an IC. I think it is different. And you can be an exceptional IC. and you should be comped appropriately for that. Or if your career passion is to mentor and guide folks, then you move into management. I appreciate that.

10:08I think it's also important for people to understand that you can be comped to purpose. I think that's the slight barrier in one's head that to break that barrier on comp, you have to become a manager. 100%. And this is something I felt strongly in for a long, long time. Google sort of pioneered this well in the early days and created this whole track for engineers to sort of keep climbing in comp and title and recognition and so on, without taking on management roles, and I've tried to mimic that at all my companies. You mentioned accountability within CEO ship in white like no one really can, who could do it with the visibility they have, and then you know the bills that could won't because they don't have the visibility.

10:43So how do you create that account for the CEO? Yeah, it's certainly not easy because you can constantly fall into a trap of thinking you're getting feedback and you're not. It's really how you set the culture of the company. So one of the things we do at Digits is we run the entire company on a weekly sprint as part of that every Friday We end every week with a full team retro and we call it anchors and breezes anchors are what slowed you down What didn't go well what you need to help with like feedback on the week and then breezes or what what well Shoutouts to people who helped you things you learned etc etc and you create this culture of just constant iterative improvement Which then allows sort of feedback conversations and one -on -ones and so on to be widely recognized by the company is like that's what we want.

11:25The whole mindset is just how do we get 1 % better each week? I love the idea, but when you get to 100 people, does that still work? Yeah, it fractalizes. So what happens is each team will run their retro on Friday, and then surface sort of the highlights like the biggest anchors or breezes to the full company -wide retro. Everyone has sort of two opportunities. You do a team -wide thing, and then you do your own small team, and that's where you get into more detail. Do you like celebrating wins? I worry that it creates complacency. We've never won. I'm always chasing someone. We both are always paranoid.

11:58I hate this. I tap on the back. Do you celebrate wins? We do. It's also, it's important to do it correctly. So I agree with your mentality. Crashlytics, I never thought was like successful in any one moment. Not when we were acquired, not when we hit a billion MAU, etc. Like there's always the bigger goal. But if you have that mentality with the team, it's very demotivating. What are we trying to go to? Like, when are we gonna get somewhere? And so it's really important to celebrate small wins. And so we use this Friday show and tell we call it basically to show off what we did each week and champion who did what and celebrate all the small wins of the week.

12:31So people feel really connected to the company and what's happening. I love the way I still use this show. Despite his size, I still use it as like this, like, mercerous testing ground for my own ideas. I love it. I love it. Tell me, obviously, I know this story being an investor. But, you know, we have crash tickets, then we have Twitter. How did digits come to you? What was that founding moment for you? Yeah, digits really came out of the crash -lidics journey. And so, you know, we got very lucky with market timing. We scaled from zero to 300 million phones in 12 months, got acquired by Twitter.

13:01Today, crash -lidics is on 5 or 6 billion MAU, roughly every active smartphone on Earth. It's incredible. Through that journey, I was struck by this dichotomy. On the product side, you have real -time analytics, performance monitoring, live dashboards, right? I knew exactly what was going on with the product and who was using it. And then on the finance side, I literally had a black and white PDF of my P &L and balance sheet once a month, two to three weeks late, that I didn't understand because I didn't have a background in finance. I was an engineer and so it was like, what is happening? And so literally that is why I started digits.

13:32That is simple premise, can we make accounting real time and intuitive for startup founders? And so it's crazy as it took us five years, but we finally just launched it. Like it's actually here five years later. I mean, that 5 -year journey is one with twists and turns. The idea that initially was digits on founding day one is different in terms of the product we're releasing today. What did you learn that led to your realization of the need to pivot? Like, why pivot and why was that enough? Yeah, it's definitely been quite a journey. Obviously, trying to make accounting real time as a lot easier said than done.

14:03When we started the company, we went heads down on R &D and really struggled with data quality for like three years. And that was because in 2018 when we started the tech to really automate bookkeeping didn't fully exist I think I was a little optimistic on how it could work And so we have dozens of patents on it now, but it was like a brick wall So in 2021 we made the decision to pivot from like the pure bookkeeping automation to collaboration tools so better financial reporting better client portals better Transaction review process and that worked we got a thousand accounting firms on the product 5 ,000 downstream businesses like that was sort of often running.

14:40But what bugged me is that wasn't really why we started the company. We had bigger ambitions. And so then last year literally all the sudden, GPT -3 comes out, chat GPT comes out, GPT -4, and we started experimenting and we're like, whoa, hold on, we're back. Like we can actually do what we set out to do. Literally overnight, just like we're back focused on this and spent this whole year building it. How do you advise founders on when they have enough data to make that pivot? because you don't want to make it too quickly where it's like, oh hold up, we'll see, they're not enough data. But also you don't want to be too slow.

15:14How do you know when you have enough data to make a decision? That is the million dollar question. I'd say it's more of an art than a science. You need to have a feel in an instinct as the founder of, do you see a path to success? If the window's closing on your path to success with your current business, that's to me when you have to go pivot. and a lot of super successful companies were hard pivots, right? Like Twitter was a podcasting startup. Slack was a game, YouTube was a dating website, it's totally crazy. To me, it's like impossible to say like, oh no, stop. Like that pivots too far afield.

15:48You have to like have this sort of founder instinct and that's how great companies come to be. The one thing I'd modulate that with is like, you need at least a year of cash left because if you don't have a year of cash, you're not gonna have time to see this pivot through. And so it's really like a founder grit and enough cash if those aren't there return your capital if those are there I would go for it. That's how like huge opportunities come about. Oh a couple of things that I always say Like do you have two to three experiments that you're still excited to run in this phase of the product and if the answer's like No, I'm kind of out you you have a real understanding that actually that that could be a sign and then second is 12 months enough I don't mean to push you there But I'm just intrigued on light if you think about you need to raise six months out of time Like, is he just six months to build?

16:32I ain't got enough traction to raise at a price as even a flat round to your lost. It's not enough. It is not easy, but I think it's rare that you would have more than 12 months of cash. Because usually you raise to have 18 months, and so by the time you figure out it's not going well and you need to pivot, it's 12. The big thing I would change from what you said is it's not an experiment. At no point where we're like, we're gonna run two or three experiments. It is pivoting on a dime, you are all in on the new direction, and that is the only thing that matters to your success. So when you advise founders on the right way to PIVAs, what would you advise them knowing what you do now?

17:06Yeah, so the key is getting your team on board. If your team loses trust in you, you literally have no one to pivot, so it doesn't matter. They can really sense the uncertainty. My other advice, as I've said, is like be very intentional and very decisive. And so both times we've pivoted digits, I gathered our core leadership team, laid out like, what are the challenges? What am I seeing? What are the options? we knew within 24 hours what the new path was and what the priorities were we were all in on that new direction. It comes back to conviction. It is still a bet, but it's like, hey, here is the information we have on the field.

17:39We need to make a decision right now because what kills companies is uncertainty. And if you sort of model your priorities and have one team try this and another team try this, no one's heart is in it and both are gonna be mediocre, I would rather see founders take like one to the moon bet on one new direction and it either works or doesn't. Do you agree with the idea of disagreeing and commit? I find it challenging. I don't think someone can fully commit to something that can give that life to it. Yep, they disagree. I agree with you. I think this is the hallmark of great founders is you need to be able to convince your team and have the trust of your team to go all in on a new direction.

18:16Disagreing and committing in that scenario is like, okay, you might as well step back and like, let's just have a smaller team and really focus on this because it's not going to be productive. Is there a need that you think are big mistakes that you see found as made when it comes to pivoting, either that you made, or you see angel investments make when it comes to pivoting? I think it's about this experiment thing, honestly. A bunch of angel investments I've made have tried to pivot, but I don't think they went all in on it. I think they saw it as a flyer that they try for a few months, and they didn't see it as life or death, and by the time they realized it wasn't really working, it was life or death because they didn't have much cash left.

18:50And so you really need the conviction like a day of to just sprint towards the new direction. I would also say that in this depth -spirited self -serving as an investor, but like, as we said, the wrong way is crucial. If you're a great founder, if you pivot and it's unsure, most of the time your investors will back you just because they believe in you. If it's a prize in their finding out through an article or a tweet, I'd leave a lot more doubt. 100%. And so, yeah, next to your team is obviously keep the investors informed and up to date, particularly your board. We're lucky to work with Peter Fenton of Benchmark.

19:23His clear avoidance on like where the large opportunity is and just relentlessly pushing us to find that and adjust like on a dime is super impressive and I think hard to do. So definitely like keep your board tightly in the loop on this. I've got a man crush on Peter. I do. I know, he knows that. I told him. My question to you is, what's been your biggest lesson from working with Peter? The power of really deep intuition and conviction, looking at a market from a very theoretical level. So one of the most interesting aspects when he originally agreed to do our A -Round. I sort of asked him why afterwards, like why he committed so quickly.

20:02And he said, well, it had flashbacks to Uber because when Uber was going against the taxi industry, the NPS scores on taxis were so bad. Even if Uber was mediocre, it would still be way better. And he said accounting gave him the exact same vibes. The status quo is just so bad that if you can make accounting like somewhat enjoyable It doesn't even need to be delightful. You've already won and so his ability to distill these markets into these like very high level Chris understandable talking points is super impressive You mentioned about kind of open AI and chat GPT kind of opening your eyes to the new possibilities that were available to you When we think about that.

20:38I'm just intrigued. Do you worry about a lot of your company being based on an external Donald Poth, he's direction development. It is unlike other times in that way. Yeah, this is such a special moment. And I'd say it vividly reminds me of the rise of mobile, which we rode in cross -lettings from 2010 to 2013. The Web 20 transition in 2005 to 2007. It's like these platform shifts are so rare. And I love them because that's where all the massive opportunities arise. And so the key, though, as a startup founder, is to be in a position to rapidly adapt to that new reality. And you need to be faster than your competition.

21:12So like for five years now, I've run digits on a weekly sprint. Every week we get to decide what our direction is that week. And I have to say that's been critical this year, keeping up with all of the changes and evolution of the tech. No, I'm not particularly afraid of it. I love the energy of the tech world moving at a huge pace. And so the key thing though is this is technology. Like we are viewing it as a tool. It's not life or death for the company. It's like databases and so on. It's just evolving faster. Let's see how we use it and it gives us more capability, but you ultimately need to stay focused on your customer and what problem you're solving first and foremost.

21:49He said that it's kind of like database, he's like a foundational technology that you build on top of. Will we see the commotivization of LLMs? Do you think, Jeff? I certainly think we will. And this may not be a popular position, obviously opening eyes, charging ahead, sort of leading the way right now. I think the market forces at work mean there's just immense energy to have an open source equivalent. meta appears to be highly motivated to open source its work. Many folks want to run these themselves and turn them themselves and so on. That is hard and expensive today, but I can't think of another thing in time and history where something hard and expensive in tech has lasted all that long.

22:25It's going to be commoditized. Can I ask you when we look at historical data on open versus closed systems? There are many examples whether it's Linux to your Apple and Android. Traditionally it's been the closed the wins. Why? I thought potentially different today. I don't know if it's different. So the closed may win in terms of having the most advanced model, but I think the Apple versus Android comparison is exactly accurate. So you're going to have something proprietary that might be best because it can be fully vertically integrated. They control all the different variables. But I think there's going to be an open source equivalent or more open equivalent.

23:02It's a very close second. and for many people and for many use cases, it's just as good. So what I'm really excited about is I can't wait to see who becomes the Android to open AI. Like, who is clearly the solidifies the second tier? Yes, I agree with you slightly on the commoditization of other lambs, but I think also we'll see the specialization of other lambs for different things. And actually, if you're a creative tool, hallucinations are wonderful, but for digits, I don't want you hallucinating with my numbers. Correct. Correct. My question to you would be like, you and Blonde, do you think the best companies will average many at the same time?

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23:37Or will it be one that we rely on? That is a really good question. So we built our ML team three years ago. We're training our own in -house models. You're right, like you can't hallucinate in finance. We've done a ton of work to make sure our math is always accurate. It'll be really interesting to see. Every model has different strengths. Like if you already look at Bard and versus GPT and so on and so on. My sense is there'll be a very common popular open source sort of base LLM and then tools to allow folks to fine tune it easily. What we've discovered is while it creates, it takes so much time, data, energy, money to train an LLM, fine tuning it can actually be done relatively straightforwardly, with a surprisingly small amount of data, as long as your data is very high quality and focused.

24:22And so imagine you basically have your sort of default Linux operating system, right? And then everyone customizes their flavor of it for their product market use case, whatever it might be. When you say about the data size, not being as important as the data quality, I'm always kind of interested like, how do we think about the importance of model size versus data size? Because we are trained that data size is so important. Yes. At the base LLM layer, the data size so far has been very correlated with performance. And so, right, the bigger the models, the more data, the more parameters, etc. the better they do.

24:54Now, they're starting to be this counter push of like, okay, can we compress them? Can we pull that back? Like, how do we maintain the performance improvements without the size? So I think that's a super interesting part of R &D. What I'm talking about is sort of the next tier of how do you fine tune the models? And that's where actually I think the quality of data is most important. I totally, either. I always say if you're just like, levers, which is like, you've got latency, you've got cost, and you have to have a trade off like anything on where you want to perform and where you're happy to have some form move degradation.

25:24And look at Apple Silicon, right? They've done an amazing job, like yes, they're fast, but instead of pushing the bounds on pure compute, they're pushing the bounds on energy efficiency, which for Apple's use cases critical. And so I think there will be a lot of really interesting R &D on how do you make these models, maybe smaller and perform it in certain use cases. You said about kind of individual cases where you'd find you on top of a core foundation model. A lot of investors today and they're honestly I see 90 % of companies that I see are like AI4, wealth management, AI4, podcast to album, artwork creation.

25:58I'm not this name, but like, it all, and it's like three weeks old, and I'm like, that can't have been that difficult to build. My question to you is, what's the difference between a thin layer on top of one of these models and a thick wrapper within Harron Valley? Yeah, this is the real problem you're hitting on. So startups are gonna get killed because they're very thin wrappers, And I agree with you most of what I'm seeing on the angel side right now are these very thin wrappers on top of open AI. If your primary product value is scripting GPT, that's a thin wrapper. If you've built it in two to four weeks, that's a thin wrapper.

26:33The key thing to me is like we are in a hype cycle around AI, much like potentially the hype cycle with crypto and other tech before it. All of these sort of fake use cases are going to get quickly washed out and replaced and commoditized. It's really important to me that people view this as a technology. Like your MySQL database, MySQL was very popular 20 years ago, right? Like it was super cool what it could do. It's still cool, but if you try to go raise money on you've built a form on top of MySQL, you're not going to be successful. In five years, that's what a lot of these are going to look like.

27:05You need to really focus on the market and like solving a core problem. When we think about it, like found us today building in this environment, who's vulnerable then? And what I mean by that is that is it in components like Zandesk? Is it like high -growth companies like, I didn't know your notions of the world? Or is it your startups? Or is it all of them? It's probably more startups. The one thing I would say is I view OpenAI probably evolving more into an infrastructure company like AWS. They will host these models that allow you to fine tune them, they'll give you all these base capabilities like you get with EC2 and S3 and so on and so on.

27:39The big companies, the big incumbents that will be able to leverage that tech. I would doubt if OpenAI goes and builds like a notion competitor or an HR sales force competitor or so on They probably want to stay at the more generic level from the startup side a lot of startups are getting killed It's funny. I use the term Sherlock. I'm an old -school Mac programmer back in 2002 Apple killed Watson with its Sherlock tour and so the name sort of stuck There's a lot of companies getting Sherlock because they're pretty incremental and they're filling gaps in OpenAI's current product without realizing that like, yes, they're just on the road map, they haven't gotten there yet.

28:14And so if you're working on a use case that's pretty horizontal, that like, OpenAI is going to need to solve within five years in order to scale, that's not a great investment, and that's not a good use of your time as a founder. One thing that I do think about, which I don't think people talk about enough, which is like, I completely understand the criticism of Google and BOD, but Google have access to compute and the ability to control compute pricing. Whereas OpenAI are the whims of, you know, and Jensen and Nvidia to his, you know, smiling appreciation right now, that's fundamentally challenging, no?

28:47It is very challenging. I like the road ahead for opening eye is not easy. What can you just help all this and understand? Why is it important that it runs on device, you know, running with their own silicon? And so, yeah, so Apple of course is super focused on privacy. They don't want your data to leave the device. The only way to do that with AI is if you can fit a machine learning model on the device and keep all the data there I bet Apple can and will and so if you project forward five years if they get to the point where they can run a sufficiently large LLM on your iPhone then open AI is out of the picture You don't you don't even need to hit their servers.

29:24It's just on your phone. I hadn't thought about it I'm like you my bro. Can we buy some more Apple? Can we load up on this one more and might have been right about them? Some things get taken out of the show. So my favorite is sometimes I'm like, I'll fuck it just leave it in. Can I ask you, how do you think about enterprise adoption? Because I speak to some of the largest enterprise in the world. And they're like, I'm not sending my customer data, my transaction data to a model that is outside of our bounds. How do we think about enterprise control of very sensitive data in this world where they want to get the benefits, but don't want to lose control?

29:59Yeah, two different thoughts here. This is a really good question. So they had the exact same reaction to cloud. If you go back 10 years, they were like, I would never put stuff on AWS or Google Cloud or Azure or whatever. That's ridiculous. Why would I share my data with those companies? Right? Now it's just not only do they all do it, but it's actually better because those companies core competency is running data centers. Most enterprises have no idea how to operate a data center. I think this will go in the same direction. You'll have very clear guidelines around how the companies use the data from model training and its off limits and so on, and sort of that trust will be overcome.

30:33The other angle though is there's also the danger of every enterprise jumping on AI because it's hot and cool. They all jumped on blockchain for zero reason even though it did nothing. And like IBM's at fault, IBM was consulting, charging for services to consult on how to adopt blockchain into your enterprise. That's ridiculous. Again, to me, focus on your customer, your market, your product need, and view this as a tool, not a panacea and adopt it strategically unlike what makes sense and where it's going to push the product forward. You said of IBM that I think that ashy AI implementation services will be one of the biggest categories in the next few years.

31:09Do you agree with me or do you actually think that enterprises will adopt natively? It'll be fine. How do you think about that statement? I think you're probably right in that it's a large market. To me, it's not a very interesting market. Like, yes, there'll be a lot of consulting to help enterprises adopt AI and the products won't be that great and they won't really make that much of a difference. What I see when you come to platform shifts is, again, this opportunity for sort of a net new approach to really take over fast. And what gets me excited is like, let's build real workflow automation for real people in massive industries that are outdated, like, for example, accounting.

31:45Like are you going to trust into it to adopt this and totally disrupt their own product lines or do you think a new upstart is going to come in and do it better? And that's where I'm excited to see a like poor energy until. If we're totally honest, you have a couple more years in this game than me Jeff. My question to you is you've seen transitions with mobile, you mentioned before databases. I'm always worried about speed of adoption and speed of transition. I always fear that it takes a lot longer than we think. Yes. When we think about the speed of transitions, Will this be a slow transition or a false transition and we give credit to you?

32:20It'll be faster for a couple of reasons. So if you look back at mobile, so the iPhone came out in 2007, they opened up the App Store in 2009 by 2011 to 2012 a lot of people were using in building apps. And then enterprise adopts are even lagged from there, so call it five to seven years. With AI, there's no new hardware to buy. So you don't need this huge purchase price, right? Locking out enterprises and people all around the world. You can do this instantly benefit from it online, and there's no new UX pattern to get familiar with, right? You don't need to be used to carrying something around in your pocket, looking at a little screen, squinting or reading things.

32:56There are chatbots. It's a very fluid interface. It does things for you. That makes sense. And so I actually think the adoption curve here will be radically faster, and industries will be disrupted probably way quicker than prior tech waves, just because of the barriers or solo. You said they're about kind of the disruption inherent there. One thing that I find people kind of don't understand as well It's like everyone's like oh Google is so slow and behind. Yes, but that golden goose is such which produces some I think it's like a hundred million a day Whatever it is they're essentially having to cannibalize their cool golden goose.

33:30Yes. What would you do if you I asked as trainer This actually from intcom, but what would you do if you were CEO of Google from here? You mentioned Apple's strong stance What do you have here to go? They need to go all in on it. I don't think they have a choice. I agree with you. I think it's existential for them. Because if AI replaces search, their golden goose has been killed. It is way more effective to kill your own golden goose than let them watch someone else do it. And again, I mean, going back to Apple, it reminds me of the iPod Nano. Apple killed their most popular product, actively killed it because they knew there was better tech coming.

34:03And I think Google needs to get bold and do the same. How do we feel about the cost of compute changing over time? You know, right now it's actually, we mentioned that kind of cannibalization cost of queries is significantly higher With you know models than it is for search today How do we feel about cost of computing cost of query in the next three? Is the traditional Moore's Law is it faster is it slower? What has been interesting to see is it's very clear the top models are memory bound as well as CPU bound So you can't just make the CPUs the GPUs faster. You need to increase memory bandwidth on par with that and open AI actually shared a tech talk a few weeks ago that talks about how they were tuning their data centers like this So it's gonna be new challenges for Nvidia for ARM for these chip companies to really unpack I would bet on the pace of technology.

34:50It will get a lot faster and a lot cheaper very very fast Speaking kind of the price per query that I think pricing is this undiscovered element of this net generation Traditioning we've had per seat pricing in the world of SaaS, will we continue in a world of per seat pricing? Will it be consumption lab? Will it be project led? How do you see the future of pricing in an AI world? So this may be just me, but I very much see AI as a tool, not a product. And so it's a technology. It's like your database. It's like memcash back in the day. And so because of that, I don't think it'll change how people price in specific industries.

35:25Like if your market does Percy pricing, that'll probably stay. If your business and product does consumption pricing, that'll probably stay. And you'll have to work that into how you use the AI. I think it'll be commoditized and seen as technology within a couple years. So you mentioned that the word commoditized. I'm really interested when it comes to the data itself. So my mind just jumps around. It's Friday evening. It's dark. It does roll with me on this one, Jeff. You mentioned the challenge in terms of acquiring clean dates earlier. How challenging do we think it is for companies today to acquire high -quality clean data?

35:59Is it as proprietary defense mechanism as some suggestive is? It is extremely challenging and what's interesting is the counter -reaction because you're seeing Reddit, Twitter, etc. Suttoff APIs, put in more strict rate limits, etc. etc. And so the whole world is starting to lock down data, which was counter to the trends over the past 20 years. So when everything was being pushed more and more open and API accessible and so on. And so I think there's been a clear realization that the data is valuable. And that's one of the things like we've been really focused on at digits is we have a proprietary data set of a hundred million financial transactions.

36:36And that's what we can train on and make sure a finance and bookkeeping eyes know what they're doing. So I do think the data is really, really important. In terms of permissioning around training for, you know, healthcare companies that, you know, have patient records for you, which has obviously financial records. Do you need permissioning on an end client basis to be able to use that data for training? You do. And this is usually sort of broadly captured in the terms of service, having access to your data to improve the product. And so we do not share any of that data externally. We train our own models internally on the data.

37:08But that does allow us to improve the product for you and make your accounting better. I'm pretty sure that one day Tim cooks, just going to come and take one of my children and say, actually, I take the degree in, you know, 2004 and now I've lost my kids. Let's step back for a moment because it's not entirely a joke. So Google Photos, potentially one of the most strategic products ever launched, because it allowed Google to collect the world's largest library of photos ever assembled. And that's how they were able to train their early vision models and so on. I wasn't aware of this. They're able to use the photos that you collect in Google Photos for their training models.

37:43Yeah, presumably. That's impressive. Why doesn't Amazon just buy on Thropic? I look at Amazon's play here and I'm It'd be quite an easy buy, and respectfully at 4 billion, whatever it is, it's a minimal amount of market cap for them. Yeah, that seems like a wise acquisition now. What would you do if you're an Amazon's place? That is super interesting. I would be very nervous about the OpenAI Azure partnership, and of course Meta just made a big deal about partnering with Microsoft as well, so I think you're right. I would look to aggressively move into the space and apply or something to bolster AWS.

38:12Which incumbent do you think is vulnerable from the top incumbents in terms of like, you know, your Apple, Amazon, Facebook, Google? because we've just said Apple actually have a huge opportunity. They're behind the huge opportunity. Yep. Who is vulnerable? I think Google's by far the most vulnerable. Because again, their business model is pretty binary, right? Search is all their revenue, and so if that gets damaged, they're in a huge problem. And they've been slow to react. They've combined two different MLAI teams. They've just punted Gemini into Q1, which tells me it's not doing very well.

38:41So I would be nervous. Final one, and then I will move on from... I'm loving this. but like every scale up is introducing an AI product. And they were just kind of like jumping on the topic de jour. They really are. And one of the funnier ones to me is Dropbox. Dropbox has a built in AI, and I don't know. I mean, I'm sorry Drew, but I just want Dropbox to store the files. So I think there is a bit of a sort of bandwagon ride the hype wave aspect. Oh, gosh. Daesh. What is fun though is obviously it's a lot of experimentation. So all these companies are trying things out and seeing what works and what sticks.

39:17And so the industry's gonna learn a ton over the next 12, 18 months, unlike where it's appropriate to use AI and where it's sort of just a useless out on. On the start -up side, do you think 90 % of investor dollars going to early stage companies today will go to zero? Oh yes, likely. Isn't that always the case though, has there been a period where there's not been the case? Yeah, I think so actually. I think this is a gross over exaggeration on the mortality rate of startups, which is like going to zero is actually rarer than people give credit for site. It could be half your money back. It could be a 1x whatever it is But it is actually rather than zero and the company's killed overnight So I actually have some data for you.

39:53I'm more than happy to share this publicly So since 2014 I have angel invested in 97 startups and I just did the count So far 30 have failed outright about a third another 19 are still at 1x So basically haven't gone anywhere and if you look at the overall portfolio really it's like 10 of them matter But what's crazy to me is, again, 2014, nine years of data, still the vast majority of the gains are on paper and it depends how these tend to, on how successful the portfolio is. You have just opened up treasure trove of questions to me, hey, do you have cash back on many of them? No, very few have returned.

40:31A handful gave cash back, but, or are you talking about on paper? I know I'm saying my actual cash back, like DPI. Oh, very, very few. Yeah, the time range on seed investing on the angel side is just like a decade plus. Okay, so we have that. In terms of the top 10, do you trust the book values? I do not know. And I think a lot of them are basically holding at their 2021 valuation whenever the last round they raised was, and it's nowhere close to the reality. I do get data from the secondary markets, and so I can see with some of them like where they're trading versus where their last preferred round was, it's a bloodbath.

41:06It's like down 80 % for many of them. So I think it'll be really interesting. What do you do if you're a founder who's sitting on a price that's just untenable? That is a really tough position to be in. And I think you don't want to get there. Like my advice has always been be really disciplined about each round and what you give away and terms and so on. If you're in one of these boats, I would look to like recap if you can really focus on growth, trim expenses, length and runway. It's going to be big shoes to build into. So, over there is 10. Would you do secondaries in any of them? How do you think about liquidity planning?

41:41I have actually. So, I've done secondaries over the time. And that's actually been my most successful outcome so far. It was via secondary. It's like waiting for them to sell. I've unfortunately had the opposite happen where a couple of my early investments went on to IPO. And so, we're extremely successful. But then during the six month lockup window went almost to zero. And I couldn't exit almost anything. I've actually had more success selling on the secondary market pre -IPO than I have had actually waiting the whole time. I mean, that is just the ultimate pain, isn't it? When you wait 10 years, it IPOs, and then you can't do shit, and then it goes to zero.

42:17You're like, ah, ah, it is crazy. I mean, I understand why, but I don't understand why small -time angel investors will be locked up for six months. And my question to you is when you look at the cohort, 97 companies at nine years, what do you know now on Angel of the Massing that you wish you'd known when you started? Yeah, big lesson learned is no matter how great you think the company is, how great you think the market is, how great you think the founder is, it is still damn hard. The odds of his success are very low and you can't get too cocky. So on two of them, actually two of my biggest failures, I was so convinced.

42:53I was like, this is a no brain or this is gonna be huge home run, I'm going to put in way more than I usually do. Usually I try to stay pretty disciplined on check size. Both of them went to zero. What can you do about it? Okay, so what gave you the confidence in those companies? It was seem to be a very impressive founder. To me, a very obvious market. I won't name their names, but I was like, hey, just like solid execution here should be a clear good outcome. And there's just too many variables to play over the course of the startup journey. And you don't know everything. Like, as an angel, or you don't do that much due diligence, so it's hard to fully understand.

43:26And so my advice would be just be very disciplined. It's like do a bunch of deals because you need a portfolio and put the same amount in every time and average it out. I'm so with you, the idea that you have more conviction in one versus another at an early stage, in particular, totally wrong. You also get known for writing a certain check, I find, oh, Jeff's a 50K, right? I don't know if you do 500 and then 50 or whatever it is, it's like, whoa, also don't buy trash. And what I mean by that is, like, dude, I was in clubhouse, I was in hoppin. I've been in some of the massive spikes. Traction doesn't mean sustainable.

43:58That is very key advice. Yes, totally agree. Yeah. On the consumer side, I'd say real traction on enterprise software. Okay, potentially more sustainable. Totally. But it's generally less that. Yes. You might get to 10 million aero in 18 months, which is amazing, but it won't be like, you know, 100 million a week. Yeah. Yeah. It was been the biggest hit for you. And what was Spinner lesson from last. Oh man, it's okay, so this is all true. This was 10 years ago, a college friend of mine was prototyping what was gonna be a new teenage social network. And I invested 10K, I was like the guy smart, let's see what happens.

44:32He eventually pivoted that into down to lunch, which did well for a bit and then failed unfortunately. Then he pivoted that into crypto, but not the coins, he started and launched Alchemy, which was like an Ethereum dev platform dev tool thing. And at the height of the Bitcoin boom, I exited on the secondary market for 200x. Holy shit! Lesson learned there? Nothing. It's all about a founder's grit and mentality, and you can't back the early idea and think that that's gonna be it. Did that pay for all the other angel investments? Yes, so that is why on paper, and in terms of cash returned, I'm actually in pretty good shape.

45:11But yeah, it's remarkable how the outliers outclass the rest. But doesn't that also tell you one other takeaway, which is market timing? Yes. And getting in very early at a very low valuation. That's another great lesson learned for folks actually. So I had the opportunity to take some money off the table in a deal. So I got a 3x return, right? Return cash in the bank, 3x return. On paper, it's gone on to do another 10 to 15x. But I'm worried that valuations fake. I don't think it'll ever return the remainder. So I only sold some of my shares, but that might be the only cash I get out of the deal.

45:44How do you feel about investors asking for cash back? Some people like you can never do that. You believe in the founder when you invest and others are like, it's a ton of your reasons we'll say, hey, Jeff, we both know this isn't working. How do you feel about it? Great question. I am biased, obviously, by the founder side, but I think it's very scenario dependent. So if the founder is still excited, the team is there, they have grit. I don't think you can ask for cash back. I think like you want to bet on the founder like let's see where it goes if the founders clearly wavering if there's performance concerns if there's been a pattern of bad decisions Then maybe there's a clear scenario in case for it But in general I would bias towards supporting the founder sometimes found is that she feel like they just have to keep going One thing I have to ask about as well.

46:30Everyone has actually I'm sure had fooled in their portfolio in somewhere or another I don't think we've seen the tip of the iceberg of it coming out. Do you agree or do you think I'm over exaggerating? No, I think a lot of valuations will still crash from here dramatically. And there's probably going to be huge layoffs going into Q1, Q2 as well. What will be really interesting is the number of companies that raised and have sort of struggled through 2023, but now are down to six months or so of cash. I think next year could be very tough because they're not all going to be able to raise follow -on rounds.

47:02What happens to talent migration? And what I mean by that is, you have some amazing talent within large companies and high growth but highly valued companies. Yeah. Do they optimize for safety and stay in the well -paid job? Or do they go and make a company that's way overvalued? I should leave and do something. Which side do you err on? Yeah, this is a great question, because a lot of folks you're right are trapped in companies with high valuations where their options are likely under water. Yeah. But it's safer than just starting something new. Right. And so it probably is safer than starting something new, but it's not safer than switching to a earlier stage sort of growing company where you're going to have real options and a real impact.

47:43I actually love sort of down markets because I think in the very hot markets, it's too easy to raise capital and you peel off all the sort of like fantastic second engineers or product managers or designers or whatever they might be and they go get funding and start something, and that actually blurs, it stretches the talent density across the entire ecosystem. Versus in down markets, you can build higher talent density because it's harder to raise your own money. So you think we'll see a migration from later stage to earlier stage? Yeah, we'll come be aligned though, because that's the big problem they just pay well.

48:15This is the problem, you're right. And that's probably the counter force is all of these big companies who raised huge rounds in 2021 have high salaries. If you switch, you'll get more equity but way less cash. And so that's probably keeping folks where they are. And so will they stay? People like cash. People are trained that cash is now king, right? You know, Ray Gatley is going, uh, cash ain't trash no more. It's very true. It's very true. The final one, but like, and it's a shit question, I can't believe I'm asking it. But like, you know, from the 97 -Langela investments, is there anything non -obvious that you see in terms of patterns from the most successful founders?

48:48I know it sounds strange, but one that I see is often the most successful founders moved a lot in early childhood. Oh, fascinating. And why does, why, if you theorize around that, the theory is that actually you essentially have to constantly reinvent yourself. Right. You align to culture, society's friendship groups. And you understand nuances, intricacies, the idea. But that's one that I found. Oh man, no, I don't have a good of an insight as you. I'd say looking at my portfolio, It's not even necessarily the most techy founders that are successful But the most sort of customer obsessed and just like really deeply personally understand the market and really want to solve it And usually have some pattern in their background like their parents were in a sort of adjacent space or something Where they've just felt this like personal identity come to bear on what they're doing and I think that gives you like an extra Push an extra drive and extra grit to make it successful.

49:43I listen, dude I want to move into a quick fire. I've so enjoyed this. I say a short statement. You give me your immediate thoughts, aren't it, okay? All right, let's do this. So what do others not know that you know to be true? Run away climate change is less than 10 years out. What do you mean run away climate change? Like just a self -building cycle of higher temperatures and catastrophic storms and droughts and everything. And so we just accept this new reality? No, I think we're too late and like I funded climate change films 15 years ago. It's still shocking to me that this is not like the singular top priority in any political campaign in the entire world.

50:18But then do we just accept this new reality of storms and unpredictable weather patterns? Yeah, I don't think you can't accept it. It's going to happen. And so the real question is, what are we doing about it? And which countries is it gonna completely impact way more than others? So it'll be really challenging. Being a realist, I think it's something like, if China hit its emissions goals for a year, it would be the same as Canada hitting them for 26. As much as we would like to, does it even matter if you don't get China on board? Yes, the impact is unfairly distributed and the cause is unfairly distributed.

50:54That's why it's basically a strategy of the comments, and so economically it's like how do you motivate that on a global scale? Do you not also feel slightly for emerging economies in terms of like, you know, for years you've downtroddened some beatiness to a terrible way of living? And finally we're increasing our, you know, standard of living. And now you want to focus on other priorities, increase tariffs. We're still scaling the pole of starvation. Right, exactly. And they haven't had the time to catch up and drive efficiency and technology and so on. The whole thing is unfair, yes. I'm asking the tough questions.

51:27I was putting another quick fire around. Yeah, you know, I was fathering about, dude, you gave me such a good one. And most people give me shit on that question. I'm like, oh, this is good. Tell me, you can be CEO of any other company for a day, which company do you be CEO of them? Why? All right, well, this is for one day. So I would go be CEO of OpenAI just so I can see the roadmap and then I'll know what to do from there. Next one, most controversial view that you have today. Ah, so I would say actually, AI won't replace many jobs, I think, actually. It'll drive productivity, not replacement, and it'll be like other technologies that have come out.

52:02Like phones didn't replace people. Now you just use them and you can do business from wherever. I think AI will let you get a lot more done in a lot less time. Why do you think the popular narrative is that it will? Is it because we like to be scared? Yeah, we like to be scared. We like to be terrified. So there's this concept in economics called the lump of labor fallacy It was literally from the late 1800s and you can look back. There's newspaper articles in the New York Times from the 30s Being like we are gonna be replaced by robots It within the next decade and it's like nope that didn't happen and it just marches forward every decade there's a fear of the new technology coming in.

52:36People hated personal computers in the 70s, because they thought it was going to take over and replace them. And so it's just it's this fallacy. Can you imagine being a math teacher back in the day with the advent of calculators? You would think your entire job is useless. But was the right way to view competition, Jeff? Ignore them completely. Focus on the customer. Really? I'm always like, it's helpful just to be aware of the other boat. I don't think so. It's like be really aware of the customer pulling you and like make sure you're going in their direction as fast as possible And as a startup maybe if you're a giant gala if you should start paying attention to some competitors But as a startup the market is way larger than you could possibly capture this year So like focus on your customers I think a lot of product managers get too distracted watching the competition and they don't have a vision for their own product What's the best piece for advice you've been given?

53:28Oh man 24 -hour hypothesis. When your team comes to you with a question, you need a decisive answer within 24 hours. If you're slower than that, you're not moving fast enough. What if he truly needs to be incredibly thoughtful, like the Mr. T. Irishman company, or really like old structure, redesign? Yeah, so this is where I go back to one of Bezos's letters, Type 1 versus Type 2 decisions. The vast majority are Type 2 decisions, they're reversible. You can undo them. What I would say is one net, it is way better for a startup to be moving in a direction than the absolutely perfect direction. Because you can keep refining that going forward, but if you pause on a decision and you're like, give me a week, what do you want the team to do?

54:11And this was one of the biggest challenges Twitter faced internally back in the day was just complete in decision from leadership. I think we constantly underestimate the value of just activity. I look back, but like the early days of doing these shows, I wasn't so good, the topics weren't so great, the questions weren't so great, but I learned and I iterated the shows, the value of evolved, guests got better, worse, what it - But like activity drives progress. 100 % And learning, if you're not moving, you're not learning, so what are you gonna do differently? So if you're not moving, you're not learning, what did you believe 12 months ago that you no longer believe?

54:4412 months ago, I thought useful AI would be years away. No longer think that. It is amazing to think of the speed. It's not even been like a year since the evolution of the net share. Jeff, 10 years. I mean, we met eight years ago. I think it was. Yes. So if we take the amount to years in 2033, where are you then? So keep in mind, there's going to be some runaway climate change. I'm going to be off growing obscure wine grape varietals in a cold climate. Where will digits be? Digits will be the new de facto accounting platform. We're really, really excited. We've built basically a completely object -oriented real -time AI -driven approach to finance to make it really intuitive for Startup founders to understand their finances as the business happens not three weeks late on a black and white PDF.

55:31Jeff, I've absolutely loved this. This has gone in so many great directions. Thank you so much for being so brilliant and it's been a highlight of my week. I love it, Harry. This was super fun. Thanks so much for having me on. I think what I love so much about that show was just the natural rapport and conversation there. I think you could tell that it was very much unscripted. It was such a joy to do that with Jeff. I want to say huge science to him for the friendship over the many years and the partnership now with digits. I really do so appreciate it. If you'd like to see the video of this episode, then you can check it out on YouTube by searching for 2 -0 V .C.

56:03That's 20 V .C. on YouTube. But before we leave you today, there is no shortage of helpful AI tools out there, but using the mean switching back and forth between yet another digital tool, what was supposed to simplify your workflow just made it way more complicated and less of course you're in notion. Notion combines your notes, docs and projects into one space that's simple and beautifully designed and you can leverage the power of AI right inside notion across all your notes and docs without jumping between your work and with a separate AI powered tool, automate the tedious task like summarizing meeting notes or finding next steps, freeing you up to do the deep work.

56:42It allows you to save time and right faster by letting Notion AI handle the first draft, jumpstart a brainstorm, or turn your messy notes into something polished. And you can try Notion for free when you go to Notion .com slash 20VC, that's all lowercase Notion .com slash 20VC to try the powerful easy to use Notion AI to stay. And when you use our link, you're supporting our show. and speak of game -changing products like Notion there. Listen to this. Mercury has been a breath of fresh air. Getting started was maybe one of the most delightful onboarding experiences I've had. Mercury is just so easy to use.

57:18The aesthetic of it is actually quite relaxing. For me, it was less a choice and more finding a kindred spirit. Imagine feeling this way about business banking. You could, if you join more than 100 ,000 startups on Mercury, The powerful and intuitive way for ambitious companies to bank, start building momentum and leave the friction behind by visiting mercury .com forward slash 20VC. Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolved Bank and Trust, members of the FDIC. I'm finally traveling in the expense and never associated with cost savings, but now you can reduce costs up to 30 % and actually reward your employees.

58:02How? Well, the van rewards your employees with personal travel credit every time they save their company money when booking business travel under company policy. Does that sound too good to be true? Well, the van is so confident you'll move to their game changing all in one travel corporate card and it spends super app that they'll give you $250 in personal travel credit just for taking a quick demo, check them out now at navan .com forward slash 20VC. As always I so appreciate all your sporting stage tune for an incredible episode on Friday where we're going to be bringing together a couple of different episodes.

58:36Combining thoughts on will LLMs be commoditized? What will the pricing model for AIB in the future? And which incumbents will be the winners and which will be the losers? That will be such a cool episode to do.

From the publisher

Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC. Jeff previously served as Twitter's Head of Consumer Product, a position he came to following the acquisition of his prior company, Crashlytics. Today, Crashlytics is the de-facto mobile crash reporting solution for iOS and Android and runs on over 6 Billion monthly active smartphones worldwide.

In Today's Episode with Jeff Seibert We Discuss:

1. The Art of the Pivot:

  • What are Jeff's biggest pieces of advice to founders pivoting?
  • How do you know when you have enough data to make the decision to pivot?
  • What are the single biggest mistakes founders make when pivoting?

2. AI: Who Wins and Who Loses:

  • Why does Jeff believe that OpenAI will transition into an infrastructure play?
  • What are the most significant challenges OpenAI will face moving forward?
  • Why does Jeff believe that Apple are best positioned to win in an AI world?
  • Why does Jeff believe that Google are the most vulnerable incumbent?
  • What would Jeff do if he was CEO of Google?

3. LLMs: What Happens Now:

  • Will we see the commoditization of LLMs?
  • What are the biggest misconceptions people have on training and fine-tuning LLMs?
  • Will we see LLMs increasingly specialise to vertical-specific models or will they remain horizontal?
  • What is the difference between a thick and a thin wrapper when building on top of LLMs?

4. Angel Portfolio in Review:

  • How many angel checks has Jeff written? How many failed? How many home runs?
  • Does Jeff believe that company valuations are being kept artificially high?
  • How did Jeff make 200x selling through the secondary market for a now failing company?
  • What are Jeff's three biggest pieces of advice for angels today?

More from The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

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20VC: Why OpenAI Will Become an Infrastructure Play, Why Apple Will Win in an AI World, Why Google is the Most Vulnerable Incumbent, Will LLMs Be Commoditised, Which Startups Are Thin vs Thick Wrappers on Top of LLMs with Jeff Seibert, Founder @ DigitsThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 59 min
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