The Exchanges

Q Not at all, but I want to kick off today with a little bit about you. So tell me, how did you make your way into the world of first angel investing and then come to found Work Life Ventures? What was that aha moment for you?

A Yeah, I mean, I think this has been a long time coming, and I'll, and I'll walk through sort of how I got started, because it's a little bit non-traditional. I actually started teaching classes at General Assembly very early in my career, so I kind of always had these two sort of parallel tracks that I was running. First of all, I was operating at Expedia, had started out in more of a performance and growth marketing role, and then scaled into a head of social media role, which Owned performance marketing, brand community, and customer support, which kind of ties into the later Zendesk experience. But in parallel, I kept teaching classes, taught over 5000 students. I had a go-to-market bootcamp that I was teaching. I ended up spinning that out into a program that I run today, twice a year, called SAS School. And SAS School is a self-funded, community-led program taught by amazing executives at brand name SAS companies. And in building that community, I had sort of progressed from From advising to then writing angel checks while I was at Zendesk. So I think like many individuals, I started with sort of the 25 to 50 K angel checks and over time, build a track record, which we can talk about later. You got into great companies like Webflow, which I know you spoke to Vlad, Voiceflow, Air Garage, which is a company that I'm really excited about. That's an up and coming one. And, you…

AI assessment note: “decided that... I wanted to... build my own dedicated SAS fund”

Q And then I'm really sad for this to be the final one, but the most recent investment, and why did you say yes and get so excited, Brianne?

A Yeah. So my most recent investment is a company called Pace. Pace enables SaaS companies to offer flexible payments on annual contracts while getting paid up front. So there's no debt, no payment risk. You can think of it as a firm for software businesses. And it's a really interesting product for sales reps. They can close deals faster by bypassing procurement and any sort of ACV thresholds that exist inside of other companies. For CROs and for finance teams, Pace Pre-qualifies businesses and handles the paperwork and complexities that come with invoicing. And it's a really game changing model for startups who can now access premium software with a lower monthly rate. So imagine having enterprise grade software, but only paying, you know, a certain MRR amount that you're willing and able to, uh, to pay for. And it's been really great to see and pace is moving very quickly in terms of product development. I think in a lot of ways, you know, it is a new financing model and there are also just Discovering a lot as well as they're meeting with both startups and medium-sized companies to figure out what are the unique financing needs that have held back SaaS companies previously? And how do we really flip the switch on monetization where it's less about a self-serve business model where you land on a pricing page and you get to choose three options, which are oftentimes a little bi…

AI assessment note: “my most recent investment is a company called Pace.”

Q Not at all, but I want to kick off today with a little bit about you. So tell me, how did you make your way into the world of first angel investing and then come to found Work Life Ventures? What was that aha moment for you?

A Yeah, I mean, I think this has been a long time coming, and I'll, and I'll walk through sort of how I got started, because it's a little bit non-traditional. I actually started teaching classes at General Assembly very early in my career, so I kind of always had these two sort of parallel tracks that I was running. First of all, I was operating at Expedia, had started out in more of a performance and growth marketing role, and then scaled into a head of social media role, which Owned performance marketing, brand community, and customer support, which kind of ties into the later Zendesk experience. But in parallel, I kept teaching classes, taught over 5000 students. I had a go-to-market bootcamp that I was teaching. I ended up spinning that out into a program that I run today, twice a year, called SAS School. And SAS School is a self-funded, community-led program taught by amazing executives at brand name SAS companies. And in building that community, I had sort of progressed from From advising to then writing angel checks while I was at Zendesk. So I think like many individuals, I started with sort of the 25 to 50 K angel checks and over time, build a track record, which we can talk about later. You got into great companies like Webflow, which I know you spoke to Vlad, Voiceflow, Air Garage, which is a company that I'm really excited about. That's an up and coming one. And, you…

AI assessment note: “progressed from From advising to then writing angel checks while I was at Zendesk”

Q And then I'm really sad for this to be the final one, but the most recent investment, and why did you say yes and get so excited, Brianne?

A Yeah. So my most recent investment is a company called Pace. Pace enables SaaS companies to offer flexible payments on annual contracts while getting paid up front. So there's no debt, no payment risk. You can think of it as a firm for software businesses. And it's a really interesting product for sales reps. They can close deals faster by bypassing procurement and any sort of ACV thresholds that exist inside of other companies. For CROs and for finance teams, Pace Pre-qualifies businesses and handles the paperwork and complexities that come with invoicing. And it's a really game changing model for startups who can now access premium software with a lower monthly rate. So imagine having enterprise grade software, but only paying, you know, a certain MRR amount that you're willing and able to, uh, to pay for. And it's been really great to see and pace is moving very quickly in terms of product development. I think in a lot of ways, you know, it is a new financing model and there are also just Discovering a lot as well as they're meeting with both startups and medium-sized companies to figure out what are the unique financing needs that have held back SaaS companies previously? And how do we really flip the switch on monetization where it's less about a self-serve business model where you land on a pricing page and you get to choose three options, which are oftentimes a little bi…

AI assessment note: “my most recent investment is a company called Pace.”

Q with you. I think it's really important to keep that friendly check size in terms of the kind of multi-stage fund component. I am interested, though, because we had Samuel Sharon show the other day, and he said founders are voting with their And bypassing seed funds to multi-stage funds almost aligned to what you're saying there. Would you agree with this? And how would you respond to that suggestion?

A You know, I think founders are going to multi-stage funds, but I will also say that multi-stage funds have done a really impressive job of really ramping up their seed practices. So I think it's happening on both sides. I think you have enough repeat entrepreneurs who are working on their second or third idea already have a Establish relationships in Silicon Valley. They kind of already have a sense for who they want on their board. And for those individuals, they already have the relationships, you know, they already potentially have a path to what they would envision for a great Series A. So I think for those individuals, they do go to the multi-stage firms. And I think, to be honest, like one of the challenges that the existing seed funds face is that because of the large fund-sized From these multi-stage firms, then they can very quickly write a check with very little diligence, or they can do it based on existing relationships. So I do find that once a company starts to gain some momentum and some heat, it is more difficult for a seed fund to compete with one of the sort of top tier multi-stage funds.

AI assessment note: “I think founders are going to multi-stage funds”

Q And that capital, obviously being work life, is a super interesting structure, actually, and so it's structured as a holdings company. Let's start with that. Why did you do that over maybe a traditional fund structure, and what does it allow you to do, Brianne?

A Yeah, this is a really interesting point. And I think this is something that I had explored very early on. So I actually had started out at Expedia and had spent a lot of time really understanding multi-product companies, kind of looking at the IAC model and looking at what are some opportunities in the future of software. And I kept coming back to this thought that to truly support SaaS businesses, I do believe that venture is only one path. You know, where I spend most of my time and where I'm most excited is more so Specifically building and helping entrepreneurs scale venture sized outcomes. But what I will say is I wanted to structure work life in a way where if I meet great entrepreneurs who are hitting some roadblocks around the five to ten million ARR mark, I do want to have the ability, sort of a separate structure to facilitate some boutique funding models such as private equity. It's been really interesting to see. I think this is something that It will be a growing trend in Silicon Valley. One example that I have is, you know, I feel like there is basically an under utilization of talent. And I think that there are a lot of really impressive ideas that get abandoned over time. So what I typically find is oftentimes, you know, there are companies that have gone through a program such as Y Combinator. There may be two or three batches outside of the program. And, you …

AI assessment note: “a separate structure to facilitate some boutique funding models such as private equity”

Q with you. I think it's really important to keep that friendly check size in terms of the kind of multi-stage fund component. I am interested, though, because we had Samuel Sharon show the other day, and he said founders are voting with their And bypassing seed funds to multi-stage funds almost aligned to what you're saying there. Would you agree with this? And how would you respond to that suggestion?

A You know, I think founders are going to multi-stage funds, but I will also say that multi-stage funds have done a really impressive job of really ramping up their seed practices. So I think it's happening on both sides. I think you have enough repeat entrepreneurs who are working on their second or third idea already have a Establish relationships in Silicon Valley. They kind of already have a sense for who they want on their board. And for those individuals, they already have the relationships, you know, they already potentially have a path to what they would envision for a great Series A. So I think for those individuals, they do go to the multi-stage firms. And I think, to be honest, like one of the challenges that the existing seed funds face is that because of the large fund-sized From these multi-stage firms, then they can very quickly write a check with very little diligence, or they can do it based on existing relationships. So I do find that once a company starts to gain some momentum and some heat, it is more difficult for a seed fund to compete with one of the sort of top tier multi-stage funds.

AI assessment note: “I think founders are going to multi-stage funds, but I will also say”

Q want to move the layer deeper now. We've discussed the camp tables around the investments. We've discussed the fund structure. If we actually talk about The fun thesis itself almost. I want to talk about that because you said before, the next great thing in consumer will touch work life, obviously, hence the name. Clearly the thesis of the fun book. What does that really mean as a starting point?

A Yeah, I mean, I think we've hit this really interesting moment in time where I think there are a number of changes happening. So from a consumer point of view, people are incredibly motivated professionally. We are also seeking creative outlets, especially as the workforce Becomes increasingly technical. The lines between work and life are increasingly blurred, and the vision for the fund was to really take a step back and imagine, you know, what does the future of work look like? Not just from a software standpoint for individuals who are building software applications for other startups, but what are some new ways that both individuals are accessing new types of work? What are new ways for individuals to make money? Thinking more even about what are some of the services and programs that need to be built to unlock, you know, human potential at scale.

AI assessment note: “The lines between work and life are increasingly blurred, and the vision for the fund”

Q Totally get you in terms of the reliance on paid marketing and having that beautiful consumer experience. The final element though that I do have to ask, it's a brilliant statement. You said this scrappy SaaS is dead. What is scrappy SaaS? And why is it dead, Brianne?

A So I think that there's been conversations for a while around freemium being a great marketing channel around the ability to quick and launch SaaS businesses. And I think one of the challenges that I faced with the category holistically is Oftentimes, the products are fairly easy to build. You get in a race for free users, and then later, you attempt to monetize. And I think with this sort of scrappy mentality, typically, you do end up having a dozen companies that are actively solving the same problem with a very similar solution. You can oftentimes find that it does attract a certain type of entrepreneur as well, where I oftentimes do find that it mirrors more of a side hustle or an applicant Application that is potentially an experiment which hopes to gain meaningful traction. I think that those sort of applications are few and far between, I think, specifically in sort of the venture world, simply because I think now you'll start to see more companies that are thinking about the way that they collect data. Like a few years ago, everything was AIML. I think that's now shifting, and we're sort of over some of the hype around AIML. And we're now moving into this world where it's more about Great consumer, great experiences. We are willing to ask users to pay from day one. I think superhuman is a great example of this where Rahul had recently spoke at SAS school, the program th…

AI assessment note: “We are willing to ask users to pay from day one.”

Q Totally get you in terms of the reliance on paid marketing and having that beautiful consumer experience. The final element though that I do have to ask, it's a brilliant statement. You said this scrappy SaaS is dead. What is scrappy SaaS? And why is it dead, Brianne?

A So I think that there's been conversations for a while around freemium being a great marketing channel around the ability to quick and launch SaaS businesses. And I think one of the challenges that I faced with the category holistically is Oftentimes, the products are fairly easy to build. You get in a race for free users, and then later, you attempt to monetize. And I think with this sort of scrappy mentality, typically, you do end up having a dozen companies that are actively solving the same problem with a very similar solution. You can oftentimes find that it does attract a certain type of entrepreneur as well, where I oftentimes do find that it mirrors more of a side hustle or an applicant Application that is potentially an experiment which hopes to gain meaningful traction. I think that those sort of applications are few and far between, I think, specifically in sort of the venture world, simply because I think now you'll start to see more companies that are thinking about the way that they collect data. Like a few years ago, everything was AIML. I think that's now shifting, and we're sort of over some of the hype around AIML. And we're now moving into this world where it's more about Great consumer, great experiences. We are willing to ask users to pay from day one. I think superhuman is a great example of this where Rahul had recently spoke at SAS school, the program th…

AI assessment note: “Oftentimes, the products are fairly easy to build. You get in a race for free users”

Q I do want to talk about another segment that's seen incredible rise over the last few years, and it's the rise of Celebrity Aim. Again, if we go back to causation, why are we seeing so many celebrity angels on cap tables today, do you think?

A Yeah, it's fascinating. I mean, I, uh, you know, I spend a lot of time in Los Angeles and even looking at my LP construction for fund one. And, you know, you do have some interesting people who are potentially a little bit outside of the traditional Silicon Valley circles. And I think there are two things that are happening. I think the first thing is that startups are going mainstream. I think, I think startup Culture is going mainstream beyond these sort of quirky shows like Silicon Valley. I think that one of the greatest talking points that I hear consistently from A-list celebrities, from athletes, from people who are not spending their day to day solely focused on building technology and sort of software is that startups are a talking point. And I think that right now, not only is it an incredibly fascinating asset class, I think that it's also something where if you can have strong brand alignment, it's a great way for a celebrity and athlete, a person of influence to really diversify their investment portfolio and in parallel, choose companies that align with their brand. So I think, you know, historically we've seen sort of athletes align with more CPG related products. But one interesting thing that I'm seeing lately is, you know, I invest in a lot of tools and platforms Platforms that do get implemented and adopted in Hollywood. I think that celebrities, influencers,…

AI assessment note: “startups are going mainstream... great way for a celebrity and athlete... to really diversify”

Q I was chatting to Vlad, as we mentioned before the episode, and he said, I'd love to hear how Brianne thinks about founders actively angel investing. How do you feel about that? We're seeing it more and more today.

A We do see it more and more today, and I think the greatest thing an entrepreneur can do today is to stay focused, and I know that that's quite a conservative point of view. However, I think that right now in the ecosystem, there are a lot of distractions, and I think that when you look at the historical track record of Scout programs, or I would say even angel investing. Like I think as an entrepreneur, the most amount of leverage you have is with your own company. I think like Vlad is by far one of the most recent and more high profile examples where if you look at an individual like Vlad, he is 100% committed to Webflow. So he, he does an amazing job on Twitter. He's recently promoted an employee to the head of diversity inclusion role. So I think that he is very much Building what I consider to be, you know, the next great cultural icon for a tech company. So, you know, I was very fortunate and really enjoyed my time at Zendesk because I think from a culture standpoint, from an employee retention standpoint, the only way those sort of things happen is if it happens top down. So having an incredibly thoughtful and focused CEO will yield a great place to work. So I think there's a lot, there's a lot of opportunities to sort of get distracted and start writing a high volume of checks. Or join a lot of these sort of separate group syndicates, and I think one of the biggest thing…

AI assessment note: “I think the greatest thing an entrepreneur can do today is to stay focused”

Q Totally aligned to you there. You mentioned that in terms of the speed of rounds, and it's something that if people listen to the show know that I'm very worried about, it's the compression of fundraising timelines. How do you feel about the compression? Fundraising timelines. And do you share my concern?

A You know, I do share some concerns around how quickly the seed landscape is moving. I think that I'm an investor in a company called Tandem, which was in the last YC batch, which very quickly became the hottest company in the YC batch. And I think that was a really good signal of just how hot the market is right now and just how much capital is freely flowing, especially for early stage companies. And, you know, I think for entrepreneurs, it's a, it's a really interesting time because I think that some of the seed funds are not able to move as quickly. They do have a smaller fund size and they are more thoughtful in the way that they engage with companies. But I think that, you know, when you choose a more boutique seed fund or you choose, especially a sort of career seed investor, then I think that the day to day will be very different. I think that, you know, they already have systems and programs and processes in place. To help you find product market fit. You don't have to be concerned with asking very tactical questions like, how do I negotiate this sublease on an office in Soma? So I think there are a number of questions where potentially the multi-stage firms typically view this as things you should figure out on your own, where I think that a lot of the boutique seed funds already have the infrastructure in place. It's sort of like they are a great first call because no…

AI assessment note: “I do share some concerns around how quickly the seed landscape is moving.”

Q I do want to talk about another segment that's seen incredible rise over the last few years, and it's the rise of Celebrity Aim. Again, if we go back to causation, why are we seeing so many celebrity angels on cap tables today, do you think?

A Yeah, it's fascinating. I mean, I, uh, you know, I spend a lot of time in Los Angeles and even looking at my LP construction for fund one. And, you know, you do have some interesting people who are potentially a little bit outside of the traditional Silicon Valley circles. And I think there are two things that are happening. I think the first thing is that startups are going mainstream. I think, I think startup Culture is going mainstream beyond these sort of quirky shows like Silicon Valley. I think that one of the greatest talking points that I hear consistently from A-list celebrities, from athletes, from people who are not spending their day to day solely focused on building technology and sort of software is that startups are a talking point. And I think that right now, not only is it an incredibly fascinating asset class, I think that it's also something where if you can have strong brand alignment, it's a great way for a celebrity and athlete, a person of influence to really diversify their investment portfolio and in parallel, choose companies that align with their brand. So I think, you know, historically we've seen sort of athletes align with more CPG related products. But one interesting thing that I'm seeing lately is, you know, I invest in a lot of tools and platforms Platforms that do get implemented and adopted in Hollywood. I think that celebrities, influencers,…

AI assessment note: “I think there are two things that are happening. I think the first thing is”

Q And that capital, obviously being work life, is a super interesting structure, actually, and so it's structured as a holdings company. Let's start with that. Why did you do that over maybe a traditional fund structure, and what does it allow you to do, Brianne?

A Yeah, this is a really interesting point. And I think this is something that I had explored very early on. So I actually had started out at Expedia and had spent a lot of time really understanding multi-product companies, kind of looking at the IAC model and looking at what are some opportunities in the future of software. And I kept coming back to this thought that to truly support SaaS businesses, I do believe that venture is only one path. You know, where I spend most of my time and where I'm most excited is more so Specifically building and helping entrepreneurs scale venture sized outcomes. But what I will say is I wanted to structure work life in a way where if I meet great entrepreneurs who are hitting some roadblocks around the five to ten million ARR mark, I do want to have the ability, sort of a separate structure to facilitate some boutique funding models such as private equity. It's been really interesting to see. I think this is something that It will be a growing trend in Silicon Valley. One example that I have is, you know, I feel like there is basically an under utilization of talent. And I think that there are a lot of really impressive ideas that get abandoned over time. So what I typically find is oftentimes, you know, there are companies that have gone through a program such as Y Combinator. There may be two or three batches outside of the program. And, you …

AI assessment note: “I wanted to structure work life in a way where if I meet great entrepreneurs”

Q Should founders always be raising or is that a misnomer?

A It's an interesting question. I think that founders should always be building the relationship. I spend most of my time in seed and I help entrepreneurs get ready for the series A. And, you know, I think that that is an inflection point in your company where you're adding a tenure partner, you know, choosing your board member is no easy feat. I highly encourage entrepreneurs to really keep in mind that at this moment in time, uh, you know, in the tech ecosystem, investors are on the sell side. And what that means is entrepreneurs can really take advantage of getting to know the potential board member by scheduling working sessions, you know, whiteboard sessions to evaluate accordingly. I think that really being thoughtful and evaluating that individual partner's network is important. So you can ask hiring questions for later rounds. I think really, you know, digging into who would be someone they suggest for a future independent board seat. I think that you really have a lot of leverage early on as Especially between seed and series A, to get to know a partner, to really understand, like, is this someone that you want to spend the next 10 years with? And really understanding their thoughts around later funding rounds, future hiring, and really investigating if this is the right partner for you in the long term.

AI assessment note: “I think that founders should always be building the relationship.”

Q stage, and they say, yeah, we built that internally. I mean, I can show it to you, and you know, ours is very similar to that. Is that a concern for you when investing in these more open source, more independent players who are open to the market versus someone who has it closed in, and would that deter you the fact that technically there's no IP in that respect?

A Yeah, it's a really interesting question, and I think this is something that I speak a lot to these consumer operators who are entering B to B. And one of the things that is important to consider is with a lot of these self-serve SaaS companies, you know, many APIs, a lot of workflow tools, a lot of the things that we're seeing in the ecosystem today, quite frankly, they're easy to build. And I think when you have a product that's fairly easy to build, then what you need to consider is there needs to be some sort of competitive advantage. Now, maybe that competitive advantage comes from From, you know, your access to other great tech companies, like maybe you are really strong on building closed products, accepting only users who meet a very specific criteria and sort of align with your product vision. And therefore you can build and scale this product alongside other great product leaders. You know, that's sort of one option. I think historically we've seen, you know, what I sort of call the opposite of hype beat SaaS, which would be scrappy SaaS. And historically we've seen a lot of landing page experiments We've seen very quick product releases on product time, and you see this sort of freemium model where I think that era of SaaS is slowly going away. And the reason for that is that the products are easy to build. You then get into this race, which is much similar to consum…

AI assessment note: “when you have a product that's fairly easy to build, then what you need to consider”

Q Should founders always be raising or is that a misnomer?

A It's an interesting question. I think that founders should always be building the relationship. I spend most of my time in seed and I help entrepreneurs get ready for the series A. And, you know, I think that that is an inflection point in your company where you're adding a tenure partner, you know, choosing your board member is no easy feat. I highly encourage entrepreneurs to really keep in mind that at this moment in time, uh, you know, in the tech ecosystem, investors are on the sell side. And what that means is entrepreneurs can really take advantage of getting to know the potential board member by scheduling working sessions, you know, whiteboard sessions to evaluate accordingly. I think that really being thoughtful and evaluating that individual partner's network is important. So you can ask hiring questions for later rounds. I think really, you know, digging into who would be someone they suggest for a future independent board seat. I think that you really have a lot of leverage early on as Especially between seed and series A, to get to know a partner, to really understand, like, is this someone that you want to spend the next 10 years with? And really understanding their thoughts around later funding rounds, future hiring, and really investigating if this is the right partner for you in the long term.

AI assessment note: “I think that founders should always be building the relationship.”

Q want to move the layer deeper now. We've discussed the camp tables around the investments. We've discussed the fund structure. If we actually talk about The fun thesis itself almost. I want to talk about that because you said before, the next great thing in consumer will touch work life, obviously, hence the name. Clearly the thesis of the fun book. What does that really mean as a starting point?

A Yeah, I mean, I think we've hit this really interesting moment in time where I think there are a number of changes happening. So from a consumer point of view, people are incredibly motivated professionally. We are also seeking creative outlets, especially as the workforce Becomes increasingly technical. The lines between work and life are increasingly blurred, and the vision for the fund was to really take a step back and imagine, you know, what does the future of work look like? Not just from a software standpoint for individuals who are building software applications for other startups, but what are some new ways that both individuals are accessing new types of work? What are new ways for individuals to make money? Thinking more even about what are some of the services and programs that need to be built to unlock, you know, human potential at scale.

AI assessment note: “the vision for the fund was to really take a step back and imagine”

Q I was chatting to Vlad, as we mentioned before the episode, and he said, I'd love to hear how Brianne thinks about founders actively angel investing. How do you feel about that? We're seeing it more and more today.

A We do see it more and more today, and I think the greatest thing an entrepreneur can do today is to stay focused, and I know that that's quite a conservative point of view. However, I think that right now in the ecosystem, there are a lot of distractions, and I think that when you look at the historical track record of Scout programs, or I would say even angel investing. Like I think as an entrepreneur, the most amount of leverage you have is with your own company. I think like Vlad is by far one of the most recent and more high profile examples where if you look at an individual like Vlad, he is 100% committed to Webflow. So he, he does an amazing job on Twitter. He's recently promoted an employee to the head of diversity inclusion role. So I think that he is very much Building what I consider to be, you know, the next great cultural icon for a tech company. So, you know, I was very fortunate and really enjoyed my time at Zendesk because I think from a culture standpoint, from an employee retention standpoint, the only way those sort of things happen is if it happens top down. So having an incredibly thoughtful and focused CEO will yield a great place to work. So I think there's a lot, there's a lot of opportunities to sort of get distracted and start writing a high volume of checks. Or join a lot of these sort of separate group syndicates, and I think one of the biggest thing…

AI assessment note: “I think the greatest thing an entrepreneur can do today is to stay focused”

Q stage, and they say, yeah, we built that internally. I mean, I can show it to you, and you know, ours is very similar to that. Is that a concern for you when investing in these more open source, more independent players who are open to the market versus someone who has it closed in, and would that deter you the fact that technically there's no IP in that respect?

A Yeah, it's a really interesting question, and I think this is something that I speak a lot to these consumer operators who are entering B to B. And one of the things that is important to consider is with a lot of these self-serve SaaS companies, you know, many APIs, a lot of workflow tools, a lot of the things that we're seeing in the ecosystem today, quite frankly, they're easy to build. And I think when you have a product that's fairly easy to build, then what you need to consider is there needs to be some sort of competitive advantage. Now, maybe that competitive advantage comes from From, you know, your access to other great tech companies, like maybe you are really strong on building closed products, accepting only users who meet a very specific criteria and sort of align with your product vision. And therefore you can build and scale this product alongside other great product leaders. You know, that's sort of one option. I think historically we've seen, you know, what I sort of call the opposite of hype beat SaaS, which would be scrappy SaaS. And historically we've seen a lot of landing page experiments We've seen very quick product releases on product time, and you see this sort of freemium model where I think that era of SaaS is slowly going away. And the reason for that is that the products are easy to build. You then get into this race, which is much similar to consum…

AI assessment note: “when you have a product that's fairly easy to build, then what you need to consider is”

Q Totally aligned to you there. You mentioned that in terms of the speed of rounds, and it's something that if people listen to the show know that I'm very worried about, it's the compression of fundraising timelines. How do you feel about the compression? Fundraising timelines. And do you share my concern?

A You know, I do share some concerns around how quickly the seed landscape is moving. I think that I'm an investor in a company called Tandem, which was in the last YC batch, which very quickly became the hottest company in the YC batch. And I think that was a really good signal of just how hot the market is right now and just how much capital is freely flowing, especially for early stage companies. And, you know, I think for entrepreneurs, it's a, it's a really interesting time because I think that some of the seed funds are not able to move as quickly. They do have a smaller fund size and they are more thoughtful in the way that they engage with companies. But I think that, you know, when you choose a more boutique seed fund or you choose, especially a sort of career seed investor, then I think that the day to day will be very different. I think that, you know, they already have systems and programs and processes in place. To help you find product market fit. You don't have to be concerned with asking very tactical questions like, how do I negotiate this sublease on an office in Soma? So I think there are a number of questions where potentially the multi-stage firms typically view this as things you should figure out on your own, where I think that a lot of the boutique seed funds already have the infrastructure in place. It's sort of like they are a great first call because no…

AI assessment note: “I do share some concerns around how quickly the seed landscape is moving.”

Q always advise founders actually like, think of it like a sports team. Each player has their individual position, so it could be enterprise go to market, it could be growth hacking, it could be whatever that specific skill is within the team. My question is, how do you keep angels engaged over the lifetime of the 12 to 18 months before the next race? How can founders really do that?

A I think that the definition of angel and the expectation from entrepreneurs has changed over time. I frequently say to entrepreneurs, if an angel sources and closes one key candidate, or they give you one to do dedicated hours per month, they've delivered their value for say a 25 to 50 K check. I think that one thing to keep in mind is like, especially with angel investors, we pride ourselves on having a strong reputation in the ecosystem. I think what that means is typically being more mindful on the types of companies that you're willing to take on. And I think that that actually has It's changed as well, where I think historically angel investors have invested more broadly. They've done a high volume of checks. They've traditionally been individuals who were successful CEOs or have had, you know, a large exit, which then has given them the financial means to actually start investing. And I think that now you have this landscape where there are scout funds, there are individuals who are raising outside money. And I think that has changed the dynamic and sort of the relationship where oftentimes angel investors are Doing it to build a track record. They want to be very mindful of portfolio construction. And I think the biggest thing is, you know, they're willing to say no to companies that they feel like they aren't able to help. So I think from an entrepreneur standpoint, you…

AI assessment note: “if you're going to evaluate an angel, how valuable is their operating experience?”

Q always advise founders actually like, think of it like a sports team. Each player has their individual position, so it could be enterprise go to market, it could be growth hacking, it could be whatever that specific skill is within the team. My question is, how do you keep angels engaged over the lifetime of the 12 to 18 months before the next race? How can founders really do that?

A I think that the definition of angel and the expectation from entrepreneurs has changed over time. I frequently say to entrepreneurs, if an angel sources and closes one key candidate, or they give you one to do dedicated hours per month, they've delivered their value for say a 25 to 50 K check. I think that one thing to keep in mind is like, especially with angel investors, we pride ourselves on having a strong reputation in the ecosystem. I think what that means is typically being more mindful on the types of companies that you're willing to take on. And I think that that actually has It's changed as well, where I think historically angel investors have invested more broadly. They've done a high volume of checks. They've traditionally been individuals who were successful CEOs or have had, you know, a large exit, which then has given them the financial means to actually start investing. And I think that now you have this landscape where there are scout funds, there are individuals who are raising outside money. And I think that has changed the dynamic and sort of the relationship where oftentimes angel investors are Doing it to build a track record. They want to be very mindful of portfolio construction. And I think the biggest thing is, you know, they're willing to say no to companies that they feel like they aren't able to help. So I think from an entrepreneur standpoint, you…

AI assessment note: “the definition of angel and the expectation from entrepreneurs has changed over time.”