20VC: Worklife Ventures' Brianne Kimmel on Why More Operators Should Start Their Own Fund, How To Structure Your Round for the Highest Signal Round & What The Multi-Stage Funds Playing At Seed Means For The Rest of The Asset Class

Brianne Kimmel is the Founder and Managing Partner @ Work Life Ventures, a very new firm focused on the future of work backed by some of the best in the valley including Marc Andreesen, Chris Dixon, Zoom's Eric Yuan, InVision's Clark Valberg and then dear friends of the show, Alexis Ohanian, Garry Tan and Matt Mazzeo. To date, Brianne has invested in the likes of Webflow, Tandem, Lunchclub and Girlboss to name a few. Prior to starting Work Life, Brianne spent 2 years at Zendesk on their GTM strategy; building Zendesk for startups, ultimately representing 3,000 startups and 250 accelerators. From 2013-2017 Brianne also taught over 5,000 students at General Assembly all things user acquisition and growth marketing. In Today’s Episode You Will Learn: 1.) How Brianne made her way into the world of startups and SaaS, how that led to her angel investing and what was that a-ha moment for the founding of Work Life? Why did Brianne choose to structure Work Life as a holding company? 2.) With the fund, how does Brianne think about portfolio construction? What is the right check size for her? Why does Brianne think we are seeing more angel funds than ever today? Why are we seeing so many celebrity names on the cap tables of great companies? How does Brianne think about scout programs? What impact have they had? Why is Brianne against founders actively angel investing? 3.) What does Brianne advise founders on how to structure a high-signal round? What are the two types of angels that exist in the world today? What can founders do to keep their angels actively engaged? How have what founders expect from their angels changed over the last few years? How does one measure the true value of an angel? 4.) Does Brianne agree with Semil Shah, we are seeing "founders vote with their feet and bypass seed funds for multi-stage funds"? How does Brianne advise founders when choosing between a boutique seed firm and a large multi-stage firm? What does Brianne believe are the pros and cons of taking multi-stage money at seed? Items Mentioned In Today’s Show: Brianne’s Most Recent Investment: Pace As always you can follow Harry, The Twenty Minute VC and Brianne on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  We are back in the land of venture on the 20 minute VC with me, Harry Stebbings at H Stebbings 1996 with two Bs and I always love to see you there. But to our show today, and I've been looking forward to releasing this one for quite a long time now. And so I'm thrilled to welcome Brianne Kimmel, founder and managing partner at Work Life Ventures. A very new firm focused on the future of work, backed by some of the best in the valley, including Mark Andreessen, Chris Dixon, Zoom's Eric Yuan, Invision's Clark Valberg, and then some dear friends of the show Alexis Ohanian, Gary Tan, and the wonderful Matt Mazzeo. Today, though Brianne's also invested in the likes of Webflow, Tandem, Lunch Club, and Girlboss, just to name a few. And prior to starting Work Life, Brianne spent two years at Zendesk on their go-to-market strategy,

• 0:40Harry Stebbings?

  building Zendesk for startups, ultimately representing 3,000 startups and 250 accelerators. And I'd also have to say a huge thank you to Vlad at Webflow, Braden at Voiceflow, and Ryan Hoover for some fantastic question suggestions today. Mojito's on me for that, chaps. But before we dive into the show today, if you have employees and they're anything like me, you need spend management. And that's where Airbase come in. Airbase is the ideal cloud-based spend management platform for growing startups. With Airbase, you can issue virtual and physical cards for card payments, as well as checks and ACH transfers for invoice payments. They also have an incredible pre-approval system for expense requests. So you see expenses as employees request them, instead of only learning about them when the statement comes through at the end of the month.

• 1:22Harry Stebbings?

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• 2:04Harry Stebbings?

  Simply fill out a 20-minute term sheet today, love that name, and within 24 hours, you could be approved for 10,000 Dollars to up to ten million dollars in funding. And the best part, they can top you up with more when you need it most. Time is running out. Make sure you're prepared to capture as many sales as possible this holiday season. Head over to clearbank.com/20minvc to apply for Q4 funding. That's clearbank with a C dot com slash twentyminvc. But there's never going to be spend without a team. And scaling engineering organizations is the hardest. Did you know that there are five job openings for every one developer in the U.S.? That's where my friends at Terminal come in. Terminal is your dedicated partner in quickly building really skilled remote engineering teams. How do they deliver on both speed and quality though?

• 2:47Harry Stebbings?

  Well, Terminal does this by focusing on everything necessary to successfully source, set up and support these teams. From really little things like managing office logistics to really big things like benefits, legal and community. They've developed this proprietary and comprehensive remote team solution based on decades of experience building remote teams across multiple continents. So they know what works, but don't take my word for this. Take the word of Avembright, former 20 VC guest Hymns and DialPad, all customers and lovers of Terminal. And you can find out more today at www dot terminal dot I O. However, you've heard quite enough from me. So now I'm very, very excited to hand over to Brian Kimmel, founder and managing partner at Work Life Ventures.

• 3:32Speaker 01

  You have now arrived at your destination.

• 3:35Harry Stebbings?

  Brian, it is such a pleasure to have you on the show today. As I was just saying to you beforehand, I've heard so many great things, both from Vlad at Webflow, Deanna at Forthor, also Ryan Hoover, actually. So thank you so much for joining me today, Brian.

• 3:46Speaker 02

  Yeah, thanks so much for having me.

• 3:47Harry Stebbings?

  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?

• 3:57Speaker 02

  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 5,000 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 SaaS School. And SaaS School is a self-funded,

• 4:42Speaker 02

  community-led program taught by amazing executives at brand-name SaaS companies. And in building that community had sort of progressed 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 50K 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 know, once I started building that track record, decided that rather than joining a fund or rather than going sort of broad as an angel across both consumer and

• 5:23Speaker 02

  B2B, I wanted to lean into the Zendesk experience and sort of the traction I was getting with SaaS School and then build my own dedicated SaaS fund to support, or specifically bottoms-up business models. Oftentimes I invest in two strong technical co-founders, where typically they need a little bit more support on the go-to-market side. So helping them determine, do they go self-serve? Do they do top-down? More often than not, it's a combination of both and you're sort of experimenting in parallels. So that was how I sort of started, was started from a teaching point of view, then started angel investing and then went out to raise some outside capital to build WorkLife.

• 5:58Harry Stebbings?

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

• 6:10Speaker 02

  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, 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 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 10 million ARR mark,

• 6:54Speaker 02

  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 underutilization 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 know, you start to hit this inflection point where you're not quite achieving venture scale. However, you have a really great SaaS business that you've built.

• 7:36Speaker 02

  And I think during that period in time, oftentimes entrepreneurs, they start to think about their second idea. You know, they start to recognize that we live in this compressed ecosystem, which is primarily fueled by venture capital. They start to feel pressure from investors. They're starting to think about like, what is that next billion-dollar idea, knowing that what they've built is kind of getting stuck and not quite hitting venture returns. So I think having the ability to really offer founder-friendly funding models, whether that's early-stage, joining at a seed round, work-life ventures fund one, it's, you know, 150K check size. And then being flexible from the point of view that as I meet great entrepreneurs, as I meet companies that potentially could 2, 3, 4X their business, simply

• 8:20Speaker 02

  By adding a great growth engineer, a great growth PM, you know, slotting in someone who likely feels underutilized as a product manager inside of a medium or a large size tech company. So I think just being flexible and maintaining this focus on SaaS is a vision for work life, irrespective of early stage, either it has some optionality in terms of is it is early stage VC best for you? Have you reached an inflection point where maybe it's time to slot in an awesome growth PM who can scale into a CEO? And maybe there's some other options for you as an entrepreneur.

• 8:53Harry Stebbings?

  You mentioned the check size there being 150K. Now, I'm a portfolio and construction model geek. So I'm super interested. Why did you choose that as a check size? And how does that play into the portfolio construction model thinking?

• 9:04Speaker 02

  Yeah, that's a really interesting point. I mean, I think for me, coming from an angel point of view, I was typically playing around the 25 to 50K check mark. What I wanted to do from a portfolio construction standpoint with work life is incrementally grow that check size. So I will say my average check is around 100, 150, and I can scale up to 200K. What I will say is I think that 150K mark, it is still fairly friendly capital. So I think one of the interesting things is for the majority of companies that I'm investing in, oftentimes they come to me with an idea, they may be pre-product, repeat entrepreneur, or potentially some product pre-revenue, and they're likely talking to multi-stage funds. Oftentimes, you know, we're

• 9:46Speaker 02

  seeing in a seed landscape, I think that the lines and the numbers and the letters are getting blurred. But I will say that most companies that I'm talking to are out actively pitching a multi-stage firm as a lead. So I found that the 100 to 150 is still a friendly check size, where I'm able to get into the deal alongside a multi-stage fund, potentially another seed fund. However, I'm still fairly nimble and able to get into some fairly competitive rounds.

• 10:13Harry Stebbings?

  Totally 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 Shahn on the show the other day, and he said founders are voting with their feet 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?

• 10:31Speaker 02

  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 established 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

• 11:12Speaker 02

  existing seed funds face is that because of the large fund size 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.

• 11:34Harry Stebbings?

  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 of fundraising timelines? And do you share my concern?

• 11:47Speaker 02

  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 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

• 12:27Speaker 02

  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 question is something that they haven't heard before from other first time founders who are potentially new to the Bay Area or potentially, you know, just figuring things out on the fly.

• 13:12Harry Stebbings?

  We spoke about kind of the changes in the landscape itself there with the different shifting movements of the players. We've seen a couple of new entries that really enter the market. If we start with the first, we've seen a lot of angel funds come into the market. So on that, why are we seeing so many angel funds today, Brianna?

• 13:26Speaker 02

  Yeah, it's a really interesting time. I mean, I think that we're seeing a number of changes. I think that from an angel point of view, there is a lot of capital that's available in the market. If you're an operator at an interesting, you know, hot tech company, it's fairly easy to become a scout for a VC fund. And I think that, you know, there's this combination of scout funds plus syndicates. And there's these new ways to really build a track record as an angel. And I think when you have these sort of programs in the ecosystem, the next logical step is for you as an individual to essentially invest in your own platform. So I know both Angelus and Carta have great productized offerings for individuals who want to start their own micro VC funds.

• 14:10Speaker 02

  What I will say is I think that there are a lot of angels who are currently exploring, do I continue scouting? Do I potentially remove scouting as an option and begin deploying my own capital? Because the economics make more sense and you have a lot more vested interest in that particular company. And then I think the third piece is there are a lot of individuals who are exploring this more boutique micro VC model where potentially you can continue operating. So I meet a lot of individuals who operate in the one to $5 million fund market. For them, they're doing it part-time and their arrangement with LPs is that they do have a lot of flexibility in terms of the number of checks that they write. And I think that they oftentimes lean on These angel networks that they've built,

• 14:53Speaker 02

  or potentially they have a very strong alignment with multi-stage funds who can help them get into some of the investments that they're making.

• 15:00Harry Stebbings?

  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.

• 15:10Speaker 02

  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 does an amazing job on Twitter. He's recently promoted an employee to the head of diversity and inclusion role.

• 15:54Speaker 02

  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 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 things is like, these breakout companies don't happen by chance. You see CEOs like Stuart from Slack, Eric from Zoom, Vlad from Webflow, in these great places to work, they don't happen by coincidence.

• 16:39Speaker 02

  They happen with a very systematic approach to culture and an insane amount of focus.

• 16:43Harry Stebbings?

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

• 16:54Speaker 02

  Yeah, it's fascinating. I mean, I, 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.

• 17:35Speaker 02

  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, an 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 that do get implemented and adopted in Hollywood. I think that celebrities, influencers, people who have historically played in these spaces, they recognize that they take a portfolio approach to their career.

• 18:19Speaker 02

  And I think the next generation of great consumer tech companies, they sort of meet at this intersection of work and life. Shopify falls under that example. You can think about that and kind of zoom out and say they have 500,000 stores, they have $40 billion in sales. Like, they have unlocked entrepreneurship at an incredibly massive scale. And now we're seeing that sort of next generation where, you know, there are platforms like Faire, which is modern wholesale, and it gives creators of artisan goods access to brick and mortar. It's breathing new life into cafes and restaurants and sort of local brick and mortar store owners can stay relevant with the latest goods. And I think that the one thing that I think a lot about on a daily basis is, you know, there's this new rise of the creative class. You have individuals starting podcasts, designers.

• 19:04Speaker 02

  Who are sharing their portfolios broadly and basically becoming influencers at these massive design conferences and sort of media, lifestyle, entertainment conferences like South by Southwest. And we see this new category of professionals who are actually subject matter experts and becoming influencers in their own regard.

• 19:22Harry Stebbings?

  I'm totally with you there in terms of the independent creators, that being one myself. And the lack of podcasting tools today still astounds me, like totally astounds me. So please, anyone listening to innovate in the space. I'm interested there because we spoke about the many different funding options that have arisen over the last two years. That leaves founders with more choice when it comes to cap table construction. What do you advise founders on how to structure a really high signal round?

• 19:45Speaker 02

  Yeah, this is a really interesting point, and this is something that I spend a lot of time with entrepreneurs on. I think that, you know, from an angel point of view, I think this is where angels have the most amount of leverage. So typically, when I meet a company, spend time grooming them, getting the pitch deck ready, and then introducing them to both multi-stage funds and potential angels, that's where the whole conversation starts to happen around like, what would a perfect cap table look like? And I think oftentimes, like, there's an interesting argument around like, how much work do you actually need to get out of an angel to make them valuable? And I typically say, you know, founders should find both show horses and workhorses. And I'll explain what that means. But, you know, from a show horse standpoint, there are individuals that are amazing social signals for follow-on investors.

• 20:28Speaker 02

  So in that bucket, I would think of investors like Alok Gill, Scott Belsky, the entire collective of hashtag angels, angels who are both helpful. But I think most importantly, they've established this track record in the ecosystem where they have the ears of series A investors, they know how to facilitate great introductions. And I think they themselves, as individuals on the cap table, help you have this sort of competitive advantage that other potential competitors that are trying to enter the space don't have access to. And I think that presents a second layer, which is what I call the workhorses. And, you know, these are up and coming angels. These are active operators who are meeting startups on evening and weekends.

• 21:10Speaker 02

  Many of these individuals have become my closest friends because we've all been in Same boat, you know, I was meeting startups on evenings and weekends when I was at Zendesk. Ryan Delk, who's the COO at Omni, same thing where Ryan, you know, really is thoughtful about the companies that he invests in because, you know, he's an active operator, he's Omni first, but really wants to give back and invest in the next generation of great companies. So he is someone who's very thoughtful in sort of the way he thinks about his portfolio construction. And then the same goes for Jeff Morris Jr., who I know you've had on the show before. Jeff is product leader at Tinder first, but also has built this amazing VC fund called Chapter One. And, you know, to see how Jeff balances a number of companies and he's the portfolio, he's very helpful across the portfolio because he stayed very focused on product.

• 21:53Speaker 02

  I think we'll continue to see these sort of emerging workhorses, as I call them, and individuals who are very mindful with portfolio construction. And they really spend a lot of time with entrepreneurs to ensure that both from an operating standpoint and from a fundraising standpoint, they help them get from seed to series A.

• 22:09Harry Stebbings?

  I'm so pleased you said about Jeff. I actually invested in Chapter One. I'm such a big fan of his. So totally with you there. I do have to ask you, because you said about the workhorses. And absolutely, I 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 raise? How can founders really do that?

• 22:35Speaker 02

  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 50K 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 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

• 23:18Speaker 02

  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's standpoint, you know, I often point them in the right direction of these are angels that I know are interested in this category. Or, you know, if you're going to evaluate an angel, how valuable is their operating experience? And then most importantly, how valuable is their network?

• 24:01Speaker 02

  Because if they are increasingly busy, or if they reach an inflection point where they're not really actively helping startups because they're busy with their day to day, do they have a really valuable network where they can help you quickly hire and close a candidate? Is this a relationship where, yes, they're going to deliver a lot of value in the first few months for that 25 to 50 K check? But likely they'll just be someone that is part of your growing network of friends, family and advisors in the future.

• 24:25Harry Stebbings?

  Totally with you there in terms of income ingratiating them into the network. But I do want to move the layer deeper now. We've discussed the camp tables around the investments. We've discussed the fund structure. We actually talk about the fund 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 fund, but what does that really mean as a starting point?

• 24:46Speaker 02

  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?

• 25:28Speaker 02

  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.

• 25:35Harry Stebbings?

  Speaking of the new kind of classes of work and new almost generation of SaaS companies we're seeing, we're also almost seeing a new generation of distribution channel availability and approach. And you described this before as the rise of hype B SaaS. So I've never heard of hype B SaaS before. So what is hype B SaaS and who's done it well in your mind?

• 25:53Speaker 02

  Yeah, it's a great question. So I think when we look at some of the changes that are happening in B two B SaaS, I often say that the traditional B two B language is entirely dead and irrelevant. And the reason for that is, is we're actually seeing that, you know, the next generation of great SaaS companies, they're actually being built by operators who are spinning out of consumer tech companies. So I think they're bringing the same sort of best practices and methodologies that they had at companies like Airbnb, Coinbase, Uber. You see really great consumer product builders who have experienced legacy software internally. Or quite frankly, you know, these companies are scaling so quickly that there aren't really tools and infrastructure that's readily available.

• 26:37Speaker 02

  So they end up building their own tools in-house and figuring out that these tools are actually widely applicable and they could be something that they can either open source or potentially monetize and turn it into an early-stage startup.

• 26:51Harry Stebbings?

  Can I ask, that's a really good question because I've seen quite a lot of tools recently in this kind of collaboration and teamwork commenting area. And I share it to a lot of founder friends who may be at series D stage. And they say, yeah, we built that internally. I mean, I can show it to you and 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?

• 27:18Speaker 02

  Yeah, it's a really interesting question. I think this is something that I speak a lot to these consumer operators who are entering B two 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, 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

• 28:01Speaker 02

  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 hypey 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 Hunt. And you see the sort of freemium model where I think that era of SaaS is slowly going away. And, and the reason for that is that the products are easy to build. You then get into this race, which is much similar to consumer product, where you end up spending a lot of time, energy, money on paid marketing. Where unless you have a competitive advantage or unique distribution channels,

• 28:46Speaker 02

  you end up spending a lot on consumer paid marketing. And then you end up finding that you have a lot of free users who aren't converting to paid. And, you know, I'm starting to see that this next generation of great software businesses are building both great consumer quality products. In parallel, they're also really thoughtful in sort of how they build a waitlist. Who are the users that they accept to the product? And how do they really start to layer in traditional enterprise faster than the previous generation, which was solely self-serve and increasingly rely on unpaid marketing?

• 29:17Harry Stebbings?

  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, and it's scrappy SaaS is dead. What is scrappy SaaS? And why is it dead, Brianna?

• 29:29Speaker 02

  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, 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

• 30:11Speaker 02

  or an 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 AI ML. I think that's now shifting and we're sort of over some of the hype around AI ML. And we're now moving into this world where it's more about great, consumer-grade 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 that I run twice a year, and his entire talk was around video game design

• 30:55Speaker 02

  and sort of the mechanics of building highly addictive video games and what that actually means for the workplace. Like if we want to build a highly addictive product or if we want to really solve some of these core like productivity challenges that we faced in the workplace, then we have to look outside of traditional SAS and we actually have to look at the types of consumer experiences that people expect in their day-to-day life and we need to figure out how to bring that into the workplace.

• 31:20Harry Stebbings?

  I'm sure that would have been an amazing talk from Rahul. I had him on the show and he was just incredible. Couldn't be a bigger fan of his, so that's exciting to hear. I do want to move into my favorite though, Brian, which is the quickfire round. So I say a short statement and then you hit me with your immediate thoughts. Are you ready to rock and roll?

• 31:35Speaker 02

  Yeah, that sounds great.

• 31:36Harry Stebbings?

  Okay, so I'm boarding a flight to SF. I need a book for the flight. What's the book and why?

• 31:40Speaker 02

  Oh, that's a great question. So I tend to read a lot of fiction, which is kind of funny. I feel like a lot of folks in Silicon Valley tend to read a lot of nonfiction. So I have been going through, there are a number of comic books that touch the future of work. So I'm quite turning into this weird like dystopian sort of comic book reader.

• 31:58Harry Stebbings?

  That is absolutely bizarre. No, I'm kidding.

• 32:02Harry Stebbings?

  Tell me, what would you most like to change about Silicon Valley in tech today? You're at the epicenter between SF and LA. What would you like to change?

• 32:08Speaker 02

  I just got back from Tulsa late last night. So I went with Bloomberg Beta and 15 venture capitalists from Silicon Valley in New York to Tulsa, Oklahoma. And the whole point of this trip, and this is part of Roy's ongoing Comeback Cities Tour, is to really take a step back, really spend time with industries from the past from sort of an investment standpoint, to really take a step back and look at Tulsa is famous for what they call Black Wall Street. And there was this moment in history where, you know, the first major US city that had an entire ecosystem of Black entrepreneurs building great businesses such as designer goods stores, movie theaters, restaurants for other Black Americans. Like, that was just a key moment in US history.

• 32:53Speaker 02

  And I think that's great when I think about the future of work, because I think there are these new tech-enabled venture-backed businesses. Ethel's Club, as an example, is basically Soho House for African-Americans. And I do believe that we can take these insights from places like Black Wall Street. We can apply it to like, what are the programs and infrastructure and companies to be built around this? And I see these new clubs like Ethel's Club really being that next generation and really creating a platform for entrepreneurs to meet other like-minded entrepreneurs. And I think we'll see really great businesses coming off the back of these sort of platforms and coworking spaces.

• 33:27Harry Stebbings?

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

• 33:30Speaker 02

  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 10-year 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, 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.

• 34:13Speaker 02

  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, 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.

• 34:38Harry Stebbings?

  What keeps you up at night, Brianne?

• 34:40Speaker 02

  I would say, right now, I've been very focused on building work life. And I think that what I'm finding is especially with something that touches the future of work. I'm very mindful of the power and impact that technology has on everyday people. So one of the things that I've been personally investigating in my free time is really understanding, what are some of the root causes of underemployment? And what are new classes of work and new ways for people to make money outside of urban metro areas? This is something that really stood out on the trip to Tulsa, where Tulsa has been very forward-thinking in building a program that they call Tulsa Remote, where essentially you have individuals who were born and raised in Oklahoma, or you have people who were born and raised on the coasts.

• 35:24Speaker 02

  And, you know, they're looking for a lifestyle change. You know, they're ready to have kids. They are potentially caregiver of an aging parent. I think one of the things that is oftentimes missed in Silicon Valley is the fact that the ecosystem is incredibly compressed in a way where you can learn a lot and you can learn a lot quickly. However, as life goes on and things start to evolve, I think understanding how your work life and your personal life come together and what are ways for tech companies to keep individuals in the workforce longer? And what are new ways, such as remote and distributed teams, where individuals can access great careers in technology irrespective of location and ones that they can potentially continue and carry into various different life phases

• 36:09Speaker 02

  as, you know, you think about potentially having kids?

• 36:12Harry Stebbings?

  Penaltima one, what advice do you hear most often that you most commonly disagree with?

• 36:17Speaker 02

  You know, I think it's really interesting. I disagree with the Traditional notion of having a mentor. And the reason for that is I often find with a mentorship relationship, I think that oftentimes the mentee is typically over indexing on information and inputs from one data point. So I'm actually finding that of the individuals that I meet who are accelerating in their career, you know, they're achieving this sort of like breakout moment where they've built something, they've become known for something, you know, they're sort of thriving in their day to day. I would say that those individuals have done a fantastic job of both building a community of like minded peers around them. And more importantly, I think that they've found individuals outside of their direct industry that they can learn from.

• 37:02Speaker 02

  I see this happen a lot where a number of my friends are in the direct to consumer space. And I'm so thankful to have both CEOs and both investors that fully focus on DTC because as a software person and as someone in SaaS, like there are so many similarities that are happening right now where, you know, we're selling software direct to consumers. We're thinking more about brand and community and all of these sort of macro trends that consumers are experiencing. Like they're also bringing it to the workplace. And I think that's something where like the more you can build a community around you and the more you can find individuals who are like minded but in different sectors. I think that's where you're going to find and unlock the most amount of learning rather than feeling tied to a formality of having a more traditional mentor, someone you meet on an ongoing basis,

• 37:47Speaker 02

  or potentially someone who is even, you know, two, three steps ahead of you career wise.

• 37:51Harry Stebbings?

  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, Brianna?

• 37:57Speaker 02

  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 upfront. 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 to pay for.

• 38:42Speaker 02

  And it's been really great to see you. 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 they're also 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 bit unclear on what you're what you're getting in terms of value. And they're really changing the way that people will buy and sell software in the future.

• 39:16Harry Stebbings?

  Now, I'm super excited for Pace, I have to say. But Brian, as I said at the beginning of the show, I've been so looking forward to this one for a long time. Can't wait to see the next chapter with Work Life. So thank you so much for joining me today.

• 39:27Speaker 02

  Awesome. Thanks so much, Harry.

• 39:31Harry Stebbings?

  I absolutely loved doing that episode with Brian. I couldn't be more excited to see the portfolio she builds with Work Life. And if you'd like to find out more from Brian, you can at Brian Kimmel. Likewise, it'd be fantastic to welcome you behind the scenes here at the 20 Minute VC. You can do that on Instagram at H Stebbings 1996 with two Bs. However, before we leave you today, if you have employees and they're anything like me, you need spend management and that's where Airbase come in. Airbase is the ideal cloud based spend management platform for growing startups. With Airbase, you can issue virtual and physical cards for card payments, as well as checks and ACH transfers for invoice payments. They also have an incredible pre approval system for expense requests. So you see expenses as employees request them instead of only learning about them when the statement comes through at the end of the month. And finally, because of all the transaction flows

• 40:16Harry Stebbings?

  through the Airbase system, they can really help you automate a ton of accounting work, like coding expenses, collecting invoices and receipts and more. And that's why Gusto, Front and Segment all love Airbase. Simply head over to airbase.com to book a demo and find out how to get up to 1.5% cash back on your monthly spend. But wait a minute, to have spend management, you have to have a spend. And my word, it is five weeks. That is all the time that stands between you. Your online business and the holiday season. Will you have marketing budget to boost your best ads? Can your inventory supply keep up with shopper demand on Cyber Monday? Are you starting to sweat? Well, ClearBank's here to help. They offer fast, affordable investments for online businesses. Simply fill out a 20-minute term sheet today. Love that name.

• 40:58Harry Stebbings?

  And within 24 hours, you could be approved for $10,000 to up to $10 million in funding. And the best part? They can top you up with more when you need it most. Time is running out. Make sure you're prepared to capture as many sales as possible this holiday season. Head over to clearbank.com/20minvc to apply for Q4 funding. And that's clearbank with a C dot com slash 20minvc. But there's never going to be spend without a team. And scaling engineering organizations is the hardest. Did you know that there are five job openings for every one developer in the US? That's where my friends at Terminal come in. Terminal is your dedicated partner in quickly building really skilled remote engineering teams. How do they deliver on both speed and quality, though? Well, Terminal does this by focusing on everything necessary to successfully source,

• 41:43Harry Stebbings?

  set up, and support these teams. From really little things like managing office logistics to really big things like benefits, legal, and community. They've developed this proprietary and comprehensive remote team solution based on decades of experience building remote teams across multiple continents, so they know what works. But don't take my word for this. Take the word of Eventbrite, former 20 VC guest Hims, and DialPad, all customers and lovers of Terminal. And you can find out more today at www terminal.io. As always, I cannot thank you enough for tuning in and for your support. It means the world to me, and I can't wait to bring you a very special exclusive this coming Friday.