Kylie Jenner, Joe Rogan and the new American Dream

I recently joined the Square One podcast with Romeen Sheth to discuss the latest trends impacting the way people work.

In this episode we’ll discuss three themes that I’ve been actively exploring as an early stage investor:

The new American Dream

How creative expression, online influence and extreme optionality ie: remote work, calendar flexibility and the freelance economy is changing how Americans define success.

YouTubers and Twitch streamers

The age of the individual   

How the gig economy exposed a need for better tools for freelancers and side-hustlers including personal finance, productivity tools and new economic opportunities for blue-collar and white-collar workers.

And why customer support is a good analogy for augmenting (and not automating) knowledge work.

Founder as a service 

Following events like Fyre Festival, we’ve seen Distrust Go Viral and a shift away from pay-per-post influencers to a new generation of creators.

In the next wave of online influence, celebrities will launch their own brands and move away from paid posts and collaborations w/ legacy companies.

Kylie Cosmetics is worth $1B+ w/ only 12 employees!

How 20-Year-Old Kylie Jenner Built A $900 Million Fortune In Less Than 3 Years

With Shopify, we saw the ability for anyone, anywhere to create their own e-commerce company.

In future, we’ll see new platforms for celebrities, influencers and aspiring creators to build just about any type of tech-enabled business.

Listen to the episode or skim the full conversation below.

But first, sign up to get future essays delivered to your inbox:


You’re listening to Square One, a podcast where we interview entrepreneurs, investors, and executives at the cutting edge of business.

I’m your host, Romeen Sheth. Today’s guest is Brianne Kimmel, network leader at Village Global.

Scale and reach are off the charts today. Joe Rogan gets more views than CNN, Kylie Jenner’s dominating cosmetics with less than 30 employees, and Conor McGregor can sell more pay per view than UFC.

But with access comes real responsibility. Fyre Festival is the latest SNAFU to fall trap to this. So what’s going on?

Romeen Sheth: The age of the individual is on the rise, and AI is automating away old world jobs while increasing leverage for new world jobs.

This paradigm shift is causing us to reimagine work. What does it mean to participate in the workforce?

How will we interact with one another, and what are the skills of the future?

Welcome Brianne, and thanks so much for joining us.

Brianne Kimmel: Hi, thanks so much for having me.

Romeen Sheth: So Brianne, really excited to have you on the show today and dive pretty deeply into your perspective on all things future of work, but before we jump in, tell us a little bit more about your background.

Brianne Kimmel: Yeah, sounds great. So I spent most of my early career at Expedia. I worked across the consumer experience and also the B2B side of the business.

This was where I got most excited about enterprise businesses and the future of work.

Expedia was one of the first technologies to really tackle a very large antiquated sector and bring them online.

So if you think about airlines, hotel chains, car rental companies, before Expedia, essentially the entire landscape was fragmented and heavily reliant on travel agents. 

Brianne Kimmel: By bringing all of these services online, it actually created a whole new level of transparency in terms of pricing, standardized star ratings and publicly available consumer reviews. 

I think what was really interesting was during my time at Expedia was the mass consolidation of these online travel agencies. 

Expedia had acquired Orbitz, Travelocity and HomeAway to bring non-traditional, Airbnb like accommodations to the platform. 

Brianne Kimmel: It was great to experience first hand the size and scale of a platform like Expedia with supply consisting of the world’s oldest hotel groups and airlines and demand

So it was really great to really understand how do you use software and how do you use a marketplace, essentially, to bring in an outdated sector or category of businesses online, and then how do you use even reviews and recommendations and really strong data science to essentially bring a whole new level of transparency to a certain category.

Following my experience at Expedia, I got recruited for a role at Zendesk. 

So I took my platform experience from Expedia and applied it to enterprise software. During my time at Zendesk, we went from one product to seven products.

Brianne Kimmel: A lot of folks know Zendesk for Zendesk customer support, which is our core product, but essentially we built a whole suite of additional services such as live chat, more robust analytics, and a number of basically new technologies that would help us not only sell better into the enterprise but ultimately compete against Salesforce.

Brianne Kimmel: It was really cool, because during this time, I started spending a lot of time with our customers, so Peloton, Allbirds. I built a program called Zendesk for Startups, which was our way to create a dedicated program of the next generation of great companies. So it was a really interesting time in Zendesk journey where essentially, as we were moving that market and tackling more large antiquated enterprise companies, we also wanted to make sure we had programs and infrastructure in place to really support the next generation of great, disruptive companies.

Romeen Sheth: Yeah, your suite of experience is really interesting to me, because I think it ties to kind of a fundamental underlining of what’s going on in the labor markets today, right? So the labor markets we’re living through right now are, I think, incredibly interesting. It’s only at certain times in history that we reach such inflection points where policymakers, business leaders, and workers, frankly, are thinking through the benefits and uncertainty at such scale.

Romeen Sheth: So it’s a huge point we can obviously talk about for a full episode, but at a macro level, what’s your view on how to think about the intersection between technology and the labor market?

Brianne Kimmel: Yeah, that’s a great question, and I’m happy to kind of dissect it in terms of how I’m thinking about how do we even just categorize work? Because I think right now, there are just so many different ways to actually think about post education. How do we classify our work? There’s a lot of conversations around things like a side hustle, or you’ll hear folks talk about underemployment.

I’ve really been thinking about four types of labor:

  1. Centralized white-collar: knowledge workers in an office
  2. Decentralized white-collar: remote & freelance knowledge workers
  3. Centralized blue-collar: manual/physical labor in factories or warehouse facilities
  4. Decentralized blue-collar: desk-less workers such as delivery, installation and maintenance professionals.

Brianne Kimmel: So what’s interesting today is that in addition to having white collar work and blue collar work, we actually are starting to see new trends in terms of centralized and decentralized.

Technology companies will talk about what does it mean to have remote teams? Remote teams are becoming more and more important. You see that white collar distributed work is actually, there’s a broader trend where people actually like working from home.

It’s great to have your own setup. They like the flexibility. We’re seeing trends, even, in terms of how does this create a more inclusive workforce, I think specifically for new parents and also for the aging population.

We’re seeing that people are willing to work longer and they’re willing to continue contributing to their places of employment longer if they’re able to choose the way that they work.

Oftentimes, the way that they work is best from home.

Romeen Sheth: I like the decentralized, centralized framing, because I think if you look at the value stack, you see kind of different dimensions of what’s going on today. You have one side of the value stack which has a ton of increased opportunity sides, right? Finding talent and high skilled workers can be challenging in today’s market. But then you have the other part of the stack, more low skilled workers in many ways are being left behind. 

You have a pretty interesting perspective actually specifically on how millennial men are less likely to work than any other gender demographic. Talk a little bit more about that.

Brianne Kimmel: There’s also a lot of research that’s been done lately on the millennial work opt- in rate, and what’s interesting is when you look at recently changes. We’ll look specifically at the US labor market. Specifically with the US labor market, we have seen a shift where millennial men, so primarily men who are 25-34, they’re actually opting in less than previous generations, and more specifically, post-global financial crisis and post the previous economic downturn.

We’ve seen a major shift where actually, there’s an element of unemployment that’s happening, or underemployment that’s happening across the board. However, we’re seeing that men in particular are actually opting out rather than accepting underemployment, which is quite interesting.

Romeen Sheth: It’s interesting too because you can cut it kind of from a demographic perspective, but you can cut it from a skills perspective. One of my favorite or most interesting stats is if you look at it from a skills perspective, there’s actually a huge technical talent shortage.

Brianne Kimmel: Yes.

Romeen Sheth: So by 2020, there’s gonna be over a million and a half software development jobs than actually applicants who can fill them. So how do you think about it kind of from a skills perspective?

Brianne Kimmel: Yeah, I think this is a really interesting point, because I think historically when we talk about software development, there’s an assumption that you need to have a computer science degree. Now that we are seeing different types of software development emerging, we’re actually seeing a whole new landscape of both software technology that will help us build faster, but also ways for people to learn how to build software faster, as well.

So I think what’s interesting is we’re actually starting to see that computer science majors are opting into much more challenging roles when it comes to the full stack of things that we need to build.

So you’ll notice, we’ll talk a lot about in Silicon Valley is the smartest and the most technically capable developers, they want to work on things like AI, ML projects.

There’s a shift towards the smartest people really want to work on these new applications and these frontier technologies where essentially you need to have a computer science degree or you need to have additional training for that.

Brianne Kimmel: What this has actually done though is it’s actually created a whole new landscape of roles and responsibilities within an organization where essentially, you don’t need a CS degree. So there’s a lot of great programs. I think in the previous tech cycle, we saw coding camps and things like Dev boot camp or like general assembly, where essentially you can learn how to build great applications and especially in sort of front end web development. You can actually do a lot of things without a CS degree, which is great.

Brianne Kimmel: So we’re kind of seeing these two paths where I think there are individuals who are technical-ish or technical enough to really be able to add value outside of having a traditional computer science degree. I think this is where we’ll continue to see programs like Lambda School, for an example, where essentially, it does make sense for us to provide new classes of work for people who would like to work for a tech companies, but they either can’t or aren’t ready to commit to a full CS degree.

Romeen Sheth: It’s interesting because I think that has some pretty deep implications for skilling capability building. I want to jump into that a little bit later in the conversation because I think there’s some interesting nuances there. I’m curious to hear your perspective on how you think about job characteristics and job skills that folks should be thinking about.

So the McKinsey Global Institute did a study pretty recently on looking at characteristics in occupations that could be automated away. It was interesting because the conclusion was less than 5% of jobs were at risk of being full automated away, but up to 40% of skills that are the underlying components of those jobs will be affected by technology.

So how do you think about kind of that conclusion or that statement both from the perspective of a startup that’s building and then from the perspective of an individual worker?

Brianne Kimmel: Yeah, so this is a topic that I think about a lot, and I think what’s great is the time that I spent at Zendesk was very much a time period where I learned a lot about various functions within an organization. I think that customer support is actually a really good analogy for the way that I think about automating work versus augmenting work.

If you look at the sort of day to day roles and responsibilities of a customer support agent, there are a lot of things that we can augment and that we can automate to make their day to day much more enjoyable.

Brianne Kimmel: So I think the question and what you sort of read in a lot of headlines is that jobs are being replaced, things are going away, and I think that oftentimes, those sort of headlines don’t really dig into how complicated and how nuanced each individual role actually is.

So I’m an investor in a company called Forethought AI which does enterprise search and they do what we call human augmentation. They’re starting with customer support.

The reason they started with customer support was this is one function within an organization where essentially, agents don’t really have the tools that they need to do their job.

What I mean by that is we have created a whole suite of different technologies for agents to receive comments from customers and to respond to them, but we haven’t gone the next layer deeper where we actually give them access to the right information internally to solve problems quickly.

Brianne Kimmel: At Zendesk, we’ve done a lot of research around this as well, as far as how long does it take to respond to a customer’s question?

Oftentimes, the reason that it takes so long is that the agents don’t have the information they need to solve the problem. So they don’t have access to internal information or maybe data is sitting in different technologies that they don’t have access to.

So I think what’s interesting is often times when we talk about replacing roles, or when we talk about workplace automation, what we really need to focus on I think in the next 5-10 years is how do we actually augment a person’s day to day and actually remove some of the daily annoyances that keep us and hold us back from doing what we’re meant to do faster.

Romeen Sheth: Yeah, I like that framing a lot, because one of the things I’ve been most interested by is this idea of digital transformation at work, and specifically two buckets of it.

One which is entirely new forms of work, and then the second which is work that can created on a scale by platform businesses. On that kind of latter point, I had JD Ross, who was one of the co-founders of Opendoor on the show, and he talked about how he’s seeing individuals actually created larger home services businesses off of the Opendoor platform.

Romeen Sheth: I think it’s a very interesting kind of nuance. I’d love to get your perspective on how do you think about, there’s obviously the gig economy, but how do you think about how the gig economy and this opportunity set particularly unfolding?

Brianne Kimmel: I absolutely love what Opendoor’s doing and I think that’s, Opendoor will be an analogy for a number of other sectors. I think the same way that the Lambda School model which basically, you can learn without any sort of fees and you don’t have to pay until you get a job.

I think these sort of models are great starting points, and I think they will carry into other sectors, which is awesome. What’s interesting about building services on top of these platforms is that it creates a whole new opportunity for people to make money.

Brianne Kimmel: So I think historically, when we think about the gig economy, I think one of the challenges with the gig economy is typically, you will not, they’re used as basically complimentary or supplementary income.

Oftentimes, Uber drivers still have a full time job or you have to essentially have multiple gig jobs to really make a true salary. Whereas I think with a lot of these platforms, I’ve spent a lot of time and done research with specifically with people who do full time HomeAway rentals or Airbnb rentals. Essentially, you could build your own services business on top of a number of these platforms.

Brianne Kimmel: I’ve been spending a lot of time lately looking at marketplaces for knowledge workers, and I have two examples. So one is a company called Wonder, which is based in New York. They do market research on demand, so essentially, if startups all the way up to Fortune 500s want to access additional individuals to help with research, so think basically early research that will then be passed to management consultants or to lawyers or accountants.

This is a job that didn’t exist before, but for the average person, especially someone who is either in college or recently graduated from college to build your own business where you’re able to do research from home is actually a really compelling alternative to driving for Uber or doing Postmates after you’ve recently received your college degree.

Romeen Sheth: Let’s dig into that a little bit more, because I think what you’re hitting on is kind of the intersection between doing new services on top of existing platforms. Then there’s another bucket which is just entirely new types of work, and you have a really interesting perspective on this with your thought process on influencers and streamers.

There’s a really good tweet that I was reading this weekend, and it pointed out that now Joe Rogan gets more views than CNN, Kylie Jenner is dominating cosmetics, and Conor McGregor can sell more pay per views than the UFC.

Romeen Sheth: I think there’s two threads there, right? One is just entirely new types of forms of work, and then the second is kind of the age of the individual and a little bit of the power of technology with distribution scale. Let’s talk about the first one first. Talk a little bit more about your perspective on not just digitally enabled work but really entirely new type of work.

Brianne Kimmel: Yeah, I mean, I think this a really interesting point where I think we’re seeing this shift where in generations prior, I think specifically post World War II, oftentimes people took the job that was open and available, and they took a job that was close to home. I actually have recently done a lot of research on post World War II, like how did we transition from a wartime culture and specifically very much a blue collar culture into these new communities of white collar workforces. Where did we actually start transitioning from kind of the industrial revolution into where we are today?

Brianne Kimmel: During this period in time, that’s when we saw the introduction of things like the Myers-Briggs and the sort of new ways of thinking about work where essentially, people want purpose. I think prior, it was how do you work hard, how do you demonstrate that you’re working hard, and how do you basically provide for your family? Where I think today it’s more about, how do we find purpose? How do we find new ways to be creative and to build? I think what’s different about our generation is that we are highly creative and we are a generation that wants to build something.

Brianne Kimmel: We see with these new platforms, Twitch is a great example. YouTube is a great example as well where we have these new platforms where essentially, you can actually create your own type of work. There’s nothing stopping you from becoming an expert in basically any field that you’d like. I think an example I have here is I recently went to TwitchCon, which was an amazing experience to spend time with a large group of people, thousands of people, actually who have either built a company on top of Twitch from a tech standpoint, or who actually stream full time.

Brianne Kimmel: What was interesting was I had a conversation with an individual who is a streaming coach. I was saying to her, I said, “What did you study? What did you dream of doing when you were growing up?” She’s like, “When I was younger, I never thought I was going to be a coach. I never thought I’d be a professional coach, and I would’ve never thought that I would be helping individuals become more animated as they’re broadcasting their ability to play video games. There’s just so many classes of work that we didn’t know it exists. I think touching on influencers and streamers, there are amazing ways to do what you love and make enough money to not only pay the bills but also become incredibly successful.

Brianne Kimmel: So I’m super passionate about these new platforms for distribution, how people are using them to create new types of work.

Romeen Sheth: That’s interesting. Let’s dig into that a little bit more, because I think one of the things that I’m seeing is as we move more and more towards this world where individuals can leverage all sorts of technical platforms, whether it’s infrastructure or distribution and have the ability to create upsized economic value and influence. It’s exciting because of the leverage, but it also requires, I think, a new set of responsibility guidelines and standards. We saw the effect of this on a really small group of influencers and how it exacerbated the impact of Fyre Festival.

Brianne Kimmel: Yeah, I agree, and I think what’s interesting and one thing that when you talk to influencers who are just getting started, it goes back to the early days of Hollywood where yes, your quality of content does matter, but also there is an element of access and of luck. I think specifically for YouTubers that are just getting started, oftentimes as these platforms start to mature, it does become increasingly hard to get discovered or to become famous.

Brianne Kimmel: So I think it’s really interesting to see over time, in the age of the individual, we actually start to revert back to very tried and true behaviors of individuals ultimately need groups. I think that’s something I saw at TwitchCon where essentially, streamers don’t operate on their own. They actually find ways to collaborate. Influencers also create this whole network of other influencers where they can promote each other’s content or work together and do a lot of collaborations with brands.

Brianne Kimmel: So I think while we’re entering this age of the individual, we’re actually starting to see these kind of next gen of social constructs being built, which is really fascinating. I think to kind of talk about Fyre Festival for a little bit, Fyre Festival was only successful because they leaned into a very human truth and something that’s very true today, where people are looking to have access, and they’re looking to actually build credibility through spending time with other influencers or experts.

Brianne Kimmel: So while over time we are kind of the age of the individual, I will say that I think with Fyre Festival for an example, these influencers that were involved in actually promoting the event, part of the hype and part of the demand was actually, wouldn’t it be great if I could get access to these influencers and I can spend time with them and I can kind of live, access that lifestyle by paying for a ticket. It turns out people are willing to pay for those tickets.

Romeen Sheth: Talk a little bit more about kind of distrust and how in kind of the age of today you have companies where reputations take a long time to build and one misstep or trust can kind of exacerbate out of control. How do you think about that from the company perspective on how to proactively manage?

Brianne Kimmel: Yeah, I mean this is something that I’ve been spending a lot of time on. I think a lot of these heritage brands that we know and love have become so large that it’s very challenging for them to be transparent. So I’ve seen this when working with Fortune 500 companies where we start to, as your company grows, and this is natural, we start to have more policies. But one of the challenges with a lot of these policies is we start to lose our transparency over time.

Brianne Kimmel: This is an area where as we see this next generation of great companies, direct to consumer brands are doing incredibly well at being transparent from day one. They’re also aligning to their, they are developing their own mission and values, which really resonates with today’s consumer, but I think one of the questions I have is long term will these direct to consumer brands ultimately consolidate, similar to the way that Expedia brands ultimately had to consolidate? And will they eventually lose their transparency over time?

Brianne Kimmel: I think it’s a little bit early for us to see that, but I’m very optimistic and excited to see these next generation of brands that are more transparent, that have better ingredients, that are really starting to prioritize the consumer. I’m just kind of skeptical and wonder at what point in time do they become large and bureaucratic as well?

Romeen Sheth: So as you’ve worked with a lot of, as you’ve observed kind of future of work from both an early stage startup and an investor perspective and you’ve kind of seen both sides of the gamut, what do you think large corporations and larger organizations get wrong? One of the things I see a lot of the time is this idea of just capturing data without having a really clear framing of the problem that you’re trying to solve. But when you think about future of work, what do you think that large companies or large organizations get wrong?

Brianne Kimmel: That’s a great question. I mean, I think as far as large companies go, I think you’ve really nailed it in terms of saying, oftentimes the problems that these large companies face is actually, it’s a problem of access and of information. So over time, as your company grows, fewer and fewer people have access to core data. Fewer and fewer people are truly connected to the core mission of the company, and I think oftentimes, this has to do with size and with scale.

Brianne Kimmel: Now, what I think is really interesting is now we’re starting to see where companies that want to go back to their early mission or that want to innovate and get access to the next generation of consumers, they are willing to acquire companies that match that profile. So I think we’ll continue to see large acquisitions, specifically in the retail/eCommerce space, specifically with consumer packaged goods where essentially it becomes harder and harder to innovate as a large multinational company. However, it is very easy for them to spend time with relevant startups and to actually acquire them and fold them into their portfolio of brands.

Romeen Sheth: Yeah, it’s interesting. I see a lot of, especially in the consumer goods space, a lot of, and R&D and innovation is just done via acquisition as opposed to any sort of internal, organic R&D. I’m curious to hear your perspective on the flip side of that same question, which is what do you think startups get wrong about large companies, right? I think there’s a lot of truth in corporates being very legacy and not adapting to technology, but I think it’s actually a lot less about sophistication with technology, which is often the conversation in startup rooms. But it’s more so about some of the things you mentioned, right? Organizational issues, cultural challenges, [inaudible 00:27:32].

Brianne Kimmel: Yeah, I mean, this is something that I talked to startup founders a lot about. I think what’s challenging is that oftentimes in the Bay area or if you’re in a very startup centric ecosystem, it’s very easy to sell to other startups. You understand their buying behavior, you understand how to partner with them or sort of what’s in it for them longterm, but one of the challenges is that selling to the enterprise is very different. It typically requires a different feature set. Oftentimes companies are looking for maybe if it’s healthcare, they’re looking for HIPAA compliance. If you are a large enterprise company, you have to start thinking about different types of contracts and different features, and there’s a lot of customizations that come when working with large enterprise companies.

Brianne Kimmel: So we see that oftentimes, startups, I feel like wait too long to talk to enterprise customers. I think that you can get a significant amount of traction by selling to other startups, and I think we see this a lot specifically with the YC ecosystems. So if you’re going through Y Combinator, you get access to not only your current batch of startups, but also any YC alumni companies. So you can see companies get to 500k, a million in MRR, and actually it’s just selling to other startups either in the Bay area or outside of the Bay area.

Brianne Kimmel: What you’re missing is actually a deep understanding of what are the nuances that comes with moving out market and just selling to larger companies, which I think this ultimately comes down to how large companies make decisions. Large companies typically make decisions based on how do you maintain current traction and kind of not rock the boat too much, and how do you think about incremental change rather than disruption. I think oftentimes that’s where startups will come in and if you’re presenting to a large Fortune 500 company, the last thing they want to hear is disruption or a complete change in structure processes, because essentially, what they’ve been doing is working well. It’s good enough and longterm, they want to figure out ways to align with partners that can de-risk what they’re trying to achieve and provide incremental change over time.

Romeen Sheth: Let’s switch gears a little bit and talk about what’s going on in the world of rescaling and capability builder. I also know Allred, the CEO of Lambda School, and Shaan Hathiramani who runs Flockjay, another interesting capability building and scaling startup out of YC right now in the current YC batch on the show. We talked about the education system at large, and I’m interested in your perspective on what you’re seeing with scaling and coaching startups. When you think from first principles, the experience can be pretty neat. Real time feedback, dynamic course experiences, flipping the classroom. How do you think about rescaling and capability building today?

Brianne Kimmel: Yeah, this is a great question. I think over, I would say even let’s zoom out over the past ten years. We’ve seen a number of great platforms that are focused on skilling and coaching, whether that be mentor mashing, like helping you find the right person to learn from, either as a peer or as someone a little bit more senior. We’ve seen education startups like Udemy and Coursera which have done a fantastic job in terms of essentially democratizing education that historically, you would have to either go get your MBA, go get your MFA. They’ve taken a lot of these really core, fundamental courses and brought them online for individuals.

Brianne Kimmel: I think in the next cycle, we’re seeing great, new companies like Lambda School, which I think what’s very interesting about Lambda School is they have infinite scale, because as they’re tackling such a large sector, which is education and more specifically an alternative to undergraduate college education, which is historically extremely expensive. Student loans are one of the largest point of stress for individuals. I think we’ll start to see new types of education and new types of even classes of work that come after individuals graduate from Lambda School.

Brianne Kimmel: Now, what I think is interesting about a lot of these re-skilling and a lot of the education and coaching startups is if you’re selling to a consumer or you’re ultimately competing for attention. I think one of the challenges that I’ve seen with specifically a lot of marketplaces that essentially offer professional coaching as a service or mentorship as a service. One of the challenges here is accountability, and it’s also competing for attention. So one of the things that I’ve seen is oftentimes with these marketplaces where one side is either an expert or a mentor or someone that is historically fairly time poor.

Brianne Kimmel: Facilitating that matching is very important, but also ensuring what’s in it for both sides? It’s very clear that there’s a whole category of young professionals who are hungry and eager to learn more, but on the supply side, it’s always a little bit more challenging to actually find the right people who a, have the time, and b, have the right incentive to actually invest in an individual for even a short, medium, or longterm period.

Romeen Sheth: Yeah, one of the things I always, and I’m curious to hear your thoughts on this. One of the things I always kind of wonder with with some of these kind of coaching on demand platforms or so, especially when they’re consumer focused, is how do they solve for the platform leakage problem, right? So if you think of, all marketplace businesses are different, but if you think of some of the kind of high profile companies that ended up not succeeding, like Homejoy out of YC, right? Raised $40 million.

Romeen Sheth: I think one of the big learnings from the nature of the transaction itself was that they were doing a great job of helping you match and find someone, but then the nature of that transaction was once you found someone to come in and service your home, you’re kind of, you trusted them and you didn’t really need to go back to the platform. So you ended up having a lot of these kind of platform leakage problems where folks would say, as a consumer, it doesn’t make sense for me to pay [inaudible 00:33:58]. Then as a vendor, it doesn’t make sense for you to take a price cut just by being on the platform. If we’re gonna develop a kind of longterm relationship, it just makes sense to take your transaction off of the platform itself.

Romeen Sheth: That’s something I think about a lot with kind of mentorship as a service, training as a service, et cetera. How do you think about that?

Brianne Kimmel: Yeah, I think that makes a lot of sense. I think in early marketplaces, we’ve seen that even with home sharing apps to an extent. We’ve seen that with the dog walking on demand services. Once you find someone that you really like and you build a longterm relationship, it is difficult to maintain a platform lock in over time. What’s interesting with a lot of these coaching applications is I think there is an opportunity to do more than just one on one matching, but also how do we think about the group facilitation of conversations.

Brianne Kimmel: I actually recently read an article that I thought was interesting that made the comparison that events and conferences are the new, that’s the number one choice for editorial. So historically, you would have magazine coverage. It was more about impressions and eyeballs and creating, brand building was actually built on a very specific aesthetic and look, whereas now that we’re in this sort of individual economy as you said. Now that we’re in this individual economy, what happens is actually people want to be directly involved in your product experience, whether that’s events or becoming an influencer in part of your platform.

Brianne Kimmel: I think there are ways to facilitate a lot of these service marketplaces by doing more of kind of a focus on community building rather than one on one matching. But I agree, I think to your point, one of the challenges with a lot of these services marketplaces is when you’re competing for attention from a consumer point of view, then oftentimes you’ll find these companies will ultimately convert to almost an enterprise sale. If it’s something that your work is paying for and it’s something that becomes a core part of your education or your career, then people are more likely to opt in and to lean in.

Brianne Kimmel: An example that I have there is there’s a company called Plato, which is also a YC company as well, and they do mentorship for engineers. What’s interesting is for Plato, they see high retention on both sides of the marketplace. So both on the supply side, these are mentors. These are mentors at top tech companies, and their goal is to essentially build a personal brand for themselves. They use it as a way to hire and recruit up and coming engineers, and then on the demand side, you have very hungry and eager young professionals who want to connect with leaders at other companies. Not necessarily even in terms of I’m ready to switch careers. I want to move to this company, but there are a lot of great things that you can learn from individuals at another company.

Brianne Kimmel: I always use personalization as an example. So if you’re working at a Bay area startup and you want to learn about personalization, then Netflix is obviously one company that you’d love to spend more time with. They’re actually located in Los Gatos and it doesn’t make sense for you to ever facilitate and in person conversation, but even getting access to someone who’s worked on personalization at the size and scale of Netflix is a really compelling offer.

Romeen Sheth: Well, let’s talk a little bit, I want to pick up on that last thread of personalization and I want to use it a segue to talk a little bit more about ML and AI and how it’ll affect the workplace. You alluded to this a little bit earlier in the conversation. One of the companies that I’m an angel in, Imbellus is doing really interesting work in the assessment space. I see a lot of interesting applications for ML and AI in helping improve the end to end talent equation. So screening at the top of the funnel by mapping the skills, matching and rerouting talent internally. Talk a little bit more about what you’re seeing in the space and how you think about it from a macro perspective.

Brianne Kimmel: Yeah, I think it’s interesting. With AI, ML, we’re seeing the impact across multiple, different sectors and functions. I think from a recruiting standpoint what’s great is we’re actually able to facilitate much stronger matches. I think what I’m starting to see as far as a macro level trend is oftentimes, the recruiting process is a pretty complex one. You can divide it into college recruiting, which historically, there has been a matching and facilitation problem where essentially you would have one person in recruiting who works at one company and they would go to a career fair which happens once or twice a year.

Brianne Kimmel: What you would find is essentially students would go to these career fairs in hopes of meeting someone. You’d wander around, and it was just sort of like antiquated version of matching, which is not great for the employer, because they can only meet a limited number of candidates. It’s not great for students, because they don’t really have the time or the ability to truly have a conversation and to demonstrate how they’re different from the hundreds of other candidates that you’d see at one of these large university or college career fairs.

Brianne Kimmel: So what’s great is we’re actually starting to see these new platforms, like I’m an investor in dev.to. Dev.to is one of the largest communities of software engineers, and the way that it’s different than, say a GitHub or from other platforms is it’s actually more about the individual. So it’s a place where you can create a profile. You talk about your skills as a developer. You also talk about what you’re looking for in terms of culture fit, and you can write your own blog posts that are related to remote work or work/life balance, or any sort of parts of your day to day that matter in both a personal and professional context.

Brianne Kimmel: What’s great about that is you can actually start to facilitate matching that extends beyond just these are the things that I’ve done. I think LinkedIn is great in terms of having a nice resume, but the challenge with resumes is it doesn’t really ensure future happiness. So with a resume, they are data points that really communicate where you’ve been, but they don’t really communicate where you’d like to go. I think that’s where recruiting and matching is really broken, because it’s actually a way to lean into any personal biases that you have. So then you start selecting candidates based on where they went to school or what their most recent job was. But it doesn’t really communicate appetite and hunger and drive and all of these things that we look for when hiring new candidates.

Romeen Sheth: Yeah, I like the framing of kind of a historical perspective versus a future oriented perspective. That’s actually one of the things that I like that Imbellus does the most is this idea of recruiting by set in order proxy or where you went to school, what your previous job was. It doesn’t really give you a great, full picture of the story, right? But if you can start to understand how people think about problem solving, critical thinking, right? Judgment, how they exercise judgment, these are the core skills that you really want to see, right? You want to see in any sort of type of worker. It gets especially interesting I think when you actually put blind screens on top, to your point a little bit around kind of confirmation bias, right? I think you actually end up getting more interesting results based on the actual kind of first order observations that second order observations might not have gotten.

Romeen Sheth: But what are the most interesting kind of specific applications of technology you’re seeing as related to the workforce and kind of workforce productivity and what you’re most excited about today?

Brianne Kimmel: So I’ve been spending a lot of time in basically three areas. We talked a lot about new platforms for distribution and new classes of work such as streamers, influencers, and some of the new workplace applications that will tie into the gig economy. I’m also looking at distributed teams and not from the lens of do companies allow you to work from home one or two days a week, but what does it actually mean for a company to be fully distributed from day one?

Brianne Kimmel: I think we have a few examples today that have proven out this model. So we have InVision, we have GitHub, which is primarily distributed as well, and we have a whole kind of plethora of new startups that are essentially starting with distributed teams from day one, because it’s a great way to reduce overall cost. So you can remove real estate from the equation. You can hire great talent from anywhere. You are not constrained to only one or two markets where you have your HQ and maybe a satellite sales and marketing office.

Brianne Kimmel: So we’re really starting to see what are the deep mechanics to build a decentralized team from day one. That’s more on the white collar and on, in terms of knowledge work. I think on the blue collar side, what’s really interesting is we’re starting to see new applications that truly understand both centralized blue collar work, which is more factories and more kind of large companies. We also see new applications for decentralized blue collar work, which the example that I use there is a company called Earnin. Earnin is backed by Andreessen Horowitz, and they allow people to get paid in between paychecks.

Brianne Kimmel: What’s great about the model that they’ve built is they’re actually using a number of models that they’ve built to understand how many hours are you working on a weekly, monthly basis? How much money can we give you in between paychecks to actually unlock new opportunities for you as an individual? One way that they do this, which is super cool, is the actually can forecast on when are you actually at work? So they can use data from your phone, which tells you on average, you’re spending 5-10 hours, let’s say if you work an hourly wage job. You’re spending 5-10 hours at this certain company. Maybe you work at a restaurant, something like that.

Brianne Kimmel: But then you also have a side hustle where you also spend another 5-10 hours. So it can actually start to forecast how much money can we give you in between paychecks because we know the number of hours that you’re working. We see that you are fairly consistent in the hours that you work. However, like most people, unforeseen bills come up. Maybe it’s as medical expense. Maybe it’s a family holiday. Whatever might come up, there are just certain times where we need a little bit of extra cash, and they’re able to facilitate that using what they understand about the hours that you’re working and more importantly, the data that goes into this model that they’ve built.

Romeen Sheth: This has been a super interesting conversation. Granted, as we round out, I’d love to ask you that kind of Peter Thiel question as applied to the future of work which is what do you believe to be true about this idea of future of work that most people wouldn’t agree with you on?

Brianne Kimmel: I think to date what I’ve been thinking a lot about is how do we augment the way that people work today? I think that makes AI, ML, fairly approachable. I think in the short term, it’s really great for us to align on the fact that there are a number of things that we do in our day to day that are highly inefficient. But I think longterm, I’m actually very optimistic about the automation of work. What I’ve noticed in terms of understanding a lot of deep nuances in terms of blue collar work is there are just categories of jobs that shouldn’t exist.

Brianne Kimmel: I don’t believe that people should be truck drivers. When you look at the overall side effects and from a safety standpoint as far as number of car accidents, but also when you look at just the overall health of truck drivers, it’s a really, really sad job to have. I think that there’s a number of ones like this where when we start to look at different categories of work.

Historically, we haven’t had the technology to automate jobs that are, quite frankly, unsafe for people. So I think over time, I’m really optimistic in terms of automating things that are incredible unsafe. We can look at a list of these are the top 20, 40 jobs that have the most amount of workplace injuries and fatalities. We can just figure out ways to solve those problems. I think that is the starting point.

Brianne Kimmel: If I were gonna start a company today, I would start with that list. I would look at, I think another space that’s really fascinating is if you look at, when we talked about millennial males opting out of work, a huge percentage is actually driven by the opioid epidemic, which is a manmade epidemic. It’s a problem that’s impacting a large percentage of specifically American males. So how do we actually find alternatives to prescription medication? How do we disrupt certain, I would call them cartels, essentially these large, antiquated spaces where essentially, we are causing harm to the average American person.

Brianne Kimmel: So I think for me, short term, very much aligned in terms of let’s augment what people are doing today, but I think longterm, we need to automate work. We need to automate certain jobs that are incredibly unsafe.

Romeen Sheth: Well, Brianne, this has been a really interesting conversation, and I’m glad you were able to make the time. Thanks again for joining us. We really enjoyed having you on today.

Brianne Kimmel: Yes, thanks so much.

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