Brianne Kimmel — WorkLife Ventures

Wednesday, May 25, 2022

Brianne Kimmel is the founder of WorkLife Ventures and an early investor in Hopin, Pipe, Webflow, Tandem and many others.

We had a great discussion on how she gets into rounds, how she established herself as a top angel investor and then transitioned into a fund manager and her thoughts on work and life.

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Brianne Kimmel is the founder of WorkLife Ventures, a fund focused on the future of work and life. Brianne was named a “Top angel investor everyone should know” by Business Insider. She has invested in Pipe, Webflow, Tandem, Hopin and many others. Prior to starting her own fund, Brianne worked on go-to market strategy at Zendesk. Brianne, congratulations on WorkLife. 

Thanks so much. And thanks so much for having me. 

I’d love to start by just knowing a little bit more about how you built your connections, how you became an expert in the future of work, how you established yourself.

Yeah, absolutely, I always like to start from the beginning, I think that’s really helpful context. I grew up in Northeast Ohio, very much a blue collar town, and tech was not part of my day to day at all. 

I actually started out as a journalism major. Very quickly realized that I liked building websites more than I liked writing stories. And so I started out using Wix and Squarespace and a lot of the lower code tools at the time, but then ultimately learned how to code.

And so I ended up spending about four and a half years in Sydney and a bit of time in Hong Kong as well with Expedia. 

I was in a more performance marketing role at Expedia. Medium sized tech company was doing go-to-market strategy at Zendesk, which was super interesting because that grew out of, more of an intellectual curiosity that I had while I was at Expedia, where we started buying a lot of saas products because it was a faster way to build, in a lot of cases, like a lot of my product roadmap was very much dependent on engineers.

 And we all know how hard it is to hire engineers. And so we, I started buying a lot of tools off the shelf to really ensure that my team was able to hit their KPIs and that we were able to have  best in class technology.

I would say throughout my career, it’s been more of a very high hustle approach. You know, I went to a state school, broke into venture as an angel investor and decided to start my own fund.

 I like that summary that it was a high hustle approach. I think a lot of us have a high hustle approach. And how important were your angel investments?

They were critical in terms of raising outside money. When I initially moved to San Francisco I was teaching classes at General Assembly. Iit was a nice way to meet startups. 

At the time I didn’t have any capital, so I wasn’t able to angel invest. And so over time I started building more of a portfolio of startups that were at least in my network. And so that’s something that I’ve continued as well, where we still do. WorkLife today does weekly community events and we do quarterly workshops.

And so I think a lot of that has come from my background teaching at general assembly. Um, you know, I hit an inflection point when I was at Zendesk, where I was hosting a lot of dinners and very startup curious. Um, I actually raised my hand and, and had asked the team at Zendesk, if I could build Zendesk for startups, which was the, the equivalent of AWS free credit program or notion for startups, they’d be like every SAS company now.

Dedicated program for startups. And so I operated as a GM, um, in, in that role and, and building out the program and, you know, for me at the time, um, it was awesome to see, I feel like there were so many great, um, solo capitalists and new funds that were getting started when I started angel investing. Um, a lot of people I don’t, I don’t know if I’ve met.

Before, but I actually, um, was an LP in funds before I was ever an angel investor, even. So I remember, um, you know, my good friend Neve drawer. Um, he started shrug capital. I loved his approach. You know, I primarily do enterprise software and I’m very much focused on the future of work. And I recognize that needs investments were always really fun.

Cool, quirky, like, you know, the, the future. And so in being an investor in Neves fund, and now I’m an LPN, a handful of funds that was great exposure to really, you know, learn about angel investing alongside other people. Um, and then ultimately start writing small checks. So I think to start, I was writing five, 10 K checks.

Um, but it was enough to, you know, have exposure to investor updates, to play an active role, to, to build more of a, um, reputation before I went to raise outside. 

Yeah. I feel like the angel investment portfolio can become sort of the equivalent of like the portfolio for a designer or the resume for an MBA student or something. 

How was it for you going from angel to fund manager?

Oh, absolutely. Yeah.

And it, and it feels like today as well. I mean, um, angel investors face the same challenges that, you know, new funds and large platforms face as well, where, you know, there’s a lot of capital in the ecosystem right now. There are a lot of great startups. Um, a lot of the best practices that I’ve learned as a fund manager.

I wish I had known when I was an angel investor. You know, I initially was writing more first checks into companies. You know, in hindsight, um, because I was spending a lot of time with a handful of companies I should have continued to follow on as an angel. Like imagine if you build a, have a concentrated position using your own capital, you don’t have to return that money to LPs.

It’s all upside for you. And so I think there’s a lot of strategies that, you know, the, the current class of angel investors are deploying, because I think in a lot of ways, Um, they operate as their own mini funds, but the nice thing is you don’t have to answer to LPs and you have complete independent decision-making. 

Okay. So following on would have been one of the things like continuing to invest, how did you get, I listed a couple of the companies, pipe, Webflow, tandem, Hoppin. Those are amazing names that we all recognize and have grown into large companies and had huge markups. did you, how did you meet them?

How did you get allocation into those rounds?

Yeah, web flows. A great story to tell. I mean, this was an angel investment and one that I made quite frankly, when I didn’t have a lot of money, it was one of those things where when you wire the money, you’re like, wow, that’s like a little bit painful. Um, but I was really excited about what they were building.

Um, web flow is a product that the design team was using it. Um, you know, I, I think across the board, Zendesk has amazing, um, product and brand designers always attracts very great talent. A lot of this stems from having three Danish founders. And so it’s like very beautiful Scandinavian design and that’s sort of the ethos of the company.

And so when I first discovered Webflow, I’m like, wow, this is really awesome. It kind of goes back to my days when I was, you know, first and second year in college where I loved building websites. Like I loved. Um, figuring out new ways to tell stories. I think in hindsight, um, you know, if I were going to go back to college today, I would probably do something related to product design, just because I think it’s such an awesome field and it’s, it’s this perfect combination of being creative and technical.

Um, and so when I saw web flow and its ability to, take not only take Wix or Squarespace to the next level, cause there’s, it’s a lot more customizable. What’s cool is that they also had this community attached to it where. Designers are actually open sourcing or, you know, publicly sharing the work that they’re doing and you could build on top of it.

  So just as someone that had started out, you know, building websites then became a marketer. And I appreciated the fact that like, you know, I think in the previous generation we would have optimized really, or a lot of these platforms that would allow you to ship as many. You know, AB tests as possible.

What I like about where we’re at in the ecosystem today is that founders and design teams have very strong opinions. And so I think it’s turning more back into an art versus just a science. And so I was really excited about web flow and I remember I had cold email. Lad the CEO, um, you know, had, had been, trying to find ways to, to just get to know them.

And like, I don’t know if they’re fundraising. I don’t know if I want to work there. Like it was one of these things where I just really loved what they were building. And so I wanted to figure out how to be helpful. And so, um, I had started hosting low-code no-code dinners in San Francisco. Um, I run this program once a quarter called SAS school.

And so I invited Vlad and Bryant to come to SAS school And so it was something where 

I kept thinking through like, what are ways to get in front of this company? What are ways to spend more time with them before ever, um, Knowing that there would be an allocation or knowing that I would be able to invest at that or that they were open to taking on more money.

And so I think it’s just a Testament to finding ways to work with smart people and to continue building the relationship. Because, at some point a startup will raise money or you’ll get to a point where you’ve spent enough time with them where, you know, maybe you can negotiate some advisor shares.

And so I highly encourage people to, you know, build the list of like companies that you would love to work with   

either, either as an angel or as an advisor or. You know, maybe someone that wants to join the company full time 

because you know, founders really appreciate when you become very excited about their product.

And when you 

make that, 

make that next step of finding ways to be helpful. 

Yep. Hi hustle. Um, what about something like tandem where. In Tandem’s case, I don’t really know the story, but they were one of the hot YC companies is, as I remember it, you had already established yourself as someone, you know, what a business insider say, you know, a top angel investor, everyone should know.

How did you establish yourself to have that reputation so that people wanted you in their rounds?


tandem. I, um, I think this is an interesting Testament to sort of how venture works behind the scenes. I think as an angel investor, I didn’t quite have the exposure to really understand how closely connected every person in the ecosystem really is. And it’s quite a, um, you know, it’s like very much a game of strategy and venture because.

while, um, you know, Silicon valley is very closely connected, the broader ecosystem of startups and in other cities are closely connected. Every individual has a different relationship with someone else. And so I think that’s something to recognize. Like, you may follow someone on Twitter, you may have had dinner with them once or twice, but you have to really figure out who has the most trusted relationship and who is influencing the round.

And so in the case of tandem, um, I had, uh, spent some time with, uh, Natalie salmon, who was the first investor in tandem. Um, she actually discovered this as a, this is a great story for Natalie. So she was at, um, Shasta, ventures at the time and she was working on a market map and looking at where’s the white space for collaboration.

Who’s working on interesting things. Like we were comparing notes on this space because we were both very excited about it. Um, I had recently, um, Left Zendesk and was really thinking about like, you know, an early stage SaaS and work-focused fund. And so we were comparing notes on an ongoing basis. She discovered tandem wrote a check very quickly, you know, had high conviction and, and wanted to make sure that, that she was an investor in the company.

And then she actually introduced the founders of tandem to join my program, SAS school, um, which had traditionally been invite only. It was something that was primarily for, um, companies that had some product and maybe. Some revenue. Um, and so it was more of a, you know, a, a go-to market accelerator, then it was, you know, a zero to one program.

And so it was an interesting one because. Tandem was a little bit early. And in the context of, you know, the types of companies that we typically partner with for the program, but in seeing their vision and then seeing what they had built already, um, I was very excited to, to spend more time with the team, um, so much so that there had been, you know, during, um, during YC things.

Uh, things start moving very quickly. I think with fundraising, oftentimes it feels like it’s going nowhere and then it goes everywhere very quickly. And so I met, um, I finally got a chance to meet with, um, Regina, the CEO of tandem during, YC pitch week. during YC things.

Uh, things start moving very quickly. I think with fundraising, oftentimes it feels like it’s going nowhere and then it goes everywhere very quickly. And so he was meeting with every firm in the valley.

He was, you know, calling angels in between each meeting. And so our first interaction was actually at the Starbucks In Menlo park close to Sandhill. And so it was one of these like very quick interactions where, you know, when it’s go time from a fundraising standpoint, you know, as an angel investor and as someone that really wanted to be part of the journey, you have to come with a lot of notes and with a lot of preparation.

And so I think I prepared for about an hour. Two hours before we met going through, you know, who were all of the interesting people in my network that can be helpful as they’re thinking about product and engineering, you know, as they make their first growth hire, as they think about, you know, their first even community manager or content marketer.

And so I came with this whole prepared. ways to be helpful. And it’s funny. Cause then once you get to the meeting, you end up just having a conversation going for a walk and that’s sort of how venture works. But I came with all of these things in my back pocket, just as a way of demonstrating how excited I was about what they were doing.

Um, the interesting thing, and this is something that I stress to angel investors a lot says specifically in this climate, is that because the fundraise, um, The fundraising process is moving so quickly. Right now, founders are meeting so many people that they forget who they met, or they forget the conversations.

And so the thing with tandem was, you know, I made sure to get Regina phone number. I was immediately texting him like I was in the Uber on the way back from Menlo park to San Francisco, texting, asking questions, offering advice. Uh, asking to jump on a call, you know, once per day, every day until I wired the money.

And so I think you have to really stay on top of the fundraising process because it’s moving so quickly. And now there are so many angels that are, you know, writing smaller checks or, you know, building a track record. And so I find that being as responsive as possible is a competitive advantage. 

Yeah. I actually think the move to text. I’m seeing that a lot more.

I agree. And I think it’s, it’s nice too. Cause I feel like it does strengthen their relationship. I feel like in the last, you know, 12 to 18 months, um, a lot of us are investing only over zoom. And so if you’re only having conversations over zoom or. You know, your communication with founders is sending someone to your EA and then they scheduled time.

And then, you know, there’s just, there, there’s a lot of relationship building that’s been lost during COVID. And I find that texting is actually great because, you know, at least there’s a little bit of banter back and forth and, and there’s a responsive nature to texting where I just see the future of work going a lot more.

personal and alone.

Corporate. And so I’m happy to see that ventures, you know, in that position where we’re building relationships with a lot of people very quickly. And I find that texting is a good way to do that. 

Oh, I want it. I will have to put a pin on that because I do want to hear about, I want to get into some of the substance of how work is getting more personal, but, but I’m just going to ask one more question and like your investors in WorkLife, including. Eric Yuan from the CEO of zoom. I have the CEO of slack, which I assume is do it better field.

Um, you’ve got mark Andreessen. How did you get on their radars? How did you build that relationship? Those relationships.


and this is a great conversation. And one that I love to have, because a lot of it was a brute force and patients, I think there’s like this combination of being intentional, um, and finding ways to be visible in the ecosystem, but also being patient. Um, I will say. For me personally, you know, I had a lot of personal growth and work to do to make the transition from being in more of a go to market strategy, role to a venture capitalist.

  Like that’s a very big leap. Um, I remember when I was first thinking about, you know, getting into venture, 

I had talked to a number. of traditional VC firms. And many of them were like, this isn’t going to happen. Like you can go get your MBA and you could probably, you know, come in as an associate. But I think what you’re trying to do is like a pretty big career leap.

Um, and one that quite a few people discouraged, which I’m happy that I did it listen, but also I think there’s a lot of truth to it. Like it’s been a lot of hard work and a lot of learning and educating myself on evenings and weekends, 

but it’s, it’s been interesting to. To see, um, you know, with building your network.

I find that tech is one of the most open ecosystems. Like if I look and talk to friends that are in Hollywood or, you know, ones that are climbing the traditional corporate ladder, it’s very hard to meet people. I think that tech is very productive and efficient with our time, but also very generous with our time.

Um, and so I found that. Whether it was, you know, sending someone a DM on, uh, on Twitter or finding, um, someone inside the company that could make an introduction to their founders, CEO. Um, I spent a lot of time sort of mapping my network and figuring out, you know, who do I. Slack, who do I know at zoom? Like figuring out, like, what are the best entry points into a company?

Um, and a lot of ways it reminds me of an enterprise sales cycle where oftentimes you, you know, you have to mind accounts or find the, the best possible, um, introduction. And so for me personally, um, You know, when I first met Eric from zoom, um, he had not invested in a VC fund before. So the, the, um, you know, the hurdle that I had to navigate was the fact that he had been an angel investor.

 He’s also very busy as a, as a public company CEO. And so, you know, my pitch to him was more or less like this is a category that’s really important. It’s something I’m really excited about. Would you. You know, did you wish something like this existed when you were first building zoom? And so it was more finding connection points and ways for us to work together in a way that didn’t require a lot of his time.

I think had, I asked for time allocations and mentorship and all of these things that would create a lot of additional work. I’m not sure he would’ve said yes. Um, and then the same as true for other, um, you know, founders that are investors in WorkLife. I wanted to make sure that it was a very founder focused firm in doing that.

It’s been great because we are specialized and focused on work and do a lot of bottom up SAS and enterprise software. And so I wanted to make sure that our LP base reflected that. Um, and so in crafting the pitch for my investors, you know, it’s equal parts. Is this something that you wish existed previously as a specialized firm that can be really helpful also, you know, is this something that can add value for your company and for your team?

  And so that’s something we’re seeing a lot where our founder LPs will send us great executive candidates who are thinking about next step. They’ll send us, um, you know, they’ll send us the right contact. So WorkLife companies can sell to, you know, and, and be adopt. Their software can be adopted by, um, companies that are part of the WorkLife community.

And so I feel like at the end of the day, we look more like a community than we do a traditional VC fund. And that’s by design. 

Yeah. Um, Um, you said a lot that I thought was interesting. One is you described the tech ecosystem is very efficient with our time and generous with our time. Right? One thing. It’s held me back sometimes. And I think some people get in this is, um, I get it. Um, know. I feel nervous about taking people’s time sometimes or 


how do you get over?

And let me phrase it in a better way, but like, how do you get over the, the need to be sort of persistent, um, to get in front of these people? How do you sort of think about that yourselves when you’re asking people for time?

Oh, you said so much. That was interesting. You described the tech ecosystem is very efficient with our time and generous with our time. Right. I feel like I have some sort of nervousness or hesitation about asking for someone like Eric, who owns time. How do you get over that? Or how do you think about that? 

Oh, yeah, this is, yeah, this is a great point.   And I would say like, I’m actually very believe it or not. I’m actually a very shy person. And so for me, um, I’m more of an introvert and more of a shy person. And so I always feel like I’m like misusing people’s time?

That’s just like my general. Style and life.

Um, but what I find is, in Silicon valley and in tech broadly, um, we’re all very efficient and we process email very quickly. Like Like I think if it’s one, if there’s one thing that’s super human has done really well, like we are naturally very inbox, zero people. And so I’ve noticed this and I I’ve, I’ve specifically noticed this with some of my friends that are.

Executives at medium to large size tech companies like sending a one-sentence email is totally fine. I think early career, you know, you, you go to college, you learn about, the format for sending emails and the intros and the closings. And like, that’s just not the way that the world works for very busy people.

And so I’m very open to sending a really short email to someone if they’re able to help by just sending them. Email or looping someone else in. And so I oftentimes craft my emails in a way where, you know, the person can either quickly forward an email, um, loop someone else in very quickly, I usually say it’s like a two tap email.

It’s either a forward or a very quick reply, um, and plus send. Um, and so I try to keep things as simple as possible. That way the person on the other side can get to a yes, as quickly as possible. 

I like that. So you don’t have to feel bad about using people’s time if you’re using it very efficiently.

I tried it. Yeah. I’m a very asynchronous person. I find that it’s, um, you know, it’s very hard to find time for a zoom or invite folks to dinners. And so if we do a dinner or if we, you know, if I do have a zoom call, I do come with an agenda or I do come with like a very specific reason for the conversation, just because I know people are.

Very busy. And I, you know, I try to make sure that like every interaction we have, whether it’s with founders or with our investors are meaningful and they go away with something that’s interesting and has added value to their day. 

Great. Well, Well, let me make sure that I talk some about the substance of WorkLife. Um, briefly what, what size check is sort of your sweet spot?

Yeah. It varies. I think in this environment, round sizes are different, although, uh, it’s always different. Um, I would say, you know, One to $2 million round, um, we’re, we’re able to, to lead those? rounds, you know, I’m seeing today with the six to $8 million first rounds, we’re usually writing a one to $2 million check.

How do you think about those? Cause I’m in the same camp by writing a million dollar check. How do you think about investing into these rounds where it’s a seed stage company, but it’s a 30, $50 million valuation or something.

Yeah. You know, I would say. The market is becoming highly efficient and for, because we’re a specialized firm, you know, there’s just companies in our category that we want to be part of the journey. And so I try to be less grounded in, um, entry, valuation, and more grounded in our ability to deliver value and to build concentrated ownership over time.  Um, you know, Um, one of the interesting things, when I talked to founders, as far as like, well, you know, what have been your, your best relationships with early investors? What are the things that you look for? You know, what are things that stand out? I find that oftentimes going into a pitch meeting or having a conversation with a founder and only talking about the price of the round is not the best way to build a relationship. And so you know, I like to stay really focused on ways we can add value and ways that the WorkLife network can be helpful. Um, knowing that, you know, we will build ownership over time. You know, I think looking at our fund one investments we’ve followed on. Almost every company. I think there’s a, there’s a handful that, that happened gone out to raise yet, but we have followed on.

And the interesting thing is that fundraising, I, you know, I believe that fundraising has gone from this start stop motion, where you would raise around, you would close the round, you’d go back to work and then you’d go out to raise again. When I’m seeing today is that founders are in a period of continuously fundraising.

And there’s a few reasons for that. Firstly, there’s a lot of demand from the last round where there are a lot of great firms. You know, are either going earlier stage or raising growth funds. And so I think every firm has its own shot into a company at any moment in time. And so there’s just a lot of demand from the last round, which leads to, you know, I’ve seen with a couple of WorkLife companies.

The next round of financing is done within weeks of the last round of financing. And so firms are willing to take on early stage risk with a much higher valuation, simply because, you know, they’re excited about the team. They want to make sure that they get into the round. They don’t want to miss out. and so I’m less grounded in price.

I will say that one of the fortunate things of being more of a solo capitalist or. Being someone that, um, still has a reputation as being more of an angel first and maybe a VC second is the fact that we invest in a lot of friends and family rounds. And so our pre-seed strategy is still very much, you know, investing in companies that have, you know, somewhere between a 10 to 20 posts, which is a low valuation and this environment.

And then we continue to follow on in the institutional. 

Yeah. So will you see rounds then? Do you see people are almost fundraising in between rounds as in there’s or notes being raised uncapped notes, or just sort of approximate valuations happening there?

Yeah, absolutely. And it’s something that I, I don’t, it’s not that I always encouraged it. I will say I occasionally encourage it for the right types of companies. Um, cameo is an interesting scenario where they, they have always had a note open. And the reason for that is they meet a lot of influential people.

And so as they meet amazing people that can really help, you know, scale, um, their efforts on the supply side, Celebrities and athletes and influential people. Um, they want to keep a note open to enable, people to invest in, to be part of that journey. And so I think this works really well in enterprise as well.

You know,   we have done this with some WorkLife specific companies where maybe we’ll open. Yeah. $1 million note, something like that, where we bring it, we do more of a customer round where if there are customers that are on the fence, are there, there are design partners that have been incredibly helpful.

It’s a nice way for us to really, um, solidify that relationship both on the customer side, where they’re giving really great feedback.  On the investing side, you know, the early believers of the product and the ones that are really doing a lot of the hard work behind the scenes, they should share an the company’s upside over time.

And so we do Sometimes open customer rounds, too.

Sometimes I’ve, challenged with what the price, what the cap should be on an, on a note, because if you make it too low, it sort of anchors for the next round. Um, are these usually uncapped or how, how are those structured?

Oh, yeah, it really depends. I would say, um, depends on the company. I am more uncap notes. Um, you know, you know, historically, and when I was angel investing, that would give me a lot of anxiety. I mean, you just never know in this environment  what the next round is going to look like. Um, But I am seeing some uncapped notes just as a way to ensure, um, to build training.

Firstly, that builds a lot of trust and Goodwill with the founder. Like if you are willing to invest on an uncapped note, like you’re in it for the long haul and you’re very excited about what they’re building. And so from the founder side of. Oftentimes a very positive and strong signal. Um, I am sometimes seeing, you know, with a, with a discount, um, you know, I think YC has made a lot of the early stage financing, really simple, you know, raising on a safe or doing, you know, in-between rounds.

You know, something was like a 20 to 30% discount. I’m still seeing that. 

Hmm.  Well, um, let’s get in a little bit more about what your initial. I think it’s sort of consumerization of enterprise is one of your big areas of clothes. Maybe you could just start by telling us what that is and what you’re focused on.


absolutely. So in the early days of WorkLife, it was interesting. I, I think, uh, having left Zendesk and being very interested in the future of work, I think the general. Reheat across the ecosystem was that I was only investing in enterprise. The interesting thing is I don’t think we’ve made an enterprise investment to date.

Um, I will say that, you know, I like bottom, bottom up business models. Um, you know, I find in the way that work is evolving over time, you know, we’re seeing even prior to COVID, um, we were seeing that, you know, the average worker wanting to work from home at least one day per week, Um, there’s been a lot of studies done on, you know, the future of freelance and, you know, the percentage of people that are either freelancing on the side today, or plan to do it in the future.

And so I felt like work across the board was becoming a lot more flexible. And so from a business model standpoint, what that means is that, you know, companies, which I view as kind of dated institutions, Need to catch up and find ways to really adapt to the changing needs and desires of consumers and consumers or people at work.

And so I get really excited about tools that start more bottom up. I mean, I think from a, from an investor standpoint, um, you know, the cost structure, has come down significantly where it’s not something where you have a large sales team you’re responsible for hosting a lot of events or doing, you know, the old steak dinners and taking people out for drinks,   which during COVID wouldn’t have been possible. And so I find that companies that have more of a product led growth angle, are scaling faster. Um, they’re able to unlock a lot of value, not just for one person. Um, That signed an annual contract, and then it’s using the software internally, but for an entire team or an entire company. 

Hmm. Is there a good example of that you want to share?

And so I, um, Yeah.

I get, I get really excited about some of those business models. Um, we do a lot of bottom up SAS. We do FinTech. Um, I was an early investor in public, which is the social network for, for stock market investing. public was an interesting one. You know, I think public clubhouse, Hoppin and put in this category as well.

You know, for me, the future of work is creating new economic opportunities for everyday people, whether that’s starting your own business using low-code or no-code tools, whether that’s becoming an expert on the internet, which public has enabled, you know, non-traditional or first-time investors to become influential people in investing, which is awesome.

you know, with clubhouse, same thing, it’s like back in the day, you’d have to have an agent or you’d have to be, specialized in radio and you’d have to have all this equipment and go to a studio today. You can just, you know, log in from home, have a conversation, post your own evening show.

And, that’s where I see the future of work going is that software is making it a lot easier for anyone to do just about anything. And so I get really excited when I see. New applications that make, um, work possible and that make it as easy as possible for people to make money doing the things that they love. 

Wait, I’m fascinated by this. So what you said is corporations are sort of dated institutions and the way you think about it, Creating new economic opportunity for people keep going on this. Tell me how, how are companies, how are companies still going to be doing this or are these like tools that enable this sort of almost outside the corporate structure?

Yeah, I will say I’m, I’m a very, um, I’m a very reasonable person. Um, you know, I wouldn’t say like companies are dead. I, I read on Twitter. There’s like this whole wave of like companies are dead. Everyone’s going to have a podcast. Everyone’s going to make, you know, 250 K per year as a writer on sub stack.

That to me is a little bit extreme. I think a lot of the things that we’re seeing today is that being a freelancer is very hard. 

And so I think to say that companies are going away and that everyone will be their own boss is a little bit extreme, but where I get really excited is the fact that we’re seeing new technologies that make it as easy as possible. Or easier than the, you know, the, the last, um, tech cycle to really start something.

It might not be your full-time thing. It might be more of like a passion project or a side project for a while. But, you know, I think the future in the future, every person will be able to say, they’re a founder, they’re a founder of a Shopify store. They’re a founder of a podcast. They’re a founder of a food truck.

Um, I’m seeing some really interesting things in the SMB space because over the last year, a lot of small businesses have had to rethink their strategy and part of rethinking their strategy. It’s not real estate dependent. So many of them have moved online. Um, it’s not necessarily. Dependent on specific suppliers or specific, you know, relationships that they’ll need to build over time.

There’s a lot of new platforms that are making it as easy as possible for someone to launch their own direct to consumer brand launch their own candle company cosmetics. I was an early investor in a company called Piatra. That’s doing this really well, where, you know, if you’re a fitness instructor and you’re.

You’re used to working a limited number of hours per week, and you’re locked in at an hourly rate and, you know, the gym or the studio that you’re working on is taking a, a large chunk of that cut to launch your own branded apparel line, to have the ability to sell your own swag is actually very cool. Um, it’s a nice way for you to have your own independent revenue stream.

It’s a nice way for. You know, you to not only make ends meet, but to really build a community and a following behind the work that you’re doing. And so I am seeing a lot happening and more of the, um, you know, to what extent will individuals have multiple different businesses that they’re running on the side?

Maybe it’s not their full-time thing, but it’s something that, you know, over time compounds into something that will at some point be equal or greater than the work that they’re doing at an hourly rate. 

Hmm. Um, and how do you, how do you still make it feel like you’re part of something, if you will, like, how do you still make it feel good? Like, I think people are. Some of our companies are talking about just making remote work, still collaborative, feel, feel good. Like have you given thought to what’s going on with remote work?

I’m sure you have.


Hmm. What do you think about the move to remote work and remote teams? 

I’m actually, I’m, I’m really concerned for companies that have gone fully remote. Um, I will say that we have painted this dream that it’s great for everyone. And then it’s great for every tech company. The challenge with remote work is that. Um, the way that we’ve created this first version of a remote company, it looks very similar to an office, which is for better, for worse.

Like when we think about the way that companies have brought documentation online, like the way that it works. You’re working in a silo, you share a doc, you pass your work to someone else. Maybe they comment a little bit, they pass it back to you. It feels very corporate in nature and not very collaborative.

It feels like you’re delivering a body of work to someone else. And then it’s up to them to, to comment and to make changes. And so I find that, um, where I get most excited about the next few years is the fact that now that we have been online for the last year, that we’ve used, like the current version of all of the tools, which essentially.

Traditional office to the cloud. I get really excited to think now that we’re all, you know, in the cloud, working collaboratively with a global mindset, what is the next version or the next iteration of all of these tools look like? Because I think there will be new design principles and new forms of collaboration that emerge that remove the traditional office entirely.

And it’s designed around. Different people’s working styles, you know, the way, the ways in which we can collaborate in a more effective way that doesn’t feel like we’re creating additional work. 

Hmm. Do you have any thoughts on those design principles? Like they’re personalized. I think you said, do you have thoughts on how that will evolve? 

Yeah, I I’ve been thinking about this a lot, and this is more of just thinking out loud, but you know, if we look at the tools that a lot of people are using today, Hoppin has done an amazing job of bringing offline. Events online. And so they, you know, went from, you know, four employees to now over 850 ish, in the last year and a half.

And so the reason for that is there was a lot of demand for their product. It’s a, it’s a hard problem to solve and creating a virtual experience where you can have thousands of people, you know, at the same event online. Um, what’s interesting about Hoppen is that it essentially looks like, you know, the.

traditional conference that we see today. There’s a main stage. There’s breakout areas, there’s networking events. They’ve done an amazing job of bringing conferences online, you know, to take it to the next level is, imagine you’re fresh out of college. You’ve never been to a traditional conference, or you don’t really have that affinity with that sort of virtual business cards and, you know, things of that nature.

Um, you know, I think in a, in a future world, a lot of this could be more streaming and experiential and pulling in, you know, ways of making it look as human as possible, as opposed to like an avatar, walking into a room or walking out of a room.  I’ve played around with and a few of these like new office 2.0 where you create an avatar and you can walk in and out of conference rooms.

But I think in my mind, I’m wondering what happens when we remove the conference room entirely and we create the next version of, of what collaboration should look like. Like maybe it’s having all of your docs in one place. Maybe it’s having, you know, a visual whiteboard and something that’s very immersive as opposed to just be.

Replicating the conference, which for better, for worse, um, you know, will become dated over time. 

 Hmm. let’s stay on this next generation of folks.  what are you seeing with the, are they gen Z coming out of college yet? Millennials, gen Z. You know, what are they, what are you hearing there on what they’re looking for from work and from life?   I guess the 

Yeah. Yeah, it’s a, it’s, it’s a really great question. Um, you know, I was very fortunate to be part of a number of gen Z communities over COVID. Um, the reason, you know, from my involvement in joining a number of discord servers and being part of the IMF I campaign, which was more of a political, um, sort of activist group that was, you know, had.

40 gen Z that work at different tech companies. So I, I like to spend a lot of time with, um, you know, people that are, uh, one or two years into their tech career. Um, it’s really helpful for me to figure out what sort of tools are missing from the ecosystem. You know, what do they look for and startup culture.

Um, you know, hiring has become really competitive, especially as we’re working from home, you know, without the office, without benefits, without, uh, an in-person interaction with a founder. You know, I find that I’m spending about 40% of my week on sourcing and closing new hires for portfolio companies. And so that’s, uh, a big chunk of my week.

And so I like talking to engineers, designers, people that are fresh out of school, and you know, many of them are making decisions based on their values. And so I think the, um, you know, the, the last generation, and maybe we could say older millennials, you know, too, Work at Google to go to a cool campus, to have all of these things at your disposal.

Like that was enough and saying that you worked at Google, apple, Facebook was a huge badge of honor and ones that, you know, uh, one that, you know, your parents were excited about. It was a great way for you to find your community and find your tribe. And, you know, I actually think in a lot of ways, work used to mirror a religion where you would go work at a company.

Um, you know, you would travel, um, be on campus, meet as many people as possible network after work. Like we basically designed our entire lives around like work as an entity. Um, Um, what’s different with gen Z is the fact that many of them are choosing problems to work on attached to their own personal values.

However, they’re doing a much better job at S you know, setting boundaries, you know, and you know, how they show up on social media, how they think about, you know, career progression. I think there are less tied to maybe climbing the corporate ladder because in a lot of ways they’re choosing problems that they want to work on and then I also find that for. Tech startups. What’s interesting is that the culture and the benefits that they offer are actually quite different in nature. You know, I think that we look at the statistics on gen Z. They have been online from the beginning.

Many of them are very active and comfortable, um, having a presence on the internet. Like I love watching the, the fun things that people are doing on Tik talk, because I feel like our generation was more posting, really beautifully edited photos on Instagram, which is great from an editorial standpoint, but not very authentic.

And so I find that gen Z are very often. And so I’m excited to see like what this means for the future of work. Like I do believe that we’ll see sort of an Instagram stories or, you know, some sort of, um, interface that makes it easy to share updates professionally. I think LinkedIn in a lot of ways has lost its way because it’s fully monetized and you know, now designed for recruiters and for salespeople.

And so I think it presents an opportunity of like, how do we enable the next generation to be authentic at work too? Build their own reputation online. And I think there’ll be a lot of new tools that mirror a lot of the things that we need to see in consumer, but they’ll be adapted for the workplace. 

What about, is it Brian Armstrong, Coinbase, who came out and sort of said, we don’t want the sort of more political discussions at work. Do you think that’s, the wrong direction? You think that’s against the trend?

Yeah. I mean, companies, it seems like there’s a, like a bifurcation that’s happening right now where, you know, companies are aligning to specific values and sometimes those values are, we want to stay focused on our company mission and we don’t want to bring politics to work. I think that attracts a certain type of person.

I think that that can on one hand create a safety net where, for. Most of us. It’s been a really challenging year. We’re already taking in so much negativity from the news and taking in so much information. Yeah. You know, I talked to a lot of people where work is their safe space. Like they want to come to work, they want to do their job.

They want to have fun conversations, but you know, if, if the day-to-day, um, is consistently negative, it’s just like, you know, another, um, layer of icing on that cake, um, where it just continues to compound and sometimes a very negative way which could lead to burnout. However, I will say, I mean, there are ways of striking a bell.

Um, you know, Nick Toby from Shopify did an amazing job of really aligning on the fact that Shopify is a team and it’s a top, performing team. Um, the interesting thing that he said that I think is a little bit not controversial, but I think it’s something that, um, you know, many startups have asked me about this were not identifying as a family, as a statements statement in itself, because I think in the early days of a startup, you’re spending so much time with each other that you do start to have.

You know, family like dynamics, where you hang out, you get drinks, you talk about your day to day. Like it becomes your support system, the challenge. And that philosophy is that, you know, your work family is not your, your family family. And so I like that. He brought up the point that, you know, your family, isn’t going to fire you nor should.

You know, your work family become more important than your own family. And I think that’s something that’s really important to me. Um, specifically as I think about, you know, women and underrepresented groups in tech, where, you know, many of us don’t have the, um, Privilege or have the opportunity to give work 100% of our time because we’re caring because we have, you know, uh, responsibilities at home because there are, you know, things that are happening in our own life that oftentimes, you know, we see, I’ve seen this personally where we hit the.

Inflection points in our career where we start optimizing for safety and for stability. Whereas maybe our male peers are optimizing with, you know, an uncapped amount of risk because they’re in that unique ability to do so. And so I like that, you know, some of these topics are hard to talk about at work, but I’m happy that companies are having these conversations where, you know, We, I think we can strike a balance of, you know,  in the case of Coinbase,  I’m not sure the context of the conversations that were happening there may have been an infinite amount of negative conversations on slack.

Like it may have gotten to a point where they had to say something. I don’t, I don’t have enough context there, but I like to see, like, what Shopify is doing is, you know, let’s stay really focused on helping merchants on helping small businesses on really changing the world. Um, and let’s stay focused on that without necessarily bringing in all of these various different elements that, you know, can be unsettling for certain people.

I think it’s, uh, I always like to go into conversations, with as much positivity as possible because we’re not sure what other people are dealing with. I think, especially during COVID, you know, we assume that the lives that we’re living at home are the same are true for all people, but everyone has unique circumstances. 

Well, let me ask one more question then. How do you navigate your own balance between work and life   and the infinite amount of email that you can’t necessarily get through all day? How do you navigate that?


Um, that’s a great question. I am, I will say the first half of the pandemic, I had no balance. I mean, I was working from home. I started WorkLife in September of 2019. Um, I had made my first couple of hires for the firm. And so we were working really, really hard. I think it wasn’t until maybe six months into the pandemic.

I realized, um, you know, if you would look at my schedule and working from home versus pre pandemic, you know, I was taking the time to go for walks with friends. I was going to dinners most nights of the week. And so when you remove those things from the equation, I was replacing it with more work.

Um, and so now I’m much, much clearer with boundaries because it became, uh, you know, not, not to the point that I felt physically burnout, but there was a, there was enough there where I felt like this is a really awesome, you know, I’m very fortunate to work in an industry where I’m safe and able to work from home.

And so with this time, you know, what are some things that I can do that will make me, you know, happy 10, 20 years from now? And I remember when I was younger, you know, I never really learned how to cook. I was always studying And so I actually, um, had started a weekly. Weekly cooking with my grandma over, over FaceTime, which was amazing. Um, you know, I had recognized I’m of Ukrainian descent, um, and grew up in Northeast Ohio.

And I remember when I was younger, you know, I never really learned how to cook. I was always studying. I think it’s like any, anyone that. Immigrant parents or immigrant immigrant grandparents, like your job is to study and to do well and to, you know, really, uh, think and more like, I would say more of a multi-generational way where it’s like, I was very fortunate.

My grandparents and great grandparents came over, um, and moved to the U S. You know, for a couple of generations, you know, we, our family had primarily been working in more blue collar trades, which I still love it. I’m very excited about the future of trade and, you know, the future of trade education. But for me, I was always very focused on studying and doing well.

You know, ultimately not, not, not intentionally, but you know, getting out of Ohio and seeing the world and, and Silicon valley is where I ended up. And so this was the first time in my life where I had time to learn how to cook and spend time with my grandma. And which was amazing. it was just really cool to see, you know, as I’m catching up with friends, you know, many of them have done the same, you know, a very close friend.

Um, she’s actually a product leader at Webflow. And, uh, she moved in with her grandma and we were like, how cool is this? Like, you know, we are in our thirties. We’re living with our family. Again, like we just have this opportunity and this time that like, we, I would have never imagined, just spend so much time with my family over the past year.

 But, you know, we, we had the combination of zoom and FaceTime and all of these tools that made it much easier for us all to become close. 

That’s a great glass half full note to end on Brianne. I’m so impressed with what you’ve built at WorkLife. I wish you so much continued success and thank you for coming on the podcast today. 

This was great. Thanks so much for having me.