YouSaid · the spoken record

Bill Trenchard

lines on the record: 64
first: 2021-12-09
most recent: 2021-12-09
sittings or episodes: 1
sources: podcast

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“I think from my mom, I learned the value of persistence. She was an ultra marathoner and would run these crazy 50 or 100 mile races. I don't know if you've ever seen anyone run in one of these races, but it's really hard on your body. Your feet get all beat up and bloody. It's just a hard thing. And I would go with her on a lot of these races and watch her do this and just push through the personal pain and the physical pain and just be able to focus on this end result. And sometimes it was just running around a track for 24 hours, which is just incredibly difficult mentally. But I watched the incredible joy that she had when she was done and the experience that would have brought to her mentally and just the joy we all had for her and her accomplishments. And that was just incredibly inspiring to me. And so I learned watching her go through that and push through that. And she was mostly in her 40s. She was running those races. She taught me a tremendous lesson in persistence.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“I love to snowboard. I fell in love with snowboarding several years ago in Tahoe. And I actually, during COVID, got the opportunity to live in Tahoe for a year. One of the best experiences is going out for a couple hours in the morning or an hour in the morning, getting the first chair and enjoying the snow. I did not grow up with board sports as a kid. I grew up with East Coast sports, soccer and running and things like that. And I just love it. My wife is a surfer, so really it was easy for her to learn. It was very hard for me to learn how to snowboard, but I do love it.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think it was an intelliger that said sometimes magic is someone spending more time on something than anyone would reasonably expect. And I think those are the things I'm most proud of when I have those moments.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Challenge of this world we live in today is there's so much happening, there's so much coming at you that you have less time to do deep work because especially as a venture capitalist, you've got just a barrage of deals showing up and different needs from existing investments. And so I'm most proud of the times when I can really go deep on a product or project and spend a tremendous amount of time to build something that I think is really fun and borderline sort of magical in some way. It could be something in my personal life. It could be like a trip and planning a really amazing trip and just turning it up to 11 and just spending an inordinate amount of time on it. Or it could be something on the workfront where I really have time to do a fantastic amount of work on one thing. It doesn't happen as often as I would like. It's one of the downsides of my day job, which is just too much coming at you. It's like a good job for someone who has ADD.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“I have another piece of software called Alfred, which runs on the Mac, which allows me to trigger all sorts of scripts I've written and other things to make my computer kind of as fully automated as I can. And so I found that these little things you do every day, if you could just trigger them with a keyboard command, it's amazing how much faster you can be in processing and getting things done.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“My latest work hack is during COVID. I realized I was sitting down too much in front of my computer and just going from Zoom meeting to Zoom meeting or paging through email after email. And so I will do these what I call email walks where I'll literally just get on my cell phone with my assistant and process the inbox with Erd going through it and responding to things. I'll say do this or do this or respond with this while I'm out walking in nature. And that just, I found completely changed my mood. So it's a bit of a personal hack and it's a bit of a work hack because it lifted my mood so much after being, you know, it's a bit draining, as we all know from the Zoom fatigue that happens from being back to back all the time. And this is also sort of crosses, I think, both as I learned from Rahul, it's superhuman, where I'm an early investor and board member, the power of keyboard shortcuts. And I've tried to keepboard shortcut my whole experience on the computer, which is I found this thing called Vimeum, which is a browser extension that allows you to keyboard, control every website.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Could be a tremendous amount of pressure. We're seeing that big companies like Apple recently had this happen in the news about how a lot of their employees wanted to push towards a more remote friendly culture versus coming back in the office. Because people know that works, that will continue, with one exception on the talent side, which is the people right out of school. I think when you're coming right out of school and your first job, it's an opportunity for you to build a new social network and it's really hard to do that remotely. And I have not found a good way to do that. But the best practices I have seen to really build culture is most teams that I've seen are moving to three times a year off-site where you get the whole team together. You basically take what would have been your real estate budget and you put it into nice off sites for the team to come together and have a combination of work time and some get to know you social time. I see a lot of teams also doing pairing or forced pairing in the virtual office, if you would, where you're paired with various people to do projects, trying to avoid the”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“A lot of people are asking where this is all going. I get asked this all the time. My founders, by other investors, and of course we don't know precisely, but I would say the industry is largely dictated by two forces, founder preferences and talent preferences. Both of them will come together and tell us what's important to them, and that will shape the future of businesses, whether they're fully distributed, partially distributed into sort of pods of people all around in small offices, or we come back to more of a centralized structure where people in an office together. The thinking is totally different today. What's possible is very different today than what I think people were thinking back in 2019 pre-COVID. And I think we all have had experience with remote work that has transformed how we think about where we work. I'd also say broadly, most talent, I think, wants more flexibility in where they live and how they work. So there's a major force there. And if you think about the talent war that's going on, I'd say that there's certainly in a lot of roles, engineering roles, data science roles, and so on, which are very competitive.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“At the time, became customers of his. And then went out from there. So often you'd see three types of innovations, product, distribution, and business model. And it's usually the people that attack the dusty industries have a little nuance on each. And it's not necessarily huge changes, but the combination of them is actually really transformative for the industry because the incumbents can't adapt very well. They don't have the product insights or the ability to deliver great products. They can't change the pricing such that they can really compete against this new up-and-comer. They don't have a distribution advantage. And so those are the things that I look for. And typically make those companies really work. You got to look for somewhat small tweaks that end up making a huge difference.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Import and export. How does it work? How do you move things between countries? What are the different chains of custody? What's the complexity? What's the paperwork? How does the bill of lading work, all that? And then when he started Flexport, these insights around, there were actually relatively small from the outside, it looked like relatively small product innovations, but they were really huge for the customer. And the biggest one for him, at least initially, was tracking of where a shipment was. So you could give the tracking of like a FedEx type of level of tracking for freight on the ocean, which was not previously possible. And so it was taking these bills of lading and manually entering them through a team that I think was in the Philippines at one point that did that. That was sort of initial product insight. And then that was enough. Plus, I think he picked the right spot to start. He really focused on distribution within the tech forward companies and then moved out from there. So a lot of these tech forward leading companies that were starting to explode.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I mean, Tusty Industries are typically these ones that were not early to the digital revolution in some way. So they tend to operate the same way today as they did 20 years ago or 30 years ago. It's a new founder with a new model that comes to the market and says, wait, there's a better way to do this. Typically, what I look for there is you're looking for a founder who's really gone deep in understanding the problem. It's one of the things that I look for in any founder that I invest in, but particularly for ones going after the dusty industries, because there's often a lot of dynamics that are just not completely obvious from a surface level look at it. And it requires you to go in and understand it. So Ryan Peterson started Flexboard, very dusty industry. I mean, these businesses that have been doing freight forwarding, which is international shipping, have been around for hundreds of years, some of them. I mean, these great companies have been around forever. He actually did two businesses prior to Flexport, where he really went deep in understanding all of the nuances of international logistics.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Typically in the industry, there's an unspoken rule that you don't scoop other people's deals if you learn about it from them. And obviously, if it's a small investor like an angel that we're doing a reference check on a founder with, we'll invite them in. We'd love to have them in alongside us in the round if they want to put some money to work. If they're part of a larger fund, typically we won't be calling them because we do not want to highlight the deal for them. But usually it's someone who is an operator who's worked with them. They may have been at Google or Facebook or somewhere like that. And they might have a small scout check that they can write or they want to write a personal check and that's totally fine with us. We support that. We think that's great. And certainly they're doing us a favor by providing us a reference. And it's a great reference if they want to invest. And that's a great sign.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Definitely created a unique challenge that I did not foresee because not only to be able to their own funds, there are also scouts you may not know they're a scout. They may be investing their own capital. You see these very odd dynamics where you're calling our references and then people are like, wait a second, I didn't know that they were fundraising. I should call them.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Pitches on the weekends sometimes if we need to. We will move as fast as needed to get in front of the whole team to get in front of an opportunity. For us, it's not a lottery ticket. This is not just taking a lot of shots on goal and then doubling down on the ones that work. This capital really means something to us. We are taking a big bet. We've sized our funds to be relatively small to a lot of venture funds today. We care about this capital deeply. And each of us only has so many, it has a relatively limited number of companies to work with actively during that seed journey. So we care deeply about it. And we're clear about that from an ownership model and clear about that with founders in terms of what they can expect from us. And we think we deliver on that in the market.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“We wrote a 500k check to 750k check, we could buy 10 to 15% of the company when we were early in the life of first round. That is no longer the case. That is not the market price clearing price for a seed round today. Seed rounds are much higher value, and our average initial investment is about $3 million these days. So we've had to move with the market. We're still the same stage, however. It's still typically a few founders with an early product and an insight. They have insight around product, they have insight around distribution and our business model or all three. But that's typically what we're looking at. And it's just that they can raise a lot more capital than they used to be able to at that stage. We've increased our fund sizes over time to be able to accommodate that and still not change the core of our business. We've also increased our cadence. We have two partner meetings a week now rather than one we used to have just one on Thursdays. Now we have one on Monday and one on Thursdays. And so you're never more than 72 hours from getting in front of the whole partnership. And we have a process for meeting outside that too.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, it's fascinating to watch him be a participant. And I'd say the first thing is Unilisten, we're all students of technology and markets. And if you don't adapt and respond to the changes in the market, we think you really can get run over by them. So what that means today is founders want capital faster and at better terms for them typically. And you could argue that's always been the case, but now there's a market to support it. And you also have to figure out, I think, when you're playing this game what you're uniquely great at or positioned to execute exceptionally well. And so we have stuck to our knitting instead of going to become a multi-stage firm, which has happened to some of our colleagues and other firms have decided to become not just a seed firm, but an A firm and a B firm and maybe even later than that, we've decided to stick to early stage. It's what we'd love to do. And it's what we believe we can deliver the best products and services around for our founders. But even there, early stages changed. It used to be that”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Awesome. I'm so delighted that he's on the team, and it's a real challenge in this business so much is this kind of unintentional social reproduction and it leads to groupthink and pattern following. Let's pivot a little bit because first round was founded on the idea that the firm could turn venture capital on its head. Venture capital is doing a perfectly good job turning itself on its head nowadays. And the cadence is just out of control. How are you guys adapting to the cadence that we see in the market today?”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Fantastic. He's an operator. He has this experience from Stripe and Mixpanel in terms of early stage sales. He's fantastic, which we think is incredibly important to help with early stage founders with how do they go to market. But we also have this question of how do you hire somebody that hasn't done the job before. He has not been an investor before. It's like, would you hire an exenior executive for a company that has not done the job before? Probably wouldn't. Or, how do you do that? We had to invent a process around that as well. And that was a lot of fun to do.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“By having this clubby type of hiring that everyone does by going to their cohorts and having these conversations and these dinners and so on. So we started at the top of the funnel, we posted publicly and rethought the whole process. We said we're hiring a new partner. We put out a post. We had a lot of people apply, over a thousand people apply for the job. We looked at every single one of them. We got a very good sense as people moved through the funnel of what we wanted. And we had a very structured process as people moved through the funnel. So it was an incredible learning experience, but we added the structure and the discipline that we had from our investing world and the things that we look for at the various stages of the funnel there into our partner hiring process we think works extremely well we've most recently hired mecca sonia who's fantastic and a great member of our team he was the first to go through that process we couldn't be more thrilled with having him on the team and with how the how the whole process worked and one of the challenges there to be honest is he's”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“You're hired. We don't think that's the way to build a really strong partnership. It's certainly not a repeatable process. It's subject to the same problems that are early investing process was focused on when we just had conversations. The person that advocated the hardest could drive the conversation to hire a new partner in one direction. It's the loudest voice in the room problem or the person with or most articulated opinion. So we've refined it and we started this last summer. And the reason that I think is important is it was during a lot of things that happened around Black Lives Matter and with George Floyd and a number of the other situations. And it wasn't a hard requirement, but certainly we'd like to diversify the partnership with putting a much higher import on it as we were looking at what are our important things for a new hire. We read this post by Brian Dixon over at Cape Port Capital, and it was called So You Want to Fund Black Founders. And his main point in the post was you're being unintentionally exclusive.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Of the different sections. And then we all sit and read it. And then we have a discussion. And usually it's a moderated discussion by one of the members of the team. And the moderator's job is to pull out the areas of dispersion and to really find in the conversation where people are at disagreement. And the reason we do it this way is we found that you would get on this train of like the loudest voice in the room would dominate the conversation and you wouldn't get those long tailed voices that tended to be or the quieter voices that tended to have some pretty interesting ideas around the business. And we weren't getting the benefit of that. We believe this has allowed us to make much better investment decisions. We take in a similar approach to partner hiring. We used to do it, I think how a lot of firms do it, which is you go through the motions of like, okay, who do you know in the marketplace and who are the people in our broader ecosystem that we like? And then start to have informal conversations with them. And then they meet a bunch of the different partners. Maybe you go to a couple dinners. You have a bunch of conversations. And then you're like, okay.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I'd say that we've gotten very intentional about this. In an interesting way, it actually flowed from some of our thinking about how to run the firm better in terms of our investing product, how do we make better decisions as investors first when a company comes in to present, how do we make sure that we as a team are getting the best ideas around the table and really pulling that business apart and trying to get to the truth as well as we can. And so there's a number of things that we do there. We have very, very structured post-meeting review process when a founder leaves the room. We don't talk. So they come and pitch typically for an hour. We ask questions. It's a relatively conversational type of approach when they're pitching the partnership. And then we literally just write for about 15 minutes. We have this structured form that we've built in Airtable that builds out a profile of the company. There's sections on product, market, and team, positives, negatives, narrative that you write for each. There's a whole bunch of different rankings you do on each.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“That doesn't happen in the early days, and it actually could be incredibly valuable for an early stage CEO to know that. So we developed a service. We've worked with our CEO to do 360 reviews as a service for our founders to a 15-person company, which is a typical seed stage company once they've started to scale up. And it's incredibly valuable for CEOs to get this valued 360 review that they otherwise don't get. And they just don't get the feedback. How important is it in the early days of the company building to learn how you are and how you can be a better CEO? It hasn't tremendous down the line impacts. So those are just two recent examples, but we're constantly thinking about ideas that help our founders and help build better products for them. And the operating team is freed up to go deliver and not be pulled from left to right by what we individually want to do as partners in any given day.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Want to break into the tech industry. People that are smart, motivated, and ambitious, to basically train people on how to be a great tech recruiter and it's a free program. People can sign up. We've got tons of people that have applied. We're launching the first cohort soon. And our goal with this is to place several recruiters that come out of the program into our companies and to have them be those early recruiters that really help with building up the teams and helping with the early transition from founder-led recruiting to now we have an internal recruiting function and the type of thing that we love to do. We believe it can scale. It also is a way that we get back to the community by helping people learn these new skills. We saw this other challenge, which is CEOs often don't get a review themselves in the early stage company. When you're a bigger company, when you're running a later stage company like when I was on the board of looker or when I was running LiveOps or any of these companies where you have hundreds of people, someone on the board will typically perform a review of the CEO and give them feedback and do things like 360s.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Independent of the whims of the GP or the partners at any given time. And so they're constantly able to deliver for founders and build and scale services and products that make for a better experience. We think ultimately a much better venture product out there. So there's lots of examples of this. We're working on some really cool new things right now. One example is what we call recruiter track. I'll just talk about new stuff because it's fun to talk about new stuff. But recruiter track is we noticed that the big challenges in the market today is and great people in your company. It's always a talent work. And it starts often for our founders with getting great recruiter in the door to go and help them scale up their team. It's very hard to find a good recruiter. So what we've realized by hiring some recruiters ourselves and starting to really learn the best practices is that you can hire people and train them. So what we're doing is we're creating a training program for anybody. This is actually a great opportunity for people that”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Fundamentally different operating model. We have an operating team. Most teams inside of firms are really beholden to the GPs. And they work at the behest of GPs. And anytime the GPs say, go do this, they go jump on that. And it ends up with this very disorganized set of things that happen, whether it's jumping on the latest deal or trying to do some initiative that maybe helps with marketing or branding. And we have a different model, which is our partnership acts like a board of directors for our operating team. And we've released a very much a board operating cadence with them that we meet every four months. And they present an operating plan to us. All the senior level senior members of the team will go through what their objectives were, what they accomplished over the time. They proposed budgets. They review what they did. And they're really operating on behalf of our customers and building on behalf of our customers in a way that's”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“On the entrepreneur side, I spent a good amount of my time working closely with my partners, especially Brett Berson, who heads our internal team, new products, services, and ideas. And we have this intense bottoms-up orientation for the customer, and we're always looking for opportunities to build new and exciting things for them that will help them in ways that just haven't been done before. Our core operating model, which I've helped with along with Brett and myself and Josh and the other partners have all been involved with this, is very different than other venture firms. I think that if a founder walked into most venture firms, I think they would probably fire half the team from an operating standpoint because it is not the thing that is traditionally driven returns is building great services and delivering great quality of service to founders has mostly been about picking and getting access to great deals. But we believe that the markets changed and the expectations and the market have changed and they continue to change. And so we have a”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“For me, scratches too itch. One is I love investing, advising, and working with great founders and hearing these great ideas all day. But also it is incredibly fun innovating and creating an innovative brand and practice at first round on an ongoing basis. That is very rare to find a set of like-minded people that are so aligned to build a better venture product in the market. That's what the firm has always been about. So we're always thinking about bottoms up, how can we serve our customer better, our customer, our founders. There's two ways we primarily do that, refining our internal processes and then to make better decisions faster and then experimenting constantly with new ideas. And to be both an entrepreneur at the firm and coming up with new ideas as well as an investor is just the combination of two things I love.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“All the areas that you're going to innovate for the business and what's really going to give you the flywheel. That's when it all comes together is during that seed round. And I love that journey. And so for me, first round was incredibly attractive for those reasons. And of course, to work with my friend, Josh Koppelman and also at the time, Howard Mooregan and Chris Frelek and Rob Hayes and the rest of the firm, I was just very attracted to the team that was on the ground. Those are some big reasons. The other thing is I think first round approached the business as a startup itself. I used to ask Josh just as a friend, I'd rib him at various conferences and say, hey, you know, when you get to start another company, because you've always thought of you as a founder, he's like, first round is my startup. He's always thought about it that way instead of culture early on of doing things that way, which permeates how we operate today, which is what makes it, I think, not only the most fun job is adventure, but it is the most fun job in venture because first.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Attraction of the industry, which has attracted me, is it's probably the most fun job on the planet. It is incredibly fun to hear new ideas that could shape the world and shape the future day in and day out, and to do it across so many different areas. We are a generalist firm. We invest as journalists across a lot of different areas, whether it's consumer, enterprise, fintech, hardware, and so on. So I hear ideas across a wide range of areas. And it is incredibly fun to do that, to pivot on the one end to some cool climate tech company to a very interesting and compelling SaaS company is a lot of fun. First round for me had at the early stage of development as a firm built, I think, one of the strongest brands in Seed. I love seed investing because it is the closest to what I did as a founder, those early days of figuring out product market fit, figuring out your early go-to-market motion, figuring out your pricing model and your business model.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Was you're not the operator anymore and you're betting on the founder. You're picking founders to operate. You're not making operational decisions yourself. So take yourself out of that role. Think about the chef versus the recipe. This is advice I got relatively early on in my career as an investor. Think about the team bet that you're making and whether they can execute this, not how you would execute this idea. A lot of times early on as an investor and a former operator become investor, you fall in love with the idea and you really need to think about the team that's executing that idea. And that's a harder transition to make because you sort of project yourself into that seat of operating. The two things I typically advise early on, and I would size your fund appropriately to and think about your strategy appropriately to whatever you think will differentiate you in the market.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“About where you're really going to stand out amongst the sea of capital that's out there. And I think it could be simple things like are you going to make faster decisions? That's simple way to start. A lot of people start there as a simple way to compete against bigger firms. Are you going to focus on specific areas like crypto or infrastructure tech? Are you going to be really great at things like customer introductions? Maybe you're going to help at hiring and talent acquisition. Whatever it is, I think that you need to pick your spot about where you're going to really stand out, how you're going to differentiate from everybody else and your service business at the end of the day. We're all in the service business. Serving founders, they're our core customers. It's relatively easy to deliver value in the short term, but very different to do it at scale for a lot of customers over a long period of time. And you really got to think about if you're going to do that, how you're going to do it and where you're going to stand out. That's probably the biggest thing. The other thing you hear all the time, which is somewhat generic advice, but something I definitely have to learn in my early days of being an angel investor.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“The first thing is think about whether or not you want this to be a business for you or not. You could just be investing here and there using your network to get into really interesting deals. And investing a small pool of capital, typically your own capital or it could be a scout for a fund or you could raise a small syndicate on Angelist or you could just raise your friends and family like you mentioned. And it could be three, four, five million, maybe 10 million. And you don't have to think that much about whether it's really a business of investing. It's more just making good investments. But if you want to be in the fund business, it's a different game. I would think hard about differentiation. Capital is a commodity now. Good founders with good ideas are making a decision about who should have their equity based on what value they bring. If they're good, they've got plenty of options for getting where they get the capital. It didn't used to be the case, but these days it certainly is. So think about how you're going to differentiate if you want to build a business.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“One of your founders said, I've got a board full of cheerleaders, but Bill's my personal trainer. I think that's a great description. And it sounds like it's rooted in your experience, which is awesome. So another thing that's interesting is you made the transition from angel investor to full-time firm investor. What are some of the pieces of advice you give to people who are moving from an operating role into an investing role?”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“And it was a lot of people driven issues as you get the skill, you find that most problems are people problems. Most problems are how do you put together the right team on the field to execute? And he was amazingly good at that. He'd run a public company called Westmarine, which is a big retail company. And so he had a very back-to-basics approach to everything, but it really worked. It resonated for me. It wasn't high-tech, hyperbole, or a lot of the cool things to talk about OKRs. It was rooted in similar ideas. That was, I think, a big help for me and it shaped a lot of my approach for how I work with founders and provide them feedback today and how we work as a firm. I'd say that broadly, Josh embodies the same thing as I mentioned. And I'd say we as a firm typically lean forward with unvarnished opinion on unwavering support approach.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Support. We know how hard it is to be a CEO. Most of us have been CEOs before. And you're taking in all sorts of contexts and different information. And you're the closest to the customer, you're closest to the market. You know what to do. You're going to know best what the data is. And you have to make the hard decision and the buck stops with you. So while we may disagree, we'll give you our full support. And that happens reasonably often where I will give advice to a founder and I'll tell them, listen, I think you're really going in the wrong direction because of X, Y, and Z, here's the data I see. Here's what I think you should consider. And they'll decide to continue on in that direction. And that's fine. I am fully supportive because it is sometimes the people that buck the convention or the words around them that they build a really impactful big companies. But for me, a lot of this came from one of my CEO coaches when I was running LiveOps, a guy named Jeff Eisenberg, who gave me a ton of tough love about all the things I was screwing up when I was running that company. He was fantastic. And I meet with him regularly probably every week or two for a while when we're really scaling that company.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“I'd say in the valley today, there's really two types of investors and most fall in the first bucket. There's the cheerleaders and the people that'll give you the tough love. And I fall in the second bucket for sure. And I think the reason why a lot of people just default to the first bucket is we're all worried about being founder-friendly and having a brand as being founder friendly. And if you have to give tough feedback to a founder, it can be perceived clearly as not being founder-friendly. And there was an old way of doing that, which has been well written about and talked about V10 a venture where people would fire founders or CEOs or they would be extremely aggressive with them. And that's not my style. I take the style of really something that I think my partner Josh actually put a nice wording around, which is we always give our unvarnished opinion. But, you know, if you're a CEO and you have to make a call that's different than what we think you should do, we also give you our unwavering.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Start to help people in the early days of being a founder and finding product market fit and finding something that was going to be scalable and really work. I fell in love with that. I didn't know if I would. I actually really thought I would go and start more companies. But one thing led to another and then sort of decided to do it full time. Founder collect was really a part-time thing. And then starting in 2012, I went full-time at first round. And that's what brings me to today. I've still been doing it for nine years.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Started by Dave Frankl and Eric Paley out of Boston. Fantastic people, fantastic investors. Got to do some really cool investments there. The most notable one being Uber, which was obviously a fantastic outcome. And that's what got me hooked was just that I loved the constant inspiration I got from founders and the ability to move from a player to being a coach to take the lesson.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Was my first real experience scaling something because jump when we sold it was only about 25 people, but LiveOps regrew from just a handful of us to about 300 people when I left and 100 million or so in revenue. And that was a lot more learning in the management ladder. And that was a tremendous amount of funds. But in 2007, I left. And that's what got me into investing because I started, I actually had enough capital at that point to start being an angel investor. And I started to invest in my friends' companies. I made one early investment in a company called Ironport, which was started by two friends of mine, Scott Bannister and Scott Weiss. And I was like, I'm never going to get this back. And sure enough, they sold to Cisco for almost a billion dollars and it was like a fantastic return. I'm like, oh my gosh, you can make money doing this investing thing. I'm going to look into that a little more. That's what got me down the road of becoming an angel investor. One thing led to another over a few years. I was angel investing. Then I started to work part-time at a firm co-founder collective, a firm that was bicoastal, mostly based on the East Coast, but also on the West Coast.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“I was at Microsoft a brief stint, then I went to a company called Idea Lab, which is the peak of the dot-com pinnacle. This is late 99, early 2000. We raised a billion dollars, which was a lot of money, an unusual amount of money back then. These days is a little more common. And then the dot-com implosion happened. And we were kind of a derivative of a lot of the companies that we had underneath us. One of the people that worked there said that we got multiples under companies multiples. And so it turns out when those multiples disappear, it's a hard place for us to base. So I left there, started another company afterwards with a group of folks that had to tell me. We started working on a platform that was kind of similar to some of the ideas around Twilio. We're just about eight years too early. And it was during the real depth of the dot com. So we had to merge with another company that actually had a real business. It was company called LiveOps. The business was a call center business with people working from their home. And our team embraced that business. I ended up running the combined company for about four years. And that was a fun.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“And just go chat with him about business. I was just so out of my depth in running a company, but he had done it several years earlier when he was just a little bit older than I was. And having that mentorship and advice early on and finding somebody that could help me think through how to be a competent, at least somewhat competent CEO, I certainly wasn't highly competent. Was invaluable. I was very lucky to have that relationship with him.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, Chris, the list is incredibly long. I would say the biggest thing for me was I had never been a CEO. And the sports I did as a kid were more individual-based sports. I was a runner growing up. So I ran across country. And so I had to learn how to really lead a team. A lot of the mistakes I made were around that, which is how do you be a strong leader? How do you inspire people? How do you get people to do their best work? How do you avoid a lot of the problems of a company that as it's growing you become, you can get the negative cultural effects? How do you avoid those? How do you make sure that you have open and transparent communication? How do you make sure that people are clear about where they're going? How do you make sure they're clear around what they're doing really matters? And all those things I had no idea how to do. So I kind of had to stumble my way through it. But to bring it back to my partner, Josh, we would talk every morning for like, I remember the summer we were building that product. I was talking to him every morning at like 7.30. He would take some time away from Infonix for half an hour. And we at that time big self.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“So Josh talks a lot about how you want to let your players make fouls. You don't want them to foul out. But if you go through a whole basketball game without fouling once, you're not playing hard enough. Do any fouls from that era maybe stand out that have where you kind of face-palmed, but you're like, wow, you know, that was a great learning opportunity.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“We're just figuring it out as we went, but we all had a passion for products. And we would talk about the cool products that were in our life. And we'd talk about the things that we're really excited about at the time. It was the handheld product, was the Palm Pilot, which is kind of really crazy to think that that was the state of the art at the time. But we would talk about building apps for that. And we'd be excited about some of the cool things that were happening in mobile. And then Wi-Fi was just happening back then. And so this was the dawn of so many things at once. And that was the biggest thing was like learning what made for a great product from these other companies. That concept of taste and really it was a consumer product. So how do we connect with our consumers, really build something that was going to be 10x better than a desktop-based calendar? So that was a lot of learning and it was a ton of fun. We had a great time doing it.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“It was fantastic fun because you were figuring it out as you went, and I was learning how to be a CEO as I went as a lot of the founders I advised today are having to do. And a lot of them are a little older than I was at that time. The key thing for us was, one, was just putting together a great team that had incredible product sense, even though at the time no one had really built a web-based calendar. Outlook was our model at the time, which was desktop software. And so how do you do that and how do you, and so I had, I was very lucky to just have an incredibly talented team. It was almost a benefit that we were all naive and hadn't had a bunch of experience before because we just started from a first principles basis. Andre Black was leading design and he's fantastic. He's gone on to do amazing things in his career. Mike Torres was leading product. He now leads Kindle at Amazon. I mean, these people have gone on to fantastic things in their career. Dean Glasgow, who was helping me run the company, also fantastic at product. He's now running a lot of the entertainment products at Facebook.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Absolutely, with Josh in particular. He's older than I am and was always a mentor and advisor and some of the best advice I got was from him over the years. Matter of fact, when I started my next company, he was my key advisor. So after I was building products for him from all, I'm like, I'm going to go build a product. I want to go build. I want to build something cool. And so me and a bunch of the team that I had assembled for these consulting projects went off and built our first company, product company, which was doing web calendars in the early days of web calendars in 1998, 1999. And we were right out of school and we just sold that to Microsoft. And that's really what brought me to Silicon Valley was that move. And that's what started the rest of the career.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“A great point, too, because in the tech world, broadly, but particularly in venture, everything, if you think about it from a game theory perspective, everything's a multi-period interaction. But in the venture world, you have these resonating relationships that go on and on, and they become particularly important because the evaluation horizons are so long. And those long relationships can pay real dividends.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't know about that. I don't know about that, but Josh would have lots of ideas, as you know, Josh really well. He's an idea machine and he would get frustrated because he had limited resources internally. So he'd bring a lot of air-brained ideas to these college kids up at Cornell to build. And that's what we did. We create a lot of cool little products for him over the years. And that was a lot of fun. The other lesson from that era was I think relationships compound. And the best businesses compound, but the best relationships compound too. Here I have a career arc with him that's really stretched for 26 years now that goes back to when I was literally just a kid, I was 19 years old. That's really cool. It's very cool to have that longevity with one person and see how they evolve and how you evolve and how you look at the world differently over time.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source
“Customers. My biggest customer was for a while was Josh Koppelman when he was doing his company Infonics. Josh is, of course, the founder of first round. But back then he was doing another company. He was co-founder of. He started out of Wharton undergrad program. He started a company called Infonotics, and he was working on that. And so he would send all these skunk projects up to Maine. And I started doing that. This was the beginning of our very long relationship, which is stretched over 26 years now.”
2021-12-09 · Capital Allocators · Bill Trenchard - First Round Capital (Manager Meetings, EP.23) · IDENTIFIED FROM THE TRANSCRIPT · source