Zachary DeWitt: How to Combine a Community-Led Growth & Product Led Growth Strategy # 192

Zachary DeWitt, partner at Wing Venture Capital and founder of Drop, explains community-led growth as a go-to-market strategy that uses passionate users to drive sales. He walks through real examples like Notion's ambassador program and Figma's plugin marketplace, then outlines a playbook: find power users, build referral programs, enable user-generated content, and keep the community fun with games and surprises.
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Hello, hello everyone. This is your host, Akhil Jabbar, and welcome back to another episode of SaaS District. In today's episode, we'll be talking about how to combine a community-led growth and a product-led growth strategy. And today we have our guest Zachary DeWitt joining us. Zach is the partner at Wing Venture Capital. They are a firm that invests in seed and Series A rounds for transformative enterprise tech companies. Prior to Wing, Zach was CEO and co-founder of a company called Drop, which built 2 award-winning iPhone apps, Drop Messages and Firefly, before they sold the technology and the IP to Snapchat in 2016. Zach also holds a BA in economics from Yale University as well as an MBA from Harvard Business School. So Welcome, Zach. Super excited to have you on the show today.
Yeah, thank you so much for having me. I'm a big fan of the show and a lot of your content, so it's great to make the connection and excited to chat with you.
Thank you. Thank you. Likewise, Zach. So a lot of exciting stuff to hear. Impressive resume. But before we get into the nitty gritty, just let's start from the top. Community-led growth. I mean, that seems to be a hot topic these days. People love it. But can you give us a quick background what exactly that means and And how does that compare to product-led growth when it comes to SaaS?
Yeah, absolutely. So community-led growth is a powerful immersion go-to-market strategy that's gaining momentum in the startup community. So what do we mean by community-led growth? The way I think about it is community-led growth is a go-to-market strategy in which companies build and foster vibrant communities of passionate users and customers who ultimately become advocates and influencers. So you can think about this instead of relying on your product to do the selling or your sales team to do the selling, you almost rely on your users and your community to do the selling. And so what are some ways in which a community can help the business? So I think there are many. So one of them is customer acquisition, right? In today's world, we tend to trust people more than we trust brands. So social proof matters a lot, and it's a very valuable currency. If you go on Twitter and you see people talking about how much they love Notion or how much they love Figma, you may try this product simply because you're seeing an online trusted community talk about it. So these referrals matter. You know, it's valuable social currency. It's a signal of strong community-led growth, and it's a way to spread the product, you know, across your community. And there are certain— we can talk into some strategies how to do that. You know, companies like Notion, for example, they have structured programs where they build community advocates and they have referral programs. And so they actually incentivize users to do that. But we can talk more about that later. And so just going back to, you know, why does community-led growth matter and what's its benefit? So another benefit in addition to customer acquisition is upselling, right? So communities often help drive engagement and they come together, they share best practices, they share their content. They share their success stories or templates, and this just creates, you know, more materials, more use cases, removes friction for users as they go deeper into the product, and they're more likely to try new features and upgrade to a more premium package. Certainly it helps with customer support too. You know, oftentimes, like Tesla, for example, is a really strong community. You could argue it as community-led growth. And, you know, Tesla, a lot of the how-tos are And the forums online are powered by users. So if you want to figure out how— why your window's stuck, you're probably going to read a forum that a user generated that content for as opposed to Tesla generated themselves. And lastly, a huge benefit of community-led growth is product feedback. A vocal community is not shy about sharing their product feedback, both in public and in private, like in Slack channels. So you just have a tighter feedback loop with your user base when you have a very vibrant community. So we're moving from sales-led, which is your team doing the selling, to product-led, which is your product doing the selling, to community-led, which is going beyond product-led growth. And it's more than just your product doing the selling, it's your community doing the selling and really supercharging them with passion and advocacy for your product and company.
Interesting. You use Notion as an example. So you mentioned their community. They're actually rewarding their community to refer and get out more customers. So I would look at that more of like affiliates or ambassadors or channel partners, I guess you can call those. I would think that would be between also PLG and community-led because I think it would be more of a transactional, right? Like, here's a link, sign up, it's such a good product. Whereas here you're saying the community is actually using the product, they're sharing case studies, how they're actually using it. It's a lot more intimate, not just of the transactional way. Would you agree with that?
I do agree. Absolutely. And so you're right, it's a very gray area between what is product-led, and some of that may be referrals, both in-app referrals or external referrals or links. And then it's a gray area into what is actually community-led. And so it may be like Notion. You can Google Notion ambassadors and the whole Notion ambassador program. It says they're passionate volunteer enthusiasts who teach and share Notion with others. And some of those ambassador programs are paid and some of them are volunteer. So I know Notion has different levels of programs. And so I think for their Notion Ambassadors program, they are free. Sorry, they are volunteer. They're not paid, but they're— but Notion equips them with materials, right? So Notion gives them, you know, special, you know, admin access to the community forum so they can, they can put their posts towards the top or they can moderate their communities, right? So, so part of what I think is powerful about community-led is actually tagging and identifying your power users, who's naturally, who's organically communicating and speaking up most in a lot of your online community forums, and then empowering them with materials, with support, with kind of a dedicated person you can talk to if there are questions to spread the good word even more. So I think you're spot on. There is a bit of a gray area where product-led growth stops and community-led growth starts. And there's certainly a spectrum. Yeah.
And imagine what would happen if you started incentives. I love the idea of using volunteers, people who actually generally want to spread word. I think that's the best way. But if you start adding incentives with cash into that, I wonder how that changes the whole dynamic in the mind. But yeah, it does.
And you can feel it on Twitter too. I mean, we've all seen people on Twitter where it feels like a promoted post, right? that is when, you know, you kind of get turned off and your spidey senses are tingling a little bit that this feels gimmicky or this feels like they're paid to do this.
Yeah.
And so, yeah, I mean, part of it is authenticity and, and actually, you know, part of my thesis over the next decade is, is brands, you know, B2B brands really need to have both transparency and authenticity. And, and so if you can really empower your, your, your true organic users, You feel that on Twitter and you see that sometimes, or sometimes people say on Twitter, what's the best tool for design for my small business? And you just scroll through the comments and you see all these people like, love Canva, love Canva, love Canva, Figma's great, love Canva. And, you know, and you can kind of get a sense of just the, the, the natural passion. And so that really, that authenticity, I, I think you said it very well, is, is, is super important to, you know, to be a part of your kind of program and your aspirations for your community.
Yeah, 100%. Authenticity, I think, in all aspects of life. But even it's kind of hard to differentiate online sometimes, right? But if you can spot it, that's important.
Yeah, exactly. Well said. I mean, you're right. I mean, you're kind of blurring the lines between brands and people, right? And so I think that's what this movement is about. You're becoming less of a brand who's talking to you and talking down at you, and you really want to become an authentic collection of people and collection of users that love your product. And that becomes the interface. That becomes Kind of the experience layer for new users. That's where they hear about the product. That's where they get referrals for the product. So moving from kind of this creepy, large monolithic brand to this organic, warm, natural kind of user nebulous community.
I want to challenge that thought around the old nebulous monolithic brand. Doesn't that attract a certain type of folks too? Folks, let's say bigger companies, Fortune 50, Fortune 500 CEOs, they would maybe look at that as better than us. It's kind of reverse psychology where it's like, no, they actually don't want the personality. They want to see a big brand company and has all this— it looks bigger than it looks like, right?
Yeah, it's a good question. So I think it depends on the vertical, right? If it's dealing with money, you can imagine a world where you want a very large monolithic organization, a faceless organization like Bank of America, right? They're trusted. They have millions and millions of customers. They've been around for, through acquisitions, but 100-year-plus. And so there's a lot of trust there. However, if it's a developer tool, or if it's a productivity tool, you really want to learn about that from users. And then you want to troubleshoot it with other users, right? You want to land on the community page as opposed to on kind of a page which is like the brand talking to you. And so I think, again, I think you're right and your instinct's right, but I would push back and say it's more on what kind of vertical dependent of Do you want a big trusted monolithic faceless brand or do you want more of a community kind of, you know, people-first experience and in company?
Yeah, yeah, it makes complete sense. And do you think that, you know, every SaaS company out there should experience or think about using community-led growth or is there any specific you would say that you wouldn't suggest as this a channel to even look at or consider?
Yeah, great question. And so there's certainly some companies who are really well set up for community-led growth. Any company that has, any product that has collaboration in it, right? And so whether it's internal collaboration with colleagues or external collaboration with customers or vendors or partners, those tools are great for community-led growth because there's natural virality in the user experience. So this could be productivity tools, this could be communication tools, this could be developer tools, this could be open source projects. So these areas are really ripe for community-led growth. As you move to more traditional SaaS, for example, I'm thinking like an HR product who sold to multiple stakeholders kind of top down, that, that's a little bit harder to do community-led growth. Now, I think it's still important to invest in the community, and that's part of when I talk to large companies, that's part of the message I'm telling them that, hey, community really matters. And so even though it may be a top-down sales process with multiple stakeholders, for kind of a, you know, like Workday, as you can imagine. You know, people still wanna go on and see the community, feel like people are using it, feel like they can troubleshoot, feel like they can ask questions and get quick responses, you know, feel like people really value the service. And so my advice is every SaaS company should invest in community. It's just a question of how aggressively and kind of, you know, what tools of the community playbook you should start with.
Yeah, that makes sense. I guess if you don't have an internal tool to talk to each other, then that's one way you probably can look at. But I imagine there's so many different channels to build communities these days that, I mean, even like a podcast itself, right? That's one way that I think every SaaS company can do. And then in terms of results, right, like you mentioned a few benefits at the beginning of the episode. Can you share maybe some results of what you've seen, maybe some metrics or a case study showing between, like, was there a company you guys worked with that, you know, between starting with product-led growth and maybe moved towards community-led and what was the results of, you know, before and after? Yeah.
So one of the companies that I work closely with is a company called Copy.ai, which is an automated writing tool and platform. And Copy is, it's still an early company. It's, you know, we led the Series A last year, so it's only a couple of years old. I think it's 2 and a half years old at this point, but they're starting to really push into community-led growth. There's a very vibrant Twitter community. There's a lot of community members that post on TikTok organically that help troubleshoot the product. So it's in early stages of moving to community-led growth. And so your question on metrics is, so what does that mean in terms of metrics? What's the impact? One, we've seen a decrease in customer acquisition costs. Because we see the percentage that come in from word of mouth or referral is increasing. And so that, that, that is your purest form of customer acquisition. There's no paid customer acquisition associated with, with that user growth. So we're seeing customer acquisition costs go down, which is really important for a lot of businesses cuz you're optimizing customer acquisition costs relative to kind of the lifetime value of that customer. We're also seeing support costs go down. And so this is if people are filing tickets on Zendesk, they can start to resolve it by asking other community members either on Twitter or on a forum. And so the number of kind of customer service reps we're seeing that we need to hire is stabilizing. And actually they can spend their time on some of the high-value, more complicated questions and problems where the community can kind of help each other out and answer some of the lower-hanging fruit questions. And then also we're just seeing more engagement across the board, right? When you have all these almost like kind of cross-user network effects where they're learning from each other, they're creating templates, they're posting about how they did something online or a new use case, it just expands the surface area for other existing users. And so that's been really powerful too in terms of seeing that plays out and seeing faster upsells and And upselling to team products sooner.
I'd imagine that on top of CAC dropping, your conversion rate might go up as well, right?
Exactly. Yeah, that's a really good point. Yeah, conversion rate goes up from free to paid.
Yeah. So interesting. You mentioned TikTok as a community. I wouldn't have thought of that for a company like Copy.ai, but that's one place. And you also mentioned a forum and Twitter. Were these things that you guys kind of thought out and say, okay, We've got this company, we're not using community right now. Here are some ways where we can start. Like, okay, we're going to start writing content on TikTok, creating content, and then are we going to add these Twitter, this location in a forum that people can go and voice what's going on and would rather just build this and let it kind of flow on its own? Or how do you guys manage it?
Great question. Yeah, really good question. I would say it's a mix. I would say it's a bit of push and a bit of pull. And so what I mean by that is Listen, we wanted to invest in Twitter, and so we started working with a few influencers to— and that was paid to get the word out there. I think at that point, what we realized is, hey, this is starting to spread. Like, if we paid 3 influencers posting about it, some of their followers started using Copy, and they would post, oh, Copy is a great way to brainstorm an essay I have to write for college, or it's a great way to write about marketing blog posts for my job. And so we started seeing that spread organically. And then there's things you can do. Like, you can create little challenges on TikTok that go viral. You can send people swag so they can wear a copy of a hat in a video. You can kind of create, as I said, some challenges and some incentives. And so you basically want to start a very small fire and just watch it for a little bit and see how it burns and see how it grows. And then you can add more fuel to the fire and invest in those channels. in a bigger way. So, you know, Twitter's the same way. Like, we see Twitter all the time, people posting about CopyAI. There's, there's a user called Easlo. His handle is @HeyEaslo, E-A-S-L-O. He posts all the time about his favorite tools. And so he was posting all the time about how great copy is. So the team got in touch with him and tried to understand why and figure out he's ultimately a power user and figure out how can we create more people sharing like you did, what caused you to share. So you can kind of study some of this behavior and invest. And then also we're going to invest in a forum as well. We want to use a modern forum service. Right now we have a Slack channel with some of our users. So just giving them more avenues to communicate with other users and giving them more avenues to communicate directly with the company and kind of giving them like a hotline to talk to the product leader or the CEO if anything comes up.
Yeah, that's super smart. I like that strategy. I wouldn't have thought TikTok, but I mean, I'm actually not even surprised. I mean, Twitter has always been true and tested and SaaS companies, I find if you know how to find creative ways like you mentioned, I think that could be great. But if I'm a SaaS company, I'm okay, I'm just building out or whatever stage I'm in of my product development, when should I start thinking about creating my community? And maybe if you can give us some steps and it's like, how can we do this right and make sure we get to success here?
Yeah, it's a good question. So the first thing I think you want to do is you want to see Who are your power spreaders, right? And so who are people that are naturally sharing already? Who are people that are posting often in forums? And then you want to have meetings with them, right? So this is the research phase, right? So why do you love our product? Why do you feel compelled to post about it in our forum? Why do you feel compelled to post about it on Twitter? What do you get out of it, right? And so really kind of understanding that psyche. And then you basically want to try to create programs that creates more ambassadors or more passionate users. And so it may be a paid program where you go out to some of your power users and say, hey, listen, we'll set up this referral program for you, or we'll set up this ambassador program for you. We'll send you a bunch of gear. We'll give you tools and tips and material you can post about. We'll give you sneak access to our upcoming product set and product launches, make them feel really special. And so I think that's really important. The other thing that starts to happen is you start to see people actually creating on top of your platform. So you wanna give people tools to build on top of your platform. So, you know, I, I use Notion as a conical, canonical example of, of great community-led growth. Because if you look at Product Hunt, I would say every day I look at Product Hunt every day, I have the app on my home screen on my phone. Every day there's 1 or 2 Notion apps or Notion templates that people are launching. That is really powerful, right?
Wow.
So not only are they evangelists in promoting Notion, and spreading the good word, but they're actually creating content tools, apps, templates that make Notion better for every other user. So there's this compounding effect. And so, so part of it is Notion, their product is set up where people can build templates, right? Their product is set up where people can build kind of custom plugins or custom apps. And so I think you want to be able to set up a product to do that, right? Where you give users power, you let them build on top of you, let them share what they're building. Figma does this really well. They have their— you can go to figma.com/community. You can see all their plugins that their users build. And so they really showcase what the community's doing and giving them tools to do that. So I think that's the second step is like once you set up this ambassador program, this evangelist program, you wanna make your app and you really wanna make it a platform where people can build on top. And so not a lot of apps do that. Figma, Notion were early to that. And I think we'll start seeing that a lot more and more.
Yeah, it makes sense. So if I'm maybe in the building stages and I'm thinking of sharing— so I see this a lot, right, on some communities where people are often sharing updates to their platform and get people excited, I guess, things like Superhuman and a few other great— they've done a really good job with that. At what moment do you think is a good time to be sharing with the community to test and say, okay, hey, we're here, or hey, we've got this new thing, right? I mean, how often should you be doing this and keeping people of the community excited?
It's a great question. I think with your power users, if you can get your power users into a Slack channel with you or a Discord channel, you want to be sharing product updates every other week, maybe every week. Just let them know you're building, let them know you're responsive, let them know you hear their feedback. That's super important. And then every company's got a different release cadence for public releases. So that may be every quarter, that may be every month. And so I see a lot of early-stage startups have very fast release cycles. Every month they're sending product email to their entire user base. Here are new features. Hey, we hear you. We hear your feedback. We're building for you. And you really make the user feel heard, right? Because if you think about this, I mean, really community-led growth is making your product and experience a two-way street. We've all used products. I mean, I'm sure you use many SaaS tools in your work. You invest in tools. And so you're constantly You want improvements, you want change. I mean, I want Slack to do certain things. I want Superhuman to do certain things. I want Stripe to do certain things. And so when you feel heard and you feel like they're really responsive to your input, it deepens your affection for that product. And so closing, I think the best product-led growth companies and the best community-led growth companies have a really tight feedback loop between product and community.
Yeah, I always feel, you know, the struggle there is always like, you know, you don't want to be bothering these folks. Like, I mean, these people have, you know, their full-time jobs or whatever it is. And it was like, hey, like, hey, can you get— you're asking them for free, I guess, stuff, right? Maybe you do give them some stuff and, you know, but you kind of feel like, hey, I'm wasting this person's time, or like I'm asking them too much. You know, if you're every week like, hey, can you give me feedback? Hey, can you give me feedback? How do you kind of think about that if I'm a SaaS founder?
Great question. Yeah. And you really want to be careful not to push people too much or annoy people. And so that's why I think if you can really observe who are these superpower users that are always talking to you, always posting feedback, always sending tickets in. And you can get a sense of like they're almost opting in through their behavior that they want to engage more. And so that's who you want to bring into this tight community of kind of product, of immediate product feedback. So it's a really important point. The other thing I'll say is that SaaS tools today become our identity, right? Like there's this movement of bring your own tool to work. The average tech company uses 50 to 60 SaaS tools today, according to the Okta Work Report.
Wow.
And so these are, these are tools that users want. You know, some users bring in Slack, some, you know, some, some users bring in Tome, and some users bring in Tango. I mean, all these kind of emerging new compelling startups, and they want to introduce it with their team, and, and they want to be first. They want to say, hey, I'm cool, I'm in the know, this is what other great startups are using, other great teams are using. And, and so they take a lot of pride in it and it actually becomes who you are and becomes your identity. And, you know, I've seen people on Twitter post the tools they use in their bio, right? Or, and so that's happened, or just post on LinkedIn all the time. And so you want to get into that. Like, I think this is true. I think the best companies become cults, right? Like Figma's a cult. Like you look at Twitter, like people are ride or die Figma. People have Figma tattoos. When people start getting tat— like when people start getting tattoos for a SaaS product, Like you've activated your community, right? And the other thing we haven't really talked about is events. And so Figma has done a great job with their FigCon, their Figma conference, and bringing users from all around the world to incredible cities to meet each other, to talk about design, to push design forward. Another great aspect that communities start doing is they actually help educate their user base. So Figma really values learning and education. There are all of these videos on Figma's website where I can learn how to design, I can learn best practices. I can learn modern practices and what's kind of cutting edge. And so reinvesting in your community, giving them content, I think is super valuable as well. So yeah, you, you know, it's, it's, it's, there's a lot of cool stuff going on with community and, and, and people, as I said, you know, people kind of get to cult status and, and, and that's, that's a sign I wanna invest in any company where there's people who are getting a tattoo with, with that company's logo.
Yeah, no doubt. I mean, that's also probably why Adobe decided to acquire Figma as well. I don't blame them. That was a great deal. Yeah. I feel like that's the trend going to be, right? Future is like, show me your resume. But part of that, you got to include your tech stack is like, here's what I can use and what I bring to the table. I think that's going to be the future.
It's fascinating. People take a lot of pride in it, right? I'm sure you talk to a lot of founders and operators that are talking about their tech stack and their tools, and they're opinionated. And so it's very cool. It's fun to watch. I mean, it's really the consumerization of enterprise. That's a term people have been talking about for a decade. But just like people take a lot of pride in what consumer products they use, what car they drive, what t-shirt they wear, What shoes they wear, right? It's the same thing at work. You wanna express your identity at work. What presentation tool do I use? What communication tool do I use? What dev tools do I use? That says something about me. It says something about my style. It says something about my aesthetic.
Wow. That's a cool way to think about it. Yeah, I guess it's like your work clothes, right? Behind the screen.
Exactly.
This is how I dress.
All right, that's interesting. Exactly, exactly. So that's why it wasn't— aesthetics really matter to me too. I probably miss companies, investment opportunities because of this, but when I look at a company's website, even if it's a seed company, I hold it to a really high standard. Do they have attention to detail? Is the brand thoughtful? Does the brand stand for something? Do they feature their community and their product right on the homepage right away? And so it's tough. A lot of teams will say, oh, we're just a seed company. We just hacked together a website. And for me, that's kind of a knock against the company if they haven't really put a lot of thought and care into the first experience, the website, the aesthetics, the color palette, the logo. Like, as you said, people love their shoes, they love their Nikes, they love the Air Force Ones, and the aesthetics really matter. And so I want to see that expressed in SaaS brands then.
Yeah, I could tell by your background just by the level of detail in your new branding. We're not a SaaS at Horizon Capital, but that was something important to me. So I feel you. Our design, everything had to be on point. So, I mean, a lot of investment companies don't care. They're old school. They're like, no, this represents me. I want it to look good.
Totally. Yeah, aesthetics matter. And so Figma, I mean, I'm just like, Figma's website is, I mean, it's sexy, right? Notion's a beautiful product. These products are clean and they have a feeling to them, they have a mood to them. They have And that's what we're going for. You want to make products, want to make their users feel a certain way, right? And so that is the state of where we are in SaaS today. It sounds a little bit silly, but that's where we are in terms of kind of the next great set of startups.
I mean, that's the basics of sales, right? Making people feel connected to your brand. I mean, now we're just learning how to do it without people to people with the actual website.
Well said. Yeah, well said.
So last question, Zach, before we get into the kind of personal rapid-fire questions. So building a community is one thing I find I'm probably pretty good at getting people in and having this huge list, but then engaging them is another. If I'm a SaaS company, product-led growth company, I'm looking to build and keep that community active, engaged. What are some actions you would recommend to take?
Yeah, it's a great question. And so there's a standard playbook we've talked about of of having a tight loop and communicating often and sending them product updates and certainly engaging them on Twitter. If someone tweets out, you tweet back at them. And so there's a lot of the basics. I think when companies go above and beyond of how to engage your community, they keep it fun and they introduce— it's like really surprising delight your customer. And so they're hiding little nuggets in the product. Like one company I work with around Around.co, which is kind of a next-gen video chat, they introduced games into their product. It's not really a gaming product, right? But they wanted to keep it fun for people in their video conferences. They had little nuggets of like, oh, seek, like find and go seek. We hid something in this product release. Who can find it first, right?
Mm-hmm.
So surprise and delight your consumers. That's something a friend would do, right? A friend would mess around with you. A friend would have a sense of humor. You know, a friend, a friend would, you know, would, would, would, would keep it fun and light and, and make you laugh. And, and, and, and so the, the best, again, like they, they make, they extend and expand the range of emotions that you experience using their product. And, and so I think that's something that, that brands should do. 'Cause you're right, you don't wanna just send 'em the boring email every week, every month saying, here's our product release, like every Wednesday, second Wednesday of the month.
Mm-hmm.
No, you wanna make it fun. You wanna have, beautiful content, cool videos, but you want to make it mysterious, you want to make it humorous, you want to make it cryptic, you want to hide something inside the product for them to find, right? And keep it fun and light and hide a little mini game. And so I think we're starting to see that more and more. People are really expressing their creativity in terms of product launches and releases and just how they communicate with customers. And so that's the next-gen cutting-edge stuff that we're seeing more of.
I like it. I mean, it sounds so simple, kind of being a little bit more bold in your communication, but I mean, it's tough. I mean, most people think that you got to keep it simple and just don't make it too personal. But I love the idea of making it like as you're talking to a friend and you're just making it. But I can see the struggle on both sides, right? It's tough, but I'd love to try it out. Yeah.
And especially today, it's just noisy out there, right? I mean, you pick any category and there's like 5 startups competing. And so you have to do something different. And I think the other thing is you have to stand for something. I think where companies get lost with community is they don't stand for something. They don't have values. And I heard a CEO talk of a very large private company recently, multi kind of decacorn company. And he was saying that every single board meeting, every single all-hands meeting, they reiterate the company's long-term vision. and the company's 2 or 3 strategic things they're working on this year. Everyone knows, prioritize these 2 or 3 things, this is what matters most. And I think that really matters too when you're engaging customers and consumers and users. You need to know what the brand stands for. You need to know what their strategic vision is because oftentimes when I'm adopting a tool, it's a Series A or Series B company, I wanna know if, hey, if I'm gonna use this tool and spread it and be an evangelist, like where are you headed? I mean, do we have the same values? Do we have the same beliefs? In 5 years, are you headed in the right direction? Right. And so, so much of it is where you're going. And so you need to, you need to communicate that to users.
Yeah, that's awesome. This is really good, Zach. I appreciate all you've shared here. I think there's a lot of good insights for people to start applying.
Yeah, I've enjoyed it.
I'm excited to try it as well, some of these things. So, all right, ready to, ready for the rapid-fire questions?
Yeah, let's do it.
Yeah, let's do it. All right, Zach, what's one activity you enjoy outside of work that gets you into flow state?
I love hiking with my wife. Just being in nature, actually leaving our cell phone behind, really, you get in the flow state. When you get your heart rate up going uphill, you stop thinking and you're really present. Listen, I think we're all struggling to be present. We're all inundated with notifications, emails, tools all the time, especially as an investor, you're constantly getting emailed and pinged. Yeah, you got to get in a flow state. I'm glad you asked about that. I don't do it enough, but that's probably where I get in my deepest flow state.
Nice. Nice. Yeah, you got to find a way how to be hiking while you're working, and then you're always—
Exactly.
Zach, what's one piece of advice you wish you had known and would tell your— I'm going to change it to 20-year-old self, not 25-year-old self. What would you tell yourself?
So I started a couple of companies in my 20s, but I never really went all in on them. I only went all in on one where that was my full-time job. I stopped what I was doing. I wish I started companies all in throughout my 20s, every 2 years. In today's world, there's so much support for founders. Even if you fail, you want to be backed again, people want to work for you again. You just keep getting better and better, and there's never been a better time to start a company. So every other year, I wish I started a new company, a new company, a new company. If it doesn't work, shut it down, move on to the next, just keep going. Um, it's the most fun process in the world. It's, it's the most challenging process in the world. And I wish, uh, you know, I wish I did more of it. I only did it once. I should have done it 4 or 5 times.
What's, uh, what's stopping you from doing it now, right?
It's a good question. Well, I think the way to actually thread the needle as, as, as a VC is I'm actually working on an incubation project right now, which we can, you know, if, if we chat again next year, we can talk more about, um, in kind of the, the go-to-market space. So that's a great way to— I'm doing all the research, coming up with the branding, coming up, um, you know, kind of with the product with one of my colleagues. And, and that's a fun way to, to build something, um, you know, but also still be able to invest? Because I'm so curious. I love working with different projects and different founders.
Yeah, I think we're the same that way. I get you. Zach, what are some of the biggest challenges you guys are currently facing in order to continue to grow your firm, Wing Partner Capital? Meaning, if anything, what keeps you up at night these days?
Yeah, it's a great question. I think the challenge is how best can we serve our founders? And so there's trade-offs, right? I mean, we're only so big, we can only make so many investments. And so Do we invest more in resources for them to grow talent resources and customer resources and marketing resources and go-to-market resources? And what's the right trade-offs at the right time? The other thing is we have companies that are seed companies. We also have companies that we've invested in 7 years ago that are about to go public. And so how do we serve companies along the whole spectrum? And how do we really be the best partner to them throughout the lifecycle? It's a game of trade-offs, and we're constantly evolving and constantly trying to figure out how to get better.
Nice, man. Rooting for you guys.
Thank you. Root for you too, man. I've really enjoyed this.
Thanks. Who or what are best 3 resources? These can be books, people, mentors, or people you follow in the space who you'd say have been instrumental to your success over these last few years. I think you guys started back in 2013, right?
Yeah, back in 2013. Exactly. So I joined a couple of years in. So yeah, just so let's go through it. So a couple, couple resources. Actually, I gotta give a shout out to someone at another venture firm. I think Kyle Poyer of OpenView, he has some of the best content on product-led growth. He, you know, we've connected, we both write a lot about product-led growth, and we've compared notes. We hopped on a Zoom together for the first time a couple weeks ago. He's awesome. He's someone I really admire, someone I really respect. And in terms of content, I definitely give a shout out, check out my newsletter, which is a Substack called Notorious PLG. Every week we feature new content. And listen, I'm a student of this. I mean, part of what we do is we have a founder guest write every week. And so he or she's talking about what they do. And so it's a great— it's not me just pontificating, it's actually advice from real-world people. So every week you learn from someone. And this is the— yeah, this is the link here. And I'll say that, listen, I think I'm very grateful to have mentors at Wing. Peter and Gaurav, who are the 2 founders— Peter was at Accel for many years, and Gaurav was at Sequoia for many years before starting Wing. And listen, it's really important to have mentors early in your career, and everyone's going to have different mentors. But you got to put yourself out there. You got to ask to go out for lunch, ask to go out for coffee. And just ask questions and learn. So hopefully that's a good summary. Check out Kyle's work, check out my work to learn how some of these early-stage startups are doing product-led growth, and then find a mentor at your firm or outside your firm.
Absolutely. Yeah, we'll add those links to the show notes. I haven't heard of either of those, so I think that'd be great for people to check out. What does success mean to you today, Zach? Whether that's personally, business, financial, life, I guess no right answer. Yeah.
When I was younger, I used to think it was financial success is what mattered in terms of success. And as I've gotten older, that is probably like the 4th or 5th ranked thing. I think success right now is, listen, is pushing myself to be the best, is self-improvement, is growth. And also the founders I work with, I want my founders to be the best version of themselves. And so I constantly wanna push 'em. to stretch and to be out of their comfort zone and to, and to help evaluate their, their blind spots. And so I, I love challenges. I love, um, you know, discomfort. I love, uh, growth. And it's been— listen, it's been a hard 2 years for everyone, uh, with the pandemic and recession. And it's just— and so I think just constantly finding ways to worry less about what everyone else is doing and worry more about how I can get a little bit better every day. Actually, my favorite athlete is Tom Brady, and he talks about that. He just wants to be 0.1% better every day. And if you do that for 20 years, you're really incredible when the dust settles. And so, that's what I strive to do and just kind of block out the noise and just keep pushing myself. And that's where I get a lot of enjoyment out of, much more so than financial success or any other type of kind of You know, more, more material success measure.
Yeah, yeah, absolutely. I love it. Yeah, we'll do the— I mean, follow the path of the turtle, not the rabbit who's kind of— or the hare that, you know, goes different directions. So I just give— you know where you want to go, and if you're sticking on your line, you're feeling pretty good, right?
Exactly. And yeah, so that's picking markets you like, working with great people, and just keep learning. And that's why doing this weekly Substack has been super helpful, because every week I learn something. I mean, it's just— I feel so lucky to that people help me work on it and I can feature great founders in it.
Yeah, absolutely. Well, thank you, Zach. Where can founders, anybody listening, want to get in touch with you, learn more about you and your company, or if they want to maybe pitch their company for— if they're looking to raise their Series A or seed round?
Yeah, listen, any SaaS company I'd love to meet. My email is zach@wing.vc, or you can find me on Twitter @ZacharyDeWitt. And love to hear from you. Always, my DMs are open and certainly excited to learn what you're working on. I think it'd be great to connect. And I've really enjoyed this. You've asked very thoughtful questions. I've learned a lot from you and I've learned a lot from your content. And hopefully we can do it again sometime next year.
Yeah, absolutely. We will. Next one will be a challenge because I know you love challenges. So I'm going to try to put you on the spot and see what you do. Yeah, yeah.
Well, listen, if things are moving so fast, it's probably going to be the next You know, the next hot kind of growth category beyond community-led growth. So you can challenge me to try to articulate what's going on, what's going on, you know, growth channel.
I love it. Look forward to it.
Awesome. Thank you so much.
Thank you. Thank you. Thank you all for watching this episode and joining SaaS District today. Don't forget to like, subscribe, and hit the bell for future episodes where we interview top leaders in the SaaS industry. If you're a SaaS company looking to grow and unlock the true value of your business, get in touch with us at Horizon Capital and myself or one of our consultants will provide a free assessment to help you get there and hit your goals. If you have any feedback or suggestions for this podcast, please comment down below and help us improve our content for you all. Thanks again and see you on the next one.
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