Meet Your Members Where They Are with TightKnit CEO Zach Hawtof
Check out Good Talk to master the art of conversations big and small
Please support the podcast - subscribe on Spotify or iTunes or with a monthly contribution here, or a one-time donation here.
My guest is Zach Hawtof, CEO and Co-founder of TightKnit.AI, a platform for businesses that run their communities on Slack. He is also a community builder for people who do or who could potentially use his company’s product. He and I are both members of Fabrik, where I host a Founder’s Forum that Zack often joins.
In this conversation, we discuss community building, the difference between an audience and community, and how to introduce yourself (and get people to introduce themselves) at events. Zach also shares his philosophy on building and selling B2B SaaS products in the AI era.
One of my favorite moments in this conversation is this question:
What if you built your second company first — the one you actually believe in, instead of the one you'd build just to prove you could, or the rational play? The one that might create real impact, rather than just another zero on the balance sheet? Zach’s metaphors for this kind of business are just as human as he is: the Costco of B2B SaaS or the Corner Deli of Startups - a place you work with because you like working with them, and you get great service!
We also get into why you can't vibe-code your way to a real community or a real product. Since the tech is the “easy” part now, the actual moat is understanding why people don't do things. The founders who win are the ones who understand a problem so deeply that people trust them to solve it for them today and in the future.
I’m also grateful for Zach being willing and able to unpack his relationship with his co-founder Stephen, whom he’s known and worked with for 10 years.
AI can’t be your co-founder. Zach makes the case for something AI can't replace: a person who can actually say "in my experience, I think you should do this," and mean it. A real human co-founder, who will disagree with him, but can trust his gut and back him 100% anyway.
Zach describes his “butterfly” thinking style and contrasts it with Stephen’s “thinker” mode, and believes that their different styles give them more surface area for problem solving.
I think that’s still core, in all the co-founder interviews I’ve hosted - respecting and even admiring your co-founders' different way of thinking and approaching the world.
I’ve been able to piece together an interesting checklist for how to navigate co-founder disagreements from this conversation - especially when the conversation is about what to do now vs what to do later or what not to do - what I’ve heard described as the Woodstock Paradox: When the organizers of the first Woodstock concert were running out of time and money, they had to make a hard choice:
Build a stage and bathrooms so that they could actually have one of the best concerts ever
Finish building a fence so that they could charge admission to every person who showed up
They chose experience over profit and created a moment that defined a decade.
How to disagree (well) with your co-founder in Four Easy Steps:
Zach leads with the most essential check:
When you feel friction, slow down first. Tension is evidence of difference. Slow down so you can notice it - like walking to a location vs taking a bike or a car. Slowing down just a bit can make all the difference in the quality of the decision and the quality of the relationship after the decision.
The second is a simple idea that's hard to apply in practice: the reversibility check. If it's an irreversible decision, slow down even more and think a little harder. If it's a two-way, easily reversible decision, it's best to optimize for speed.
The third is a strategic check, a set of questions to suss out ROI: will solving this meaningfully move things forward for our customers? If we don't solve it, is it going to become our biggest problem later? This comes down to really being able to define the return on investment and work through the trade-offs with your co-founder.
The final check, which he doesn't mention in the opening clip - it comes up later in the conversation - is that the real challenge after feeling the friction, having the reversibility and strategy conversations…is that sometimes, if your co-founder still feels strongly about something, to trust that there's a real reason behind it, even if they can't fully explain it.
Making low-signal gut decisions is sometimes necessary, and trusting someone else’s gut over your own is part of being in a good relationship.
About Zach
Zach Hawtof is the Cofounder and CEO of Tightknit, a platform for businesses that run their communities on Slack. He is also a community builder for people who do or who could potentially use his company’s product. He’s a big lover of the darkest and driest stand-up comedians, snowboarding back in Colorado, and if there’s something on a menu that he hasn’t tried before, that’s what he’s ordering.
Links
Summary
[00:19] Why "founder" feels weird to say once you’re in the trenches — Zach goes straight to the facts ("I built a B2B SaaS company") rather than backing into it, and why "I'm starting a company" never quite stops feeling true.
[02:18] "What's your story?" — his go-to opener, delivered with a straight face, and why an open question lets people tell you what's actually on their mind.
[09:00] Building your "second company" first — choosing something on the good side of business over an AI dev-tool wave he'd have hated waking up to.
[10:19] Why you can't just vibe-code a community — anyone can build the tech now; the real moat is years of understanding human behavior and why people don't do things.
[12:51] The "conductor" — when everyone can build tech, the winner is the builder who understands the problem deeply and has a following, not the one with the slickest code.
[16:08] Location, location, location — the "meet your members where they are" mantra, and why he built in Slack instead of pulling people out of it. Plus the meme-curve of over-engineering a platform jump and the customers coming back to the basics.
[23:28] Chase the problem, not the solution — his number-one rule for founders, and the webinar/content playbook for starting a community from scratch.
[24:30] Audience vs. community — why they're not the same thing: an audience is the first layer of trust, but you only have a community once people are asking follow-up questions and want to keep discussing the problem.
[25:55] Step one vs. step two — prove it's a real community worth building before you pick a platform (the chefs are on Instagram, not Slack problem).
[29:40] Co-founders do what AI can't do — AI is great at transactional answers, but Zach doesn't trust it to have his best interests, and (no offense, Claude) it can't say "in my experience, I think you should do this." The value of a co-founder who actually disagrees with you.
[34:51] Key Co-founder Conversations: impact vs. value and navigating decisions— the Woodstock "stage or fence" decision as a frame for impact over revenue, leading into how he and Stephen navigate friction: move fast on reversible calls, think hard on one-way doors.
[43:37] Co-founder dynamics: the butterfly and the thinker — Zach the outgoing "butterfly" who speaks before he thinks, Stephen who thinks first, and why two different lenses give them far more surface area for understanding a problem than two yes-men ever would.
[47:28] Good person, good company — closing thought on building the "Costco of B2B SaaS," why you can't fake being a good person, and loving a company for the people behind it.
Transcript
Daniel Stillman (00:00): Welcome to the Conversation Factory.
Zach Hawtof (00:01): Amazing.
Daniel Stillman (00:04): Thanks for making time to do this, Zach. I appreciate it.
Zach Hawtof (00:05): Yeah, thank you. Thank you for having me.
Daniel Stillman (00:06): Okay. What do you tell people you do when you have to talk to them at the parties? 'Cause that's a — and, which is by the way a terrible way to start a conversation usually. In a party, "What do you do?" Like, there's some people who — that's their reflex. It's not the best.
Zach Hawtof (00:19): I definitely don't try to, like, back my way into it. I don't go like, "Oh, I help people build communities," and then people just go, "So what does that mean?" — because they have to ask that question. I usually just straight up say I'm a startup founder. I built a B2B SaaS company that then — I say — helps people build B2B SaaS communities. I try to just be super upfront about it. It's one of those — I hate saying, like, "I'm a founder." It doesn't feel right, I don't know what it is. It feels like an ego thing, like to say you're a founder is like, "Oh, wow, so cool, so noble." But I'm like, no, I really had to build this thing. And that's the title that they give you.
Daniel Stillman (01:00): So you go straight for the facts. But there's an internal, like, "Oh, it feels weird to claim founder" — although you are, in fact, the founder and CEO.
Zach Hawtof (01:07): And I still — it's very odd to say. Like, for a long time I used to say "I'm starting a company," but that's not true anymore. Now I'm running a company. And sometimes I do catch myself still saying "I'm starting a company," because it never feels like you're not. Like, we have a small team now and I'm like, it still feels like I'm always starting the company. You know, I came from Salesforce. That's an 80,000-person company when I left. That was like — yeah, I mean, in my head that's what, like, the size of a company is. But that's not true. That's a massive company.
Daniel Stillman (01:41): Yeah. Yeah, it's a massive company. Right. Not a startup anymore.
Zach Hawtof (01:45): Absolutely. So I think it was just kind of one of those, like, okay, I am always starting a company. I've come to realize that. And when I say "starting a company," people assume I just started this thing. But yeah, that's not the case.
Daniel Stillman (02:00): Right, which is why you don't say, like, "I'm starting a company." "I'm building a company."
Zach Hawtof (02:05): I say now — I say, yeah, I run a small team, basically.
Daniel Stillman (02:10): What do you ask people when you meet them at an event or a party? Like, what's your opener? Where to start a conversation is always, like, an interesting question.
Zach Hawtof (02:18): The first thing I always ask somebody is, "What's your story?" That's the first question I always ask. It says, I want to know who you are, but I don't want to give you exactly what I want to know.
Daniel Stillman (02:33): Now, how do you find people respond? 'Cause I actually — like, "Tell me your story," or "What should I know about you?" I ask sometimes. Sometimes people find these sort of open-ended questions a little overwhelming. They don't know — they're like, "Well, what do you mean?" So do you ask it... I don't ask it where —
Zach Hawtof (02:50): Sometimes I'd say, like, half the time I get, "What's my story? Oh, where do I start?" Right — that's so common, that's the answer I get. But yeah, then people kind of, like, stop, pause for a second, and go, "Oh, he's asking me one — either where I came from, how I got here, what I'm doing right now." And it kind of gives them whatever they want to be able to tell me about. And usually people have things that they want to tell other people about. You know, you don't walk in a room and there's not something on your mind. So it gives that person the luxury of — if they're open — I meet some people where 20 seconds in they're telling me, like, their top problem, and I'm like, that's awesome. Now we can jump right into it.
Daniel Stillman (03:35): Do you offer any help for them when they say like, "Oh my God, what am I — what is my story? Where should I start?" Do you say, "Start at the beginning," or "Start in the middle," or "Well, tell me the end"?
Zach Hawtof (03:48): I usually say, "Start where it's most interesting." And then, yeah, it's another open question — they get to choose. But no one thinks they lived a boring life in some way, right? Some people do, but everybody has something where they can say, "Oh, there's something that I can tell you about."
Daniel Stillman (04:07): That is — I mean, I think that's a very pro-social perspective. I definitely remember being at a party and this guy was like — I was like, "Oh, what do you do?" 'Cause he'd asked me, and, you know, to be pro-social. And I was like, "Well, what do you do?" He's like, "Oh, it's really boring." I was like, "I mean, everything's interesting." And he's like, "I work in finance," and he listed out a bunch of words that just, like, turned into, like, a high-pitched — I couldn't — I was like, okay, yes, you're bored by it.
Zach Hawtof (04:15): Derivatives. Tell me more.
Daniel Stillman: Yeah, but he was bored by it.
Zach Hawtof: Yeah.
Daniel Stillman (04:34): And so he thought he was boring. So obviously it's hard to tell a story that's exciting if you think it's —
Zach Hawtof (04:38): But that's the thing — that's why I don't ask "What do you do," or I try to avoid it, because I do think there's a lot of people that do think what they do is boring. But guarantee you that guy trades comic books, you know? I mean, that's not boring. I'm just saying there's something about that guy that says, "I wanted to make a lot of money so I could do X, Y and Z." And so — there's some, you know, I think a lot of people have something to prove. He's got something that he's still —
Daniel Stillman (05:12): Right, right. So the fact that his job may not be the most interesting thing about him. So his story could be like, "Well, I do finance full time, but my hobby is blank."
Zach Hawtof: Like, have I met truly boring individuals? Yes.
Daniel Stillman (05:15): You go to a lot of events, so your chances are higher.
Zach Hawtof (05:17): I have met people where I'm like, I really can't — I'm just, like, trying to coax out of them something where I'm like, I need to get out of this conversation. But very, very rare.
Daniel Stillman (05:30): Very rarely. Very rare. Well, so there's a couple things I want to accomplish today, and I'm going to follow your lead more than — because we know each other in the context of Fabrik, and we can talk about Fabrik. We can talk about the founders forum. But most of what happens in those conversations is bound by the Chatham House rules. So I want to be careful not to, like, ask you any leading questions.
Zach Hawtof (05:52): Chatham House rules on camera. Yes, carry on.
Daniel Stillman (05:55): Yeah, well — but you know what I mean. It's like, those conversations — [gesturing] over to the other room where we usually have the Forum. So those conversations are confidential. So, but — there's some things I'm curious about.
Zach Hawtof (06:11): I mean, yeah, but you can ask me, right? I'm not gonna bring up what others have brought up.
Daniel Stillman: No, no, totally. Hence the rule.
Daniel Stillman (06:15): Okay, that's fair, that's fair. So — well, I'll ask you your question, which is like, well, tell me your story. Wait — let me make sure. How do you ask it? Like, 'cause I think intonation and intention matter. So when you say "What's your story," you're saying, "So, what's your story?"
Zach Hawtof (06:23): Definitely — "What's your story, dude?"
Daniel Stillman (06:36): Or, like, "Oh, what's your story, man?"
Zach Hawtof (06:39): No, I think I say it as benign as possible. I go, "Hey, nice to meet you. What's your story?" Just get into it, 'cause you're —
Daniel Stillman (06:48): — an easy-going guy, easy to talk to, and —
Zach Hawtof (06:49): I love a straight face. Nothing like a straight face.
Daniel Stillman: "Hey, how's it going?"
Zach Hawtof: "Yeah, what's your story?"
Daniel Stillman (06:56): Yeah. Is that close?
Zach Hawtof: You even had more intonation than I give it, but close. Yeah, I mean, we have the Jewish singing-song thing, play a little too — I know, I know. I've been fighting it my whole life. So, nu. Yeah, I try to at least start — stop with the hand motions until about 30 seconds in, you know. But — where do I start?
Daniel Stillman: Where do you start your story?
Zach Hawtof (07:18): I mean, it's so funny — I'm a boring guy. No, I'm kidding, right? That would be — no. I think I start my story — I usually, like, depend — and this is the fun thing, right? — and I kind of know what I want to tell someone. But if I was, you know, meeting somebody and it was work-related, I know that they want me to actually get to the work-related stuff. Whereas if I'm not at a work-related event and I have to answer that question, I go — you know, I kind of tell, like, how I came to be. I was born in LA, I grew up in Denver, I went out to Berkeley for school. I, you know, ended up in computer science, went to San Francisco 'cause who didn't get sucked into it? And then said, "You know what, I gotta go try something new," because there's no good reason to leave San Francisco if you're in tech. And I was like, I gotta move to something. And so I thought I would go to Berlin. That was in early 2020. That didn't pan out. And then I was like, "All right, New York is gonna do." And here we are.
Daniel Stillman (08:20): So let's talk about why you started the company you started. And I'm also curious about this transition. My friend Alyssa Cohen, who I had on my podcast a while back, wrote a book called From Startup to Grown Up. And I think you're definitely in this interesting transition from the purely existential. I mean, obviously, as you were saying, like, every day in a startup is existential, I think. But there's this moment where you're like, okay, well, we have customers, we have a model, and now we have a team. It's a very different situation when it's just you and your co-founder, or just you.
Zach Hawtof (09:00): I mean, I think the reason we started this company versus any other company is I really wanted this kind of company to exist. I wanted to build something where I was like, okay, this is a company where I wake up and I go, "This is actually kind of doing good." This is actually a business where it sits in that realm of, like, the good side of business, and it proves that you can do business in a good way and still make money. I could have built an AI dev tool, and I probably — we would, you know, have caught some crazy wave, and I'd be waking up every morning and just diving deep into the chaos of, like, "Oh God, what am I doing?" And I didn't really want to do that. I think it was one of those — seeing the AI wave, I was like, you know, I definitely want to build a company, but I really love people. And it was going to be a painstaking journey to build a company that I felt, like, disagreed with some of my moral beliefs. And so I was like, okay, how do I — in a weird way, this is, like, what a lot of founders almost call their second company, right? They have the luxury to go and build that second company, the one they always wanted to build. And I was like, what if I tried to go build my second company first?
Daniel Stillman (10:16): I think that's very, very bold. I like that.
Zach Hawtof (10:19): Yeah. And so that was kind of TightKnit. It was this new B2B community. I really wanted to help build more community in the business landscape. And I was like, okay, there's an op here to do so, and I knew it from working in it for years at that point. The innovation had stalled completely. Honestly, it's even crazy to watch the way that — I think, in my opinion — companies are trying to layer on AI, and I still think it's stalled. It's funny to say, like, I think these AI features, they're cool to show in a demo, but a lot of them are not working in practice, if that makes sense. And this is one of those things where people are like, "Couldn't you just vibe-code TightKnit?" And I'm like, you could. You could totally build all the tech. You could probably try to get other people to buy your tech — they might not trust what you've built. But there is so much learning into, like, what human behavior you kind of have to pick up over years of, like, "Why don't people do X, Y and Z when this happens?" Like, what is creating a barrier for them to entry? I think the whole area of human behavior is going to have to be a growth side of the business world. Because it's also why I think enterprise sales is a fantastic job to get now. What an amazing relationship-building job at a company. Like, your job is to build relationships. That's your literal job. And you sell business as a side gig. Right? Like, if you can build a relationship, it's very easy to sell. That's kind of the new stance that I have — like, okay, I think if you're an engineer, you maybe go look at sales. Go sell a really technical product, because there's a lot of sales folks that have been in it that can't sell that product as well as you can, maybe. You understand it.
Daniel Stillman (12:23): Yeah. So let's — I feel like we should talk, like, maybe at a slightly more meta level on why community is a business, or an advantage for businesses, and also just, like, fundamentally essential and important. 'Cause I think you're a people person, but I think there's also — yeah, people who need people are all the people. And creating community around a product or a brand is maybe the only advantage.
Zach Hawtof (12:51): It's definitely one of the biggest, right? I have to look it up — I feel like this is, like, a Charlie Munger quote or something like that. But there's a quote that says, you know, all things equal, people like doing business with their friends. And so build a great product and make a lot of friends. And I think that same mentality to business goes — look, we're watching every month a new Claude or OpenAI update that beats the next one, beats the next one, eliminates the next layer of engineers. At the bottom tier, it's just eating up layer by layer of the engineering stack. So you start to go, okay, is technology as big of a moat as it used to be? No. Especially in the B2B app space — which is mostly object-oriented, very simple in its algorithmic kind of state. AI is very good at building B2B apps, we've learned. And that means now everybody can build tech. So if everybody can build tech, then who's going to win? Well, it's this — I call them this conductor — and this is kind of back to the community space. It's somebody who understands the tech, is a builder at heart, right? Can build, but is really good at building a following, and is really good at deeply understanding a problem — so much that people know that that person understands that problem deeply, and goes, "I don't want to vibe-code this thing. I want to put my money into somebody that understands it so deeply that I'm actually getting a higher return on investment than anything I could build myself." Because they're going to give me answers that I didn't even know I needed. Yes — because they're going to be thinking about this day in and day out.
Daniel Stillman (14:40): Yeah, well, I mean, you're speaking to something that's very important. You know, one of my first lives, or second lives, I don't know, was in user experience design. And you just live in edge cases and think about interaction models and information architecture. And I think someone can build sort of, like, "Oh, I want this to do that," or "I want this data connected to that data and make a dashboard" or something. And that's very exciting for them. But for someone to think elegantly through everything, and for someone to go, "Oh my God, I didn't even know I needed it to do that" — and it does — is magical. But I think there's another piece here that you're pointing to, which is, like, TightKnit builds on Slack.
Zach Hawtof (15:22): Yeah, we do.
Daniel Stillman (15:24): And you could just vibe-code Slack and integrate all the things that you think an online digital community should have. But I think you're also pointing to the reality that, like, Slack has a huge install base. It's in your pocket, it's in my pocket, and it's where people already are for business communities. And so why build something —
Zach Hawtof: Totally. Yep, it's in your pocket.
Daniel Stillman (15:54): It's hard to get business customers to — it's hard to get anybody. I don't know what metric you put on it. I think it's like, it's gotta be twice as cheap and, like, twice as easy — plus something else. Like, switching is hard. It's hard. I mean, you could — it'd be hard to go to a company and say, "Yes, this does everything, and this, this, this and this, and it's cheaper," and they still would be like, "Well..."
Zach Hawtof (16:08): I mean, it's this field-of-dreams problem. I went and built this amazing — like, you know, "Come to my restaurant, it's incredible." And the first question you go is, "Where is it?" Sometimes it doesn't matter how good the food is. It just matters, can I get there? And I think most people don't think about — it's the same with software. Location, location, location. I mean, it is our mantra — our tagline is "meet your members where they are." I actively do not try to build software that pulls your members out of where they want to be. People get this confused all the time. They think I wanted to build a community platform for Slack. No — I did the research and I said, oh, actually people want to be in Slack. So I want to be where they are. So I built a platform in Slack. The reason that I got to Slack had nothing to do with me going, "Oh, I'm obsessed with Slack and Slack is the future." It didn't start like that. It started with most people agreeing that Slack is the central forum for business, and I wanted to be the merchant hanging out in the central forum and selling to people where they actually were. And so I was like, okay, that same location, location, location mentality is so important. I run into so many customers — especially, I think this is — you've seen that meme at least, where it's like the people at the very beginning, and then it kind of goes through this chart, you got the overthinker, and then it comes back down and you end up with the genius who kind of ends up at the same level as the beginning. This is very related to community building, in that there's a lot of folks that start on Slack. It's very common — a very new community builder very commonly starts on Slack. They go, "Slack is not the right community platform for me, it's missing X, Y and Z." Right? They hit this new phase, they've learned what they want, they go and they try to jump to another platform.
Daniel Stillman: "I'm going to use Circle, I'm going to use Discord."
Zach Hawtof: Yes. Name a competitor of ours, go for it. There are many of them that work if you're going for people that live in those worlds. But if you're trying to, again, meet your members where they are, and make it as frictionless as possible to be a part of their day-to-day lives, you end up in this situation where, yeah, you've started to over-engineer — when you forgot that the real feature, the kind of unaccounted-for feature of a platform, is: how close am I? The location element of that. And then we get — I mean, I'd say 25% of our customers are customers that left Slack and regretted it and want to come back. And so it's this beautiful journey of doing it scrappy, falling into it, thinking that this is the right answer, and realizing it's all just about being scrappy and meeting your members where they are.
Daniel Stillman (19:31): Yeah. Right now, there are obviously some pluses and minuses to being an add-on to a platform. Like, there's some things you don't control. But it sounds like for you, the rational choice is the install base, the habit people have — like, Slack has just won the hearts and minds and pocketbooks of so many companies, that that's where professional conversations are happening already.
Zach Hawtof (19:55): And, I mean, you know — so here's a good way to put it. People call us an add-on all the time. But if I told you, like, okay, what are the top — I love this.
Daniel Stillman (20:05): Sorry if that's — I didn't mean to —
Zach Hawtof: No, no, no, no. You hear it all the time. And I want to — we are almost an add-on. I like to say we're an add-on that gives you full enterprise community capabilities. And we charge that way too, right? We have a low plan that starts for kind of smaller customers, but we can actually support, you know, your top B2B SaaS businesses. But here's a good example of, like, another add-on. Honey is what I used, you know, four or five years ago — coupons and all the things online and digitally. And the thing that I then ask is, okay, was there another couponer? And I couldn't really think of one that wasn't a Chrome extension. Every single one of them was a Chrome extension. And you start to go, it had to be a Chrome extension — because that's how I shop. And you start to go, okay, how do I communicate? Well, that's in Slack and WhatsApp and text. And I go, oh, that's where the community has to be in some sense, because I live there. And anytime that someone makes a community outside of that, they're putting the onus on me to have to go to them. It's so frustrating. I get so frustrated when people think that I want to go to their community when I haven't ever been before, and they're saying how great it is, and I have to just crawl through the mud with my logins and my emails. And I'm like, I have enough emails, I have enough logins, my 1Password is a mess, it's everything — and now I have to do one more, and I have to remember your URL. There's so many things that I feel like — why did you — it depends on the community, of course, but sometimes it feels a little rude.
Daniel Stillman (21:58): Well, so we have our friend in common, Carrie Melissa Jones.
Zach Hawtof (22:02): Yes — who quoted you in her post about our CLG. I was obsessed with that.
Daniel Stillman (22:07): No, Carrie's the best. I did, like, a three-part interview with her, because she obviously is a wonderful authority on community. But —
Zach Hawtof (22:14): My God, she — I took, like — we've been — I've been using all her little, like, ideas on that post. I've been like, "I'm stealing this, and stealing that."
Daniel Stillman (22:21): She's got good language. And she did talk about this physicality of, like, the onboarding, the whole customer journey. And I think it sounds like you also have a very strong mental model of the piping, the levers, the sort of force fields that are guiding community. And maybe we can talk briefly about what your mental model is about community — why people, what some of the mechanics are of how you think about community that the sort of normal tools don't do, that help make community actually a community.
Zach Hawtof (23:00): I mean, I try to —
Daniel Stillman: He said, putting his fingers — for those people not on video —
Zach Hawtof: Do we narrate our hands? You and I are hands talking. How do you do an audio podcast? Okay. So I would say, I usually tell founders to chase the problem, not the solution. That's, like, my number one rule. Like, you got into this business to solve a problem — you're getting into solutioning very quickly, I can tell.
Daniel Stillman: There will be clips, so —
Zach Hawtof (23:28): And what if you took a step back and said, "Let's go chase the problem." Let's go find the problem. You have half of it — let's go find the whole thing. And so I think that's the thing that really helps, especially if you're building a product community. And this is the thing — there's different types of communities, right? And there's different goals with each one. But I run into a lot of product builders, and these product builders are chasing a problem. And so I say, build around that problem, go and teach people about it. You have two choices. Either you're an expert and you can teach people, or you better know the experts, and you better be able to bring those people in to talk about the problem. And so that's one of the best ways to start a community — to go and create a space or a piece of content that is kind of an amalgamation of all the things around the current state of that problem. And so go find three people that are experts and say, "Hey, I'm going to set up a webinar. I really want to discuss this key problem in this key area. I'm going to do all the work, I'll send you the assets so you can share it to your social, we'll make clips for you," and you give them enough time as well to do it. And you really promote it in all the right channels, and you try to find people that are interested in that problem. And it better be an interesting problem that people care about, because that's what gets them to come to your event. And that's a good way to start it. Or you build a piece of content around that. So you've interviewed people, you've written a piece, you've created a video — and that is another great way. So it does start a little bit with this whole audience-building, right? I do think there's a difference between an audience and a community, but it's very helpful to have an audience in order to build a community. It's that first layer of trust — that you know what you're talking about, or you know people that do know what they're talking about. That's a big one. And then once you can get past that layer, you kind of have to evoke the "what's next." Like, by the end of that piece of content, or the end of that webinar, if people aren't asking follow-up questions, you haven't found the right problem. That's not a problem worth solving, then. But if people have follow-up questions and they want to learn more, and they want to discuss that problem and they have things to say about it — that's a great community.
Daniel Stillman (25:52): Yeah, then there's energy. It's not a push, there's a pull.
Zach Hawtof (25:55): Yeah. And, right — it's not just products, right? It can be about roles. We run into a lot of communities that are built around, like, a role, an identity. We have a lot of — especially Americans, more than anybody — have a lot of identity in the role that we have at work. And there's a lot of communities built around that. There's virtually a community — I run into almost everyone for every single role. And if it doesn't exist, go start it. Because there's a lot of people who love that job and they want to be able to discuss best practices. So anyway, that's my, like, starting-from-scratch, very beginning. A lot of people get into, like, "How do —" and this is so funny, having a platform that sells gamification and all these onboarding things, I'm like, that's great, I'm step two. I really am step two. Step one is proving this is a real community worth building. Step two is choosing the platform that fits the community that you want to build around. Too many people start the other way around. They start with the platform and they go, "Why are my chefs not joining Slack?" And I go, look, you never should have chosen me for your chef community. Chefs are in Instagram. Go to WhatsApp — a lot of them are international. Like, what are you doing on Slack? But if you're building a community for B2B SaaS marketers, and you're in, you know, Discord — and most of them maybe are 35, 40, primarily female audience — you should not be in Discord. You know, it's like, you really gotta meet your members where they are.
Daniel Stillman (27:30): So it sounds like, in a way, the initial spark has to be based on something real and durable, like a real desire for people. But then there's the second part, which is, like, the mechanics of onboarding and connecting people. And Slack doesn't help people connect. It's just threaded messages.
Zach Hawtof (27:53): Right. I mean, it is a tool that humans use to connect with each other. It is just a tool. It's the phone. It's whatever we can do to connect with it. Like, since the beginning of time, every time there is a new piece of communication tooling, we kind of level up in some way. It just always happens. Once we could have carrier pigeons for the first time, we could warn each other about incoming hordes, right? Like, what a wild concept that was. "Oh my God, I know when the soldiers are gonna hit the fortress. Oh, crazy." But every step, we keep going up and up. But at the end, it's always just humans. Cave art was — "watch out for the cliff at the edge of this, you're not gonna see it." So, yeah, there's all sorts of little communication habits that we've formed over a million years.
Daniel Stillman (28:31): People like to talk. People like to talk. And we can leverage that — we can make certain things easier and make certain things harder. So — we only have a little bit more time, which is shocking.
Zach Hawtof (28:56): Wow, look at that. We got, like — yeah, we got 15 minutes.
Daniel Stillman (28:59): We're chit-chatters. Fifteen minutes. So, like, one of the things that I really wanted to talk about is that — you know, there's the what you're building and the problem you're solving, but then there's the who you're building with. And that's sort of like — you know, they say, if you want to go fast, go alone; if you want to go far, go together. And I feel like — I literally saw a Reddit post where somebody was like, "Is it worth finding a co-founder?" And a lot of the people on the thread were like, "No, it's just so much — you know, just hire people and own everything yourself." And then one person's like, "Well, actually, it's really hard to get someone to care as much as you do about this problem." And so I think there is this idea that obviously other people are hard — but also, when there's a situation where working with another co-founder can be exponential.
Zach Hawtof (29:40): Yes. Absolutely. I mean, just like — I went to the Grand Canyon two weeks ago, hiked into the Grand Canyon. I would have had a very different mindset walking into completely no signal for a day and a half if I knew that I didn't have somebody there to help me and to lean on. And, you know, when they're gone — like Stephen, my co-founder, who's been with me since the beginning — it's very nice to be able to bounce these ideas off of, and to ask, when even you know the answer, to be able to just validate, like, "Is this the right thing to do?" Because while Claude is very good at, like, helping you solve an answer, this comes back to why community is never going to go away. AI is incredibly good at transactional experiences. "I need something solved, I need a problem answered, I need something." But when I don't know the right answer, and it's not a fact, it's more of an advice — it's not particularly good. Because it can't say these words: "From my experience, I think you should do this."
Daniel Stillman (31:14): Right, right. What's important about that to you? Say more about that, that's really interesting.
Zach Hawtof (31:17): I don't trust an AI to have my best interests.
Daniel Stillman (31:23): It's funny, 'cause you can ask it to be slightly less sycophantic — which I did recently when I was starting up a new skill in Gemini. I was like, "Hey, by the way, going forward, can we give me feedback in this way?" And it was like, "Great point! Thanks for giving me feedback about my feedback." I'm like, tone it down, buddy.
Zach Hawtof (31:47): God, what a loser. And you know what's so funny? People get — this bothers me. If I call AI a loser, there's about 10% of the room that goes, "Don't do that." That concerns me. Because obviously it's a joke — I could never attribute — I'm not calling your computer a loser. You wouldn't be offended by that. It's just a computer, it's just a machine. There's this problem of treating a machine that is algorithmic by nature, that is being trained to feel and sound human. And as soon as you start to question that, and you start to question, "Is it an algorithm?" — you start to go, "Maybe if I do call it a loser, it will be offended."
Daniel Stillman (32:32): So, in a way, it sounds like you're saying, like, with Stephen you can complain, you can yell — I mean, but he's a person, so you have to treat —
Zach Hawtof (32:42): He's a human being. He's a good guy. He has good opinions. He has real opinions formed from, like, his experiences. And he has my best interest in mind. I know that.
Daniel Stillman (32:56): Right, which is real. You and Stephen have what we would describe as an actual human relationship, where he disagrees with you sometimes and agrees with you other times, and that actually makes you trust him more.
Zach Hawtof (33:07): Yes, totally. Like you said, it's the sycophancy of, like, trying to make me happy in the weirdest way of, like, "Oh yeah, if you really insist, then I'll go with what you suggest."
Daniel Stillman (33:18): Well, so how do you two manage? I mean, 'cause I guess my mental model is — given that you have a certain view of community from, like, the mechanics perspective —
Zach Hawtof (33:31): Yeah.
Daniel Stillman: — things a system must do. Like, when you think about the system that is you and Stephen doing this thing together, what do you think are the structures and systems that make it possible for you to get through difficult conversations? Or do you just vibe-code it? You know, is there a way you look at it, or think about it, or talk about it? Are there structures and systems that you have to work through some of these things?
Zach Hawtof (33:53): Ooh, that's a good question. I don't know if I could even properly explain it. He and I have known each other for a decade. So there's a lot of just, like, unspoken trust of, like, you know, the long-standing relationship elements to things. We kind of, like, know when to back off of each other in some ways. Like, he knows when — if, when something needs to get done. And he knows, like, okay, Zach has some reason, this is important, and I should probably help him go accomplish it. And I know when Stephen says, like, "No, no, we really do have to do this before all the other stuff," I go, "Okay, let's try to find a way to fit it in." But I don't know if — you know, I think it's all back to communication and being able to have that trust to be able to speak to others. But I can't — I couldn't put a finger on the pulse of how it actually works with the two of us.
Daniel Stillman (34:51): Yeah, that's really interesting. So there's a couple of things to peel apart there. One of my favorite stories is, when they were building Woodstock, they ran out of time and money. And there was this sort of, like, "Okay, we can either build a stage or a fence." And it's like, if we build a fence and no stage, we can charge for the show, but there's going to be no show. And if we build the stage, there'll be a show, but we're going to lose a lot of money.
Zach Hawtof (35:17): And they built the stage.
Daniel Stillman (35:18): They built the stage, and had one of the best shows ever. And maybe they didn't make as much money as they could, but —
Zach Hawtof (35:25): There was not a second one, was there?
Daniel Stillman (35:28): I mean, there was — there was Woodstock '99, which, you know —
Zach Hawtof (35:30): — which is terrible. You know, this is a different way to put it, in some ways. Like, would you rather be — there's some companies out there that have more impact than their revenue. I think about Wikipedia a lot. I think Wikipedia is, like, a company that I admire. What an incredible story. People made some money on it, but not that much money. No one is a billionaire because of Wikipedia.
Daniel Stillman (36:00): But not, like, democracy-damaging money — which is fine.
Zach Hawtof (36:04): No. If anything, what an incredible feeling to be able to have educated the world, right? And I think those are choices you make. You can build companies that make more money than their impact. You can also build companies that make more impact than their money. And it goes back to the same thing with Woodstock. I mean, here's one way to look at it: they might not have made that much money, and they probably could have made more money — and none of us would be ever talking about that concert for the rest of our lives.
Daniel Stillman (36:35): The reason I brought this up is that it sounds like you and Stephen have what I think is the sort of, like, stage-or-fence conversation of, like, "What is actually the thing we need to do first?" Stephen's like, "No, Zach, I know you think this thing is important, but this thing is actually slightly more important." And so it sounds like you do have conversations regularly about what goes first, what goes second, what needs to wait, what needs to happen now. And it sounds like some of that is just through trust and listening a little bit more deeply to somebody's reasons.
Zach Hawtof (37:10): I think Stephen also knows I am an obsessive voice piece for our customers. A little bit too much at times. But, like, I obsess over how many features we're building that work for our customers, not from us. And I think that's always the right way to build. And I think it's, like — you know, again, it goes back to the conductor. Your job is to be an incredibly good listener and synthesize all of this into a product. You have to have good taste. You have to be able to actually take five ideas and understand it's just one with, like, a few toggles, and be able to turn that into something meaningful. And I think that's hard. It's something you kind of learn over time — of, like, when to say not "no," but kinda. Sure.
Daniel Stillman (38:03): So if you were to write a manual for how, like, to take the best aspects of how you and Stephen work through the "what should we do now versus what should we do later" conversation when you hit friction — what do you think is the sort of, like, the mantra, or the steps?
Zach Hawtof (38:17): When you hit friction, I think you do have to take a quick second and a step back and say, okay, if we do solve this problem, is it going to meaningfully help our customers move things forward? And then, if we don't solve some technology-platform problem, is it the same with the flywheel? Is it — can I trace it back to the problem? Can I say that if I don't solve this, it's actually going to become our biggest problem? Or, if I solve this now, is it going to save the team 10% productivity for a year?
Daniel Stillman (39:07): So it sounds like two things I heard, which is really interesting. Which is, like, when you feel friction, slow down a little bit — which is great. It's like a signal to say, "Okay, wait a minute, we think differently here." Sounds like the second step is then to say, bring in a little bit of objectives and key results here. And say, like, what is the real —
Zach Hawtof (39:20): Don't overthink two-way doors. You know, there's that one-way-door and two-way-door thing. Identify them quickly — if this is something you can undo later. And then make really, really quick decisions on two-way doors. And think long and hard about, "Is this one-way door going to be the right move for us?" I can tell you, like, we are a community platform built for Slack. I don't know if that's forever. Right? We've always used Slack as, "Why don't we take the stairs instead of climbing the mountain?" That has always been the attitude for us. But we're still hitting the top. And I know that we're going to have features and platform functionality that don't have anything to do with Slack one day. And I think that's the one-way door that we say, "Okay, how are we building around this solution, knowing where we're still going at the end?" We had multiple doors to get there when we decided, "Let's take the stairs."
Daniel Stillman (40:30): Boy, it's so funny. Just as, like, a tiny little side note — one of the things that I learned as a facilitator, you know, running offsites and team gatherings, is: literally getting people from one room to another is hard. Like, people are not — even in Zoom it takes time to get somebody from one digital room to another. And even if everybody wants to go from Slack to someplace else, and they say, "Yes, I'd like to go to that other room," they're going to get lost in the hallways. Like, you're going to lose them. This is why — if it's something you're thinking about — people are like a fluid, it's like a — there's a lot of friction in the fluid.
Zach Hawtof (41:07): There's always friction in tech. To get anybody into tech has a lot of friction. And so, again, why make more than less, you know? Slack is not easy for some people. It's one of the easiest apps in the world, and yet it's still not easy for everyone. And I hear it all the time, like, "Oh, I'm not sure our audience is going to be — we have an older audience, and I'm not sure they're going to be able to get into Slack." And I'm like, your alternative is easier. And then they start to go, "I guess you're right." And so this is a very funny reality of almost all software: you're trying to pick the best of the worst in almost every category. Most of us wish we could just live our lives and software solves the problems for us. That's the dream of what AI is supposed to solve.
Daniel Stillman (41:53): Well, I gotta say, you're the most optimistic pessimist I've ever heard. This is really amazing.
Zach Hawtof (41:57): I mean, that is kind of what I am. I'm an optimist. I actually do really believe that AI is going to solve immense problems, create immense problems, and then solve them again.
Daniel Stillman (42:07): But there's this, like, fundamental — I wouldn't say Jewishness of your, like, "Well, things are hard."
Zach Hawtof (42:12): Totally. I mean, it's a hundred percent — shit's gonna get bad, it's always going to be better in the long run. It's one of those. We don't realize that, as time has gone on, the problem is that our ability to communicate has actually created this weight on us. But the whole world, everybody, is getting a little bit better, step by step. And we just can't see it, because we're so in it. We can't watch grass grow. And that's exciting to me as an optimist. But the pessimist is that the lawnmower keeps coming out, right? And so it's hard to see it, because it's growing taller. But every once in a while, patches form.
Daniel Stillman (43:04): So we really — you're gonna have to go in moments. We have, like, probably time for one more question. And I would love to see if I can squeeze any other co-founder-dynamic wisdom from you. 'Cause I know you've talked about, like, the different roles you and Stephen have — in terms of, like, the driver, or the creative, or the visionary, or the dreamer, or the doer. I don't know how you would sort of think about how the two of you work, and how you fall into those roles, and if you intentionally try to step out of them in any way, or —
Zach Hawtof (43:37): Yeah. I mean, Stephen and I have very different personalities. I am an outgoing little butterfly of, like, trying to meet as many people as possible. But I'm a butterfly, you know. And he is a thinker. He — I speak before I think, and he thinks before — you know, he thinks first. And we get frustrated with each other, right? Because of that. We have very different approaches to solving a problem. But at the same time, we're coming at it from two very different lenses. So what's nice is we have way more surface area of understanding a problem. If I was working with another yes-man founder — because I'm a yes-man, I love to say yes — that would be very tough for me, because we would conflict on what to say yes to all the time. There'd be too many ideas on the board. There'd be so many things that we would be fighting over, because we would both want to be the yes-man. And I think it's one of those things — to find a co-founder that is going to complement you. And to be able to be — we both want the same wins, we just solve it in different ways.
Daniel Stillman (44:56): Do you think you've, like, learned to not just value his cognitive style — do you feel like you've learned to play the other side of it? And if we talk about, like, the sort of deep generative versus analytical — I don't know how we would divide it, but it sounds like there's a polarity here where it's like, there's good aspects of both of your approaches, and there's downsides of doing one versus the other. With regards to, like, if you only spoke before you thought, there are minuses. If you only just said, like, "We're gonna meet the customer, we're gonna meet the customer," versus, like, "How does this work and what's the strategy?" — there's an interplay. I think what I've heard a lot is that there's a deep respect for the other person's mode of thinking. But I'm also wondering if it's sort of, like, not just respect — if you've learned to sort of inhabit his way, or vice versa. If that makes —
Zach Hawtof (45:52): No, it's good. I think — I mean, I think you have to put yourself in someone else's shoes, right? With any conversation, the "What's your story" is going to all come back and say, "What do I want this person to tell me in some way?" How do I build enough trust that they trust me? And genuine trust — that's the thing. I think there's just — to kind of close it out — like, you gotta be a good person to build a good company. It's very hard to fake being a good person now. And I think we've been sold a little bit of this lie from the current founders of these big companies that I can't imagine are that pleased with themselves in their current lives. And it's hard to fully admire them because of the way some of them have just kind of fallen from grace. So if you can be a good person, build a good company, and maintain some semblance of "it's not all about the money" — and, like, I think, you know, lean into that. Build — I like to build the Costco of B2B SaaS. I'd like to be the company where it's like a corner deli. I go in, they know my sandwich order, or they just have the products that I love and want. And I have this association that goes, "I love that frickin' company" — not because of the company, because of the people that they hire and what they represent.
Daniel Stillman (47:28): It's not just the naan dippers, which are great at Costco. It's everything. It's the whole gestalt of it. Well, that's a really — boy. You can't build a beautiful — a real company without being a real person. And I think that's a great place to close. Where should — I mean, we're going to put all the links, and people can go to TightKnit —
Zach Hawtof (47:34): Yeah — TightKnit.ai. I send people to our community. I say, go to community.tightknit.ai if you want to learn how to meet, you know, a thousand-plus B2B SaaS community managers that are solving similar problems, getting started just like you. And that's where I send most folks, because my website is just static content, but my community is a dynamic place that is full of humans solving the problems that people want to solve. Boom.
Daniel Stillman (48:19): Well, I think we can call scene. It's 11 o'clock. You've got some place to be! Zach, thank you so much. This was really fun. I'm really glad we did an in-person chat. It's been a real pleasure.
Zach Hawtof (48:22): Love it. Yeah, I gotta jump to the next one, but thank you for having me. Me too.