385: CommandBar: Mastering Cold Emails to Grow a 7-Figure SaaS - with James Evans

James welcome to the show thanks so much for having me do you have a favorite quote something that inspires or motivates you that you can share with us I don't have a quote but I have the modern equivalent which is a YouTube video uh it's a Steve Jobs interview very on brand for founder to choose I love this video so much that I quoted it in my wedding vows believe it or not and I'll try to yeah know right uh I'm a fun guy I'll I'll try to summarize it I'll probably butcher it everyone should

just go watch the video but basically Steve Jobs talks about how there are two people two types of people in the world people who sort of play the game of life that's given to them so sort of the quests of like rising in the career ladder saving a bit of money going on increasingly you know nice vacations giving their kids a get education stuff like that and then there's another group of people that sort of pushes against the walls of the game and realizes that all the stuff like all the the items in this Quest

and the quest themselves were created by people who are no smarter than they are and really like no different fundamentally you know maybe different circumstances but fundamentally exactly the same type of person and it's not really like of course like a lot of people see that as a call to Arms to like be a Founder create products create companies like influence the way people live leave your mark upon the world I don't think it like needs to be that like I don't think everyone should be a Founder but I think it is really empowering to

realize that like everything you experience like the wallpaper the uh you know the rewards program on your credit card like all that all those things are created by people that are no really different than you are and you can be one of those people if you want to be yeah yeah I love it uh I I I know the video you're talking about I haven't seen it for a long time but when we publish this we'll include a link to the video where will'll embed it obviously after your video that will come first okay uh

so tell us about command bar what does the product do who is it for and what's the main problem you're helping to solve so we call command bar a user assistance platform which is a three-letter or three-word phrase that we've agonized over and we've used a lot of different ones over the years user personalization platform ux optimization platform but we've stuck with user assistance platform but I realize it doesn't actually describe what the product does the context oh I'll get into that but the context for why we exist is I think it's pretty crazy that

like we have these things called computers that make us like so much more productive and give us access to like the entire sum of human knowledge imagine explaining this to someone from like 200 years ago we have these magical things but a lot of the time like the way we interface day-to-day with computers like the net experience we have is frustration is the frustration of like I want to make the computer do something I have some intent and I have to translate that intent into the language of the user interface the key strokes the you

know which file which menu do I click on which tab you know what is the feature I want called and so we end up getting really frustrated so much so that sometimes we like do this thing called rage click where we like jam on the mouse because we're so frustrated and that has always like been a very weird Paradox to me like these computers are so powerful and so magical yet so much of our experience with them is frustrating and the best solution that has existed for a while to sort of help users use software

and help users learn how an interface can be useful to them are popups those thing you know those things that show up in interfaces that are like we just launched a new feature or like you seem new here take a tour those never really felt like the Pinnacle of user experience to me so much so that I think like most users just dismiss them they have you know fatigue or blindness for those types of experiences and so they don't end up actually being very helpful okay so what is command bar with that context command bar

is basically a platform for other software companies to make their products easier to use that are uh through the form factors that are not just annoying untargeted popups so we have a variety of ways that product teams customer teams marketing teams can embed experiences into their products that can help users in a personalized way all the way from kind of a natural language co-pilot interface where user can just sort of describe what they're trying to do and get a kind of personalized walk through or have the co-pilot actually just taken action for them to nudge

that show up in the interface kind of guide a user to what they're trying to do and give us a sense of the size of the business where you in terms of Revenue size of team number of customers and all that yeah so we're about uh I think 40 people we've raised like 24 million uh so far in a couple of rounds seven figure AR business uh been going for a little over three years and in terms of uh users or customers uh hundreds of customers so far Okay cool so I I think one of

the the things that when I heard about command bar I should say command bar my British accent is still can't shake it off completely but when I heard about it I imagined you familiar with Alfred right or raycast or something like that right so I was like a command bar right and I think it might make a little bit more sense when you talk about the story of how you guys started and what the first version was and I think basically with if I had to describe it today it it sounds like you're you're kind

of helping with some kind of user adoption type stuff it helps some with onboarding it can be helping help people with support so there's a whole bunch of use cases that command bar and can help with uh one thing I wanted to try and understand was when you said that you you you interface with other software products and let's let's take the example of like a chat widget or something like that are you are you powering their chat Widgets or are you the chat widget and everything else that happens behind there like I I was

just trying to understand like where where do you draw the line in terms of what's their product and what's your product it's a it's a great question yeah so the the physics of command bar we are a layer on top of our customers products so most of our customers are software companies you know we work with web apps mobile apps desktop apps some websites as well you don't have to like identify as a software company to use command bar um and we actually are you can call them widgets we call them experiences users interact with

those directly so another way to think about command bar is it's a product for any team at one of those companies to shape user experience without having to go through the kind of standard engineering flow we're not trying to be like a no code app builder there's tons of stuff that I think you know should be built by engineering the kind of epd team at a software company we're trying to peel off what we call the user assistance experiences so that could be a nudge that could be Spotlight search we actually call we've started calling

the original product that you alluded to Spotlight um so similar to Alfred our copot interface these are experiences that users interface with directly and then teams can shape without having to write code um and we just feel like we felt like there was an opportunity to kind like I said peel off this assistance layer that's relatively or we think should be relatively consistent across products and then tell us a little bit about co-pilot because I watched a a little demo you put together about that and I think people might hear what you're saying and say

well that sounds kind of similar to some other products that maybe I've used for onboarding support blah blah blah whatever I I think co-pilot kind of took it a little further so just just explain that a little bit in terms of what end users can start to do yeah so co-pilot is our newest product and and it looks very much like a chatbot and like kind of the the basic physics of it are very similar to a chatbot the key difference between co-pilot and a chatbot in our view is that we refer to co-pilot as

a quote unquote user assistant not a chatbot what does that actually mean we call we call our product a user assistance platform so it's like pretty high praise to call one of the products a user assistant the big difference is uh we don't think responses the most useful responses are often not textual in nature so imagine with a chatbot you ask a question like how do I create TPS reports in some B2B app that your employer is forcing you to use the chatbot there's like a zillion of these will probably answer with like a list

of 14 steps in in a good in a good case you know first you go here then you do this a bad case it might just say like oh here's an article you should read about that topic well that's like a lot of work like in our experience users really don't enjoy like reading multi-page manuals for doing kind of flows that they think should take like 30 seconds and so what is C co-pilot approach that problem if you ask that question to co-pilot yeah it can respond with a text based answer if that's how the

company Tunes it or if co-pilot thinks that's the best way to respond but it can also it wields other tools so one tool it wields are walkthroughs so instead of here's steps 1 through 14 oh it sounds like you're interested in creating a TPS report click here I can show you how and then it's going to looks and feels very similar to a product tour but it's initiated by the user asking a question and it's personalized for them where they are in the product what features they have access to Etc another thing it can do

is take action on behalf of a user and that could mean completing a flow end to end or it could mean starting a flow so going back to the TPS report example I want to create a TPS report okay great what do you want to call it do you want to copy the one you made last week and then that could either take the user where they need to go to you know finish completing the report or it could just ask them a series of questions to complete the report for them using the company's API

so it's basically like more helpful than a chatbot the mental model we have for how a user assistant should work is imagine you had a human like imagine every company every software company employed human user assistance and they would send them you know as part of the package you sign your 100K Enterprise software deal or whatever as part of the package every user gets a human user assistant who shows up at your house or your office and whenever you're using the product is kind of leaning over your shoulder there to answer questions if you go

off track oh NOP are you sure you want to go there that kind of mental model is how we want co-pilot to feel for end users so where did the idea for this come from Yeah you mentioned you mentioned our original product earlier the name command bar is kind of a vestigial name it refers to our original product the command bar so the context was we my co-founders and I Richard and benene we were working on a completely different product it's one of these classic you know working on one thing uh dog fotedar is today

we were a team of three uh we were really good at talking to users and we we basically built anything they asked for for that product you know uh there were a ton of feuture requests and we saw our only competitive Advantage was just like speed and so we built everything users asked for and so pretty quickly like the product became really topheavy no one was using all the features uh people were struggling with like basic flows we getting a ton of support requests and so we really didn't want to like redesign our UI from

scratch we felt like that's what like big companies do constantly re you know redesigning their whole UI taking account all the jobs we've done Etc we wanted like a relatively quick solution uh and so at the time there was this pattern called a command pallet which was like sort of becoming popular in some apps it was it was most popular in Dev tools like Sublime and vs code there were some products like superum and linear that really leaned into this this Paradigm this is the interface you can trigger with command K in these products and

we thought this was like a really great idea for our situation because it would allow us to create create one interface one like escape hatch where if a user on our product is trying to do something they could just like type what they were trying to do and then we could route them in the product where they could go to complete the thing they were trying to do they could use their own words as well they wouldn't have to learn like our vocabulary and so we built uh a command pallette for our product and it

worked amazingly and it had all these like cool side effects like for example we started getting all this amazing data about what users were trying to do in our product because they were telling us in our own in their own words in the search bar their intent um and we got just super fascinated by this idea but it felt like kind of a weird like comp like idea to turn into a company like are you really going to create like a component as a service and like put it in other people's front ends like it

just didn't feel like kind of a normal company or normal software structure and so we basically treated YC as like a good idea Oracle which I don't recommend doing by the way like YC is not going to tell you if your idea is good but in our case like we just needed a nudge to like start working on the idea so we wrote up the YC app for this new idea command bar the command bar and then once we got into YC we started working on it uh well let's talk about the first 10 customers

what did you what did you do to try and one like validate the idea you said you were talking to users and adding a bunch of features so you you you joined YC at what point for how long did you keep selling this kind of version of the product and at what point did you you sort of realize hey this isn't quite the right product or Market or whatever and we need to we need to change things so just just tell us about that process in terms of figuring that out validating the initial product and

kind of on the path to those first 10 customers for sure so we entered YCA with like basically nothing um which by the way for people I think sometimes there's a misconception that like YC only accepts products or companies with like meaningful traction definitely not true we had zero traction we just published our YC app and like the answer to the question of like how much traction you have is awful it's like oh we have four companies committed to using command bar in fact like one of those four companies ever ended up using command bar

and they didn't even pay us anything so like want to dispel that misconception so we showed up with nothing we just started we just started building quickly and like trying to get other people in our batch to use it that was one of the things that excited us YC is we were like oh there's a bunch of software companies in YC we can probably get them to use command bar and it went really well in the batch like we got our first 10 customers were all came from our YC batch they weren't paying us very

much it was like 50 bucks a month 100 bucks a month but it definitely made us feel like okay this has some legs so the the problem with these wedge products they're great in the sense they're narrow um clearly defined the problem is in our case like at that time summer 2020 no one was like waking up no product manager was waking up in the morning going today I'm going to look for a vendor that makes a natural language search bar as a service no like head a product was delegating the task of assessing natural

language search bar as a service vendors to like someone on their team so we had to create both budget but also time for people to like understand our thing and be like yeah this is something that I want to experiment with because at the end of the day like every novel Mouse trp company starts off in the mind of a buyer as an experiment like I'm gonna try this see if it works because it's not a proven thing and we would have like you know early conversations with people who found the idea interesting but um

sometimes they wouldn't go anywhere at this is sort of like to the towards the end of YC and the solution we found to this was actually was inspired by a PG program article where he talks about for his company I forget what it was called back in the 90s I think it was basically like a Shopify early version of Shopify he talks about how people didn't really want to pay them for the the software to create a digital store but they were happy to pay them to create a digital store and if they used their

software then so be it it's kind of like sell the work not the tools um and so we took inspiration from this and we started doing we've always been doing cold outbound to other Founders especially YC Founders um but we changed it up and we started we built a Chrome extension that let us actually sort of mock up or semi spoof what command bar could look like in other company's products and so instead of like a cold email where we would describe the product and its benefits we would just include these Loom videos and they

would say things like Hey we're command bar we do X we noticed these three flows in your product that seem hard for users to do seems like they're generating a lot of chatter on your Forum or whatever here's how easy they could be if you're using command bar let me show you and I think we sent like 200 of those emails and got like a 20 to 30% reply rate and that's how we ended getting our our first 10 like real customers besides the the folks in the B not that they weren't real but they

were just you know much earlier stage okay let's unpack that a bit so when you had that Chrome extension what exactly was that doing was this when you introduced kind of like a chat widget or were you still in this no this is just a search bar we were just a single Product Company just doing that search bar through our series a got it okay all right so you you use this Chrome extension and you you basically like recording like did you record like 200 videos was was it like a video per website you it

wasn't just some generic thing that you were sending out to everybody of like no no it was like a c it basically allowed us to it's not that fancy for CH just allows us to allowed us to embed command bar is basically just JavaScript and so it allows us to embed command bar on any site for the person who's currently browsing obviously we can't make it available to company's users they have to install for that and so it would make it appear and then there's a bunch of things you can do in command bar no

code today you can do a lot back then you could do a few things no code and so we could set up some use cases and mock up others of users encountering a problem in the product you know typing selling into command bar and then seeing some result whether that's like an action they can complete or takes and teleports them to the right page but yeah we created yeah like 200 of these Li videos I think we whittel it down at my Peak I think I could do one of these in like 45 minutes because

there's stages to it right like you find the company you got to log in create an account which you know we all know onboarding flows are super painful sometimes like you got to fill out the 14 questions or whatever get get an account become acquainted with the product identify like three we always did three three things that could be better and then you create the you mock up the command bar and then you do the video got it okay and so you were using the product each of these products yourself identifying like potential points of

friction and then showing them how they could solve them yeah it was visual it was like it kind I it kind of made it seem like we had solved them honestly I think that that was part of what worked was it it made it clear that it was pretty easy to get a basic version of command bar going which like you can say oh it's only going to take a day to get command bar up and running but like No One Believes you because you know anyone who buys software is is burned by claims that

software is easy to set up that up not being true and so I think it was a bit of like a show me don't tell me situation where if we could create this video clearly we weren't spending like days building one loom video for one cold email so I think it was a bit of a proof point that actually was like pretty easy to use so it strikes me that you know you're basically creating a new category here and the loom video is pretty smart because you don't have to try to figure out like how

do we explain this in an email in a way that they understand what the product does right like we'll show them a video but rather than just a demo video we'll actually show them what this could do on their website right and and so I think that's that's like super smart I mean it's it's a lot of work to totally to do that right it's not like hey upload 200 email addresses into some Outreach tool and write a 10 you know one email wish it's gone this takes a lot of work and I think that's

probably why you got uh such a high response rate from from people what did you do beyond that when when when you use that to start those conversations get to the first real 10 customers as you said was was that basically kind of your playbook for getting more customers yeah there there was a a second piece I'll actually Circle back to something you just said about the the time required yes these this is not a kind of a quick marketing or sales hack like it it definitely requires a bet but I'll go as far to

say that I love recommending this strategy to Founders not because it's efficient but I believe maybe this is somewhat of a spicy take I believe if you try this and it doesn't work like you don't get replies or the replies are tepid uh I don't think your product is good or at least you're maybe it's good but you're really bad at talking about it or you have the wrong audience if you really put the work in to identify pain show how your product is solving that pain in a extremely customized way like this isn't about

sequence writing this is like oneoff emails and it doesn't work something is deeply wrong and I think that makes it worth it because being able to assess I don't have product Market fit in 200 hours is way faster than most companies determine they don't have product Market fit I think can save a lot of like waste wasted building but to answer your question about what we did after that pretty simple process we get the meeting with this this Loom and then our whole pitch was like try us it's really easy we've already done like 80%

of the work put into the product and see what results it drives from users and I think and then we did that did that and I mean ultimately you have to create value to convert those into actual contracts but I think people like that we were confident they saw that we' put in a lot of the work to get them ready to go and I think you know every if you incredibly convince someone that you can move a metric they care about that's like basically what sales is yeah okay great so when when we're trying

to go out and sell a product like that there's there's a number of questions or objections people have initially it's like what exactly do you do what problem do you help solve is you you know is this thing right for me and and so you you talked about a number of things in terms of using the loom videos as a way to explain very clearly in a very relevant way way what the product does and how how they can use it and what problems it helps solve and so I think that takes away a bunch

of those issues but then the next part of it is what's the integration like how much work do I have to do to actually get this to integrate with my product and I think you've described that you know whether it's JavaScript or you know some code I need to add to my my you know Pages or it's Chrome extension okay that sounds pretty easy the second part of this would be is like well what about all the information that you're you're delivering through this search bar how much work do I have to do to get

that data you know your your you for your product to access that data so what was actually involved and how did you make that easier so more people were you know willing to to give this a try yeah I mean the the way it worked then is is is actually still the way it works now we just have more ways of kind of packaging the things people are putting into command bar for users and so we can show them in more situations but basic principles are the same it's just a mix of sucking stuff up

via Integrations and manual curation I think probably the Insight we had is like you kind of need both because some people really just want to import all the content they've already created and sort of see how command bar does with it is it surfacing the right things at the right times is it picking up mult multiple ways users might be describing some feature using our sematic search or natural language stuff and then there's also manual creation because there are certain situations where when a user types in like how do I upgrade my plan like you

really want to make sure that does exactly what you want it to do and is the fastest possible path to the user converting because those are like you know real dollars at stake for that particular query so there is a there's a way to curate kind of specific flows in command bar whether that's when a user searches for something or asks co-pilot a question or if you really want to show like a particular nudge on a particular page a particular type of user you know something like that and there's also a kind of more of

an autopilot mode where you kind of let command bar decide when it thinks it should uh interact with the user in certain ways some people do all of One some people do all the other our recommendation is a mix of both kind of curate the the flows that you know really matter you're really opinionated about and let command bar kind of pick up the long tail and it's obviously iterative but to answer your question specifically in the beginning the Integrations and the kind autopilot Focus are really helpful even if the the customer is ultimately going

to do a lot of manual creation those Integrations make it so they can get into a Sandbox and experience like what the product is going to be like quickly time kills all deals it's even worse with trials we started a bunch of trials in the early days where people just like would never even use the product we were like what the hell like we thought we were like doing something wrong I think the learning there is honestly just like people are busy uh and if you don't make it like super easy for people to get

that initial kind of 10% and get the dope mean Loop of like oh this is really easy I should keep building this they might just never get there because something might come up and so the Integrations and autopilot approach I think really help with that okay were there any other growth channels that that worked for you let's say you know beyond sort of first 10 customers as you try to get towards the first million in ARR beyond the cold email with loom videos which sounds like it was working really well and you shared that link

with me with the with the Reddit AMA you did I think we'll definitely include a link in the show notes to that so people can deep dive a little bit and there's actually a you shared a loom video with me as well right what an example of one of those videos yeah one of the ones one of the I think it was I can't remember if it was successful or unsuccessful video but it's definitely from that crop yeah but they'll people get the idea when they watch that so uh so beyond that were there any

other growth channels that you you tried that you got working or got working not really uh for us honestly we we cruised through our initial Revenue Milestones with the loom videos and just Word of Mouth like basically all of our big customers um in the early days just like came inbound which I'm incredibly great before I I still think might just have been like dumb luck I think you know I think the product experience was pretty good so I think the kind of referral Loop was working but we didn't really do anything to stoke it

it just sort of happened um one learning from the early days on growth we tried a lot of content Marketing in the early early days if I tried I mean like we would do you know two or three articles about a topic like we we weren't you know investing months in these things our approach was like let's sort of try to uncover the channels that work for us and with content Marketing in particular I think unless you can invest in it and feel okay about doing it and not worry about measuring Roi you probably just

shouldn't do it at all you know write the few blog posts that you want to refer your customers to over and over again and leave it at that until you get to a stage where you can do content marketing and not care about the ROI because I think at the early stage probably through like series B measuring Roi on content marketing is fruitless and instead we talk about it internally is measuring it right today in our company's stage we measure success of our content marketing basically by vibes like are our customers telling us oh this

is a cool article like are we getting comments when we post it on Hacker News like do people talk about it um we don't really measure like how many leads do we generate from each post because it's so hard to determine like okay this person read an article and then they went away for two months and they came back like yeah you can try to torture HubSpot other tools to kind of figure it out but my thinking today is just don't measure it and don't do it if you're not prepared to be okay investing it

and not measur right right yeah yeah yeah I had an experience with with um some Founders who I I think got into that I don't know what I how I describe it but it was like they they wanted to do content marketing would try a little bit of it for a few months and then want to wait to see before they invest in it again right what top of funnel does it drive yeah which which makes sense but the reality is I think with content marketing is you either need to just say we're not going

to do it and you like you just said we just put some core pillar content out there that we think is useful and relevant or we're just going to keep doing it and we're just going to say this is part of the strategy this is a bet that we're making but you're right it's a huge attribution problem because the chances of somebody going on unless they're like the the you know they have really high buyer intent and they're searching for one of your articles designed to you know convert them start a trial the chances are

most people are going to visit your site multiple times they might go and come across you on social media they might talk to somebody else and whatever and so what do you give attribution to okay it's you I don't know right I think you can do it at scale like I think there's you know you know plenty of companies that are doing a good job of it I've just seen so many early stage Founders they hear the advice like you should run experiments and then they're like okay great I'll run experiments I got to measure

the results to run the experiment and they get so lost in the sauce of the measurement that they first of all it takes away from actually investing in the quality of the content they kind of think of and I think this is how I used to think about testing out different channels they think of it as like flipping over a card it's like either this channel is going to work for us or not and like our job is just to kind of do the minimum viable exploration of the channel and like see whether it works

and I think for some channels like you can approach it that way like ads good good way to or a good Channel where you can actually be extremely Roi oriented from the beginning I would caution like most early stage companies from doing any ads at all or even trying to experiment with it but if you do you can be Roi oriented whereas content marketing like you just said like we've been talking about like it's one of these things our SEO is another good example where like it's a bet and it's okay you can be a

good founder who runs experiments and still make some marketing bets but just know their bets going into it and don't be dismayed when three months in you've generated no leads by the way it doesn't mean you can aband you can't abandon it if you've been spewing out content and you're getting no signal that it's useful like no one is reading it to your knowledge you're not getting any up votes on Hacker News like okay yeah then maybe there's something something with your content but don't abandon it just because it's not it's not converting leads yeah

yeah totally agree let's talk about the category creation challenge a bit more so you were you were initially in this position where it's kind of a new category you're having to spend a lot of time and effort explaining it to people like what does the product do then you moved into sort of digital adoption world where people start to get get what you do more easily but now you're also being compared with a whole bunch of other products like I was doing when we started this conversation I was saying oh chat B onboarding you know

inapp stuff and whatever how easy or hard has it been to make that transition and what are some lessons you've learned about how to stand out from the crowd yeah so context was uh we were a single Product Company through our series a and what we kept hearing over and over again from our customers was are you a replacement for x and x could be a number of different tools most frequently X was a tool from this category called digital adoption that is they're basically the popup companies so at the top of the show when

I described command bar I said like we saw the same problem is those in product popups but we're not annoying so we kept on getting compared to these other companies and we would sort of just like shrug and be like we don't really care about those other companies we don't really maybe we kind of do the same job we're both trying to help users maybe if you help users so much with command bar you can get rid of those vendors but like we don't really have a take like that's old school we're new school and

we sort of just shugged it off for a while and we were like we're creating category our product is totally different like you can't compare us to anything else but we kept hearing this over and over again and like you said it wasn't lost on us that although we were growing well we were spending a lot of time explaining what our product did to people like in a 30-minute Discovery call we might spend 20 25 minutes like really helping someone understand what jobs did we do for them what metrics could we move what other tools

we integrated with who would the company would be using this tool who would be the champion would it be them or someone else in their team and eventually we were like okay maybe we should take a look at this digital adoption category like maybe this there is something here like maybe we should say start saying we are a replacement for x or you know substitute for X um and we took a look at it and we basically came up with some ideas for how we thought we could make it a lot better we were like

oh my god there seems to be like a lot of opportunity here and it kind of made sense structurally like people were already doing things in command bar to make it personalized for users like you one of the things you can do in command bar is you can create audiences which are basically like crosssections of your user base defined by like what things they've done in your product what plan they're on what channel they came from Etc if you're doing that for the purposes of personalizing the search bar experience you can reuse those audiences in

other ways to influence us your experience so we were like okay let's actually let's lean in to what the market seems to be telling us and instead of talking about ourselves as a totally novel mouse trap let's talk about ourselves as a better version of this existing category that's trying to solve the same problems but is doing it in a in a new way um and that was a very challenging like really a for for me and the team because for so long we had been like very dismissive of these old school tools and it

was like wait a second we're going to build like we're going to build a way to do popups in command bar for for so long we've been talking about how we hate popups now you're going to be able to create a popup in command bar like that's blasphemous um but I have to say like it took a while for us to get noticed and there are some kind of nitty-gritty tactics that we employed things like leaning on review sites like cap Teran G2 to really like create some social proof in the category and get noticed

um but if you compare like one of our Discovery calls from this week to one of our Discovery calls say last January so we went on this position Journey basically all 2023 started in December today we probably spend like four minutes of that product explanation part because the people we kind of have B signaled to anyone who encounters command bar this is what we do this is who buys our product these are the jobs we do if you know anything about digital adoption digital adoption is like pretty mature category it's already done the job of

educating the market about why it's important to help users let's you know stand on the shoulders of that instead of starting from scratch so the tldr I would say is for most in most situations and for most Founders creating a category is vastly overrated it feels really fun it feels like a grand intellectual adventure and you're like changing the world how could you be like a me too product but the the uh dynamics of selling into existing Market are often far simpler than selling into a totally new market that might never exist so you said

it took about a large part of 2023 to figure that out what what were you trying along the way I I'm trying to sort of think about if somebody is in that situation today where they're getting on Discovery calls and they're spending nearly all the time trying to explain what their product does what are some of the steps that they can take to uh make a similar transition the first thing I would say is always listen to product comparisons I think Founders are really eager to talk about how their product is new and special and

so when someone says oh are you like X the default answer is like oh sort of but uh here's how we're different and I I think whenever you hear that first of all you should listen and identify Trends if people are constantly comparing you to X like you should go look into X but I would often if someone is trying to compare to a tool that's their basis of understanding and if you should answer in a more of a yes and way and you should say yeah here are the ways we exactly like that tool

because at that point you've created some you know groundwork for you to explain how you're different if you just jump into how you're different they might be like okay like I just don't get this tool at all so that's the first thing I'd say is listen listen to those comparisons um also seek those comparisons if you're not getting them one of my favorite pieces of advice for Founders that is applicable like so many scenarios is ask open-ended questions especially in uh conversations with prospects how did you come across command bar let them talk a card

I used to play in the beginning was like people would ask okay like can you demo the product like what does it do and I'd be like yes I'm absolutely going to demo the product we just readed our marketing site I'm really curious what you think we do because you know we want to make sure our marketing side is doing a good job and then you have to deal with the awkwardness because people thought they were showing up for a demo and now they're showing up for a quiz and you get them to explain what's

in their head about your product and that will tell you what they're attaching it to whether they get it they might just get it in which case amazing like maybe you don't have a category creation problem but if they don't get it and they're constantly comparing you to something else then maybe you should consider leaning into that comparison yeah I like the way you you describe that like if someone's saying are you like whatever starting by instead of jumping straight into why you're different starting by saying yes we also do X Y and Z but

in addition to that this is what we also do which is different or whatever right so I think okay great so now I understand you're similar to that product I understand what are the things that I would still be able to do if I was using your product and then I understand what's different on top of that it sounds so simple when you break it down now I know right in the moment it's like a heat a battle it's really hard I think a a little framework you can use in these situations is when someone

Compares you to X you can start with the problems be like that that solves this problem we also solve this problem however we do it in a different way to X here's how we do it so at least you know they probably understand the problem and care about the problem and so you can attach to that yeah yeah that's pretty cool okay one one kind of clarifying thing I want to just understand is you said that the Cod email Loom was basically the primary growth Channel nothing else really worked today you're doing a bunch more

content marketing and is is the is the email Loom thing still the biggest growth channel for you today we I mean we do do outbound and we do do looms um it's one of many channels we don't really have like a one and if we did I probably wouldn't tell you uh one like amazing uh Channel I think the my mindset shift on marketing in B2B SAS has been in the beginning like I described earlier I think I was playing this game of like what channel is going to work for us because you hear these

things like you got to experiment you got to focus you've limited resources you can't do everything at once now I actually have adopted the perspective of you kind of just got to be everywhere all at once always and try a lot of things and not expect any one marketing investment to 10 your top of funnel but just do it all whether that's the content marketing whether that's ads whether that's SEO like do it all have a perspective on how you're going to do it different and faster and cut things that clearly aren't working but don't

cut things just because they're not they don't have the potential to be your biggest growth channel in in terms of being a Founder what and you look back over the last few years what have been you know maybe one or two of sort of are the biggest struggles or challenges that you look back at on this journey uh for me like personally I think something I've struggled with a lot is like how much to work how much I should work like what is the right amount of myself that I should be pouring into the company

and I've tried a lot of different things over the years and I've s a lot of advice and I've kind of just come to the conclusion um and I started Angel Investing and this is what I talk to Founders who I work with as well about is like there's just no right answer to this question and like you just got to feel it out I'd say if you're someone who like wants to work 120 hours a week on your company and like that works for you and you've structur your life in a way that that's

like reasonable like I think that's a beautiful thing and like don't let anyone shame you for doing that I think if you're a 40-hour person and the company's doing well like amazing that's awesome like there's no glory in like pouring hours into your company and for the sake of pouring hours and by the way most people who say you know these grind set people like who say they're working like 80 hours a week they're probably doing like 15 hours of like actual work there's a lot of like getting lunch like you may be in the

office for 80 hours but I doubt you're doing 80 hours actual work because that's really exhausting some people can do it um and so I think just sort of like letting go of trying to optimize this and just like you know intuitively working and sometimes that means you got to work more and I think part of the part of the advice here is like the answer can change and and knowing when you should lean in when your team should lean in is a I think a superpower that some Founders have and everyone should try to

cultivate because it's even worse with the team because there's no way the team is going to Sprint for 80 hours a week every week it's just not going to work uh and so you have to know when to push and when to rest and that could be team-wide it could be when a specific team needs to push whether it's like sales trying to meet a number or like product trying to meet a deadline you kind of just have to apply this intuitive feel to your your own work but also the whole company and just realize

there's no right answer and and no investor is going to like yell at you or no one's going to yell at you because you didn't put in 80 hours a week I think hearing that is uh helpful for I certainly would have been helpful for me so so do you do you feel like you have a better control of that like do you feel like you found the right balance it abs and flows um I think like I tend to overwork just because like like a lot of Founders I think I have an obsessive personality

and by overwork I mean like put in hours that where the marginal utility is like fairly low so I don't think I've like nailed it my wife is very helpful biggest life hack founder hack is like get a partner who can support you and check you and we go on Hikes all the time where I you know our topic of conversation is like a work problem it's like really useful you can do like a mix of a mix of leisure and work but no I definitely don't think it's like a problem you solve because it's

such a dynamic one yeah no my my wife is a therapist and uh she's she's very helpful in in uh keeping me under check and I remember when there was a lot of talk about uh the 4-day work be week and there was a whole bunch of companies going on about that and um you know I was like oh maybe this sounds really interesting right maybe that would be like something I could try and I said to her you know I've just been reading about this stuff and maybe that's what you know I should do

and and she was like so nice and and kind of sweet about it and she just said said I think that sounds like a great idea but maybe you could start by going from 7 days a week to five days a week before you do the 4 day thing I was like oh okay all right uh we should wrap up let's get on to uh the lightning round I've got seven quick fire questions for you uh what's one of the best pieces of business advice you've ever received ask more open-ended questions I think people tend

to see question asking as an opportunity to sound smart and show like the integral of all the research they've done but whether it's like a candidate or a prospect or a customer asking a super openend question that requires like zero research often gives you way more insight than the smart question what book would you recommend to our audience and why it's a book called Never split the difference I wonder if it's come up before it's a a book about negotiation that taught me to ask more open-ended questions I think it's Chris Voss right who wrote

that book so I I think he did a master class as well uh what's one attribute or characteristic in your mind of a successful founder I call this like Scout it's not a really clean word uh there's a book called jul by Julia galif called Scout mindset that basically describes how like there are two types of people or different situations you might be a soldier where you're trying to like defend a point of view or you could be a scout who's trying to like uncover truths about the world forming a hypothesis disproving them forming new

ones um and I think there's a time in place for being a solders is a Founder certainly there are plenty of successful Founders who've like had a vision of the future and just like made it happen and not listened to signals that might have said it was a bad idea but more often than not I think it's the Scout Founders who succeed Scouts who say I'm going to go build X and then they learn something about the market and said you know what x was a terrible idea I'm now going to build X Prime and

exploit what I just learned about the market especially at the early stage I think a lot of Founders think they need to kind of pitch an idea to an investors then go like realize that idea and if they don't do that they'll be considered idiots in reality like at the early age investors are betting that you're going to make a company work not or a product work not the the specific product that was in your seed deck yeah cool by the way I I came across that book uh recently it's on my reading list so

I I definitely want to get around to it it was when I was exploring this whole idea of like rational thinking uh one of the books uh the other books I came across was um Harry Potter and the methods of rationality which which is also kind of a related thing I don't know if you've seen that it's kind of like this basically um fanfiction thing on Harry Potter where it's all about applying rational thinking to this the story so I've been trying to go through that and then I was like yeah Scout mindset definitely want

to read that too uh what's your favorite personal productivity tool or habit I'm one of these these people who thinks we spend too much time on productivity tools and strategies so I'm just like an Apple notes guy write everything down triage later I wish they would let me change fonts that's the only thing I don't like about Apple notes it is I I wish they had toggles that's my feuture request who knows maybe one day maybe Tim Cook is listening I doubt it very much what's a new or crazy business idea you'd love to pursue

if you had the extra time uh I feel like this maybe already exists but it seems so obvious to me like an llm based accountability uh coach who can text me the same way my wife text me to keep me accountable did you out today and then if I don't respond like pester me it just seems like such an obvious use case yeah love that uh what's an interesting little fun fact about you that most people don't know I'm a super boring person like my team gives me about this all the time I think the

two facts I think the most interesting facts about me is that I um used to be play based in a heavy metal rock band like not a good rock band like in high school and my wife thinks the most interesting fact about me is that my favorite dessert is uh raw marshmallow love it and and finally what's one of your most important passions outside of your work um I started Angel Investing I think like the topic of uh Founders Angel Investing kind of controversial I think more Founders should do it it's really fun and therapeutic

to step outside of your own business and think about someone else's business in the context of like should I invest in this or not it's also just a really great way to meet other Founders and like I think there's this Dynamic sometimes investing where it's like oh if you're the investor you have to like bring the knowledge and it's like a very one-way relationship but I've learned so much from the founders I invest in like it's a great hack for just getting I think a lot of times Founders like work in a vacuum you don't

really like see other Founders at work the strategies they use how they write investor updates what kind of progress they're making what's what experiments they're running and Angel Investing is is a great way to do that cool uh so thank you for joining me James uh it's been a pleasure if people want to check out uh command bar they can go to commandbar domcom and if folks want to get in touch with you what's the best way for them to do that Twitter or uh think D Twitter I'm daoy okay great so we'll include links

to those in the show notes we got a lot of things to add to your show notes it's cool well thank you so much it's been a pleasure and uh I wish you and the team the best of success thanks so much take care cheers