427. The Playbook to Finding Product-Market Fit, When Founders Should Begin to Scale, and Lessons from Building Attentive (Brian Long)

427. The Playbook to Finding Product-Market Fit, When Founders Should Begin to Scale, and Lessons from Building Attentive (Brian Long)

Brian Long of Attentive joins Nate to discuss The Playbook to Finding Product-Market Fit, When Founders Should Begin to Scale, and Lessons from Building Attentive. In this episode we cover:

  • Entrepreneurship, Product Development, and Market Opportunity
  • Strategic Decisions for Early-Stage Companies
  • Customer Discovery and Feedback in Product Development
  • Product Market Fit and Customer Acquisition Strategies
  • Customer Problem Evolution and Startup Success Strategies
  • Sales Strategies, Company Growth, and Founder Experience

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Transcribed with AI:

Our guest today is Brian Long, the Co founder and Chairman of Attentive, a mobile messaging platform company that has grown to be the unequivocal leader of the marketing communications market.. Attentive has raised more than $800M from the likes of Sequoia, Coatue, and IVP and was most recently valued at over $6B. Prior to co-founding Attentive, Brian co-founded TapCommerce, a mobile advertising startup specializing in retargeting ads for mobile users, which was acquired by Twitter in 2014. Brian, welcome to the show!
Hey, it’s
great to be here. Thanks for having me.
Yeah, of course. So I want to talk about a number of different topics today. And we may jump around a bit. But first, even prior to attentive, I was wondering if we go further back and talk a bit about your upbringing? Were you always entrepreneurial? Or, you know, can you share a bit about life before becoming an entrepreneur?
Yeah, I can’t really remember a time when I wasn’t interested in entrepreneurship. My parents would joke that I was kind of always coming up with business ideas from a very young, very, very young age, and had all sorts of concepts and notes and things I wanted to do and stuff like that. So it’s always it’s always been something I’m interested in it. Does
anything stand out from growing up? Like any business by the rich trading cards or anything more nuanced or esoteric?
Yeah, this is like in the 90s, I had a business making websites and designing digital materials for people when I was in middle school, and what else? And all sorts of weird concepts like I remember and this concept for making a better soda, where you could actually mix how much syrup you wanted a new soda to determine the sweetness seat, kind of do it on a scale, which is funny is, you know, it wasn’t entirely wrong, as we’ve seen, you know, Seltzer and flavoured Seltzer, and all these sort of lighter, not as sweet versions of soda get really popular, you know, give it used to think it was like watered down, but as long as it’s got the bubbles deep, you still want it today?
Yeah, well, I think you were somewhat pressured, because those those machines do now exist, but I think he chose the right path and are building a hardware business. So I you know, now fast forwarding, I will get back to tap commerce in a minute. But what was the founding moment or the insight that led to attentive, you
know, for, for just, I guess, the start of it, 10 of it came from selling our last company, tap commerce. And I would say, you know, the day after we sold it, I knew that I will be doing another company. And I remember I have this meeting with an entrepreneur, who had also sold this company to Twitter, we both sold our companies to Twitter, and I was having lunch with them. And and he was talking about going and doing venture other things afterwards. And I just knew that I had to go through another company, wizard
regret for selling the company, or I guess, if you knew you wanted to start another company that quickly, like, what was the thought process then behind selling tab to Twitter? Yeah,
I mean, look, there’s a lot of elements of a company on why you might decide you want a salad or why you shouldn’t be the person running in anymore, whatever it is, some of the things people don’t talk about, and was definitely a factor for me for Tabqa versus the cap table. So I was a inexperienced entrepreneur, when I started that company, you know, a while ago, almost almost two years ago. And as an inexperienced entrepreneur, you raise money at very low valuations, you know, if you’re lucky to raise anything, so you end up giving away a lot of the company to investors and other people and all that sort of stuff. And ultimately a by the end, you know, I thought if I kept raising more money, I’d be giving up one more company, and then be the second thing is that as a first time entrepreneur, it is a lot harder until you’ve you’ve got a win kind of on your belt, right? And I saw a lot of value in selling it just so I could have some sort of way that I could point to when doing future companies. And that part is definitely the shrew having some sort of real when made a lot of the future companies easier.
So how did that actually materialise with a tonne of like what did you do? What are one or two things that you did radically different the second time around with attentive versus tap? Beside from the cap table construction?
Yeah, I think that for me For a tenant, we had a couple of false starts in the beginning, but I think that what we what we got on the right, were two things. One, I think that we talked to a tremendous amount of customers, before we started building things. So we have learned to hear their problems, hear their issues, and then start building assault those, you know, rather than kind of just jumping right into build, build, build, so that I think saved us a lot of time. Whereas for the first company, we just had a bill that said, hey, it’d be bad. And then after we built it, we’d see if people wanted it, which, which led to a lot of wasted time.
In hindsight with tap, do you feel that you guys got lucky? Then they because you didn’t take the same approach? And you built in found a chord that clearly struck? Or how do you reflect?
There’s always some element of of luck, and actually, these things, but I think that with with tab, commerce, we, you know, we probably pivoted like five or six times on the business. So there was a balance between luck and just being persistent in trying over and over and over again, find something at work. So we had a lot of at bats. But certainly we were, we weren’t, I don’t think we were lucky that the business ended up becoming a real business, I think that we were lucky to sell the company and kind of find that a good partner to sell up to when we did, because selling businesses is very, very hard. And most most m&a does work out. And I think this idea that when you want to sell your company you can is it’s very hard, unless you have something that’s very profitable, and you’re willing to take a price that is, you know, pretty, pretty reasonable to discount. Otherwise, finding, making m&a happens very, very hard.
Yeah. Yeah, I, you were talking about iterating and finding product market fit. And I want to go into that in a minute. And you know, the art of asking good questions and how to pull that out from the market. But I’m curious, like, as you compare and contrast, tap and attentive, did your conviction in the opportunity differ between the two, the market opportunity? Like how much uncertainty did you have? Whether a market would exist for either tap or attentive?
Yeah, I mean, look, I think that one’s idea of success, success may change over time, like for TAP commerce, you know, selling the waiter for reported around 100 million. That was a big success for that company. But when it came time to do the next company, you know, success would have been that wouldn’t have been success, right, like doing something much bigger, what’s the goal? I think that it does come back to market size, what you were saying, like, having a much bigger market that you can go after, does make it a lot easier to grow over time. And the market for attentive, failed, and I think is much bigger than the market was for TAP commerce. There were there were ways you could have expanded the market for TAP commerce and kind of tried to shift it into a company like Appleton, which is, you know, a public company tend to tend to build a more public company, then that would have been a radically different product than than we have today. Yes. This also
brings up an interesting topic that a number of investors in the VC ecosystem debate and that is first time for a second time founders. And you find that investors are actually split on this, some prefer the first time founders, some prefer the second time founders. And part of the rationale behind preferring those starting the business for the first time, is that they’re somewhat naive. They don’t know how difficult it’s going to be to be successful. All the roadblocks that you’re gonna have to overcome, et cetera. I, I’m curious, like, what is? I mean, you you’ve started multiple businesses now, but what is your take around that specific part of being naive? Like, did you find that you had any blind spots? Second time around? Is there anything you underestimated the second time around when founding attentive? Or how do you react in general to hearing the debate between first and second time founders from the investment side?
Yeah, I mean, my reaction is that I think it’s an it’s an important data point. But you know, every person is different. And there are other data points that you need to see they kind of put the puzzle together on, you know, team and market and you know what they did last time but they think they weren’t the last one what they want to do this fun. How is that different? I do think that there were things I was I was a significantly worse CEO of my first company that my second company, like, like much, much, much worse. So I think as far as hopefully things you’ve learned from the first to second company, you gotta keep an open mind, do those I was I think we’re pretty trying to try to be a different times I want sir busted, but try to be open minded and get better, and trying not to have an ego about that. And before the second one, I think that I’m continuing to get better. And even then I look back at my second company and think of all the mistakes I made with that company, and that I don’t want to repeat them, you know, with with my third company or a company. So I think it comes back to me around someone who wants to get better.
So how when you say that you’re a much better CEO the second time around? What did you specifically do differently? The second time around, aside from choosing a larger market opportunity, we talked about choosing investors and cap table construction, but tactically in the business? How were you different as a CEO? How did that manifest in you, like your leadership style, or your strategic approach? Whatever it might be? Yeah,
I mean, I think it’s with the first company, I think I push at all times to be in just to complete sprint. And I think we also had much more of a short term focus. You know, it was it was it was very much just about, you know, the next month, the next round, the next whatever, instead of seeing, hey, wait, here’s where the world is going to be in five years, 10 years, 20 years. And here’s why we’re building to that world. And that’s, that’s where that compound growth and compound business is going to come from. I think we didn’t have that that true long term sort of thesis driven thinking at the core of the business the first time, whereas the second time did, and I think that led to a more thoughtful and colour execution against against those views. So
now moving forward to actually finding product market fit. How did the product evolve from the time the business was incepted, to the time that you felt that you had product market fit, I know, you guys had to make a number of trade offs along that path. But I think those are very interesting stories to highlight here, because a lot of founders Chase revenue, and they may chase the big contract. And I know that you guys had to make some difficult decisions that most entrepreneurs probably wouldn’t have made. So we’d love to hear, you know, what your journey was from having the idea, but to ultimately landing on the product that you felt you wanted to scale the business with? Yeah,
I could give a quick break bar, medium size, length story on that works for both companies that are setting up with with CAP Congress, we started off building a bunch of Android apps for just various random use cases, when the market was very early as like a side game. And one of the apps he took off was an app that offered people coupons, so they could go in and get coupons. And we said, You know what, what if we also start selling products out of the sack, so we started selling products out of the app as well, which was basically drop shipping from Amazon other places. And it quickly turned into a lot of sales fast, like, we do like 50 grand a month in revenue on like our second record and on. But the business was not a good business. Like we were losing money. There wasn’t a path and a body. And the minute that we increased prices large enough to make money, you know, sales would go down. So we were also recognising that getting people to come back and use our application just borrow. So we built some tools to bring people back to our applications. And we realised we could sell those tools to other applications and make money selling that software. So we have a whole suite of tools to sell other companies. And at first we had this big suite we’re going to do all these different days. But for a bunch of other things it was hard to sell. But eventually we sell one thing mobile app retargeting, which is like, if you’re on the eBay app, and you’re looking at a watch and then you open up Spotify and we you see an ad that watch it you click on it takes you back. That’s a that’s a retargeting ads. We found the most interest in doing those types of ads. And using that we built that out made that work and then that turned into The product that took off, and just from kind of like founding to finding that product and the business taking off, you know, in total that took about a year. So there was there was a, there was a year period where, you know, it seemed like the business was going nowhere. And we had raised, you know, like 1.2 million. And we were running out of money to the point that, you know, we were pretty close down on loan. And we had to go back to our existing investors. And they were saying, Oh, maybe we’ll give you a little more money, but there was not a lot of enthusiasm, then all of a sudden, the business claims it took off when we raised the Series A. So that was the story on on tap. I’ll pause for a second, if you have any questions on that before doing it for
Yeah, no, I, I that’s actually my first time hearing the story around tap in the background is how you guys ultimately landed on the product that would eventually be acquired by Twitter. But we’d love to hear the story about an attentive because I’ve I’ve heard versions of it. But you know, hearing it firsthand is something I’ve been looking forward to. So,
man, well, you know, the Senate who was big 32. We didn’t sort of started it was there was a book called Amana, that talked about artificial intelligence being able to manage big workforces. And I was interested in doing that, and basically using text messaging to manage workforces. So we built out a whole bunch of products to manage workforces that included like a ship scheduling application and communication applications, the attacks and things like that. And after working on that forbid, and getting feedback, where customers seem to like it, we went out, we pitched that to over 100 customers. And, you know, I would explain how you can use text messaging to communicate, manage your workforce, and you know, maybe even use it to talk to customers. And it was funny, people overwhelmingly either weren’t as interested or not motivated, talk to their employees via text, but they actually really wanted tools to communicate with their customers via tax. So we heard that feedback. And we sort of blew up the prior products we built into them away. And we spent about half our money through the private products away, and instead decided to just focus on building communications via text with the customer. And I guess I just call out that the part of this that I think was was was kind of interesting is that the first business that was not like a lose your failure business, we had customers for it. And we actually had a really big kind of summer that I just gone through all week overview when we sign one one big contract with us. So there was something there. And there are businesses today that do this. So there’s there isn’t real business. Yeah. But we didn’t see the dynamics in that business that we thought it could be a really high growth business like we wanted to build. So we got rid of that and focused, you know, wipe the slate clean and change the company then you know, the original company name is Frank when we changed the name to attend. And we moved everything in the southern direction. And then 2.15 product market fit you know, I’ll tell you what I knew it was working and then I’ll tell you in Product Market Fit actually happened. So we attended the the idea turn to we’re going to do text essence marketing with a focus on E commerce and retail companies because we thought it was an underutilised marketing channel, we convinced the customer to run a trial with us when I knew it was working is that they ran the first trial with us. And in their first day, they had a tonne of people sign up to get messages. And then they sent a message and they made a lot of money. Like they made out a new times the money they sent sending us. And I was like, Okay, this business is gonna work. Now we just need to go and evangelise that to all these companies and most companies that decided did not have a strategy want to do tax. So then it just turned into convincing companies that this was a good idea and figuring out how to reduce friction on doing it. Now when we truly hit it, so that is kind of where I knew it was gonna work. When we truly get product market fit though. We had two relatively early customers like first 50 customer type customers that our products was working so well for. They actually quit what they were doing to start a competitive company to start a company that was basically just a copycat of our company. That is really, they saw how good our product because of how much it was working, that they decided to just send this one company in particular its company in Los Angeles, actually that the guy was was running this one company There was an apparel company. And he literally stopped doing the apparel company and meet a like direct copycat of our company. And also didn’t pay his bills to us and started a new company that was a copycat America. So when I saw that, I was like, Okay, this is really working, people are quitting their jobs to make it better. God
you’re giving me like, there’s so many different angles or paths that I want to go down based off of the stories that you just shared. But I guess quickly with these two companies, one of the things that I was interested in as a space was unfolding, I think strategy is often something that’s not talked a lot about at the zero to one phase, like thinking about, okay, we’re going to get to zero to one, but how are we going to be that company that emerges from the pack to become the attentive that we know today, the market leader, multibillion dollar company? What did you guys do early on from a strategic focus standpoint? Like, what were some of the trade offs? What did you What were some of the decision points that you felt put the business to, in a position to succeed versus these competitors, that we’re coming fast to market and even though there may be we’re a bit behind? It sounds like you guys. were, you know, a 10 100 million dollar company at that point in terms of revenue? So what did you do from a strategic standpoint that you felt like, best position that company to succeed?
Well, first of all, I think entrepreneurs need to be paranoid. Like, with my first company tab, ours, we, we held off for a little bit, and doing sort of press and saying what we were doing and stuff, but we, you know, we probably had too much ego and pride. And we eventually did come out and talk about it. And within doing that, within a couple of months, we had Uverse copycats, and that was a problem, because the copycats came out. And they were just muddle the story. And you know, what’s happening. And, you know, there was one particular copycat that, you know, caused us a lot of issues in market because they created a lot of noise, they eventually went bankrupt, it was fine. But like, you know, there was a lot of noise, it was very similar, actually, with a 10, of where we held off, and I could be held off for longer, much longer in getting press and pushing things out there and getting a high profile probably too long. But so we had copycats, but we had enough of the Head Start that I think it was very challenging for them to catch up. And as a result that the copycats ended up having a move into different niches. So we wanted to be larger mid market to enterprise for tactics, because we knew that’s a that we felt that was me like most of the money. Yeah, there have been other guys that are copycat at all, since then they’ve had to kind of move into the small business segment. But they’ve struggled to get into larger Midmark and enterprise, because we really sort of cast ourselves in that area. So I do think that be early, but then also being aggressive moving fast, you know, in terms of like strategic decisions we made to see something a little obvious, if you will get us on CrunchBase, or something like that, we raised a teeny amount of money. And that was very purposeful, we raised the money to be aggressive than also to be a deterrent. So that on the aggressive side, it allowed us to scale up our sales, marketing and engineering very fast. So we could just go very fast to catch a market. And then on the deterrence side, if you see another company that’s raised, you know, a tonne of money and they’re coming to clear market leader, then it gets pretty hard to want to invest in a competitor, that that you know, that you’re betting a lot of being number two, or three or four, and no one noticed the returns for two, three or four are much worse than the returns from number one. So, you know, I think that that made it a lot harder for people to get around investing competitors now. Late 21, God blankie, and we did have competitors that still raise money, because there was just there was and continues to be too much money and ecosystem and you know, companies that shouldn’t raise money get it, but particularly, you know, the top tier guys, no, like, you will really see a lot out here and sort of these kind of copycat third or fourth place companies, because up here is looking for better returns. But you know, mid tier VCs, for sure. You know, they’re looking for Randy anything, they can do a modest return that they’re still pretty excited about.
Yeah. So when you when you go back and you think about creating a product that customers are really going to fall in love with and that you want to scale with. I know you weren’t the cheapest at the market and you were very focused with who that that persona was like, here are our customers that were that we’re after, but we’re not going to try and be everything to everyone and So that’s obviously informed by talking to the market seeing where you guys are getting traction. I like having just listened to you talk so much about the problems that customer faced and how you ultimately navigated the maze, to position the business to succeed. There are a lot of questions that need to get answered a lot of customer discovery that needs to be done. What have you learned about the right way to do customer discovery? And more specifically, or what maybe what I’m more curious about is what have you learned as to the wrong way to do customer discovery? What did what do you find founders do in make the biggest mistakes around when talking to customers to get feedback to navigate that maze,
the biggest mistake, or founders and early teams, even medium later stage scams, in customer discovery is confirmation bias. So you say I want to prove x, and then you go on YouTube recall. And whatever they say you’re only listening to the things that prove your existing thesis. And instead, I think, going in with an open mind, and being willing to change direction is very helpful. The second thing I say is, I think that while qualitative and anecdotal information can often be helpful and help good product ideation, the quantitative side is really important too. And, you know, something I’d really like to do is ask people to give a quantitative score, say on a one to 10 scale on how they feel about a particular product. So I can’t tell you how many times I’ve done pitches. And I think the pitch has done really well. And I think that the person just wants the pitch. Oh, my God, they love it. And then you’re like, Okay, can you just rank on the one through 10? Scale? One? Not at all interested? 10? I love it, you know, how do you feel about this product? And they’ll think about it for a second, they’ll say I’m between a seven, seven to an eight, right? Which means said. And when you hear that, you know, you just went from thinking, Oh, this is a great pitch to this person’s like kind of neutral. I tend to underline how important it is to get past the politeness. I think politeness will kill you. In buyer to sessions. People are inherently polite. People just thought they are and particularly someone at a professional context, and they have a real job, they’re going to be polite. So in most 9% cases, see, had to find a way to get past that politeness to to get actual nuggets of feedback, which is part because most people follow up for themselves to be polite. Have you learned anything
tactically in those conversations to provide a safe space to be very Yeah,
I think I think the reading thing helps, but I also think of buying them to give what I think is like a balanced feedback. So you say, Okay, great. What do you like? And they can say all this stuff. Oh, it’s so positive. You want them crater and should sandwich so they say, Okay, here’s all the positive stuff. Okay, great. That’s, that’s awesome. And what do you wish was better? It’s much easier to get the answers to what do you wish was better? If the person just gave you a bunch of things they liked? They don’t feel bad about telling you what was what they wish was better than even if the stuff they liked. Oh, yeah, I you know, I like your logo. And I like the colours. And you know, I think it’s smart idea. Okay. And then, you know, what do you not like? Well, it’s way overpriced that I would ever buy. Okay, so you get better information when you allow them to give positive inferior feedback first,
how important was it for you to find strangers, aside from people on your network to validate your product?
I think people in the networker are very dangerous. I would I would avoid when possible people in this network because they want to stay on your network, they care about your relationship. And as a result, they’re probably going to give you a much rosier feedback than they actually think. So you kind of have to deduct those scores to get realistic numbers. Where’s strain news? They don’t care less, right? It’s more transactional, and you’re gonna get more honest feedback.
Yeah, it’s circling back to product market fit I. I know it’s, it’s ultimately not a binary question. Do you have product market fit or not? Generally, these things are on a spectrum where there’s strong product market fit or weak product market fit. Now, having seen this play out across a few different companies, how do you know when you have the inflection point of product market fit when it’s ready to scale versus, hey, we have some interest here, but maybe it’s not flying off product is not flying off the shelves to the point where we’re ready to ramp up our go to market And perhaps we should go back to refine our ICP or we need to do product refinement?
Well, I think that I break it down into things. One, does the product work? And what a but I see just the product work, does it solve the buyers problem. So your buyer, they could be a consumer, they could be business, whatever, but they’ve got a problem. And your product needs to solve that problem that’s at the crux of every business, right. And I think if you can understand, do my metric show, that might my product actually solves the buyers problem is the first and most important thing, because if you’re not solving the problem, it’s never going to be a big business. And as an example of that, with a with a tenant we talked about earlier, the buyer problem was that they needed to find ways to drive more revenue for their business. And using text messaging, we found that they could build a big list and send a message and travel revenue, which meant that they could drive you know, 20% more revenue for their business. So player by a probable burning travel, the important problem with a clear solution. If you’ve got that, you’re in a pretty good place to make a business work, that the second thing I’d say is looking at the core metrics of the business. So how much does it cost to get a new customer? How much money do customers spend with you? For the lifetime customer? You know, what we use the the abbreviations, CAC and LTV? So how much does it cost or wire customer and what’s the lifetime value of the customer, if you find that you can spend a lot less money than how much money they’re going to spend with you. So a lot, it’s a lot cheaper to acquire people than how much you’re gonna make from from them as such first, then you get a great business, that markets really big that you can do that all day long. So I think that actually solves a problem. And you know, you can acquire customers for substantially less than the lifetime value of your customer, then, you know, it’s time to step.
You know, I want to circle back to that first point solving the customers problem, because that’s also a continuation where the problem may change for the customer over time. Like I mean, you’re almost a decade in now do attentive, and I’m sure that the customer problem has changed, maybe not drastically, maybe slightly. But as you think about the evolution of the customer problem, how do you it’s a two part question here, like one, how do you ensure that you have an organisation that at scale can react to how a market may be changing how a customer problem may be changing? And to what have you found more specifically, through scaling attentive, how has the customer problem that you initially solved in the early days, how has that changed over time for for you guys as a business?
Yeah. So that the customer problem was always changing. And that’s why startups exist. So it’s a very good thing for startups. And it’s a good thing for really nimble and well wrapped companies. But it’s really hard to keep up with the changes to the customer problem. And I think that’s where you often run into this MBA to sell out, right, where they’re solving a customer problem now, but that problem is changing, but the solution or what they need to do change, it can ruin their core business today. And you know, this, this is to help do that. So it’s very hard to keep up with with the customer problem. I mean, some of the things you can do is continue to really get feedback from customer understanding and put that in into your customer, your product roadmap and change your your product based on, you know how that problem has changed. And we’ve done that at attendance by constantly listening to customers having certain sets of customers that we’re kind of always on board with, and hearing them out, in order to adjust. I think you’re also looking at things like NPS, you know, that’s a close look at file, you know what your net promoter score is, because if that number starts dropping, it’s often because you’re no longer solving the problem. Now, the customer probably is cheating. But of course, the marketplace of solutions is also changing. So that’s the other the editing factor, right? Someone might have found something that’s better than what you found solve a problem. They might have invented a better mousetrap. They might have invented a cheaper mousetrap. And you know, that can that can change things pretty radically fast. And so you get to keep an eye on the customer problem, but also understand this solution options they have.
How do you see the customer problem is shifting over the next five years specifically within your guys market?
What do you tell the business? I think that the last 10 years has been For a lot of people still a lot of harvesting on channels like social on Mata x like that. I think that those channels are saturated now. And I think that the buyers and marketers across wide swaths of companies, they need to find better ways to engage us areas where they’re not saturated. So I think that’s a great, you know, for tax, we’re still early in our journey, you know, we’ve never been around for a minute, the vast majority of people we talked to do not have an existing solution. So they’re still figuring out if there’s something there, they’re not doing something. Whereas if he talked about something like that, everyone’s on that, to some degree. I think also, you know, obviously wanted a bit technology advances in AI are offering new opportunities that we’ve had of this coming out, and that has a bunch of very cool AI products that are creating personalization within messaging that I think can can really try and have incredible performance and work, you know, for both the marketer and the consumer. So that, you know, I always like the movie Minority Report where, you know, everything is kind of personalised to the character. And I think we’re going to see that happening more and more across channels.
Yeah. A couple other things I wanted to touch on. Quick before I let you go. One is I heard you talk about the importance of hiring recruiter very, very early in the company’s life. I I’m curious if you can share your thoughts on why you feel a recruiter should be one of the first hires that a startup makes?
Sure, I mean, whether they’re VCs or entrepreneurs who have everyone loves to say, the talents, the most important, the People’s the most important making a bet on the right. But yet, we don’t have some of that the company in most companies who’s focused on people that will say, Oh, well, the CEO should be doing that. The CEO should be spending a lot of time doing that. But that’s not the CEO did on the job or focus. And just because of that, the reality of life and running a company, is that you’re not going to get it as much time as it yet. I think that there’s an underlying and true companies that have full time pretty teams, because you interview 20 people for a job rather than three,
then you can improve the experience of the candidates, et cetera. So that makes a lot of sense. I mean, hand in hand with that is, if you’re an enterprise SAS company, or your b2b SaaS company, when when should STRS be joining the team? Like when would you hire your SDR team?
Well, when a tendency to get higher than before we hired engineering, so I would, I wouldn’t hire three or four of them very early. You know, think about it this way. In SDR cost these days, probably 1/3 of what an engineer costs. But you can go out and get it a tremendous amount of meetings and learn from customers and all that sort of stuff very early on, which will shape your product roadmap. So I would have that team very early on. And I would use that team to learn about, learn from the buyer learn about the marketplace. And then you’re also building your sales saw, so that when you when you are ready to test market concepts, when you are ready to roll a problem down, you’ve got to help people to do it, you’re not you’re not sort of playing catch up, because you need that in order to figure out what you should be building. So tactically,
how did you? How did you embed yourself in the sales process? Did you have your STRS do a number of meetings per week, you find patterns, and then you pick the customers you want to follow up with? Because founder led sales is, you know, it’s obviously an important part in the zero to one phase as well. So how do you recommend that founders work hand in hand with the SDR team,
go join the calls, you know, either leading the call, or listening to the call, you can always read the notes. But being in the call and doing it, it’s very different than reading the notes. You can you can listen like if you’ve recorded you know, I will record it for sure. They’ll make sure you watch the video recording because there’s a lot of body language that happens that may not be any audio. But I would just join calls, go join costs.
And now with your third company, what are you doing different this time around versus tap and attentive?
I think that we’ve taken an even longer term focus. I think that we we know what can be big. And and we know I you know it’s always dangerous to start getting an ego to think you can do things because it’s always very hard. You’ve always gotten the guests and all that system, but I think we have a caller Demeter towards taking a longer term view, having a thesis around that view, and then understanding how the pieces can come together for success. You know, even with the tab, I think the idea of getting to over 100 million in revenue or 500 million in revenue, that was a hard thing to imagine, for the first couple years of the company, I’ve never got there. But it was hard to imagine that I think that with, with companies we’re doing now you can imagine it now. You can see, okay, here’s how I can get to the US Civil War companies that have done that. Here’s the path to getting there. And once you understand that, you can kind of work backwards to say, Okay, what do we need to do in order to make that happen? And it becomes more possible, you kind of you put the pieces together much easier.
Do you think part of that is also just the confidence that you’ve built, like in yourself as a founder having done it before? Like it’d be that’s a very, you know, 100 million in revenue is a huge milestone that a lot of people almost don’t believe that they can reach in the fact that you’ve surpassed it. And I don’t know if you guys are at 500 million or not, but it’s got to add confidence similar to finding product market fit, and how much how much do you think that plays a role this third time around?
And you know, I will tell everyone, that there’s not a reason that they can’t do it, as long as their markets big enough that the curse of most of these distances is that the tanks just not big enough. So as long as you can is there, then you can do it? And you’ll get
Brian, if we could feature anyone on the show. Who should we interview and what topic would you like to hear them speak about?
I would talk to our the we’ve had a CRO with Brian now percent for the last, really since inception, the company, he joined when we were signing our first couple of customers, and today he runs a team of 500 plus people on just the sales and CS teams. And I think he’s got an incredible bag of tricks and strategies and strategies set to get to where he is.
What book article or video would you recommend to listeners, either something in recent memory that you found informative or inspiring?
Well, I’ve got to show my book, which is called problem hunting, the tech startup textbook. So go check out problem hunting. If you’re looking for additional reading beyond problem hunting. I’ve got a lot of this this books I love. In particular, recently, I was rereading Disney more, which if you haven’t read Disney word, it’s a fantastic book about Disney from like the 80s to the 2000s. Interesting.
And then last but not least, what is the best way for listeners to connect with you? I’m
usually good as email me, I’m Brian.
All right, easy enough. Well, Brian, thanks again for coming on the show. And best of luck here with your third venture.
Mate, thanks so much for taking the time and then appreciate Of course.
All right, that’ll wrap up today’s interview. If you enjoyed the episode or a previous one, let the guests know about it. Share your thoughts on social or shoot them an email, let them know what particularly resonated with you. I can’t tell you how much I appreciate that some of the smartest folks in venture are willing to take the time and share their insights with us. If you feel the same accomplishment goes a long way. Okay, that’s a wrap for today. Until next time, remember to over prepare, choose carefully and invest confidently thanks so much for listening