Dave Rogenmoser: Building lessons and gaining momentum in the AI revolution

Dave Rogenmoser:

We get on some Zoom calls with some of these customers that were in my coaching program and I was like, “Hey, can I just run this thing by you? Type in your business name and it’s going to spit out like a headline.” And that was magic. And people would just be like, “Holy bleep, give me access. How can I get this today?” And it was just like people were ravenous on these Zoom calls. And up until then, everything we’d ever done, I had never had that reaction before.

David Cowan:

Welcome to Wish I Knew, the show about the revelatory aha moments that founders, CEOs, and leaders discover along their own business journeys and why taking risks leads to growth. I’m your host, David Cowan.

On today’s episode, we’re doing a dive into arguably the busiest sector of technology of the moment. That’s right, we’re talking AI. Now for many, the idea of AI, which stands for artificial intelligence, can be daunting. And although it’s recently taken the world by storm, the term artificial intelligence was actually coined back in 1956 when four people, John McCarthy, Marvin Minsky, Nathaniel Rochester, and Claude Shannon organized the Dartmouth Conference and laid the foundation for AI as a formal research discipline. And while the term artificial intelligence has been around for decades, it’s at this moment that the technology’s being applied at breakneck speeds to healthcare, finance, transportation, and even to marketing, which is where we find ourselves for today’s episode, exploring a company that’s leading the charge in AI generated marketing copy. And that company is Jasper.

Jasper uses AI to create original content for just about any marketing need you can think of, from Instagram captions to YouTube topic ideas, blog posts, article headlines, maybe even this podcast intro.

David Cowan:

It’s like having your very own robot sidekick with an infinite supply of ideas.

David Cowan:

Exactly. That’s right, Jasper. So today’s guest is none other than Dave Rogenmoser, co-founder and CEO of Jasper, a company that in just 18 months went from launch to unicorn and is now valued at $1.5 billion. With such acceleration, there’s a lot to learn. And as computing power continues to increase and data sets become even larger, the possibilities for AI are virtually limitless. So with that, let’s get into today’s episode featuring Dave Rogenmoser, which is moderated by our mutual friend and my partner at Bessemer, Sameer Dholakia.

Sameer Dholakia:

Well, welcome everyone to the Wish I Knew Podcast. We’re so excited to welcome a friend and amazing CEO and entrepreneur Dave Rogenmoser from Jasper. Please say hello, Dave.

Dave Rogenmoser:

Ready to rock and roll. Thanks for having me.

Sameer Dholakia:

This is going to be a super fun conversation. So let’s get started with the basics. Go ahead and just introduce yourself, tell us your name and what you do.

Dave Rogenmoser:

Yeah, I’m Dave. I launched Jasper about two and a half years ago. We basically help marketing teams write really high quality content that’s on brand and in their tone of voice and do it much, much faster so they can get great marketing results from all their efforts here as we’ve been using the AI to help do that and been scaling really quickly over the last two years.

Sameer Dholakia:

I have had the privilege of getting to know you over the past couple years. And a huge part of our interest, my interest in investing in Jasper was you. So the next question for you is, how would you say that others describe you?

Dave Rogenmoser:

They would probably describe me as a guy that likes to think strategically and I’m the guy that’s kind of coming up with the new ideas, or I’m the guy convincing all my friends to buy Bored Ape Yacht Club, JPEGs, all of that. Yeah, you know, family man. I’ve got three little boys, five, three, and one that are wild.

Sameer Dholakia:

You left off amazing golfer that can hit the ball 300 yards off the tee, but I’m going to throw that in.

Dave Rogenmoser:

I appreciate that. I do like playing golf a lot.

Sameer Dholakia:

All right. Well let’s talk about your entrepreneurial journey because it’s been an extraordinary one. You co-founded Jasper with two amazing guys who I’ve had the pleasure to get to know, Chris Hall and JP Morgan. But Jasper was not the first venture that the three of you worked on together. Maybe just share with the listeners a little bit about how you met those guys and what made you want to go into business with the three of you.

Dave Rogenmoser:

Yeah. So I was working for this campus ministry at the University of Missouri and thought that I needed to go learn how to start a business and didn’t want to go get a regular job and was reading some books on what that looked like. I didn’t know any founders. I didn’t know what that was. I grew up in Topeka, Kansas where we didn’t have founders. You might have the… There was a guy that owned a few Wendy’s. That was the big business guy that I knew of. And so I went to this wedding, I sat down next to Chris, who I knew loosely, and I was like, “Hey, what are you doing these days?” He said, “Well, I’m starting a software company.” He goes, “I’m taking this course that teaches you how to start a software company with no idea and no money.” And I was like, “That’s me.” He’s like, “And best of all, you don’t need to know how to code.” So no skills, no idea, and no money.

David Cowan:

And as you can hear in Dave’s voice, this opportunity was music to his ears. So he took the leap and enrolled in the course officially kicking off his founder journey.

Dave Rogenmoser:

So I went through this course that taught how to do that and you’d talk to customers. You’d basically let them describe the product to you. The kind of idea extract this thing out of the market and then you’d go hire somebody on Upwork to go and build it for you. And eventually, he and JP were working on one company. I was working on this other company and we kind of made an agreement. We’re like, “Hey, whenever anyone starts making money, we’ll just team up together on that thing.” And so I ended up pivoting and started this marketing agency that teaches you how to start a marketing agency with no money and no idea and no understanding of marketing, and basically got that working and convinced them to come over and work with me on that. We just really wanted to build a business around our friendship and be committed to each other in that. We didn’t have any grand plans of building something huge. We just didn’t want to have to go get jobs and we wanted to just enjoy the process.

David Cowan:

Dave and his two buddies set off on a new venture back in 2014 to try to build a successful marketing agency. But once that business was built, it was time to set some founding goals.

Sameer Dholakia:

When the three of you got together and said, “Hey, we’re going to start this business,” what were your expectations around how much revenue the business could build or how much it would be worth someday or anything like that?

Dave Rogenmoser:

I had written down on this note card years before, “By the age of 30, I wanted to be financially free by starting multiple profitable businesses and creating passive income streams.” And my goal on there was to make $30,000 a month, was total freedom. I never have to think about money again and all these things there. At some level in my mind that was the goal, even though I wasn’t kind of aiming for that necessarily. But yeah, we just wanted to build a nice little business, have some employees, play some golf, and just enjoy doing it together.

Sameer Dholakia:

Yeah. So what happened from there?

Dave Rogenmoser:

We were making revenue, but that’s when we found out profit was different than revenue. So maybe the theme of the show, what I wish I knew was that revenue and profit are two very different numbers. We just weren’t making any money at the end of it after all the work and we were exhausted and worn out. But we’d learned so much about marketing because every client, I’d have to go build a brand new marketing campaign. It was like an air conditioning unit company in Birmingham was one of them. And then I had help this guy in Hawaii sell ozone generators. And then I have to sell this PT services in Boston. So it was just like this crash course every week in marketing, but then turned that into a course and a program on how to go basically start a similar business.

I was really good at this sales part of the agency work, but kind of bad at delivering it. And so I went and just started this course on how to go land clients and kind of scale out a little consulting business and help others do that. Selling a course is hard work because it’s a commodity or it becomes one very, very quickly. And so you kind of just live and die off of how good your marketing can be. And so you just get amazing at selling a product that’s kind of hard to sell at scale. It seems to be incredible at funnels and optimization and all of that. Learn how to build community, learn how to build a tribe of people that care about this common thing.

Sameer Dholakia:

Which we’re going to come back to is-

Dave Rogenmoser:

Yeah, yeah. These are skills that all kind of add up to Jasper. But ultimately, built that up, did a bunch of coaching stuff, started selling 30,000, $50,000 a year packages to people on how to grow their business and was selling $19 a month memberships to a Facebook group that’s just for entrepreneurs. So kind of the whole gamut. And then we just got tired of that too as we made the next pivot, which was a more productized version of that. We basically said, “Hey, we’re teaching people how to run ads and get increased conversion rate. What if we just did it for them?” And so we started this company called Proof.

David Cowan:

Proof was Dave, JP, and Chris’s first software company that they created in 2017 with Y Combinator, a startup accelerator that’s helped launch thousands of successful companies including Airbnb, Reddit, and Dropbox. And Proof was a product that helped build social proof by displaying recent customer activity on a company’s website.

Dave Rogenmoser:

It was based on a little popup that you put on your site and showed how many people had purchased an item in the last 24 hours, or it might say, “Sameer bought this pair of pants six minutes ago.” It increased conversions just through social proof. It was this whole new thing of building software that was really new to us and how do you scale it. We ended up making a bunch of mistakes there that, again, all of those things combined kind of led us to being the right people at the right time for Jasper.

One of our biggest mistakes early on, and there was so many mistakes, and we still are, we built ourselves into a corner where it got really hard to do any development on it. We had all this tech debt and it wasn’t kind of built using microservices basically at this point where it was like, “You can’t do anything else on this thing without having to rewrite the whole thing.”

Sameer Dholakia:

Oh, interesting.

Dave Rogenmoser:

I remember going into Jasper-

Dave Rogenmoser:

Having to rewrite the whole thing.

Sameer Dholakia:

Oh, interesting.

Dave Rogenmoser:

And I remember going into Jasper, like JP, our CTO had learned that mistake and built it to be more componentized and easier to switch out. It wasn’t just this kind of monolithic app, but it was something that if one part got obsolete you could just go and rebuild it and a week. It wasn’t this big thing. But again, if we hadn’t learned that with Proof, we probably would’ve done that with Jasper and four months in we would’ve painted ourselves in the corner that we can’t kind of get out of there. But fortunately we didn’t.

Sameer Dholakia:

Totally.

Dave Rogenmoser:

Yeah, I think we just never figured out how to make this into a bigger platform. We ended up getting to about $220,000 of MRR. We did Y Combinators, so raised 2.2 million bucks there. And I think a big mistake we made was once we raised that money, we kind of thought, “Okay, we’ve got this money, we’ve got time to solve this platform thing and so let’s build this platform, but we’ll launch it in a year.”

We kind of just kicked the can, the pain of the market down the curve a really long way, to the point when it kind of got time to actually launch it, we realized we were just not in touch with what users really wanted. The people that we’d kind of been talking to were being nice to us and we’re friends and we’re just kind of saying they didn’t want to break our hearts. And we ended up letting go of a lot of the team at proof and figuring out what was next. But we kind of looked at each other, we said, “You know what? We are never doing that again. Everything else we ever do, we will launch and get a user on it within a month and we need people to start paying for it as quickly as we can.”

Sameer Dholakia:

Totally. What should listeners who, or founders, what should they look for to know whether what they’re working on is a feature versus a company?

Dave Rogenmoser:

It’s basically a set and forget kind of thing where you just put on your site and then if it works, you never come back. But it’s not really good to have a set and forget company in most cases. Again, sometimes that’s the value prop, but in most cases you actually want your users using it and logging in and it becomes part of their workflow and part of their life. And there just really wasn’t anything else to do. And then also as the market got flooded with competition, pricing power drops, but we just couldn’t think of anything else to build. And even as we talk to users, there was nothing to do. And it’s funny, no other competitors to us back then ever figured out the next thing to build at all. Proof is still probably the biggest social proof popup tool in existence, and nobody else ever iterated past that.

We tried to make this move into website personalization, which was tangentially related in that what we felt like we sold was conversion rate optimization. We needed to sell to the enterprise and we were selling to SMBs. There was a lot of work to set up. There was a bunch of edge cases around hooking into websites that a was real pain. And we would do all this work for company, for our customers and they would pay us $200 a month. That’s costing us 10,000 a month to service this customer. And we never saw a path to it being something great. I think just obviously make sure that you’ve got a path to building something that you could continually iterate on and otherwise you could just end up with this feature that’s easy to get commoditized and hard to keep building on.

Sameer Dholakia:

And where the unit economics have to make sense and all the churn rates. And does that all map to the segment you’re pursuing? All those things. It sounds like y’all wrestled through, you had mentioned earlier that y’all ended up having to lay off a big chunk of the company and layoffs, boy, I tell you, I know they are the worst things that I have ever had to do in my professional career. They’re heartbreaking, they’re difficult. Any things that you learned in that process in the spirit of I wish I knew?

Dave Rogenmoser:

Yeah. Proof, as much of a technical learning lesson, it was really a big crash course in people management. And if anything, that’s kind of maybe the biggest thing that we got from it. And I think a few things that we did wrong. One, we hired everyone and we just thought we’ll teach them what they need to know. We ended up hiring this cousin of Chris, great guy. He was like an accountant. We hired him and ultimately we’re like, “Hey dude, you’re our VP of sales. You need to go figure out how to do this.” And I don’t know how to run a sales team. He doesn’t know how to do it. We look around, nobody here knows how to do it

And I’m asking to scale this thing out and we end up just like it doesn’t work out, not for lack of effort. But I think with Jasper this time around, I’m looking for both and I’ve learned to hire people that have seen greatness, have seen the role, have some level of competency, but are still super hungry and maybe haven’t had the big win yet. And that has gone so much better and taken so much stress off of me from having to figure out how each function is supposed to work and operate. It’s like that’s what I wish I knew, was hire people with more real life experience doing what you’re asking them to do. Which again, maybe it sounds obvious, but I think a lot of startup advices also just hire the person that’s the go getter that’ll figure it out and turn them loose.

So I think we left Proof thinking we’re never going to hire anybody again because layoffs are painful. I felt bad, I felt like I had sold some of my friends on this vision and then let them down.

Sameer Dholakia:

So hard.

Dave Rogenmoser:

But also it’s just so much work and so many problems and I wish I knew that there were good managers that are just really, really good at that. That’s what they offer to the world and they’re trained in it, they’ve developed themselves in that. And it wasn’t totally obvious to me at the time, I just thought all the founders had to be all the managers and that totally changed with Jasper.

Sameer Dholakia:

I know I’ve seen plenty of examples in my career of startup size companies going too far and then wanting to hire somebody who has an unbelievable resume and pedigree and has done all these things but they can’t even remember what it was like to work in a startup.

Dave Rogenmoser:

Yeah, yeah.

Sameer Dholakia:

It has just been so long ago. And then they are just not used to working at that frenetic pace. They’re not used to the lack of infrastructure and support that is so common that they got when they were at the big company. And so I think your advice there of find both is really instructive for the founders out there listening.

Dave Rogenmoser:

You’ve got to have a mix of those kinds of people. So I think you can have the just hungry person that hasn’t seen it but pair them with people that know what they’re doing.

Sameer Dholakia:

Totally agreed with that.

David Cowan:

Coming up, having made and learned from a few missteps in his previous ventures, Dave brings his harder knowledge in hiring, goal setting, and revenue building into a sector emerging from the research labs into the hands of developers, artificial intelligence, and how Dave pivoted his career into devising his biggest creation yet, Jasper. Plus, the significant impact of Chat GPT on Jasper since it became accessible to the public.

It was early 2021 that Jasper was founded. Our moderator, Samir, remembers when Dave took that leap to enter the AI space with Jasper.

Sameer Dholakia:

I always love to joke about how this overnight success story of Jasper’s, in my mind, a decade in the making. How do you know, if you’re a founder, whether you should be making the pivot? Whether it’s time?

Dave Rogenmoser:

One of our companies before this or our shell company for the course company was called Pivot and Scale. It’s even for early days, we love to pivot. Just been a huge part of our story. I think for us, we would just become demotivated on something. I’m not waking up looking forward to working on this thing anymore. And if you spend a little time thinking about something a little bit different, a lot of times we would get so excited about some new idea that it was like, “I can’t possibly spend another second working on this old thing and I cannot wait to get out of bed tomorrow and work on this new thing.”

And usually we were always pulled into pivots, but I don’t think people pivot enough or fast enough and they end up kind of grinding it out because they think that they’re so close. And in my experience, everything we’ve done well has had signals of being really great very early on. And the things that have taken us maybe six months or a year of grinding before we kind of see into that typically didn’t turn out very well at all. So if you’ve been grinding for a long time, at least take a week or two and kind of think, “If I wasn’t doing this, what would I do?” And I think oftentimes you’ll find something that you’re just like, “That’s it. I can’t believe I didn’t see that.”

Sameer Dholakia:

I think that’s great advice and I think it takes a lot of courage to execute the pivot.

Dave Rogenmoser:

It’s so hard that you’ve got to be excited about it in order to again, put in the effort and the thinking and you got to be thinking about it while you’re at dinner even though you’re not supposed to be because you’re with guests and it takes that kind of zeal. And so if you’re not excited about, it’s just not going to work anyway because somebody else in the other end is excited about that thing and is going to beat you. You’ve got to make the pivot for it to even have a chance anyway.

David Cowan:

Dave and his co-founder’s next pivot was to found the startup now known as Jasper. Their startup went through a number of name changes from conversion.ai to Jarvis, named for Tony Stark’s AI butler. But Marvel wasn’t thrilled about that last one.

Dave Rogenmoser:

People obsess over these startup names and then I’m on name number three of a pretty good company, so don’t spend too much time caring about all that. Apparently you can change it later multiple times. But basically, we kind of spun down proof in October 2020 and I went back to kind of my old roots right after that and I was like, “Oh, I’m going to start this coaching business on how to do Facebook ads for B2B SaaS companies.” It’s like that’s what we had done well and that’s kind of always been my fallback.

And it was funny in that, I think it was week four, was how to write great ad copy. And I’d had this formula that I’d kind of developed that we would use to run ads for Proof and all of our businesses. And it worked really well. Then I would teach it in this course and I would meet up with everyone the next week and most of it was not good. And I was like, “Why are they not able to follow?” I’m not teaching this well enough or it’s just new or whatever. And because it wasn’t good copy that they were writing, their ads weren’t going to convert, my course wasn’t going to work. And I was like, “Well, I could write it all for them,” but that’s kind of these…

Dave Rogenmoser:

Yeah, my course wasn’t going to work. And I was like, well, I could write it all for them, but that’s kind of exhausting. And I’d seen GPT-3, I’d seen some tweets and I was like, oh, AI looks like it could maybe handle this. And so I had just seen a way to get access through Y Combinator. And I remember texting JP, if we make a really simple front end to this API, we could build a really nice business, help people write marketing content. And he is like, “All right, I’m on it.” And so JP builds this MVP over the course of a month or so, we get on some Zoom calls with some of these customers that were in my coaching program and I was like, “Hey, can I just run this thing by you and type in your business name and it’s going to spit out a headline.” And that was magic. And people would just be like, “Holy bleep, give me access. How can I get this today?”

And it was just like people were ravenous on these Zoom calls and up until then, everything we’d ever done, I had never had that reaction before. Nobody was ever beating down the door for our product. And so I was like, okay, this feels different. This feels like maybe this product market fit thing that I’d heard about and always wanted. And then it was probably the second week we decided, “Hey, let’s open this thing up and just see what happens.” So we built a signup flow, which wasn’t even there when we were onboarding people. There was no cancellation button for the first month, which is a good way to defeat churn. You’re like, “You can’t churn.”

But just to show people how bare bones this thing is and all the stuff that people build that you don’t even really need to go and launch. And then it just took off week three and people were loving it. We were out of $20,000 MRR think at the end of the first month. And it was just like, all right, this is off to the races. We kind of pivoted all of our work. We had a couple remaining employees that were like, “Stop what you’re doing. This is the new business.” I’m calling the team that we had just let go. And I’m like, “Hey, get ready. I’m coming back for you soon. I think we got something here.”

Sameer Dholakia:

That’s awesome.

Dave Rogenmoser:

It ended up just kind of being on the wild ride that was conversion.ai and turned into Jarvis and turned into Jasper.

Sameer Dholakia:

We also talk a lot about product market fit. I love talking about founder market fit and I think there are certain problems in the world that need to be solved, but I think that the ones who are most successful at solving them are the right people for the job. And it really does help to have some real depth of understanding of a problem and real expertise in the area, which clearly you guys have.

Dave Rogenmoser:

Yeah. And I think it’s important to your customers, and maybe that seems like a little trivial, but I see people start businesses with customers that they don’t even like and they don’t really want to be around and they don’t really want to hang out with and it doesn’t seem to ever go well.

These marketers were like our people. They were our crew, they were our friends. I liked hanging out with them and I liked sitting around and talking about marketing copy formulas with them. You’ve got to spend so much time with customers to make this work that if you don’t like them, you’re never going to put in the required amount of time to do that, and you’re not going to have the empathy for them that I think you need to go build really nice products for them. And so that would just be a lesson too. It’s like, do you actually even enjoy this market problem that you’re solving because it’s just a lot of work and making money alone is not a big enough motivator to get you over the hump of not even enjoying the process.

Sameer Dholakia:

So obviously with Jasper, it was incredibly popular from the jump. I remember when we were first talking, you’re like, “Yeah, man, you won’t believe it. We’ve got customers that are getting tattoos on their arm.” And I think that was actually when it was still Jarvis. I don’t know what they did with that if they had to rebrand their tattoo.

Dave Rogenmoser:

One guy still has a thigh tattoo with Jarvis and the logo.

Sameer Dholakia:

Oh, my God.

Dave Rogenmoser:

And just the old name. But he actually loves it. He’s kind of like it’s vintage memorabilia that nobody else has.

Sameer Dholakia:

I mean, that had to be an incredibly powerful moment for you all as founders to know the customer love for the service you had built was so strong.

Dave Rogenmoser:

Oh, yeah. No, there was a lot of moments that first year that we just would pinch ourselves and just think, is this real life?

Sameer Dholakia:

That’s awesome. Now you brought up something just a minute ago too. That’s also one topic that I know I have wrestled with my entire life, which is when you’re so in love with a problem that you can’t turn your brain off on it because… So it’s got to get solved and you’re just always thinking about it even when you’re not supposed to. And yet, I know for both of us, we care a ton about family, about being good husbands and being good fathers. How have you managed to strike that balance in your own life? Any words of wisdom for the listeners out there who are going on their own journeys here?

Dave Rogenmoser:

Yeah. Back early days, I would wake up, I don’t know, maybe around 9:00. This is when I was single. And I would sit at my desk until midnight working and it was amazing. I was just doing so much learning and it was fun. Again, my palms would be sore from sitting on top of the desk. But then I got married and my wife wasn’t about that life and I had made this commitment to her that I would be about her over work. And that was important to me.

And so started finishing up by 6:00. And what I found was I actually got just the same amount done just in a short amount of time. Cause I just knew I didn’t have all day to do it. And so I just kind of compressed it all and still got to do really great work. And then you have kids and it kind of gets eaten more and more. It’s like you can just work smarter and you can find the hours in various places. And at the end of the day, I signed up to have a family and made those commitments. So I’m just trusting that I can do both well. If I had to choose one, I’m not doing Jasper anymore. Unfortunately, I don’t have to choose one, but it’s like I’m the only dad that these kids will have and I’m the only husband that my wife will have, and I want to be good at the things that are ultimately important here.

Sameer Dholakia:

And having that mental clarity on the prioritization helps drive lots of other smaller decisions throughout your life.

Dave Rogenmoser:

It’s motivating to have a family. Yeah, it makes me work better at Jasper and I’ve got other people to do this for and I’d love to have my boys work for Jasper someday. And it’s just like it’s all woven together. So these are not two different things, but it’s just a different life for sure.

Sameer Dholakia:

Let’s talk a little bit about scaling. Company obviously has been growing a weed. You have so many more employees than you did a year ago, let alone two years ago. And maybe share a little bit about what do you wish you knew about team building, leadership development, any stuff about scaling?

Dave Rogenmoser:

Yeah, we had a very weird path for scaling. I mean, the first year we basically were still like, “Hey, we’re not going to hire anybody. We’re just going to use Zapier and automate as much as we can.” Which was actually a pretty… It’s remarkable how far we took this thing. At the end of the year, we had think 35 million in ARR and nine people, two customer support people serving 40,000 customers. And so we actually pushed it really, really far before we decided, hey, let’s go for this thing here. But I wish we would’ve started hiring and built up a team a little earlier, even six months earlier. We wouldn’t have had to ramp up last year so fast, which I think it’s hard and probably unwise to go from nine to 180 in a year. We ended up getting to this point where we had all these new great people, but no one knew what we were doing and their boss joined a week before them, and the boss’s boss joined a month before them.

And so it’s just a lot of context sharing all the time. And so I think I wouldn’t recommend hiring that fast and get out ahead of it a little bit. This is something we did right, and we hired an executive recruiter for the first time to help us go find some real good leaders in these new pools and ended up hiring a president that was a guy that I never could have hired or even talked to without an executive recruiter because I just wasn’t in those circles. And ended up hiring a really good executive team with the help of that recruiter. And it’s $150 grand. And I was like, that’s insanity. I would never pay that. But it’s like the most ROI positive money I’ve ever spent at Jasper. And the trickle-down effect is so big there. That’s something we actually did right.

Sameer Dholakia:

No, it is a great ROI because the benefit of having the right leader in seat over a given function is the difference between success or failure. And every function needs to be hitting in stride for the whole company to be successful. I always use the analogy of the rowboat. If the oars aren’t hitting the water at the same time, you’re going to be spinning around in circles as opposed to going in a straight line as fast as you want to go.

Dave Rogenmoser:

We’re looking for this president role, and I talked to this guy that I thought was really good. Now I remember talking to JP and Chris, we were like, “I just found this guy. He would be amazing.” And I showed him to the recruiter and he was like, “What do you see in this guy?” And I was like, “Yeah, this, that.” And I was like, “What do you think?” He goes, “Well, he’s not somebody I would’ve ever shown to you.”” He’s like, “I think we can get somebody five times better, but if this is the route you want to go, I guess we can go find some more guys like this.” I was like, well, okay, just show me who you got and then shows me these profiles. And I was like, I had a wrong perception of ourselves at that point. It leveled me up so much from the type of people I wanted to hire to the type of people we were able to end up getting.

David Cowan:

Hiring an executive recruiter was something Dave had control over, but there were other things this past year that Dave and his co-founders had to learn how to deal with on the fly, including the launch of ChatGPT. You see, Jasper was created in partnership with OpenAI, an artificial intelligence startup. And on November 30th, 2022, OpenAI launched an AI chatbot called ChatGPT that people could use for free, and Dave could feel it instantly. This chatbot was going to be a game changer in the industry.

Dave Rogenmoser:

I remember the first time I saw in Slack, we have a Slack channel with them. They’re like, “Hey, we’ve got this new thing called ChatGPT, check it out.” And I was like, all right, let’s see what this thing was. I kind of started playing around with it. I was like, “Ph, this is pretty cool.” And then, you see it quickly explode on Twitter. And then my dad’s asking me about this thing and I’m like, “Dad, that’s kind of like what we do. This is the space I’m in.” I think for the first few weeks it was like, yeah, I don’t know what to think. It’s like is OpenAI a competitor now? Are they a partner?

Dave Rogenmoser:

… because Open AI, a competitor now, are they a partner? At the end of the day, it brought a lot of awareness to the market, and all these people that we’d been trying to get interested in AI were finally now at the table saying, “Hey, I heard about this over Christmas, I’d love to talk about what Jasper does. It looks like it could help me too.” And then there’s other people that were using Jasper lightly that were saying, “Hey, this thing’s free, I’d rather save the money.”

And so we saw more of the low end churn out, or start asking more questions. But then again, all these new business customers in January came to the table and like, “Hey, we’ve got to buy this for our marketing team. We want collaboration, we want role management, we want some of these other bells and whistles that Jasper been building over the last two years.” And these are people that would’ve gotten fired for buying an AI content tool six months before. Now they’re going to get fired if they don’t. And that was a really quick education of the market that we weren’t really prepared for. But it ended up, yeah, really focusing our company.

Sameer Dholakia:

It’s a great lesson, I think, for founders who are thinking about when you see these big disruptive events, I think sometimes it’s natural for folks to overreact, when oftentimes it ends up being a great thing for the business. Because it brings, as you described, Dave, an unbelievable amount of market awareness. On generative AI, obviously one of the most talked about categories in recent memory, anything that you see on the horizon for that technology or the space at large and its potential for the impact to business and the world around us?

Dave Rogenmoser:

Yeah, I think it’s going to be enormous, and I think we’re still scratching the surface on the application of this. And that is opportunity for people listening. If you can take this technology that is cool in demos, but bridge the gap and make it useful for regular people? You’ll be a hero. But I think we’re just going to see these tools do more for people in sophisticated ways. Right now, Jasper will write content or make an image for you, and you’re working with the tool, and clicking the buttons and all of that.

But in the future you’ll be able to say, “Hey, build a marketing campaign over this product on our website.” And it’ll just create 400 assets for you, it’ll load them up in active campaign, or HubSpot or whatever. It will send them for you at the right time for each segment, and that’ll all just happen. It’ll be like having this whole marketing army just working for you all the time, and that should free up marketers to just do much better work. And it doesn’t mean that creativity goes away, it doesn’t mean that empathy for the customer goes away. It doesn’t mean that really understanding people deeply goes away. Those get heightened, and those become more valuable in that world.

But I don’t think you’ll spend as much time fighting with email automation like stuff, and writing out all these different assets and all of that. So I think it’s just going to do more of the end-to-end staff for you, and obviously you can take that and apply it to every team at a company. That’s just a marketing example, that’s what we specialize in. But it’ll be that way for sales, and for CS, and for engineering and all these different places. The end-to-end problem will be solved in a magical way.

Sameer Dholakia:

Love it. Okay. So Dave, to get to know you a little more personally, I have five rapid fire questions for you. You ready?

Dave Rogenmoser:

I’m ready.

Sameer Dholakia:

What are you reading or watching currently?

Dave Rogenmoser:

I watched Succession the other day, which is interesting. And I’m reading a book on how the Chicago World Fair was built back in the late 1800s.

Sameer Dholakia:

Oh, interesting. All right. What’s your favorite place that isn’t your home or your work?

Dave Rogenmoser:

Driftwood Golf & Ranch Club down the street.

Sameer Dholakia:

If you could have a stage walkout song, what would it be?

Dave Rogenmoser:

The Chicago Bulls intro theme song.

Sameer Dholakia:

Love that. Which skill would you love to learn.

Dave Rogenmoser:

Hunting.

Sameer Dholakia:

What do you wish you could do more of or do less of?

Dave Rogenmoser:

I wish I could spend more time playing with the boys throughout the day.

Sameer Dholakia:

Yep, all right. Final question. On the Wish I Knew podcast, we end each episode with a parting thought for our listeners as they embark on their own personal and professional journeys. So I’ll ask you the same question. What do you wish you knew either before it all began or as it was unfolding?

Dave Rogenmoser:

I wish I knew that the journey itself was the reward, and that… I don’t know that I’m any happier than I was early days when our business was making a dollar a month. It’s just different, and that learning to enjoy the journey and the process and doing it with people that you makes it effortless. Almost effortless to build something. And just learning to enjoy the ups and the downs of it is so key. Because it’s a marathon, and you’ve got to endure. And if you get taken out of the race because of founder issues or because you burnt out or whatever then it’s not going to work. And so I think yeah, just learn to enjoy the journey and you’ll probably show up enough days in a row to make something work.

Sameer Dholakia:

That’s fantastic advice. So thanks for the time today, bud, we’ll catch up soon.

Dave Rogenmoser:

Yeah, thanks for having me. It’s been fun being on the journey with you. Thanks for all the help, and I’m sure that I’ll look back and laugh at all the things I didn’t know on this podcast many years from now, and I’ll go learn them this year.

David Cowan:

That’s it for today’s episode of Wish I Knew. You can find and follow the show on Apple, Spotify, Amazon Music, or anywhere you listen to podcasts, or at bvp.com/wishiknew. A special thanks to our guest, Dave Rogenmoser for coming on today’s show. Wish I Knew is a podcast by Bessemer Venture Partners. The show is created by our very own Karen Lee and Christine Deakers. I’m your host, David Cowan. Our show is produced by the team at Filia Media. Our lead producer is Molly Getman. Our executive producer is Kate Walsh. We’re engineered by Evan Viola. Our theme music is by Terry Devine King at Audio Network. Additional Music by Blue Dot Sessions.

And remember, if you’ve been grinding for a long time and aren’t seeing results, ask yourself. If I weren’t banging my head against the wall trying to make this work, what other exciting opportunity would I pursue? We’ll see you at our next episode.

 

 

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