How Ramsey Shaffer is Navigating the Challenges of Scaling a Tech Startup

[00:00:00] Hector: Hello and welcome to another episode of the How to Scale of Business podcast. My name is Hector San Esteban, and I am your host for today. We're here with Ramsey Shaffer and he is the well ceo. What do we, what do we call you?

[00:00:13] Ramsey: Yeah, I kind of, I go back and forth between c e o and co-founder. Co-founder feels more genuine from the roots. But, nowadays, I guess you could call me CEO O.

[00:00:23] Hector: CEO and co-founder of uptrend.ai, a a cool trading platform that's really built for d i y traders I'm so far from that world, but Ramsey's gonna give us a little bit of insight on how he's built it, and a big rebrand that they just went through.

[00:00:36] Hector: So, Ramsey, thanks for hanging out with us today.

[00:00:38] Ramsey: Yeah. Thank you for having me. It's, it's really cool to be here.

[00:00:42] Hector: go back as far back as you think is relevant, but give us the story on Uptrends. Cause I know you recently, you guys just changed your name and like, but take us back to like the journey and tell us the origin story, if you will.

[00:00:53] Ramsey: Sure. Absolutely. So uptrends.ai, we were previously called Babble. we can go into why we changed the name, but we do stock market news monitoring for everyday retail investors. So we essentially aggregate all of the chatter from news outlets, blog sites, Twitter, Reddit, everything that people are saying about stocks in real time online.

[00:01:14] Ramsey: And then we use some AI to detect the mood being expressed about each and every stock so that we can find. Trends and events that matter to retail investors over the short term without them having to be constantly doom scrolling through the news. I think it's a pretty relatable thing for investors, and that's kind of what it started out as.

[00:01:32] Ramsey: three, four years ago, myself, my co-founder, Sam, we're both two college students just trying to make some supplemental income trading stocks on Robinhood and learned pretty quickly that we were spending 10, 20 hours a week just scrolling through Twitter. Through C N B C through Yahoo Finance, trying to keep tabs on what news was moving the markets over the short term, mainly for fear of missing out on the really important market moving events.

[00:01:58] Ramsey: And so we looked at ourselves, we were two guys with computer science degrees at the time and said, well, there's gotta be some sort of way to automate the legwork here. And then that kind of commenced a three, four year journey to build a platform for retail investors that does all that for them. And now here we are, in 2023 with a platform called Uptrend that, does the job.

[00:02:21] Hector: Yeah, so cool. And you just spit it off and I'm sure it was just so easy and it was just so smooth and, and stuff. we're gonna get into some of the challenges I'm sure. I'm curious, you know, if you were to think about what type of. Business you're in, right? You know, you always hear like, we're not in the car business, we're in the, you know, whatever kind of business.

[00:02:40] Hector: Has the journey been more about finding a product market fit and really like trying to figure out what the product looked like? Or did you guys nail the product? And then the real journey was about how do you scale and build a company behind that product?

[00:02:55] Ramsey: Oh boy. I mean, yeah, you make it sound like it was easy. I probably did that too, but in reality it was a lot of trial and error, throwing stuff at the wall, seeing what sticks. A little bit of spray and pray, if you will, and like very early on, as two guys that are. Technical in nature. We don't have marketing backgrounds by any stretch of the imagination.

[00:03:14] Ramsey: We were just writing code and throwing it on like a very, very crappy website, and just seeing if anyone would click the button to create an account like that was our first. Two years of existence was, okay. What if we put a chart on the page that shows you the overall mood of conversation today or the past seven days?

[00:03:35] Ramsey: And it, I would love to say that we got it right the first try, or the first 10 or 20 tries, or that it's even perfect right now, but. Well, the truth, reality of the situation is that it's been very, very much iterative process over the past two, three years, and I think it's gonna continue. Being that I think, you know, that's the beauty of creating a startup is that you just keep taking steps, gradient descent your way towards something that seems to be working, and then lean into what you see it success with.

[00:04:05] Hector: Was there any big breakthroughs in that, development process that were, you know, either big ahas or things that you stumbled on, or, you know, kind of surprising parts, of that process?

[00:04:15] Ramsey: Yes, def. I'm surprised, like on a daily basis, honestly, a few of the big ones, early on we were leaning very heavily into like the AI, technical, very, very complicated type of metrics in our early days. And learned that like for people that aren't super n big nerds like ourselves, that's just not super palatable on a website that you're looking to pay for.

[00:04:39] Ramsey: So we really, really had to think hard about how to simplify what we're presenting on the page, what to include, where in the, the flow of the onboarding, if you will. so that was number one. And then number two that we've learned a little bit more recently with the rebrand and, and now going more paid feature.

[00:04:56] Ramsey: First is that a lot of our audience we thought was going to be just US based stock traders. We're learning that. 60% of them are actually people based outside the US either in Europe or Asia or Africa or South America, who wanna know what's going on in the US stock market in the news, but maybe aren't speaking English as a first language.

[00:05:18] Ramsey: And so they don't have that aptitude for deciphering, you know, the little nuances of sarcasm or negation in language. or they just don't have the time to be spending, you know, looking at US news because it's coming out at a different time of day than just typically works into their schedule.

[00:05:34] Ramsey: So, long story short, those were kind of the first big two realizations for us that really made us stop and think about what direction we were leaning.

[00:05:43] Hector: Yeah, it's always interesting.one of my mentors talks about getting into the corridor and he talks about the fact that you oftentimes don't know what the answer is going to be until you're, you're actually in the corridor and it's only when you're, there can you actually start to, and you try one door and this is not the door that lets you, and you try another door, and, but you've gotta kind of try these doors.

[00:06:02] Hector: you can't just look at the outset and, and guess which door is gonna open.

[00:06:06] Ramsey: Yeah, I got a mentor that says something similar. I think he might have paraphrased it from one of those masterclass like episodes, but it's, it was on writing and applies to startups too, like building a product is like driving in the night with one headlight. It's foggy. You can only see, you know, 10, 20, 30 feet in front of you.

[00:06:24] Ramsey: And it's just about making those decisions over the short term that get you through the doorway down the road a little bit further. So I think it's beautiful.

[00:06:33] Hector: Yeah. you mentioned not having a, a kind of a, a marketing background initially, but you just kind of had a Brigg rebrand. I looked at the site and I was like, whoa, this is, this is really, I'm like, I get it. This is like, it was really easy to understand. There was some cool graphics and visuals.

[00:06:47] Hector: So what was that journey like and how did you guys, I don't wanna say compensate because that sounds like a, a weird word to use, but how did you guys, you know, adjust or, or you know, what were your guys' decision making to account for the fact that you guys. You know, didn't have as much experience or initial skillset in that area.

[00:07:03] Ramsey: Yeah, I'd like to say we figured it all out in a bubble, but the reality is, is that we leaned a lot on people in our sphere, people that we were connected with the local community to really figure out what buttons to push. I think one of the early decisions that we made on the marketing side that has paid dividends, we went through an accelerator program called Generator based here in the Midwest.

[00:07:24] Ramsey: It's actually in Omaha. I'm in Minneapolis, so we've been, we were doing the commute back and forth the six hours, but. That program put us in touch with literally 50 or 60 mentors that had backgrounds in marketing or scaling SaaS direct to consumer businesses. And just picking their brain and getting those connections that led to other connections in other places to look was like the best thing we could have done.

[00:07:49] Ramsey: So that was really huge for us early on. And then two more recently, as everyone in the world is seen with the AI. Like giant trend that we've seen over the past six months. Leaning into that and focusing more on being an AI company that we are has really helped. I mean, you think 12 months ago before Chat, G P T or Open ai, we were doing AI stuff, but it was a little bit more taboo to call yourself ai.

[00:08:16] Ramsey: Even just a year ago because there weren't these large scale AI companies that were, you know, breaking the fourth dimension of direct to consumer products. Now that fast forward to the past six months, we changed our name from babble dev to up trends.ai to capitalize on that. There's all of these really, really impressive aggregator sites nowadays, like edia.io that just list trendy, cool AI tools, and we got ourselves featured on there pretty early on in the rebrand and that like 10 X star visibility on the top of the funnel.

[00:08:52] Ramsey: And so, Yeah, I mean, I guess to summarize, distill all that down. It's all about, you know, the classic cliches of who you know and leaning into what's popular at whatever time it may be.

[00:09:06] Hector: In that process, was there any things that you, Were hesitant to that. You know, maybe like coming from where you were coming from, it's like, ah, this doesn't really make sense, or I don't think this is gonna work, or, you know, but it was advice that, you had gotten and, and just kind of went with it.

[00:09:22] Ramsey: Anything that I was skeptical of from the get go that ended up working out maybe.

[00:09:27] Hector: Yeah.

[00:09:28] Ramsey: I mean, the trendy stuff was definitely a hurdle for us right away, believe it or not. Like when Open AI and Chat G P T and Mid Journey and all this stuff started coming out we're like, okay, like is it really that easy to just throw a.ai on the end of your name and increase your visibility?

[00:09:45] Ramsey: Like that felt kind of like cheating to me because it wasn't a thing before chat G P T and now all of a sudden, We did it and it's working. and so

[00:09:57] Hector: And to clarify the, the product stayed relatively the same. It was really just a rebrand.

[00:10:02] Ramsey: It was a lot of the rebrand. Yeah, the product didn't change too much. I mean, we've been improving the interface of it, how it looks, and to your point, like it, it looks a lot better than it used to. But the technology on the back end is the essentially 95% the exact same. And so is really just the positioning within this market.

[00:10:21] Ramsey: And I mean, granted, there are plenty of AI tools that call themselves AI tools nowadays that. For better or worse, or really just like fancy stats. And so you can't say it for everyone, but I think that was a really big thing for us. The hindsight is like, okay, I wish we would've leaned into the AI a little bit sooner.

[00:10:40] Hector: Well, or perhaps not. Perhaps you did it at the exact right time. You know? cuz it, you know, that's just, it's cool to see that pay off because, You say that it shouldn't be that easy and perhaps why not? when we get back from break,

[00:10:52] Hector: I'm curious where your head goes to next. And so we're gonna talk about that, right when we get back from break.

[00:11:01] Hector: Hey y'all, thanks for tuning in today. Today's episode is brought to you by Amplify Media, and we are a podcast and content production company. Well, we like to think of ourselves as as genius makers because chances are, if you're listening to this, you probably have a, a mission, a message, a passion, a product, a service, something you wanna get out to the world, but don't have the time, the tech skills of the team to be able to do it well.

[00:11:20] Hector: If that's the case, we can probably help. Go to amplify media.com. That's A M P L A F Y media.com. You can also check the show notes for details. And with that, let's get back to today's episode. So, Ramsey, you mentioned that you're the co-founder and as the. Product is growing as things are catching on. How is the organization evolving internally? You know, are there new systems or structures or new people that you've had to add or layer on to kind of account for just this moreness, if you will? What, sort of steps have you guys taken in that, in that regard?

[00:11:59] Ramsey: Oh boy. Yeah, I mean, thinking about where we were before, kind of catching a little bit of fire and getting some growth here over the past few months, like early on it was very much just a couple of dudes, myself, the co-founder and our developer, Hamza. Just kinda hopping in Discord like once every day or so and saying, all right, what should we build next?

[00:12:20] Ramsey: And that was what got us a lot of the way. Now thinking about where we are currently, we've got all these systems in Notion and that we use different Trello boards that integrate with GitHub, and there's all this Zapier automation stuff that's on top of it. I can't take credit for much of it. That's more my CTO that's kind of designing a lot of that, but.

[00:12:40] Ramsey: We've really had to think hard about how do we go from, you know, something that's on the website, then iterate on what people are doing with it, how are they interacting with it? What should we prioritize next? And so we've got the system now where we meet once a week. We go through all of the feedback points we've gotten from customers, whether that's a small little bug where, you know, text is overflowing a certain, you know, card on the page, or.

[00:13:06] Ramsey: Big giant feature suggestions, like you guys should be able to have a, a leaderboard of which stock market news outlets are the most credible, that type of thing. And just planning out on a roadmap what things we need to get done by day has been huge on the development side. So that's number one. And I guess on the marketing side, it's gone from just like, let's tweet a bunch of trades based on the news and let's, you know, try to get on some blog sites now to, you know, having.

[00:13:36] Ramsey: Budget and campaign to say, okay, this month we need to get this many visitors to our website, assuming the conversion rates that we have are gonna stay the same. And then from there, how do we actually, you know, acquire that like a thousand, 10,000 visitors. It's doing things like, you know, Twitter outreach, influencer campaigns, podcasts like this.

[00:13:59] Ramsey: and so yeah, it's definitely evolved for sure.

[00:14:03] Hector: Yeah, that's cool to hear, and especially because it seems like things are happening. Quickly. I'm sure they seem slow in the moment, but, I'd imagine that from an outside perspective, they've kind of accelerated, a little bit, for you as a. founder, as a leader, you know, who, where this thing kind of goes from, you know, not to be diminishing, but like, you know, kind of a shoebox kind of project that's just kind of you're tinkering with to all of a sudden now there's this, this real thing that, you know, I would imagine people are going to regularly and it's part of their routine and they're trading with it and all these kinds of things.

[00:14:37] Hector: I would imagine that you as a founder, there's gotta be something happening for you To maintain that? Right? what's that been like for you?

[00:14:46] Ramsey: Yeah, that's a good question actually. I mean, first few months of going from shoebox phase to now kind of the beginnings of the real deal. I wouldn't say we're quite there yet, but it was very easy early on to get a little bit down at. The growth curve looking pretty horizontal. But I guess that's kind of the thing about exponential or geometric growth, is that any growth curve early on in the grand scheme of things is gonna look pretty flat.

[00:15:11] Ramsey: And then we just stuck to our guns, kept talking to users, building in feedback to the site and iterating. And then before we knew it, we were at 60% month over month growth and we're like, okay, we're actually doing the dang thing. So that was like, that really didn't. Occur to me until the past month or two, to be completely honest with you.

[00:15:32] Ramsey: Now that we've kind of established and validated that we can do that, it's been, you know, a lot of just the same. Sticking to our guns, believing that if we continue to talk to users and build features that they want to use that. It, the rest will work out. And I think sometimes it's easy to think like of all the opportunity cost of I could be doing this or that, or spending my time here when I shouldn't be doing it over here.

[00:15:57] Ramsey: But the, I think that's the most reassuring thing is like product-led growth. If you build the right things and talk to users that a lot of the other stuff kind of takes care of itself. So that's what I have to keep reminding myself.

[00:16:09] Hector: how does that actually look practically in terms of talking to users? what do you guys do to get that sort of feedback?

[00:16:15] Ramsey: yeah, it's kind of a mix of art and science, I would say. Where anytime a new user signs up subscribes to the platform, we send them an email right away saying, you know, first and foremost, thanks for being here. Here's how to get the most out of the platform. And then we offer 'em an incentive right at the bottom saying, if you do a 30 minute usability, Orientation test with us.

[00:16:35] Ramsey: We'll give you, your next month on the platform completely free. And so that's worked out pretty well. We didn't get that right, right out the gate. It was a lot of just me. Manually emailing users and begging them to talk to me, basically. I still manually email a lot of our users from time to time, so that I don't think that ever goes away, but that's number one.

[00:16:57] Ramsey: And, and number two, we have started finally using some of the technology tools to kind of help. Figure out what users like and don't like passively. So Mixpanel is a good example of that for tracking what buttons or events are happening on the website and prioritizing them. Sentry is another tool that we use that's more on the error handling side of things.

[00:17:18] Ramsey: So we know immediately if someone tries to create an accountant there, something goes down on the site, that we can diagnose it. But early on it was a lot of just site went down, oh crap. Like. What the heck is going on? Like two days of debugging and then just like trying to ask users to talk to us, and now we're finally kind of through the doorway of getting that systemized.

[00:17:40] Hector: Yeah. did you have an entrepreneurial kind of, you know, you mentioned having a computer science background. Would you say that this is your, your first like, entrepreneurial venture or was there inklings of that, you know, earlier on.

[00:17:53] Ramsey: definitely my first bonafide entrepreneurial venture. Like I had a day job. I quit it, you know, eight months ago. But before that I think I've always been kind of an entrepreneurial guy. And middle school I was selling Mountain Dew outta my locker until they told me I couldn't do that anymore. Was in all the entrepreneurial clubs in college, did all the pitch competitions that I could really just to ki because I knew it.

[00:18:16] Ramsey: Some point that I wanted to do something and that, you know, getting outta your comfort zone and doing that stuff is really what helps you grow, as cliche as it sounds. So, yeah, I mean that, I think that's kind of what led here. I knew that I would wanna do something like this eventually, and that after this I'm gonna wanna do something else.

[00:18:33] Ramsey: but yeah, this is kind of the first time that we, we've got, I've gotten paid subscribers and gotten some other people to gimme money to build something, so it's cool.

[00:18:42] Hector: Yeah. And how, how far out do you look for I was about to say babble because that's, you know, this

[00:18:47] Hector: whole time I'm like, oh. I'm like, oh, no, Ramsey, you know, babble. And when, when I looked at your, you know, I was doing some research today, I was like, wait a minute, is this the same guy? But

[00:18:56] Ramsey: the glow

[00:18:57] Hector: things that's changed, yeah.

[00:18:58] Hector: How, far ahead do you look, or what's your vision for Uptrends? and how far can you see, out for that?

[00:19:04] Ramsey: I mean, right now with the rebrand, it's, I'd be hard pressed to say that we aren't super short term focused. Just making sure that the transition works. Thinking about our next three months worth of features and how we can build those in to get into, you know, our M R R benchmarks over the short term, but, Realistically, we're looking at five years out from now and thinking how can we get in a position to not only build this where we want it to be, but ultimately, you know, sell it to a large brokerage or a strategic partner like, you know, a major news publisher.

[00:19:37] Ramsey: That's ultimately the goal that we have in mind. Trying to get to, I mean, As a 25 year old, it's hard to think any farther into the future than five years. Like I know you, you hear Zuckerberg and Ba Bezos talking about 10, 20 years into the future. Like I've only lived two and a half, 10 year periods, so I, it's hard for me to do that.

[00:20:00] Hector: True. Those are facts. Ramsey, this has been so fun and, you bring such a, great, energy and, and youthfulness. You might be our, our youngest guest on the show here, so you might, you might take that, that honors. where can people get more connected with you or, you know, what's the website for, for uptrends?

[00:20:15] Hector: Can you give a little more info there?

[00:20:17] Ramsey: Yes, absolutely. uptrends.ai is the website. Simple as that. you can go on there, create an account, start monitoring stock market news today if you like outside of that, you can find us on our blog market mood.com and we're on all the socials Uptrends ai, that's us.

[00:20:38] Hector: Sweet. Go do it. Y'all. Thanks for sticking around with us. If you got some value outta today, which, if you made it this far, I know you did. We would love and appreciate a rating or review wherever you get your podcasts. And if you know someone who is in the midst of scaling their business or, or even as a trader and needs to be on, on Uptrends, make sure you send 'em this episode and, Go take action on, on something today and, let Ramsey or me know how it goes.

[00:21:00] Hector: We'd love to hear about it. We appreciate as always, for being a part of the tribe. We'll see you on the next one later, y'all.