Transcript: Ryan Schreiber on Entrepreneurship, Networking, and Building Streamline

Good morning and welcome back to the show. We are here with U.S. graduate of the class of 2009 and the founder and CEO of Streamline, Mr. Ryan Schreiber. How are you, Mr.

Schreiber? I'm great. Thanks for having me, Charlie and Jack. Really appreciate you guys having me on and spending the time over your winter break to learn a little bit about Streamline and myself.

Yeah, thanks for being on. So, no, but no, I really am impressed with what you guys are up to. You know, I think U.S. has changed a lot. I'm fortunate to still be involved.

But what I'd say is I built really great relationships in those years at U.S. My closest friends today are my closest friends that I met starting when I entered sixth grade at U.S. at the lower school in Shaker. a phenomenal experience at the lower school. It's why whenever I hear parents or folks saying, oh, maybe to the upper school, I always say, you know, those few years at the lower school were a real highlight for me. I made really great friends there.

I had great teachers. I started to play, you know, on organized sports teams beyond just kind of rec sports, right? And that kind of, those are some really formative moments. And a lot of those happened for me at the lower school.

You know, I think as I transitioned to the upper school, once again, met new friends, right, that are still close friends of mine, really incredible teachers like, you know, Mr. Perry, who you guys know, and Coach Stevens and Senior Plower, a couple of my other favorite teachers. I had Mr. Gallagher as my sophomore English teacher, believe it or not, who was incredible.

That was a great, great class. I remember Macbeth and a lot of the things we did in there. But, you know, I think that the mission statement of U.S. responsibility, loyalty, consideration are legitimately words to live by in things that are pounded into the education, the relationships you build there are truly lifelong and have been a real blessing in my life. And just learning how to work with other folks on a team, being on successful teams at U.S. were highlights.

So all of those experiences in and out of the classroom were just, you know, an incredible opportunity. It's, you know, the thing I'm most grateful for in my life outside of being a parent and getting to go to U.S. was just such a privilege and has continued to pay dividends for me personally and professionally in so many ways. Do you have any activities or clubs that you specifically think have kind of shaped you into who you are today? That's a great question.

So, you know, sports were a big part of who I was. And so I think that absolutely the people I played sports with, the expectations to succeed on those teams, you know, and the ability, you know, and need to balance, you know, what you have going on in the classroom and then also bringing your best after school to that team. I think, you know, has shaped how I've approached, you know, my career and balancing now, you know, personal and professional versus in classroom, out of classroom. Trying to think what, you know, so those are kind of sports.

What other things, you know, I wrote for the school paper, which was a fun experience and another kind of layer to my U.S. time. So, so absolutely all of those things contribute to kind of who you who you are becoming and who you become. No. Did you kind of have any teachers or mentors who kind of helped shape your vision for what life was kind of going to be like after high school?

Yeah, I think that what I valued about teachers and mentors at U.S. was they weren't looking at you. kind of through one lens. And I think kind of from the first couple of questions, if you listen to my answers, that's kind of the theme so far, right? Is that U.S. kind of knows the whole boy. And I remember Senior Pla spending an incredible amount of time with us.

You guys probably don't know Senior Pla, but he was a legendary Spanish teacher that taught at U.S. for probably 30, 35 years. We were kind of at the back end of that. He was there a few years after I was there, but he just had great life lessons. His family had left Cuba to come here, you know, when the communists took over there 60, 70 years ago, and he left there as a young boy, came to Florida, his family built a life in America, and he just had incredible perspective and lessons.

You know, our head football coach, Jim Stevens, was not only my coach, but also was my English teacher and I remember just you know the amount of time he spent with me on my writing at that point in time it was specific to my college essays but it's certainly a skill that's you know you know helped me throughout my college academic career and into my career just in terms of being efficient with words and writing so those are a couple teachers that just almost more from a personal perspective than an academic or professional perspective impacted my outlook on life, my value system, all of those things. Today at U.S., there's a big focus on creating a brotherhood. Was that a focus when you were at U.S.? Yeah, there's no doubt.

You know, I hate to just like hammer home on the mission statement, but I think, you know, it's the responsibility to the people there. It's your loyalty to them. It's being considerate to that, right? That's what it's really about, is how you interact and building a brotherhood.

And it is a brotherhood. You know, I am very close with the guys in my class and the class below mine, even, and a couple guys, you know, a year or two above me. But what I've found amazing in being back in Cleveland and building a career in different industries is how it really goes outside of generations. And it's not just your friends' dads who might've gone to US, but there's guys now that are 10 years older than me that I consider good friends that I went to US with.

There's guys six, seven years younger than me that I've worked with now in my last job. And one of my senior advisors for my current business is a U.S. alum that's 20 years older than me, right? So those connections, you know, that brotherhood, I think, has always been part of what U.S. is. I think, obviously, it's a great institution, you know, when you look at the arts and the sports and, you know, the academics, but what differentiates U.S. to me is that it's a community and that you have that brotherhood.

So I think that's, I'm so happy you say that that's a point of emphasis because I I think that's really what US is about. Yeah, for sure. And I think every class kind of creates that brotherhood in their own way. How do you feel your class kind of built that brotherhood Well what I tell you is it wasn particularly clicky right like there yeah are there core groups of people that are still friends or closer absolutely but i think what's nice about us is that you have friends with different interests and then it wasn't like it was just this one group of people there really was kind of that broader um you know ecosystem what was cool our year was it's the only time us has ever won four state championships.

And we won the Ohio Sports Cup that year, which acknowledged you as the best sports school in the state of Ohio. And so I think that experience, what was unique about it was because there are so many often, you know, juniors and seniors and even sophomores on sports teams that there was kind of that cross class bond. So my class 09 and the class below mine 10. If you look at like a lot of the weddings, it's like there's a good chunk of guys at both.

And I think that there's something to be said for, you know, winning on the sports field together that further, you know, deepen some of those bonds. Not that you don't have cross-class bonds elsewhere, but to your point, you have your class identity bonds, but I think that experience of people winning together had a real long-term effect, you know, on what that brotherhood looks like. You know, as someone who's achieved so much professionally, looking back, What was one of the biggest takeaways that you had at university school that stayed with you throughout your career? That's a great question.

What would be I think accountability, right? Like, I think that, you know, I even see it now. I don't mean to be like the old man in there. But like, I think in a post COVID world where people aren't in person as much, it's harder to build a bond in a relationship and trust and ultimately accountability.

And so I think at US, those are really foundational things that expectations are high. And they're not just high from your parents or, you know, your teachers, they're high, you know, amongst your classmates. And so I think that that was something I learned at U.S. that continued when I went off to Middlebury, that being surrounded by people with high standards is really good for you, that that's going to raise the bar. And so I think, you know, when you look at U.S., you know, there isn't a low common denominator, right?

There's a high bar. And I think being surrounded by people that are competitive, that are ambitious, but that want to do things the right way is really important to kind of everything that, you know, I've, you know, been a part of in my life. and I think a lot of people say they lose touch with their friends after high school you've talked about you've been able to stay in touch with those friends how have you been able to stay in touch with those people that's a great question so you know I came back to Cleveland after college which is a little different so that made it a little easier because over holidays I would see people but what I'd say is my core group of friends in Cleveland is not my high school friends there were some guys that went to rival schools and were other classes at U.S., but it's really just in the last couple of years that a couple of my good U.S. friends have moved back. You'll see once you're in your 30s and people are having kids and trying to buy a house that it's like, oh, Cleveland looks a little better now. So I think I was lucky from that perspective, but I think it's just, it's what you put in, right?

Like it's sending that group message about the Browns games, It's asking who's around over the holidays. I've stayed involved, as I'm sure you guys will ask me about, with the school in and of itself. So being involved with reunions and fundraising has been another way to stay connected to people, which I would certainly encourage you guys to explore after you graduate as well. You know, we're going to talk about it in a second, but your current role as the founder and CEO of Streamline, this kind of revolutionizing streaming app.

But before we get to that, we first want to know, what was your experience like before that? What was your jobs or roles? And how did it apply to that current role of yours? Yeah, no, that's a great question.

So nothing prepares you to start a business from scratch. Let's start there. We're learning every day and we're learning by trial and error. So that's a lot of fun.

But going back, so I left US, I went to Middlebury, which is great, but it's a liberal arts school, right? So it's not like you have this business or finance degree or some vocational degree, right? That's clear what you're going to do. To my point about being surrounded by really smart, motivated people, Middlebury was a source of that.

And a lot of my friends were going into finance and investment banking. And that was something that I had from some mentors even heard would be a good first job, especially coming out of a liberal arts school. So I came back here and I worked at Key Bank immediately out of school. I had great mentors there.

I went through a great training program there that gave me some hard skills to complement my kind of soft liberal arts skills. So, you know, finance and accounting and capital market skills. And I worked there for a couple years out of school. It was a rotational program, really great experience, really built a great network.

And it's funny, that network in starting a business like my U.S. network, like my Middlebury network has been a big part of my, you know, fundraising, team building, networking, all sorts of stuff. So I really met a great group of people there. And I think that's the theme at each stop. At U.S., at Middlebury, at KeyBank, I really met great people and was able to surround myself by great people that pushed me.

I really enjoyed investment banking. It was challenging. But there were a lot of my skills that it didn't necessarily bring to the forefront or wouldn't over a long period of time, like sales and communication skills. So I wanted to be in a position where instead of just working on transactions, I had more ownership of what I was doing and could really impact the growth of a business.

So a couple of years out of school, I went to a tech company based here in Cleveland called Vertical Knowledge. I knew the founder, Matt Carpenter, who really became a mentor of mine as a tech founder and gave me the opportunity to manage some of the key accounts that that business had established on Wall Street. So hedge funds that were using their data, vertical knowledge, collected public data, its scale from the web and public APIs and the public sector defense were big users of that. And financial services, hedge funds, banks, private equity to use that data for investment research were big clients.

So I, you know, I went to that business to help with some key accounts. I ended up really taking over the sales function for the financial services business and then building a really great team around me. So I was there for nine years till this June. I just left there.

Vertical knowledge was acquired by a private equity backed business in January. So that was a great learning experience. I got to touch all parts of the business. We really were able to be successful in growing it over a long period of time.

So that was an incredible opportunity to do something like that. And then, but you don't leave a big stable finance job go work in tech if you don't have some entrepreneurial ambitions um so i think even if it wasn't at the forefront part of why i made that move was because i knew i would ultimately want to do something like i doing now um but i kind of pause there and see you know if you guys have any questions any questions on that 11 year period of time Well ever since I kind of like heard about you and Streamline almost two months ago I actually dialed in on my own phone I have been trying. I've really been liking it. Can you take us kind of.

Awesome. Thank you. Can you take us through the journey of the last seven months and what was your idea? What was that entrepreneurial idea that you had for Streamline?

Yeah, no, that's a good question, Charlie. So it really goes back a couple years. So I was just sitting on my couch one night trying to watch TV, looking for what to watch. And I was like, this has become so frustrating.

I wish all my sports and my shows were just on my calendar with a link of where to watch. So that was just my like consumer frustration and the thing I wanted to solve it in that moment. It was not a business idea. I wouldn't even say it became a business idea for a couple more months after that.

I have that original note pinned in my phone. But, you know, it became more of a business idea once I started to talk to people and understand their frustration. Scrolling on Netflix, which is one of the five or six apps they pay for, for 20, 30 minutes a night. their inability to agree with their partner on what to watch, how often at dinners or in social settings, asking people what they're watching was the topic. And then, you know, don't even remember what they told you.

And even if they, if you make a note in your phone, you still got to Google where to watch it. So I'm kind of looking at this whole problem set and I'm like, all right, there's something here. So I kind of start to explore it. I'm reading more about the media business and some of the challenges that the streaming platforms are going through with churn and profitability to understand there's not just a consumer problem here, but there's also an industry problem.

And during that time, sports start to come to the forefront of this problem. So you might remember last January that the Dolphins and Chiefs played in an NFL playoff game that was exclusively on Peacock. There was a lot of articles written about it, big point of frustration for NFL fans that a big game was in streaming only, right? And then they put five games on Peacock this year.

The NBA rights are moving next year to more streaming exclusive places. You guys know the whole story. I'm sure you feel this pain. But in addition to the sports stuff starting to come up front, sports fans had been ignored by some of the apps out there trying to solve this problem that you guys might be familiar with.

Apps trying to help navigate what to watch, where to watch it. Totally ignored sports and sports fans. Sports fans are the biggest consumers of streaming by time spent. So when you start, actually a US friend of mine that was just like, who are you going to go after first?

Look at the data of who consumes the most. So, you know, looking at all of that information, it started to be clear that this wasn't just a problem around shows and movies. Sports are kind of the why now, and we want to solve this problem, you know, for sports shows and movies and do it in one place, like hadn't been done before, and build a social environment around it, right? So for books, you've got Goodreads, you know, you've got Strava, you've got Belly around restaurants, you've got all these other social platforms around affinities and consumption and broader socials become so toxic that some of the conversation around sports and big shows that used to happen on Twitter doesn't necessarily happen on X anymore.

So just kind of, you know, this problem continued to mount and it got to a point where the fear of seeing someone else solving this problem exceeded my own fear of failure and all the things that you know come with leaving your job when you've got two young kids and a wife that doesn't work to make it happen and my wife was really all in so as we looked at the problem you know it became something that we really wanted to solve and got excited about and can you guide us through how that app works please yeah so i you know we don't have a shared screen but but really the way i use streamline every day is that i first and foremost open up my calendar like i talked about the original idea if there is a show or a sporting event on that i already know i like and it's on my calendar i go and watch it done If there isn't, I've already curated a list based on the Discover tab, the homepage, what my friends like of shows that I'm either watching or want to watch. So I always have something now ready to go. The social part of it is really fun and enjoyable. I think where we are seeing the sticky behavior is where people are using it with friends.

So getting on there, being able to see what your friends are watching, sharing it, you know, there's some features that will improve the social interactive nature of it. And we're just we're just a month into going live. So there's a lot of features we we still want to build, but we're we're constrained by time and money and resources like any startup, which is a good thing because it forces you to solve the most pertinent things first. But we've solved the most pertinent things of what should I watch, where should I watch it, when is it available, right?

So we've fundamentally solved that problem. And it's now how do we make it easiest for the consumer to navigate it? And then ultimately, how do we drive distribution for the streaming platforms to help them with their challenges around churn and profitability and create a really sustainable business model here that can scale? You know, being the founder and CEO, I'm sure you've had to do many different jobs and learn many different skills to kind of succeed.

What skills have you learned that kind of looking back, you didn't think you're really going to have to pick up? Yeah, that's a great question. So, like, I'm wearing a ton of hats right now. But, you know, I've got a technical co-founder that really runs.

We've brought some great people on the marketing front. But I think the marketing piece, I hadn't been in a B2C business before and trying to launch a B2C app has definitely taught me a lot about like the different marketing skill sets. I thought I'd just be able to find like this one magic bullet person that would be able to do social and SEO and ads and creative. And it's like those are a lot of different skill sets.

Um, so I think putting that team together and iterating there has definitely been something that's been a great, great learning experience for me. Um, you know, because of the working in finance thing, because of working in sales, doing some of that, um, both in terms of, you know, in-house financial management, as well as capital raising, like has generally been things that have come naturally, but I'd also say are harder than I ever imagined. Like, I'll tell you this fundraising, free product, free revenue, free team is not easy. Luckily, I had, you know, I think I have a lot of people that, you know, believed in me and believed in this problem and our ability to solve it.

But definitely the fundraising piece is harder than I ever imagined. Luckily, you know, I think of our 32 investors, nine of them are U.S. alums. So the U.S. network has definitely been helpful in terms of getting this started. There's no doubt about it.

And what is the biggest financial lesson? I know you probably handle a lot of that with your background. So what's the biggest financial lesson that you've learned? And then can you maybe explain it to us?

Like we've never heard anything about finance Yeah I mean I think it just having an eye on the burn at this stage How much money are you burning Justifying those expenses Every expense needs to be justified at this stage, right? We have to force rank what is most important and what we need. And so I don't think it's anything that novel. It's not some big complex equation. it's just kind of being incredibly disciplined um and really scrutinizing everything but also willing to take some chances right like if you don't say take some chances it's really hard for anything to stick so i think it's it's trying to balance that discipline with the taking the shots and i'm not saying we've figured that out yet either right but but it's that's definitely kind the, you know, needle I'm trying to thread every day.

And I'm sure everything was not smooth sailing. So what was maybe a failure that you had to work through in starting this company? Yeah, what I would tell you is, so I kind of skipped over a little bit of a time period of kind of validating this problem was real enough that I wanted to chase this to like, actually raising the money and getting going. I had a few false starts with trying to find partners to build MVP.

So ultimately, a software development shop that was kind of in my network of the business I was previously at, built us an MVP in a second version, and helped us get going. But I had a few false starts on partners to try and get it built, which was extremely frustrating and kind of covered a period of call it seven, eight months last year, where I just was like, am I ever going get this built and just the first version of it let alone anything you you wanted to put in front of anyone's eyes so um that that was something that took real persistence and belief to kind of to kind of power through um we asked this question to a lot of our guests i think we have to continue asking it to you obviously as you're extremely motivated person making your own company kind of pushing it to where it is today mr schreiber what is your why and what makes you decide to keep on pushing on and only achieve only more every day that's a great question um there's there's probably multiple wise is pro is probably part of the answer um you know in terms of doing something entrepreneurial i think you know my dad was an entrepreneur so i think there's kind of that bar was set i don't think like i've worked at a big company and then a company that got big and so i think being able to build something um and really having that not just ownership from an equity perspective but really like putting your heart and soul into something and being proud of what it becomes um is important to me um you know i i think there's a lot around wanting to prove something that is a b2c tech success can be built in Cleveland. That was a thing I heard a lot early on from perspective investors is like, sounds like a Silicon Valley idea. And I, you know, when you look at the culture of entrepreneurialism here, going back to Rockefeller, it really is incredible.

And there's no reason in the tech world, we shouldn't see innovation. You've obviously seen it in other areas, medical innovation, right? And otherwise, but like with B2C tech, there has been a huge winner in Cleveland. And so people kind of look at an idea like this and kind of question whether you can do it here.

So I think that the Cleveland ship on my shoulder is definitely something that drives me, right? Wanting to do something here, wanting to prove you can do anything from here is definitely a motivator. Wanting to positively contribute to the world while this problem we're solving is very much a first world problem. I mean, wanting to give back and be successful to be able to help others achieve is important to me.

It's part of why I give back to US because I think that was such a foundational experience for me that I think I want to see more guys like you have those opportunities that I've had. So maybe not the one answer you're looking for, but those are just a few of my motivators. Yeah, those are great. It's interesting.

All of our guests have a different answer for that so we love asking that question um mr schreiber do you have any uh books that you've read that have kind of helped you on your journey that you've learned a lot from that you'd recommend yeah i think in terms of what i'm what we're doing now um the walter isaacson steve jobs biography was was one of the more um one of the one of the books that made me kind of want to go into the consumer tech product world and solving these problems beautifully and simply how we're approaching it was a real inspiration we talked about rockefeller i mean titan's a awesome book the cleveland um the cleveland stuff there is great um so those are a couple that i love you know if you could kind of give a piece to advice to a senior or recently graduated student about what they can do to succeed and kind of hit that next level what would it be yeah i think you hear this right and you guys even asked me some questions that are tied to this early in our conversation but it's the networking piece like i think you heard as i was telling my story there are people at each stage that are still like really intimately a part of what i'm doing right now. And not that it's just about like that, but I think always having that in mind that like to build deep relationships to take the time to get to know people. You know, even if it's for no other reason than just to learn from people and get different perspectives. You know, you guys are about you know, you guys have a couple more years at us, you'll obviously build that brotherhood.

But one of my favorite parts of my US brotherhood has been getting to know everyone's like college friends, right? And kind of, you know, some of those guys are now parts of our group in different capacities too. Like I have, you know, some of my U.S. friends, I'll hear playing golf with some of my Middlebury friends, you know, in New York or something. And I love to hear that, right?

So kind of, you know, taking, continuing to bring people together, getting to know new people, but maintaining the old relationships and bringing that together, I think is important, no matter what you're doing, you know, in starting a business, networking is really important. And I like, I think I kind of knew that. And then I would hit points where I was like, Oh, I need to be talking to more people. Oh, I need to be talking to more.

And it was like, it just kind of continued to ramp because there's no way, you know, you can raise money, build a team, you know, get the word out on what you're doing, unless unless you're talking to a lot of people. And so that's just been a big part of of what I have found to be successful and what I've enjoyed. So, you know, it can be really, it's a lot more fun to do things with a team. And when is a team than to do it by yourself?

That's probably something I learned at us, right? Yeah, for sure. Mr. Shriver, it's been great having you on the show today.

Thank you so much for taking the time to share your insights and experiences with us. And to our listeners, thank you so much for tuning in. And we hope you join us next Wednesday for another episode of Wait and Start Show. Thank you, Mr.

Shriver. Thanks, Charlie. Thanks, Jack.