Scale Like a CEO

Building Legacy and Trust in Entrepreneurship: Scott Conine's Journey

• Justin Reinert • Season 1 • Episode 27

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What does it take to grow a business from $10,000 to a $100 million exit without venture capital? Scott Conine's entrepreneurial journey reveals powerful lessons about leadership, talent, and trust that any business leader can apply.

Scott opens up about co-founding Rise Interactive and the innovative approach they took to hiring. Recognizing that analytical skills were harder to teach than marketing tactics, they implemented rigorous testing that only 22% of applicants passed. This strategy attracted talent from diverse backgrounds – NASA scientists, derivatives traders, even oil field workers – creating a unique culture of analytical excellence that became their competitive advantage.

When the 2008 financial crisis hit and Rise lost half its revenue overnight, Scott's leadership principles faced their greatest test. Rather than layoffs, he proposed temporary pay cuts across the organization with a promise to repay everyone. Within five months, every team member was paid back in full. This transparent crisis management built extraordinary trust that fueled their continued growth and created remarkable team loyalty.

Scott shares how they abandoned traditional annual reviews for Weekly In-person Meetings (WIMs) that provided immediate feedback, and how they codified their culture through "The Rise 5" principles that everyone learned from day one. These operational innovations were so fundamental they even designed their office space around them.

Now as CEO of TrueData, Scott reveals how he navigates preserving an existing culture while implementing necessary changes. His approach identifies the non-negotiable elements of organizational DNA while creating transparency around performance metrics and empowering his leadership team.

What drives Scott goes beyond business success – he shares his personal mission to create 50 millionaires throughout his career because of the transformative effect this wealth creation has on families and communities. His vision of business as a vehicle for community transformation provides a powerful purpose that transcends typical growth metrics.

Whether you're building a startup or leading an established organization, Scott's insights will transform how you think about talent, transparency, and the true purpose of business success.

Scott Conine:

I remember saying to John, my co-founder at Rife, early on, is my goal is to create 50 millionaires before I'm all said and done throughout my career. And he's like well, what do you mean? I go. I said, john, if we could do that, think about the economic opportunity that creates for the communities that we live in, for our employees, for families of our employees. I think it's such a powerful way to really transform the communities we all live in. And if we can find a way that the businesses and the enterprises that we create can do that, wow, how amazing would that be for our own personal legacy to be a part of something like that.

Speaker 2:

Today we have an incredible story of entrepreneurship and perseverance. Our guest is Scott Conine, who started his business with just $10,000 and grew it into a company that sold for over $100 million. In this episode, we'll dive into Scott's journey, the challenges he faced, the pivotal moments that shaped his success and the lessons he learned along the way. Whether you're an aspiring entrepreneur or just love a great success story, you won't want to miss this conversation. Let's get started.

Justin Reinert:

Scott, thank you so much for joining me on Scale Like the CEO. Just to get us started, if you wouldn't mind give us a 90-second intro to you and what you're up to these days, yeah, Jason, thanks for having me on.

Scott Conine:

My name is Scott Komanoi, ceo of ad tech company named True Data. Before that, was a co-founder and COO and CFO of an advertising agency named Rise Interactive, based out of Chicago Grew. That bootstrapped that from $10,000 in year one to selling the business at over $100 million when we sold the business To get real fun. Before that, I was a performing musician. Even before that, I worked in a series of family businesses, so I have a whole host of talent, war stories to share today around leadership and a whole host of different things that I think will hopefully provide a great conversation.

Justin Reinert:

Yeah, thank you. Sounds like you've had a fun journey. I'm curious just to start present day, if you wouldn't mind. You've worked in ad tech for many years and I actually spent a number of years in ad tech as well, so I'm curious what do you see as one of the biggest challenges in that industry and how are you solving that today?

Scott Conine:

Well, there's a couple of things that I think are challenging in the ad tech space today. That make it not only equally exciting but also challenging is, I think, with the advent of AI, I think we're seeing a whole host of innovation that's needed to be able to understand how do we reach net new customers in the market, so as OpenAI, chatgpt, gemini all of the different platforms are starting to become the way that we as consumers interact with information. If you are a marketer, how do you reach those consumers in a meaningful way? Perhaps in a zero-click world? Do you reach those consumers in a meaningful way? Perhaps in a zero-click world where you're not going to Google anymore and just doing a Google search or just finding your answers on platform through ChatGPT or through Cloud Engine?

Scott Conine:

Does your marketers need to still find a way to have a high-fidelity, personalized conversation with their consumers and customers, and how do they do that in a meaningful way? And I think that creates an awesome opportunity to create new, new innovation in the ad tech space and for consumers, which is probably that change in the ecosystem has created a whole new wave of exciting, new developments and and I think everyone is chasing that to figure out how to create really compelling marketing solutions. I get super excited and geeked out about that. I think there's a lot of innovation that's happening At True Data. We're trying to think about different ways to bring one-to-one marketing data solutions to our customers. But I think that's what's exciting today in the ed tech space, but at the same time, it's challenging. What you did before probably isn't going to work anymore, so you have to think about how you're going to innovate to survive.

Justin Reinert:

Yeah, as I look across different industries that are being materially impacted by AI and gen AI, it does seem like marketing and advertising are really shifting very fast from content generation to search. Seo isn't the only gig in town anymore, and so there's a lot going on there, so definitely an exciting industry to be in if you're into change and adapting to change.

Justin Reinert:

Great, I agree An exciting industry to be in. If you're into change and adapting to change, great. So let's go back. Let's go back to the beginning of Rise Interactive. So you're a co-founder of an architect firm a number of years ago and then continue to scale that business. I'd love to hear about some of the beginning, the first couple of years in growing that business and getting it off the ground. Tell me what were some of the challenges that you faced as you started to build the team.

Scott Conine:

Yeah, I think we. My co-founder was an individual named John Morris and John had just come out of at a booth at the University of Chicago. We had won second place in New Venture Challenge. That was the original seed capital used to launch our business, and, you know, one of the things that John and I were very committed to was organically growing the business. We didn't really want to raise any money, you know. We wanted our own cash flow to create our breaks, and so from day one we had to figure out how do we leverage our own IP, which was our people, our talent and then our technology, and we realized, if we were going to compete against some of the bigger competitors in the market, we had to find ways to have a compelling, differentiated story around what we brought to the market.

Scott Conine:

So we first started with search and this was early 2000s when we started this business, and so search was hot, it was in vogue, it was the way that you could reach customers. But we found we struggled to find talent from the trade. We were a small little bootstraps, little marketing agency, and it was hard to poach from some of the big holding co's, and so we found that to create a unique talent strategy. We had to think differently, and so our approach at very first was we figured we could always train someone to be a digital marketer, but it was very difficult to train someone to be analytical, and so we started from day one building. We built an analytical test to vet our team to make sure they had the analytical chops to perform, and one of the things that we found is we started to deploy that that only 22% of the people that took that test actually passed. So we wouldn't even continue talking to people unless they passed that test. What was even more surprising was that when we gave that test to people from the trade or from other agencies or competitors, only 15 to 16% of them passed. So it was actually a great selling point after we started to grow and build the business was that we knew that our team was more analytical than our point.

Scott Conine:

After we started to grow and build the business was that we knew that our team was more analytical than our competitors because we had the data to prove it right, and so we started using that test as a way to really find and identify really analytical people, and it really shaped our whole approach. We ended up finding people from a wide array of different experiences Over time. We had a NASA scientist who worked in the agency in 2008, when the world kind of ended from a financial service sector we had about at that point in time we had, almost 50% of our billings was in the fintech and financial service sector, and so in October of 2008, we lost half of our revenue, and so we realized to solve for those problems, we had to think about different ways to carve our way out of that, and what we did is we found talent that was sitting on the sidelines Former hedge fund guys, derivatives traders, option traders and so we ended up bringing them in because they were super analytical and we were able to continue to build a very unique analytical workforce that I think was super differentiated. Other areas where early on I'll use the 2008 example, you know we found ourselves when we lost all that revenue how do we keep our team and build credibility with our team? We asked our team hey look, if you guys can bear with us through this time, I think we all can win.

Scott Conine:

So we asked the whole team, including ourselves, that like, let's take a pay cut versus having to cut everybody.

Scott Conine:

Let's figure out what the exact amount that we need to survive and ride the wave out.

Scott Conine:

And we explained to our team is, if we did this pay cut, it wasn't a lack of a better term, it was a temporary way to augment cashflow.

Scott Conine:

And we said, look, we will pay this back to you and we will pay this back almost like it's a loan. And our goal too was and we committed to them that we would pay them back before pay the team back before we, as the leaders, would pay ourselves. And I think what all was said and done we had after we started winning back deals and winning new engagements, we had paid the full team back within about five months from the cut. So it was just a huge way to build trust and I think that that served us in the long run in profound ways, because our retention was super high after that and people really believed when we said we would do something and we delivered on it. They really believed us, and so I think we built a culture that was super unique around providing trust, accountability and really living true to our word and allowed us to really grow the business in some pretty profound ways.

Justin Reinert:

There's three key things I want to pull out of that and in no particular order working backwards. The trust thing, I think is so key because there's and I don't think you said it explicitly, but there's a message and I've gone through this with an organization more recently in the 2020 timeframe when you can communicate to the organization hey, we have a choice to make. Cash flow is not great right now, and so we can either part ways with some of your colleagues or we can all take a hit, but keep us all here and surviving and we'll pay you back. And when you can see that through to completion, it does build a lot of trust and loyalty because they also know when times get tough, you're not just going to get rid of me. You're going to find a way and we're going to band together to try to navigate this storm. So I think that's so amazing for building trust and longevity in an organization. I think that's so amazing for building trust and longevity in an organization Agreeing that.

Scott Conine:

That trust was, I think, critical to when the other problems hit right. It gave us a lot of freedom to say let's solve this together, and I also think it created a playbook for how we show and exhibit leadership to our new managers that were starting to emerge in the business is like guys we want. This is how we work and solve solutions together. Is we transparently work together. We put the problem in front of the team and and we discuss the material issues that are out there, we solve it together and then we all suffer either the consequences or reap the benefits. But we did it together as a team and that there wasn't things that were obfuscated or hidden. We found there was no benefit of being opaque.

Scott Conine:

That trust really comes from a place of an appropriate amount of transparency that allows the team and the organization to react, and everybody's reacting off the same variable, so not a lot of weird subversive politics. That starts to happen. It starts to be we're all marching to the same beat, we're all paddling in the same direction, and so it allows you to be able to solve problems and identify opportunities in really acute ways and you don't spend a lot of agita and a lot of time wasted. You're trying to deal with slightly opaque communication. So trust became a huge part of, I think, our success, but it also became something that I found to be a compound force multiplier and leadership that I've taken and I believe have applied throughout my whole career.

Justin Reinert:

Yeah, that transparency is so key. I often repeat, in the absence of information, we make up our own, and it's always worst case scenario and so if we're not being transparent with our people and giving them all the information, they're going to make it up and it's probably going to be a story that that isn't true or we don't want them to believe. So key. The other thing I wanted to pull out of there was it's kind of two in one is when you were talking about I can teach anybody digital marketing, but the hard one is the analytical piece, and I think too often we look for people who have the most number one presenting thing that we need, I have to have. So we're looking for, I have to have, this digital marketing thing, but is that actually teachable? Is it easy to teach? And identifying what are the hard to teach things and hire for those and then build in the mechanisms to be able to teach those other things, and that's something.

Justin Reinert:

In around a similar timeframe, I was at a startup ish. We were beyond a little bit, but beyond the startup phase big machines here in Chicago and we did a lot of cognitive testing for hiring and it was so great because it actually opened up the field. We didn't require college degrees because we were going to test for cognitive ability, and so it kind of didn't matter. But let's get people who are really great at those analytical skills, who are great at solving problems, and then we'll teach you everything else you need to know. We'll teach you about SaaS and we'll teach you about configuration software. We'll give you those things, and we also had kind of built up a reputation of how hard it was to get into the organization. There was a bit of this level of respect if you could get a job with that organization. So I think that's key there is identifying those hard to teach things and hiring for them. However, however, you go about assessing for that.

Scott Conine:

Kirsten, you said something there too and it does. It does remind me that a lot of the thought times at RISE, one of the things that we saw I think that was a very unique value crop, because we focused on analytical acumen and analytical ability is that people's experience by leveraging analytical aptitude was very diverse, right attitude was very diverse, right. And so what we found is when we would start to kind of onboard all of these hopefully analytical people into our organization? Where they came from was from very unique, different fields of enterprise and, like I mentioned, we had this nasa rocket scientist, we had trading managers, we had I had a roughneck from the oil field, services, drilling wells but was super, super analytical and and so what you started to realize very quickly is that every one of them had this unique perspective, was unified through their ability to leverage data but at the same time, just would open the aperture of what we could potentially do and how we could deploy performant marketing solutions for our customers in ways that was incredibly diverse.

Scott Conine:

And so we found that we started to what started as a qualifier for entering into our business being strong analytical acumen. What we realized is it unlocked all of these secondary and tertiary initiators around diversity of thought and unique value proposition, and so it started as a way just to help us provide just cleaner reporting and easier insights for our customers actually became something that was super valuable to our business and actually created, I think, a much more rich culture in our business. That was, I think, just created a very different vibe that even today that the risers and the alumni that sit in the market, when we see each other, there's this kind of, you know, camaraderie that we all share and that we experience this very unique moment in time. That was a really fun and exhilarating place to be.

Justin Reinert:

Yeah, that diversity of thought I could imagine was really beneficial, I would imagine, to the organization and just bringing those different perspectives in. So, looking back at the time at Rise Interactive, I'm hearing a couple of clear themes. There was number one about how you approached hiring and who you're sourcing. Number two was really about transparency and trust building. I'm curious if there's one more like a third key factor of success that you could pull out from your time at Growing Rise. What would that?

Scott Conine:

be. One of the things that I think we did, that was built into our DNA, is truly defining what success was at every kind of operational level of the business, of operational level of the business, and being able to take really complex things and define them into simple, simple statements. So we had like the Rise 5 as an example, and the Rise 5 was literally like you were onboarded on day one talking about the Rise five. It was our way and method of doing things. So I think that that was I would. Every leader in the organization would walk the halls or walk the floor and say, okay, let's repeat the rice five, tell me what they are right. So it was one of those things that we were super intentional on, if really codifying our core processes, codifying who we are. In fact, from day one of when we started the business until we sold, I always did the orientation. I'd spend a full day onboarding and walking through people. This is who we are, this is why we do what we do, this is what we believe, these are the values of our organization and this is how we are going to be. This is how we're going to help reinforce your success in the organization, and that flowed itself into all sorts of operational kind of skill sets and things that we built.

Scott Conine:

One of the other things that we did that I think was probably that started to build upon that whole kind of theme was what I realized very early on is, given the nature of our business and the speed and velocity that we had to compete in, having an annualized performance review wasn't going to work for our engine. It just was not a way to help our team members be successful. It wasn't a way that we could create, I think, actual meaningful feedback, and so we shifted to an agile performance management framework and we started implementing what we called WIMs, and WIMs were weekly in-person meetings that a manager would have with their direct report every week, and in those WIMs we give them tips which is how are you spending your time, what do you need to improve on and how do we drive performance and how can we help you drive performance? We'd have these placefats made for every manager, which would give you a way to construct the conversation in a way that would help drive performance.

Scott Conine:

One of the things that we were really trying to offset and kind of make sure that we weren't living in is in a halo or an effect around performance. We didn't want to have this annual performance review and you crush some performance on an account but for a year you were a horrible manager. It's like, well, wait, let's actually build real feedback in real time and let's see if we can help you become a better manager through time. We just found that to be, I think, a huge force multiplier for our business, because our team had real-time feedback, we were doing comp adjustments in real time, we were helping the business understand what are material problems at any given moment in time. The other thing we did too is as the byproduct of that was, it was so successful for us that when we did our office build out, we built the office to be able to have all of these spaces for people to do WEMS, so we had all these kind of private booths where people could meet, and it was just a huge part of our ability to give people real-time feedback to help the business just be more performant. And so, and those that feedback aligned to operational kind of sops and standard operating procedures that we spent all this time codifying how this, this way, we, this is our method of operations, the way we work. So everything started to build upon itself and enabled our I think it truly enabled us to grow from day one to when we sold.

Scott Conine:

We took one round of funding like two years before we sold and that was really for liquidity Right and that was just taking chips off the table. We didn't really need the cash, the cash, and so our ability to grow was built off of our ability just to really build and reinforce our team structure in a way that really allowed us to be wildly successful. We really didn't raise any capital, we were cashflow positive from day one and we didn't have any debt. So I think that speaks to really the hallmark of just a team that was committed, that knew what success looked like and had very clear goals on how to perform.

Justin Reinert:

Yeah, two big things that I'm hearing is one being just so explicit about the culture and how we operate and how we do things, which I've also found to be critical in high performing organizations. And then the second part of high performing organizations is that performance piece giving people regular feedback. I totally agree with you that the annual feedback loop or annual review process is just in today's world is far too infrequent. And then you've got leaders and managers who feel like that's the only time that they give feedback and that's just not enough at all. So I like this kind of weekly cadence of just regularly giving feedback about how we're performing.

Justin Reinert:

So, speaking of culture, I want to transition a little bit to a little more present day. So now you are working at TrueData You're not the founder of TrueData, but you're now leading TrueData and so I'm curious how do you go about preserving? There's people that grow with a company, really value the culture, right, they're the ones that kind of made the culture. So, speaking of culture, how do you preserve that culture as you transition to be the leader of another organization?

Scott Conine:

Yeah, that's a delicate dance, for sure. Right, you're brought into an organization naturally and instinctually. You want to make sure that your impact is felt, but you want to do it in a way that is respectful of what has been built before and the culture that exists. When I came into True Data, the business had existed for about five years. It was founder-led, vc-funded, and the CEO, who still is on our board, has this amazing charismatic personality that just engender people, clients, vendors, partners to him, and so it was a little bit scary, honestly, when I came into the organization, like realizing that this, this individual, has a reputation that looms large in the industry and has been very successful, so being mindful of what he had built was super important. I think, when I came into the organization, first and foremost was really understanding what were the non-negotiables in the culture, what were the things he built that this business need it.

Scott Conine:

Just you had to preserve respect and they are part of the actual DNA. You can't change the DNA of an organization. You want to complement the DNA but you can't change it. And so it became super important for me to really understand what those kind of assets and what those things were. I think what was part of why I was super excited about the opportunity at True Data was realizing that trust was built into the DNA. So if you hear kind of the part of my first part of my story, like that is something that I seek and I pursue rigorously. So you know that with True Data there was built into the culture and to kind of client offering is that we want high fidelity data that is, a hundred percent consenting, so that our customers, our employees, everyone knew that we were way above board when it came to kind of the type of product and solution that we were. It was part of really why we existed. So I think that was really super important.

Scott Conine:

I think one of the things I realized too when I came into the organization is how do you build trust and credibility as a new leader? Where are the areas that reinforce that? And one of the things that I first set out to do was just to create clean transparency around the performance of the business. We recast the financials, we rebuilt the GL, we did a whole bunch of financial work and we made that transparent to the whole organization. This is what we're doing really well. These are our opportunities that we can, where we can perform better. These are the areas that we want to keep leaning in, and so I think that when you, when I did that, it actually now created a common language of what success was going to be on a go forward basis. That really is. It's hard to argue. Well, here's how the business is performing, here's where we're not. What are we going to do? How the business is performing. Here's where we're not, what are we going to do? And I think just posing that question over and over and over I think started to engender a lot more support in the organization.

Scott Conine:

The thing, too, that when I transitioned to the CEO role, what was really important for me in that transition and I said this to the board was that I really want the founder to stay heavily involved in the business. I don't know if I want that person involved in the operational function of the business, because that's going to be a little bit difficult if the team doesn't know who to take direction from. But I think if I could have him on the board, I really would prefer to have that, because his voice is super important. His voice has been the leader of this organization for such a long time. We need to continue to leverage that and give that voice power, but just in a different venue. To do that, the board fully agreed and so that we worked through a transition plan to really move and migrate him to the board, celebrate the achievements that he had achieved in the business. But I mean, as a founder, he was super nervous. It was like this is my baby. I founded this business. I've got now new adoptive parents of my business. You better make sure that it works right. You better make sure that it grows and delivers.

Scott Conine:

And so I think that my role very early on was being overly communicative, overly supportive and just show here's what we set out to achieve. Did we achieve it? And here's what we're going to do if we didn't and just being super transparent, right, helping all parties know that I think this organization we also had to make some from the very beginning. We had to make some harder decisions.

Scott Conine:

When I took over the business, we found the business in COVID. We had to change some of the product offering and so we went through a lot of staff changes. We had to make a couple of rifts to get the business right size for what we needed to achieve, and that was really tough to step into the role and then really start to make some of these hard decisions from day one. And so I think I really leaned into the trust that I had built from day one in the organization to say, hey, these are hard decisions, but here's what we're, here's what success looks like, here's how we're going to come through. On the other end of that, and here's I need you all, as leaders in the organization, to step up. I'm going to give you a whole bunch of autonomy, a whole bunch of responsibility, and I'm going to give you the ability to elevate your own.

Scott Conine:

I think, when all was said and done, after we did those rifts and personnel adjustments, I think our retention on our team now is maybe three plus years. We just we don't seem to lose people, and I think it's because everyone has this amazing sense of autonomy now of what they need to do what success looks like. We give them their own sense of agency to do that. We give them their own sense of agency to do that. We give them training and upscaling when needed to rise to that. And I think we now sit in a very incredibly proud of the leadership team that we've built, because this team is pretty autonomous. They can do and operate and drive considerable success for the business and I think we've been wildly performing as the byproduct of that.

Justin Reinert:

Great. So what does the future look like for True Data and for Scott?

Scott Conine:

I think that my hope with True Data is that it will continue to accelerate, continue to grow. Ideally, at some point, truedata probably over year, it is, I think, is for a data company in the ad tech space is a phenomenal success story and so I think we will see, hopefully, continued success in the business. For me, I think I'm always looking for opportunities that always continually kind of stretch my own intellectual curiosity and enable me to create more and more performing outcomes. If that's at True Data, if that's elsewhere, I think my goal is to really engender economic prosperity for as many leaders and proper people as I possibly can.

Scott Conine:

I remember saying to John, my co-founder at Rife, early on is my goal is to create 50 new, 50 millionaires before I'm all said and done throughout my career. And he's like well, what do you mean I go? I said John, if we could do that, think about the economic opportunity that creates for the communities that we live in, for our employees, for families of our employees. I think it's such a powerful way to really transform the communities that we all live in and if we can find a way that the businesses and the enterprises that we create can do that, wow, how amazing would that be for our own personal legacy to be a part of something like that? If that's in places that I invest my time and energy and capital, I'm all about finding ways to do that and help more and more people transform the communities that they live in through private enterprise, small businesses and really just running businesses to generate cash flow that creates opportunity for employees, owners, everyone, and that's what excites me about today to morning.

Justin Reinert:

What an incredible goal. So, scott, if folks want to get in touch with you, what's the best way to do so?

Scott Conine:

I think there's the easiest way is just leak through me and LinkedIn. My name's Scott Conine. That's probably one of the easiest ways to do that, and then would love to keep having conversations. I love the other things I go deep in. I mean, justin, we connected a couple of weeks ago and last week about these types of conversations. I love to chat about these things. They're fun. I love to have these types of conversations. That's cool.

Justin Reinert:

So I love it. Well, scott, thank you so much for joining me today. Yeah, maybe we'll have you on again.

Scott Conine:

Awesome. Thanks for your time. I really appreciate it.