Talk CNY Miniseries: Leadership Lessons - Dream, Build, Lead: Lessons from a Serial Entrepreneur

In this episode of Talk CNY: Leadership Lessons, presented by NBT Bank, serial entrepreneur Jeff Knauss shares the personal and professional philosophies that have shaped his dynamic career. As an angel investor, 4x Inc. 5000 founder and the CEO of Arcovo AI and Opin, Jeff reflects on what drives his business decisions and his passion for building things from the ground up and bringing them to life in ways that provide real value.

Beyond business, Jeff’s leadership is deeply grounded in personal values, especially his commitment to family and the intentional use of time. Tune in to this episode of Talk CNY to hear Jeff’s advice to aspiring entrepreneurs, as well as his take on the importance of reverse-engineering big goals, taking a leap, and striving for daily improvement—emphasizing that regret is more frightening than failure.  

Talk CNY: Leadership Lessons is presented by NBT Bank. 

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Jeff Knauss Website | LinkedIn

Host: Brittni Smallwood LinkedIn

Transcript

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Welcome to the Talk CNY mini series Leadership Lessons, where we sit down with business and community leaders to discuss their personal and professional lessons that led them to where they are today and serve as a guiding light forward. Our guest today is Jeff Knauss. He co-founded his first company, Digital Hyve, in 2014. It was ranked by Inc. magazine as the 52nd fastest growing company in the United States in 2018. After selling it in 2021, Jeff went on to serve as an angel investor and partner in 13 different businesses, where he provides his insights for continued growth and innovation across various sectors. Jeff, welcome. Thank you so much for joining us today. Thank you so much. Oh my gosh, that was amazing. That introduction was incredible by the way for the viewers at home no teleprompter. She's just doing that. It, it was amazing. Well thank you. We're so excited to have you here. I'm happy to be here. So you are a serial entrepreneur? Yeah. As you're making a decision about which companies to invest in. How do you make that decision? It's a great question. So as an entrepreneur, I love to build things. I like to be involved. And being, involved in any startup, whether that's monetarily, like I'm investing my money or investing my time or investing both. You're right, there is a criteria, kind of a rubric in my mind of how I like to think about it. And so if I'm investing money, if it's purely at it as an angel investor, I look at the founder, I think to myself, are they qualified, capable to make a dent in the universe, to build enough of a company that can scale to enormous heights and, will, my, not only my money, but my expertise, how be helpful to them? Will I be additive to that company? And if so, you know, I may choose to invest. But if it's something that I'm going to start myself as the entrepreneur and I'm going to be the CEO of the company and founder of the company, for me, that really I need to make sure that I'm leaning in all the way into my skill sets. I think that one of the most important traits of an entrepreneur is self-awareness. And so you have to know what you're good at. But almost more importantly, you need to know what you're not good at. And so if you are going down the road of building a company, you have to understand and try to think through what are the things that this company will need to hit a point of scale that you want? What skills will be needed to hit that point of scale, and are you qualified to do as much of it as possible in the beginning stages? And then are you qualified enough to find the right people to do the things that you need, all those skills that you don't possess? Or you're not good at, yes. I saw you mentioned somewhere that you prefer the startup stage process, and then you like to give it to someone else if they're going to scale it to the next part, right? Yeah, that's that's some really good research. First of all, because I've only said that a few times, but it is true, I find that, you know, again, going back to self-awareness for me as an entrepreneur, what I found out, especially after selling my first company, I realized that what I love more than anything is the building process. To take something that doesn't exist and bring it into the world. And then for that thing to provide value to others is an incredible gift. That I just am so fortunate to be a part of. And so, for me, the startup world is such an incredible puzzle that you get to solve every single day. Oftentimes it's like into you're flying an airplane. You're flying an airplane in the air while building it at the same time. Right? Because that's really what it is. There's no predetermined rules. When you when you invent a new startup, you're having to figure it all out yourself or with your business partner and maybe with your early teammates. But it's a really fun puzzle to figure out every day. Eventually, what happens is you hit a point of scale and it turns more into operational fine tuning. You're not so much reinventing the way the business gets done, how you're serving your clients. You know, certainly at times, you know, more mature businesses will have some digital revolution they need to go through or technological evolution. But ultimately, you know, that startup phase is where all that really fun, crazy kind of pull your hair out. Stuff happens, and then over time it's more fine tuning. And I find that I'm a better CEO in that early stage of that. Like craziness, wrangling a group of people that are really invested in a mission, getting everybody to kind of sell on the right the same direction, and build something of significance. And then at some point, you know, I evaluate, am I still the right person to continue and build this thing to what it could become, or does it really need to be taken on by somebody else? Or can I find a team? Can I build a team that will help to fill in again the spots that maybe I'm not so qualified to? I love that I love watching people go from having a vision and then bringing it to reality. It's it's I love it's fascinating. So for you this year, what would you say is one of the biggest problems that you're looking forward to solving? So know over the last couple months, about a couple a few months ago I started a company called Arcovo AI with my business partner, Jake Tanner. As everyone knows, AI is just completely taking the world by storm. It's in every conversation, as it should be. You know, the tech is evolving. Every single day. The latest stat that I saw is that there's 3000 new AI businesses built every single week. Wow. If you can imagine that. It's because AI’s made it so much more accessible to build things, software development, all these things. And so these tools are incredibly powerful. And, you know, the CEO of Google said that the invention of AI is a lot less like the invention of the internet, and it's a lot more like the invention of fire or the wheel. That's how impactful it will be to human evolution. And I agree with that. But we're in the very, very early stages of it. And what I, found that I wanted to solve was big enterprise level companies, huge nationwide companies. They're investing millions, millions dollars investing in AI to help build, create their companies and make them much more efficient, using AI but small to medium sized businesses. There's almost no one serving them. There's almost no one helping them navigate all of the crazy tools, all the things, all the potential that they have. And it's really hard as a small to medium sized business owner that I've been doing for many times. Once you've built a company, it's hard to go backwards and look because you're in it every day to figure out where are the opportunities for businesses, how can we build better processes? And up until this point, it's been a big lift to try to do that. Now with AI, you can plug AI right in the business as it exists today, with not a lot of digital transformation outside of the AI implementation and solve a lot of a lot of problems automating out the repetitive, mundane tasks that humans do, reporting, data entry, things like that. Now, AI can do that. And so, that's the that's the opportunity that my, my partner and I saw. So we started a business that we are helping small to medium sized businesses leverage AI technologies to help automate and create efficiencies in their business. And that's really exciting. Okay, so then as you are tackling these big tasks like you just mentioned, what habits or routines kind of help you stay grounded and resilient? That's a great question. I mean, you know a and not to be cliche but but genuinely everything that I do comes back to my family, you know, and I'm sure a lot of people would say that. But I've also, you know, just being in the entrepreneur community for a long time, I find that people and I get it. This is not a judgment, but they tend to think I'm going to work really hard right now. And then I'll spend time with my family. And I've never had that mindset. I will not compromise on the time that I spend investing in making my kids the best possible human beings. They can be trying to raise them actively coaching my kids soccer teams. I am heavily involved as dad because I want to be, and so I don't, I don't. Yes, I work incredibly hard, but I work around my family because they are first and foremost We build a very family friendly culture in any company that I run because I know that's what I want. And it's only fair to allow my employees to do that if they're if they're working towards the same mission and vision that I have, I want them to enjoy the same thing. And so I think that's the thing that keeps me grounded in the way of like, no matter, you know, how successful you are no matter how many wins you have, no matter how many failures you face, your kids, still look at you like you're their hero, right? At least for today. They're seven and ten. I know what a teammate is going to be like, am I right now? I'm enjoying the spoils of being the being the hero, dad. Absolutely. I love listening to the things that come out of their mouths. Like, really, they're just they're fascinating. It is. Oh, that's so cool. I'm so happy for you. Yeah. So the what would you say is a defining moment within your career that has kind of shaped who you are as an entrepreneur? Defining moment. I mean, certainly, taking the first leap. Right. And I think that that to me is where a lot of people struggle. Right. We all know people that, you know, have said, oh gosh, I have this brilliant idea. I think it would change a lot of people's lives. But it's just not the right time. Right. And I get that, trust me, it's, it may not be the actual right time, but I'll also say that it kind of never feels like the right time. When I first started my, my first business, it was a Digital Hyve digital marketing agency. My son was three months old, and he was our first kid. My wife is from Finland and in Finland they have three years of maternity leave, paid maternity leave. Did you say tree years. Three years. Trace anos. I had to hear that. Yeah, yeah, yeah, yeah, it's a real thing. And so, I said, you know, when we first started dating and then subsequently got married, I said, you know, whatever you would if we have if and hopefully when we have kids, you'll get to enjoy the same, you know, privileges as you would in Finland, because that's where I'm going to work really hard to make happen. That's beautiful. And so. And she wanted to be a stay home mom. And so, that was the agreement. And then three months into having a kid, I went to her and I said, hey, look at there's an opportunity for me to start a company. I was in a really great job with a really great boss and really great team. And, I was in television, said to her I was like, so we're not going to make any money for a year. We're going to lose our health care. I'm going to get health care. But it's, you know, on the marketplace and all that stuff was gonna be expensive. Our expenses are going to go up. Our payments pay is going to go down to zero. It's probably gonna be that way for at least a year. If the if the business works out at all, it's going to be really scary. And, I remember to this day her exact quote was, if you think it's the right thing for our business, do it. That's literally what she said to me. And so I can't emphasize enough how important it is to have an incredibly supportive partner, because that's what allowed me to take that first jump. And taking that leap in that moment, I think, solidified in me. There's never a good time. And what governs how I make decisions is I am much more fearful of regret than I am failure. I don't mind if I had done that and try to start a company and didn't work like that would have sucked, but I would have been. At least I tried. Whereas if I was 80 years old and I was looking back on my life, I was like, man, I wonder if I did that. That to me terrifies me way more than failing ever could. And so, that that I think just starting that's the thing I always encourage people just just do it. That's so beautiful. But you you hit the nail on the head when you said you pick the right partner. That's so beautiful. How you can remember your wife's words to that moment. I was very oh, you have a beautiful family. Oh, thank you All right. So next we're going to switch things up just a little bit. So we have a rapid fire section. So during this section I'm going to hand you these cards. You can go through them pick out which ones you'd like to okay. You're welcome to go through them all or whichever ones speak to you most. And then the goal is for you to answer them in 30 seconds or less, and then go on to the next one. Great. All right. Well, you've heard me ramble. So that's going to be the biggest challenge of the thing I'm going to do. I'm gonna make it fun. I'm just going to pick a random one. Okay? Okay. So the one that came up was, if you can achieve one thing this year, what would it be? I would say that I actually run to, multiple companies. I would say that I would like my businesses to be in a, I would like both of my businesses to create a foundation that we can scale, infinitely. That's my goal. So. So this year is a building year for me. I've started a few new companies over the past couple of years, and I want all of them to be in a place where foundationally we have all the the teams, the SOPs, all the things in a in a in a solid place where all we need to do is whether it's add revenue, add people, whatever it is. But all of our systems are in a place that can scale infinitely. That would be my goal for the year. And it was under 30 seconds. Who inspires you as a leader? Rob Simpson, I’m on the CenterState CEO Podcast. And I would be remiss to not mention him. He has been there for me time and time again throughout my life. I actually went through a particular hardship that I always think about. I've been very fortunate in my career where I, you know, can name on the, you know, my hand, the macro failures that I've faced. And one of them, that I went through, I reached out to Rob because I was really struggling with it and within, you know, 20 minutes, he was me. He made me feel 180% differently and better. So, I really appreciate his his leadership approach, the way that he thinks about team building, the way that he cares about his teams, the way that he thinks about our community. He is, he's a great guy. And not just because I'm on the podcast. No, no, he just happened to jump to my mind. But I have probably a that's not a 30 second answer because I could go through about 100 people that I admire. And I've learned a lot from, How do you incorporate fun into your personal life to stay energized? And here's how you do it. Here's the trick. You learn to love what you do. And there's an old cliche of, you know, learn to love what you do in your work day in your life. It's it is very true. That's at my dad when I was young, said that if you have a job, no matter what, your job will suck. And I used to love skateboarding. I, I still actually skateboard and snowboard, do all these things. And he said, if you ever became a professional skateboarder, there would be days that you hate skateboarding because you're going to be forced to because it's a job. And so you have to understand that nothing will be 100% good, nothing to be 100% bad. So for me, I've learned to love my work. I really, really love it. I wake up excited to tackle the opportunities I have. And that I that I have the privilege of solving. So I love my work, and I answer to a little bit like, I like to snowboard and and do fun stuff and kid stuff. I like to coach soccer and fun. Yeah. Super fun. I love it all. Yes, it's a good reprieve, but I could work 24 hours a day because I love what I do. So, so that was three, number four. What personal values guide you guide your leadership and decision making? Personal values. I would say that if I had to narrow down to 1 or 2, the first one is, time. Time is a choice. We tend to think of time as a prison. Time is a thing that we have to fit so much. And you always hear that phrase, I don't have the time to do that. Not sure you have as much time in the day as everyone else is, is a great equalizer until the day you die, that's the one day you get robbed of the same amount of time as everybody else. Until that time you have the same exact time. And so you are choosing to spend your time. And most people don't think of it as a proactive choice. They think of it as a, thing that happens to them, not their thing that they control. And so the best way to create an amazing life is to realize that I am making my choices with my time and then how do I create a rubric for how I use my time most efficiently? So I use that to help guide me and my personal choices. But also I teach that to my teams. So that they can make really good choices and how they spend their time to best grow the company and move in the direction we want. You've done such so many great things. So many great things. I've learned a lot from great people. Oh, beautiful. Well, thank you so much. We're coming to a close. I figured our last question could be about entrepreneurs. Okay, so if there's an entrepreneur who's watching this and they're saying, you know, they really want to push the envelope, they really want to grow, what are some things that you would give them as advice? Choose your time wisely. Right. Like it goes back to literally everything you do. If you do that one thing, choose your time wisely and make slight improvements every single day with how you choose that time. So, so don't think of it like first of all set goals. Set really big, ambitious goals, in a five year period, a one year period. And then and then what you do is once you set those goals, you reverse engineer those to say, okay, if I want to hit $100 million in five years, what are the steps I have to take to get there? The step before that would've been this step before that would have been that step before that. So reverse engineer that to figure out the steps you actually need to get to that goal. And then you think to yourself, okay, now that I know the steps, here are the actions that I need to take. Here's how I need to use my time. When you every single day you use your time. The best you possibly can. You evaluate your day at the end. like the choices that you made at the end of the day. And then you say, how can I be 5% better tomorrow? Oh, I like that. At some point throughout your day, you will deviate from the day before you'll wake up and you'll choose to go right instead of left. You'll brush your teeth before you eat whatever the thing is. So you deviate. So you can by definition, you'll never have the same day twice. And so if that's the case, why not choose to be better than you were the day before? Well said. That was a great way to close it. Thank you so much. Thank you. Brittni it was great. Great job. It was a pleasure speaking with you. Well, if you'd like some additional information about Jeff's responses, they'll be available across all the social media platforms for CenterState CEO. CenterState CEO’s, Mini series, Podcast Talk CNY, Leadership Lessons is presented by NBT Bank. It's available across all major podcast platforms and it's available on centerstateceo.com At NBT Bank. We know that this day starts with this one. This day starts with this one. Because no matter how unforgettable the extraordinary days are, there's a lot of every day that leads up to them. You can count on NBT Bank to help you get started. NBT Bank. It starts here.