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A Founder's Life
Join me as I explore the powerful intersection of entrepreneurship, health & wellness, and parenthood. In each episode, I’ll be interviewing inspiring individuals who excel in one or more of these areas, sharing their stories, insights, and lessons. My goal is to provide valuable takeaways that can help you thrive both personally and professionally.
A Founder's Life
How Saying “Yes” Built a 16-Year Business - Scott Leff - S6 - E4
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👤 Connect with Today’s Guest
Website: http://www.leffcommunications.com/
Substack: https://substack.com/ @lefffield
LinkedIn: https://www.linkedin.com/in/scottmleff/
What does it really take to build a business that lasts?
In this episode of A Founder’s Life, Scott Leff shares the honest, unfiltered journey of building a B2B content agency over 16 years, from freelancing without a plan to leading a 28-person team serving global clients.
Scott breaks down the realities most founders experience but rarely talk about: uncertainty, saying yes before you’re ready, learning through failure, and figuring things out as you go. He also dives into the importance of health, agency, and building a life that works alongside your business.
If you’re building something or thinking about it, this conversation will challenge how you think about growth, success, and the entrepreneurial path.
In this episode, we cover:
•Why most entrepreneurs “fall into” business
•The power of saying yes (and when it backfires)
•Lessons from failed and unprofitable projects
•When to say no — and even fire clients
•The role of failure in long-term success
•Why agency and control matter for mental health
•Balancing work, family, and personal life
•The importance of learning from others
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Welcome to a Founder's Life. I'm your host, Leo Gestetna. On this show we dive into the real stories behind the highs and lows of entrepreneurship and how we pursue a more balanced and meaningful life along the way. This podcast is brought to you by Thanks, helping founders like us scale with reliable remote talent. Email founders at Thanks.com, that's T H A N K Z dot com with the subject line of founders' life for preferred pricing. Now I'm joined today by Scott Leff. Scott, thanks for joining. Would you like to introduce yourself to the audience?
SPEAKER_00Yeah, great to be here, Leo. Thanks for having me. My name is Scott. I run Lef, which is a B2B content marketing agency. We serve primarily global consulting firms and other B2B companies, and based in Chicago, but with employees across uh Europe as well.
SPEAKER_01Excellent. Um would you like to talk a little more about your journey that brought you to where you are today, and then a little more about the current business, sort of you know what the customers look like, what you're doing for them, etc.
SPEAKER_00Sure, sure. And I think like most entrepreneurs, I didn't have a plan to get into this. The opportunity presented itself. I got my start in business publishing with McKinsey and Company, working as eventually managing editor of the McKinsey Quarterly. I left McKinsey to go work at uh Chicago's Olympic bid. The city was was trying to get the 2016 Olympics. We didn't. Rio got it. They were they were better at bribery than Chicago was, uh, which is ironic. And after that ended, I think I was I was casting about for what was next. And uh my wife said, Why don't you just try freelancing? You're a writer and editor. I know companies you know will hire you. And uh so I started doing that, and it was very probably a couple years of feeling my way through the fog, trying to understand uh how to talk about what I did, what companies would hire me for. And over the course of that time I got busy enough that I brought on a partner and then uh incrementally built uh from there. So we're we're 16 years into the journey now. We are about 28 people, and it's been interesting. Again, like most entrepreneurs will attest, it's not a straight line. And there are lots of listening, lots of connecting the dots, trying to understand what clients want and how you can adjust to to uh give them solutions.
SPEAKER_01Yeah, um I think that makes sense, and it's uh you know the the the path is rarely on purpose with entrepreneurs. People have a habit of falling into things, it's spotting the opportunities.
SPEAKER_00Yeah, well, and I think anyone who's been around for for for a few years can look back at some attempts they made where they thought this was going to be a big offering, didn't go anywhere. But you need those experiences, right? Because at the least you're developing that test and learn muscle. At best, you're figuring out how to put the pieces together in a different way that might be marketable. Very true. And tell us uh how family looks for you. Uh family? Yes. Married with two kids, 21 and 19. Uh so that's been an interesting journey. Anyone with kids will agree that watching them learn, grow, and develop is a humbling experience, but also enriching because you can't help but go back to your own experiences and think about where you were at that time, how you developed, what you learned along the way. So give a lot of thought to how to gently guide be a resource for them without without uh solving their problems myself, because that's not how people develop and grow in the long run.
SPEAKER_01True, avoid believe in sort of treating our kids like adults as much as possible, letting them make the mistakes.
SPEAKER_00Yeah, w my my wife and I uh agreed that it was important for them to make mistakes and fail when it didn't really matter. Which is, you know, through sometimes even through high school. You have to you have to go through those times. And and if parents are always there to catch you before you before you fall, then again, you just don't develop that those muscles, the resilience, the grit to figure out for yourself.
SPEAKER_01Yeah, I think I wrote a blog the other day talking about, you know, we learn more from failure than we do success.
SPEAKER_00It's true. And uh I I think most of us can I don't know what what your banning average is for success to failure, uh or how you define failure. I think uh hopefully I'm I'm batting at least five hundred, but you don't know from time to time, depending on how you define success.
SPEAKER_01As a non-American I get what you're talking about, but I haven't got a clue if five hundred is good or bad.
SPEAKER_00But if you're uh um What's it out of? Yeah, i in in baseballs. If you're yeah no no, I get that, but what's it out of? What's uh is there a oh uh 500 out of a thousand. Uh so that's that's 50-50, uh which uh if you're failing half the time, I I guess you can say you're learning half the time if you want to be optimistic about it.
SPEAKER_01Yeah, I think you know we uh you know anyone who thinks an entrepreneurial path is is easy in all success is uh either lucky beyond all belief or it's just waiting for the failure that's about to come. Uh yeah, it's it's it's a roller coaster. It's hopefully a fun roller coaster in the end, but uh it's definitely a roller coaster.
SPEAKER_00Well, I know you've talked a lot of entrepr to a lot of entrepreneurs, and I'd be interested to get your opinion on how many of what drove most people to become entrepreneurs? If it was the opportunity was staring them in the face, they couldn't avoid it, and so they had to to plow forward, or if they had an experience that made them think, yeah, I can do this. But where how would you describe most people's inspiration for going out on their own?
SPEAKER_01Yeah, I mean it's an interesting question. I think you know, anyone who says they're going to becoming an entrepreneur to make money, that's a mistake. Because like I always say to young entrepreneurs or to high school students when I'm talking to them, it's it's you'll probably make more money getting a job. Now, hopefully long term you'll make more as an entrepreneur and you'll have more fun, but certainly in the short or medium term, you'll make more with a job. So, um, you know, I think you know, entrepreneurs come from a number of different places, but I think a lot of it is a bit like USEB, which is almost falling into it. Like, you know, there isn't a business plan behind it. It's more you're seeing an opportunity and and that then becomes a business that you build upon.
SPEAKER_00Right, right. And I think for for me there was the I knew that there were a couple of things that I was good at. I didn't know if I could run a business, but I knew I could write and I could edit. And so some of those skills that you need to actually be successful in a business come to you incrementally as the business grows. You always wish that they would you could acquire them faster or write on time when you uh when you face a certain challenge. But I think that's heartening for people who who want to go down this path. You don't have to know everything, have it all figured out, have all the experiences because every day is gonna throw something new at you. And I think the the main skill you need to have is just being ready to respond and and figure it out. Yes.
SPEAKER_01I think ducking and diving or pivoting is you know, whatever form that takes. I think it but that that is the entrepreneurial journey, which is you're spotting an opportunity. It may not be the same opportunity that you had originally. You suddenly say, that's a great opportunity, I'm gonna go that direction. That's you know that that is the journey. It it's finding, you know, those opportunities, those uh little diamonds in the rough as you go along the road.
SPEAKER_00One of the main points in the development of our of our agency, as I said, we started out mainly writing and editing, we added some design capacity. But a friend from the Olympic bids said he worked at a large consulting firm. He said, We're getting ready to we we want to do some videos around the Olympic movement. Can you do video production? And we hadn't before, right? But as an entrepreneur, the rule is say yes and figure it out. And hopefully you don't get too far uh beyond your capabilities so that you're you're letting the client down. But in this case, we were able to pull a production team together, created the videos, the client was really happy. And then that has led to a 12-year relationship with his client where we do lots of video every year, everything from uh more modest productions to 10 or 12 person crews, more sound stage, not quite Michael Bay or Spielberg, but ambitious productions. And and so had we not said yes and figured it out twelve years ago, we would never be in that place now.
SPEAKER_01Yeah, I think you know, the the and and what you said sort of you know, saying yes when when the client asked, I I think in the end, you know, with a lot of things, unless you've got a really, really focused business, I often say to my business partner, it's it's it's a yes to most things, unless it's a definite no. I mean, there's some things you're like, this just is not a fit for us. We can't add value here. Okay. But if it's slightly off from what you do, well, okay, you know what? We we we can uh adapt, and if that's a good client, and you know, 12-year client is definitely a good client.
SPEAKER_00Right, right. But we also have there have been times we've said yes and then gotten in the middle of a project and thought, how are we gonna get out of this? And one was we were asked to do uh an ambitious online survey that had lots of different options. It was almost like a choose your own journey survey, and the output was an auto-generated PDF, which at the time, now that that doesn't seem like that big a deal. But six, eight years ago, that was there was lots of coding involved, lots of figuring out a platform, lots of working with a client, trying to manage their expectations. And we eventually got to a great place, and the client was happy, but it's still one of the least profitable projects we've ever done. And and we haven't done another one in part, we we'd love to take it on, take another one on, but it was it's such an uncomfortable feeling when you realize we are in a place and we don't quite know how to move forward, and you don't want to disappoint the client, you don't want to be in those situations where you're not making money on a project all the time. So it was valuable earning experience.
SPEAKER_01Yeah, that's that's true. And I think it's the other thing that that wasn't one of those clients, but the other thing I think comes with experience is uh not being afraid to say no to the wrong client or not being afraid to fire clients. I've definitely fired clients that you know fall into the uh you know, when when you're doing the no arsehole rule, you know, there's definitely some that fall in to the other side of that and you're like, life's too short.
SPEAKER_00Yeah, uh definitely been in that situation, and it's it's it's difficult because when you start out as an entrepreneur, if the rule is say yes and figure it out, that means that you're not saying no to much. And at a certain point you can't say yes to everything and define yourself in the market. Saying no to a client that is uh uh that is difficult to deal with uh or or or firing them is that next step. It's I mean that's that's tough to uh we've gotten better at it, but it's it's never easy. And it's hard to know where's the line. At what point have we have we crossed to uh uh a point where it's this relationship is really no longer good for for us or the client. And it's a little bit like relationships generally, right?
SPEAKER_01Yeah, and and it's never easy, but at some point, you know, if if you don't want to deal with a client, you're probably not the right fit for them, so you're actually doing them a favor as well. So um you may not be doing the next person a favor who they become a client of, you know. Um and uh uh tell us what sort of health looks like for you. So mental health, physical health, nutrition, fitness, however that looks for you.
SPEAKER_00When it comes to physical health, it's a huge part of my regular routine, whether it's running, stationary bike, some kind of exercise. We're sitting in the chair eight, ten hours a day, so you gotta move. And I also find it meditative and sometimes solutions to those problems that you've been trying to solve over the course of the day come to you when you're exercising right after, so it's also important for that. For uh mental health, I come from a people whose uh uh general approach to mental health is push it down. And uh I should probably spend some time on the couch, but I'm not going to, at least right now. I feel like I I love what I do. I don't expect it to be easy. Uh I don't expect there to be an infinite amount of time to do everything you want to do. So so I'm I'm fine with the choices. And I I feel like in some of the interactions we've had with our with our employees when they're having difficulty with clients, it often comes down to that feeling of helpness helplessness or lack of agency. And it's a terrible place to be. I've been in in on client projects or in jobs where you feel like you're being asked for things, you don't understand how it fits in, you want to ask questions, you don't feel like you can. That's a terrible place to be, and I feel like that is a huge contributor to challenges with mental health or well-being just because we need agency in our lives. We need to be able to make those choices and feel like we're have some kind of control. And when you don't have that, I feel like some of the other things compound. And uh, what do you like to do for farm? I was a musician in a former life. And so music is is everything to me. At at this office, we have a a turntable and 600 uh records here that we're we're playing music all day. I play music on the side, so I'm producing uh a monthly acoustic concert series, uh very intimate kind of gathering thing, tiny desk concert, something like that. And and that's and then going to see music, traveling a bit. I was just in Memphis recently, making the pilgrimage to one of the great U.S. music cities. Those are the things that that um end up recharging the battery when uh work starts to uh become a bit oppressive.
SPEAKER_01I love that. And how about so you know, obviously recharging the battery, but if you look at that sort of balance, that center line on a balanced life, uh how do you find that uh you balance between the different aspects of work, family, health, and uh having some fun?
SPEAKER_00I don't pretend to do a very good job of it, really. And I think it's it's a challenge, particularly after the the pandemic when those lines between work and life blurred initially when we were working from our homes. That was a challenge. And so as an entrepreneur also the work is never really done, right? You could if you wanted to to work around the clock, you could. And so it's it's easier now that the kids are are grown, and I don't feel like I'm not neglecting them by spending time on work. But I think it's for all of us, you have to make choices, you can't do it all. I don't watch a lot of Netflix, for instance. Binging TV isn't my thing, but that's not something I miss. For others, that's how they recharge their batteries. So I I feel like again, coming back to agency, if you're if you're thoughtful about how you want to spend the twenty-four hours of the day uh each day, and and you've done what you need to, f find some time for yourself. I think that can look different for for everyone. But um uh I feel like uh like I said, I I know I could do better, but I'm I'm I'm maintaining I'm feeling all right.
SPEAKER_01Excellent. That's that's all we that's all you can ask for. And um what has been a pivotal moment in your life?
SPEAKER_00Trying to think. Uh there are a couple of uh there are a couple of uh times early on the uh in sports in playing music that were uh uh that were huge failures. Uh in in a in a somewhat public way where it felt like the whole world was watching and you didn't quite meet the moment. Uh as traumatic as those were at the time, I think they gave me I don't want to say a fearlessness, but a willingness to do some of the challenging things, not be afraid of failing. And I think we talked earlier about uh testing and learning, being okay with failure. That's a muscle. And when you know that the worst that can happen is really not that bad, then it makes it easier to charge forward. How how about for yourself?
SPEAKER_01For me, I don't know. I mean I've had sort of probably a few pivotal moments, you know, and I I I look at it as chapters, I should do a book at the moment, but you know, the the different chapters in my life, whether it be, you know, I got married young, my first business actually was as a teenager, whether it be um the uh there was a big tech business which I founded with my brother. That was definitely a pivotal moment, and the learnings that came from building one of the market leaders across uh UK, Germany, Sweden, and France in two and a half years. Moving to America in 2010, with my family, uh sort of moved halfway around the world again. Pivotal opened, you know, so many different opportunities, especially for my kids. And you know, another pivotal moment is you know the the you know COVID and the relationship with the kids, and then the chapter I'm on now as a sort of digital nomad, and as I sort of move forward to the next stage of my life now, my kids have left home. So I think for me, uh those pivotal moments are chapters, and yeah, there've definitely been a few, and there'll hopefully be more. You know, I'm I'm enjoying the journey wherever it takes me.
SPEAKER_00Your answer was much better.
SPEAKER_01Can I have a do-over?
SPEAKER_00I want to give you another pivotal moment.
SPEAKER_01I'm gonna give you a more positive one. It's whatever. You know, people I I find you know there's a whole mix people give, and I and I love that. It it's one of those questions that you know um it it's whatever comes to mind. Yeah.
SPEAKER_00It's it's it's hopefully not a prepared one. Yeah, well, and it's it was nice hearing you go through the series of pivotal moments and realize that it's not as if you get to an age and your pivotal moments are over. There can always be another one around the bend that changes the path forward, creates some new opportunities. You don't know it at the time, but in looking back, it's it was a really meaningful thing that happened.
SPEAKER_01Yeah, I think life's a journey, and I definitely embrace that journey. It'll have lots of twists and turns. Um you know, and that's that's fine with me. But yeah, you you never know what it'll come. Uh what's one piece of advice you'd give to a respiring entrepreneur?
SPEAKER_00I think the biggest thing, as I look back at at my own journey, is you tend to feel that you're the only one that's ever gone through this, that the problems you have are unique to your venture, which couldn't be further from the truth. And so the best thing that you can do and the thing I wish I would have done more, particularly early on, was reach out to people who'd been in that situation and get their advice. Because I always used to think that, well, there's no blueprint for what we're doing here. Actually, there is. Lots of people have done it already, and they can help you and save you some time. I guess in the age of Chat GPT, you can just put it into the bot, but it's also helpful to to talk with people, have that group of of entrepreneurs, advisors, friends, whatever you'd want to call them, to talk through these things because because that's also a process and it's a little bit of therapy, and it can make you feel much better that you're not alone in this journey and that others have been there before.
SPEAKER_01That's very true. You know, the other thing I think to add to exactly what you're saying, which is people are happy to help. I mean, I for example, I've had a hundred plus people on the podcast, and every single person when I've asked that question has said, reach out to me, happy to chat. So that that's my next question is how can people find you?
SPEAKER_00Uh well you can find us at leftcommunications.com on LinkedIn and and other places. If if anybody, if any aspiring entrepreneurs want to talk, I'm always around. I've benefited so much from the generosity of others. So I want to repay the um the favor. But yeah, but we're out there, we're at conferences and other things, and and and hoping to continue to uh uh to move the company forward. Well, thank you for joining us today.
SPEAKER_01Uh it's been a pleasure. Thank you for uh having me. And thank you for listening to today's episode. If you enjoyed the conversation, don't forget to subscribe to the channel, tell your friends, and please leave a review.