The one ability that separates okay leaders from great leaders with Dave Kerpen

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Today on 3-Minute Marketing, I’m speaking with the one and only Dave Kerpen — bestselling-author, speaker & serial entrepreneur. He’s currently Co-Founder and Co-CEO at Apprentice, the platform that connects entrepreneurs and business leaders with smart and motivated college students. Dave and his wife also successfully exited his agency Likeable Media in 2021.

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Dave joined me to answer the question, “What’s the one ability or trait that separates ‘okay’ leaders from great leaders?”

Show notes:

  1. Great leaders are effective because they know how to delegate.
  2. Leaders struggle to delegate because they either are afraid to give other people the work, or they’re wired to micromanage.
  3. To delegate effectively as a leader, follow the SHARE model.
  4. The leader’s job is to do 3 things: Set the strategy and vision (S), Hire the right people for the right seats (H), and Assures access to resources and capital to get the job done (A).
  5. When a task comes a leader’s way, if it’s not “SHA” they Remind themselves to delegate it (R) and empowering the right person to get the job done (E).
  6. The “right person to get the job done” doesn’t have to be an employee — it can be a freelancer, contractor, partner, vendor, etc. Thinking through who that person is is the leader’s job.


– You’re listening to Three Minute Marketing, where we interview the world’s top growth marketing leaders and distill their knowledge into actionable, bite-size insights. Now here’s your host, Chris Mechanic.

– Welcome everybody to another episode of Three Minute Marketing. I’ve got an amazing guest on the show today, Dave Kerpen. Dave is basically everything that I would like to be when I grow up. He’s a serial entrepreneur, he’s on company number five, he’s a four-time New York Times bestselling author, or he is got four books so far, he’s a speaker, he’s got a massive engaged community on LinkedIn, he’s an awesome dude, he’s grateful, he’s kind, he’s, I think a marketing mastermind. I’m super-duper excited, I could go on and on Dave, but-super excited to have you man, thank you for being here today.

– Thank you so much for having me, and giving me a couple minutes, maybe even three to rant for a bit. And, I’ve been very, very blessed with a wonderful career as an entrepreneur, six, seven companies, depending on how you define things. As you mentioned earlier, my wife and I exited our first company last year. Likable was a social marketing agency that we sold for eight figures, and I’m proud of that. And the books, but speaking of the books, I’m going to rant for a bit on my next book because the thing that I have identified that really, differentiates an okay leader from an amazing leader, is the ability to delegate well. And I’ve encountered, mentored, coached, invested in, partnered with, probably, roughly 2,000 business owners at this point, right?

– Wow-

– I’ve been fortunate enough to deal with quite a few business owners. Now, some business owners are quite brilliant, but what they struggle with doing is delegation. And they either, are afraid, they’re fearful and mistrustful, and they can’t give other people the work, or on the other end, they micromanage and they manage things very, very closely.

– Yeah-

– And so the Share Model, I’ll give you a sneak preview of the book which is called “Share”, the Share Model is as follows: “A good leader does three things and three things alone. 1, “Sets the strategy and vision.” That’s the S. 2 H, “Hires the right people for the right seats,” and 3 A, “Assures access to resources and capital “to get the job done.” Everything else, should not be the role of a leader. That leaves, everything else to delegate to. So, when a task comes my way, if it’s not setting the strategy, hiring the right people in the right seats or assuring access to capital, I will R, remind myself to delegate it, and then E, empower the right person to get the job done. And when I empower someone, it means tell ’em the task, and I get the hell out of their way. That’s the Share Model, and that’s what can make somebody go from a good leader to an amazing leader that can really delegate well.

– Wow, that’s sick, I love that Dave. Perfect timing as well. Let’s continue talking about the Share Model. You know the drill here, we like to keep it very brief, but if it’s not said in the strategy, if it’s not hiring, if it’s not ensuring access to capital, that I am reminding myself to delegate, and I am, oh, gimme the E.

– Empowering the right person to get job-

– Empowering it! Love it! Well, that’s a wrap-

– And by the way, in the new world of work, sorry to interrupt, but in the new world of work, empowering the right person to get the job done doesn’t necessarily mean an employee. It could be a freelancer, it could be an intern, it could be a contractor, it could be a partner, it could be a vendor. So, thinking through who that right person is, or that right resource is to get the job done is also part of the work of the empowerer.

– 100%. So hey, real quick, before we wrap, tell us a little bit about Apprentice. We didn’t talk about that, but I know it’s your latest thing. What is it? What, is Apprentice?

– Yeah, so pretty amazing story. You know, for the first 13 years of my entrepreneurial career in the first three companies, I would hire college students to work for me while they were in school, and then I would sort of mold them, and when they graduated they would come work for me full time. And I was able to do this with great success because I would handpick really smart, driven people, I would teach them everything I knew, and then they’d come on and join my companies and they’d immediately, like, frankly have an unfair advantage over the rest of our employees. So, I brought on college students who ended up co-authoring books with me, running departments, running marketing, being a chief of staff and helping manage big, big projects and big budgets and big teams, lots of really important roles.

– Wow-

– For these young people. Well I had this one young man, Rob, who worked for me for a couple of years while he was in Hamilton, co-authored a book of mine, the third edition of “Likable Social Media,” worked on a million dollar project for a big client, and, you know, he approached me and he said, “Dave, I know you’ve hired a lot of college students “in the past, and this has been so valuable for me, “and I know I’ve done some really good work for you too.” He said, “I think there’s a business model here.” And I said-

– Yeah?

– Right. And Rob went from being my apprentice, my executive assistant while in college, to being my co-founder and co-CEO of Apprentice, the purpose of which is to connect the world’s top college students with great entrepreneurs, business owners, and leaders. And, so we’re off to the races, we’re already in seven figures, Rob is a million dollar entrepreneur at the ripe old age of 24, how amazing is that for him? And, it’s been a really exciting journey because we’ve got two sides of the marketplace. Very, very big, right? So there’s millions of college students, there’s millions of entrepreneurs, small business owners and business leaders that can benefit from working with college students. And so I’m just incredibly excited about it. The biggest thing that’s holding us back is peoples’ poor delegation skills, which is why I’m writing the book on it so that I can help them, and hopefully the idea is to do what for Apprentice with our next book, what we were able to do for Likable with my first book, which was called “Likable Social Media,” and really helped to build a brand.

– That’s awesome, man. Well that is a really, really cool story. Let’s wrap the official episode here. If you guys like this, drop us a like, a comment, I’m definitely going to check out Apprentice. Let’s continue talking about Apprentice and about delegation here. If you guys want to hear Dave and I’s conversation continuing, check it out on the website at, or on YouTube. So thank you very much. And Dave, you stay online just a minute. There’s a couple of follow-up questions that I have for you, and I’m actually, I mean I’m a leader and I would self-rate myself as a poor delegator, right? So I’m really interested in getting better at that, and I think that your model definitely makes sense. I just want to drill a little bit deeper into some of ’em, like on the setting the vision piece.

– Yeah.

– So with setting the vision, I’m wondering, and in our world, like we’re performance marketers. So a lot of things are, they’re tangible, but they’re, you can’t pick them up and feel ’em. Like, I’ve got a vision right now, and I think it’s shared but it’s a little bit squishy in some people’s minds. Our latest thing is called RDO or Revenue Driven Optimization, and the idea, the big idea behind it is that we basically use post-conversion signals to help the algorithms, the ad algorithms, more effectively find the leads and prospects that become customers. So to give you an example, most advertisers, they’re, you know, driving traffic to a site, they fire a conversion when somebody fills out a form, and then a whole slew of things happen after that, like within CRM a salesperson picks it up, they mark it as a deal, but none of that post-conversion activity makes it back to Google or makes it back to Facebook. So Facebook has no way to know which leads were good and which leads were bad, right? Not the case in E-Commerce, but in lead generation. So our thing that we’re hollering right now is RDO, which is this idea of program, you know, training the algorithms, and I’m having trouble articulating that vision well I think, you know what I mean? Like so that S, like, I have it in my head, and I’ve, like you see back here I’ve got charts and graphs and stuff, and I’ve got like written documents about it but like, in your experience, what are some effective ways to, you know, get that vision to be heard, understood, shared, you know, motivating.

– Yeah, yeah. Good, point, and cool concept by the way, I like it. The marketer in me likes it.

– Yeah.

– So, couple of things. First, we can virtually never communicate enough internally. And we think people are paying attention to us, so we often under-communicate because we assume that people are paying attention to us the first, second, third, fourth, fifth time that we’re saying something.

– Yeah.

– They’re not. You know, people really don’t, I mean, even the very best employees in the world that I’ve had, that would run through a wall for me, care a lot more about their friends and family than they do about me. And that’s okay. What the hell’s wrong with that? That’s life! Like, of course they do!

– Yeah-

– So, with this insight, when I am setting a strategy and vision, when I am, communicating that strategy and vision, I am maniacal about over-communicating it early and often, and via every single channel. Email’s the worst channel. So, I never ever, ever send out an email and then expect that literally anyone would’ve read it.

– Right.

– So, it’s wrapping up, I’ll give you an example. You know, along with strategy is core values. So we open and close our team meetings at Apprentice with mentioning our core values. Mentorship, bi-directional mentorship, grit, and being enterprising. And we are constantly drilling those in, over, and over, and over again. There are so many companies where core values are like an afterthought and people couldn’t even name their core values. Like to me, whoa, then what’s the point? So, I’m maniacal about communicating out that strategy and vision over, and over, and over again and via different methods, email, Slack, in-person meetings, Zoom meetings, phone, you name it.

– And so you’re verbally communicating it for the most part. Or is there some kind of document, or-

– Yeah, I mean, in writing, on Slack and email too but again, with low expectations around readership any given time, that something gets sent out. People just have too many messages from the world and they tune out most of it, including mine. So, that’s one major principle. And the second principle that I would just say, and I’m sure you already know this, but I’m just going to say it anyway at the risk of sounding slightly patronizing. I keep things as simple as possible. Acronyms, short, simple. You know, any concept, including the one that you just described can be drilled down and simplified, and then do that same thing again and again, and again. Which is why I’ve written an entire book, 200 pages, that’s basically, I gave it to you in three minutes. You don’t need to read-

– Yeah-

– But no, sorry, you don’t need to buy or read the book, sorry my publisher! But really, being able to drill things down. Simple, simple, simple, like I’m talking to a first-grader. And I have a first-grader, so that’s a good use, you know, a good opportunity. By over-communicating and by simplifying the message I can ensure that as many people as possible hear it.

– That’s good, that’s good. I would love an example, like a Likable. ‘Cause when I think about a vision, like that could be, you know, like that could be a long document. It could be like a five-pager kind of a vision, but like, I’m interested to hear a Likable or an Apprentice, like, as an example of how you would deliver that.

– Sure, you mentioned Likable, so I’ll give you a couple examples, even though this is years ago, and my wife’s been running that company for the last seven, eight years. We co-founded it, and I ran it towards the beginning, but I stepped aside. So let’s do one Likable example and one Apprentice example. When we launched at Likable, we were really focused on subscription business, which is rare for agencies. Most agencies operate on a-

– Projects.

– And we basically drew a line in the sand and said, “We’re not pitching, “and we’re not doing project work anymore. “We’re doing retainers. “This is the focus, period, end of story.” Now this was very hard for people to hear. That’s in the counterintuitive and counterthetical, but we just did it and we just repeated it over and over again, and we lived by it. So we had that mantra, and we made a decision at the strategic level and then we executed against that. We communicated it, we had some tough decisions around things to say no to, but we were able to build a really valuable business because we were focused exclusively on subscription retainer business. Apprentice. We recently re-launched, we recently, reiterated on our core product. So one of the real differentiating factors of Apprentice over like other sort of college student internships is that we’re year-round, right? So you’re not just getting somebody for the summer or for a semester, you’re getting a year-round commitment. But we recently, iterated a bit in creating six-month rotations, so that individual apprentices would be expected to do six months with a company, and then typically the new model is that they will move on. And they will be replaced by another apprentice. Now if both the apprentice and the entrepreneur really want to keep the same apprentice and they both want to, they can, but the new default is going to be six-month rotations. So a major shift in strategy, and so again we’re communicating it early and often to all of our sales people, to all of our account managers, to everyone that would have potential client contact, so that the new model is in their head. You know, of course it’s in the new sales deck, but more than that, it’s being communicated very frequently by all of our leaders, and of course it starts with me in order to help it really get drilled down. And, I mean sometimes I’ll sort of make fun of how maniacal I am about something like this, you know, but I’m still maniacal about it because I’ve just seen too many times where, new things get lost and not really focused on because there isn’t a maniacal leader that’s really driving that strategy down from the top. And, because they’re too busy doing other shit, that they shouldn’t be doing.

– Got it, got it. So in the case of Likable, it’s like the core values that you had, plus the idea of retainers together, sort of form the vision. ‘Cause that would make sense. I thought that you were… so it’s almost like a BHAG in a way, kind of thing.

– Well, okay so, forgive me. The specific ideas, both specific ideas I gave you for Likable and Apprentice were more, they were strategic, but they were less huge 50,000 foot view. The 50,000 foot view of strategy and vision, is every quarter, I meet with all of our team leaders for each company and we do a one-page strategic plan, the model of which is from Verne Harnish, the founder of Entrepreneurs Organization, and-

– Oh yeah.

– And a fantastic, you know, author, thought leader, an entrepreneur.

– Yeah.

– Has a great coaching company called Gazelles that works with lots of great business owners that might still be watching or listening. And, so we use that to set the overall, the vision really should never change. The vision of Likable, you know, was for 10 straight years, to create a more likable world. Like more likable content in every feed.

– That makes a lot of sense, yeah, and we’re an EOS company. So very similar to that model.

– Great.

– And in EOS they call it the VTO, the Vision Traction Organizer that lists out the core purpose, the core values, so I guess, it makes perfect sense. So is it right to summarize it, like, okay. So a vision, like in setting or sharing a vision, we’re not talking about the company vision necessarily. It could be a vision for a specific initiative, or a specific program, like, hey!

– That’s right-

– You know, or whatever one of your quarterly rocks are.

– That’s right, that’s right, exactly. Because what I’m trying to do, I mean, yeah. The reality is, on a day-to-day basis, you’re not doing all just totally grand strategy and vision stuff, you are doing, you know, more quarter-to-quarter stuff, which is fine. The challenge isn’t doing that, the challenge is doing all this other stuff, like, you know, just random stuff that we all get bogged down on because we think we’re the right person for the job, we don’t want to train somebody else for it, we think we can do it faster, you know, we think we can do it better, that’s the stuff, that keeps us from focusing on the big quarterly strategy and vision.

– Right.

– And the grand scheme of things, right? So that’s what I’m focused on helping folks get, with this next book get, unblocked on.

– I’m absolutely going to read that book, and I would love it we had an hour or two marked off. I feel like I could just talk to you for many, many hours on end, and it’d be delightful. I’m curious though, like for the last few minutes that we have here, I’m curious, just like, kind of about your background in growing up. Like take us back to Dave the kid, and just like walk us through the steps. Like what were you like as a kid, where did you go to high school? Like, how did you you become you basically?

– Okay, cool! A big change from all the previous stuff, but fun. I grew up in Brooklyn, New York. A very big part of my growing up was having a bipolar dad, which was a great struggle, but forced me to become much more independent and responsible for my younger brothers at a very early age, and of which I wrote about in my next fiction book that comes out in June. It’s a YA book called “Normal”, about four kids growing up in New York city. One of them is very, closely based on my growing up story, and I went to a amazing public exam school in New York City called Hunter College High School, that I’m very, very proud of because it’s free, but the education is phenomenal, and the network is phenomenal. In my class, one of my buddies was Perry Chen, who founded Kickstarter, multiple New York Times bestselling authors. I mean it’s just an amazing, Lin-Manuel Miranda, I was his TA in math.

– Wow-

– Elena Kagen, a Supreme Court Justice, just an amazing group of people at Hunter. And then I went to school in Boston. My first job in Boston, was sort of pseudo-famously as a ballpark vendor, selling up and down the aisles, and that gig is only based on commission and tips. And it’s a seniority based system, so you have to work for years before getting the beer or the hot dog. So I sold a product called Crunch ‘n Munch, which was the worst selling product in the building. The first night sold six boxes, came back the second day and ended up developing a shtick that helped me sell many, many thousands of boxes and get quite a bit of media into Boston, on ESPN Sports Center. And the makers of Crunch ‘n Munch flew me down to do a Monday night football game as the Crunch n’ Munch guy. So, that was sort of my falling in love with marketing and PR and entrepreneurship, sort of the beginning of that journey.

– Fascinating, so you just killed it in that stadium. What did you do? What was your shtick?

– I sang and danced a lot, I juggled boxes, I tossed them and then, I’ll tell you though, I’ll tell you a story about the one smart thing I did. ‘Cause I was, really the only thing that I did was I had courage to be laughed at, and I really wasn’t afraid of being a total goof, right? I wasn’t actually talented at singing or dancing, but I was just out there and able to put myself out there. But the one smart thing I did was, after my very first Boston Herald feature, they did a big two-page kind of spread about me, basically saying the Celtics and the Bruins won’t make the playoffs this year, but this guy is getting everyone’s attention right? So that night, somebody was sitting in the front row, who obviously brought a Sharpie to try to get autographs from one of the Boston Celtics. He asked me to autograph a box of Crunch ‘n Munch. So, I signed the box and then I thought, you know what? Huh, this is actually an opportunity. And the one smart thing I did during my three years as a Crunch ‘n Munch guy was, I asked that young man if I could borrow his Sharpie for the night, and I proceeded to sign every box of Crunch ‘n Munch unsolicited, for the rest of that night. And what I was actually able to do in literally one night, was create a perception in the building that not only did you need to buy a box of Crunch n’ Munch from the Crunch ‘n Munch guy, but you needed to get it autographed. And in that moment, sales skyrocketed and my income went from 300 a night to like 1,000 bucks a night. You know, for a college student, it was really remarkable.

– Wow, so a natural promoter, a natural marketer, that’s awesome. And then, so from there, and I know we’ve only got two minutes but from there, was Likable your first, yeah, Likable was your first like, real company? Or did you do other things-

– Yeah, I did a small sort of consulting company first, but yeah, Likable was the first real company and it really came out of another crazy story. I ended up getting married at a baseball stadium and we couldn’t afford a traditional big wedding, but I wanted to have a huge wedding. And so, we partnered with a minor league baseball team, the Cyclones, and we took over all the sponsorship inventory for the game and resold it to our wedding vendors, in exchange for getting them some PR. So, sponsored our flowers and Smirnoff sponsored our alcohol and David’s Bridal sponsored our bridesmaids gowns, and Entenmann’s sponsored our desserts, and so on and so forth. We raised $100,000 in sponsorships for an amazing wedding, got married in front of 5,000 baseball fans and 500 friends and family, and the event generated so much media that after the event, our vendors said, “This was awesome. “What are you guys going to do next?” And we couldn’t get married again so we started a marketing company instead, and 1-800-FLOWERS and Entenmann’s were two of our very first clients for Likable.

– That’s so cool, man. You are, just fascinating. Can we be friends in real life?

– Let’s be friends, link in with me if we’re not LinkedIn.

– Dude, I’m about to go and buy all your books, including the new one that’s about to come out. I’m going to go to Apprentice and hire myself an apprentice probably, and just study the stuff that you’ve said man, because you are definitely a brilliant person.

– Well thank you, I very, very much appreciate it and love what you guys are doing, and performance marketing is very, very smart and underutilized by many, many, many companies. So, I’m delighted to hear that you are at it building what sounds like a great team and a great vision with WebMechanix.

Dave Kerpen

Dave KerpenFounder & CEO

Chris Mechanic

Chris MechanicCEO & Co-Founder

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