If you’re an entrepreneur stuck trying to find the perfect mentor—someone two steps ahead who will take you under their wing, give you the playbook, and stick with you through thick and thin—this episode is a must-listen.

In this episode of the Unsexy Entrepreneurship Podcast, co-hosts Charles Harris and Dr. Seth Jenson debunk the myth of the “mega mentor” and reveal a smarter, more realistic path to growth: building a portfolio of micro-mentors. This isn’t about chasing gurus—it’s about curating your own board of advisors who can help you with real-time, tactical decisions in the trenches of business.

We cover:

• 👎 Why the idea of a “forever mentor” is outdated—and potentially harmful
• 🔍 How to identify and approach the right people with the right questions
• 🛠️ Why a mentor is more like a contractor than a guru
• 🤝 How to build relationships with mini-mentors without feeling awkward
• 💬 Why mastermind groups, DMs, and 15-min Zoom calls are more powerful than you think
• 🧠 How to use social capital to get answers when you don’t even know the right question
• 🚫 Why even Mark Cuban can’t answer all your questions (and why that’s okay)
• 👣 Why your journey to expertise can’t be skipped—and how every “failed” convo is part of the process

Whether you’re just getting started or looking to scale, this conversation will help you reframe how you think about mentorship, connection, and building your business support system.

Got questions for Charles and Seth? Submit them HERE.

and welcome to the Unsexy Entrepreneurship Podcast. I am your host, Charles Harris, and as always, I am joined by Seth Jensen. All right, Seth, how are you today?

I'm doing all right, I'm doing all right. It's a good Monday.

But it's funny because we were just talking before we started recording about an active question in your business and it just conveniently coordinates well with what we wanted to talk about today. Tell me about your mentoring dreams and desires.

Yeah.

Yeah, so this is always hard, right? Because I worked at a big CPA firm, and then I worked for a big startup, and then I worked for a mid-sized company, and then I started my own firm. So I don't have many people I personally know that are the next step ahead of me. And that's what I've always heard for mentoring, is that you should find someone that's

the step ahead of you or maybe even two steps, right? I don't know many people in that situation. And I know a few, but not well enough to say, I pick your brain over this idea or this idea? And then even if I do know them well enough and a lot of...

Right.

A lot of cases they're my direct competitor, right? They live down the street or we're communicating with the same people. And so, I mean, I can ask them, but it also still feels a little bit odd.

Yeah, yeah, exactly.

Yeah. You know, it's funny you say direct competitor because my career was, you know, especially my consulting business was built not from competitors per se, but like the big thing that jumped started my career as I did a tour of all the best entrepreneurship programs and incubators in the world and collected best practices and people really willing to share. And of course I shared back.

But in some ways, universities compete with each other, and incubators compete with each other, accelerators compete with each other, so it was interesting that they were willing to kind of open up their books and show me their best practices and their secret formulas. And to be perfectly honest, in my field, there weren't a lot of eggs or silver bullets, and so I don't think anyone was giving away some secret formula. I think they were more hoping that I would come back with secret formulas for them.

But it was an interesting experience because at least universities, even though their competitors are willing to be open, and so I was able to have kind of 20 mentors in early in my career all helping craft. And now I'm going back and giving back, and now I have something to add to that conversation, which is really rewarding. But it does kind of, in most industries, that's a problem. Most people aren't willing to just be like, yeah, here's all the best practices, competitor. Go use them to take my customers from me.

And accountants are

great. I've mentioned accounting influencers before. That's where I've gotten most of my ideas and direction. But it's very different than real people working in the field right now doing the thing.

And that's such an interesting concept. It's kind of new to our day and age that mentoring as an influencer is a thing. Like people go to these people for information, which ironically their job is not the thing that they're mentoring on anymore, because now they're influencers. Their job is to make YouTube videos and things like that. And so it's a really fascinating thing where it's like...

Yeah.

the mentor influencer, their incentives aren't quite aligned always because they're driving engagement and they might have really good information, but they're probably, their day to day is no longer building the company you're trying to learn how to build, right? Because their day to day is now producing content about it, which is a different thing. So yeah, it's like nice to have all these free resources and there's definitely gems to be had, but it's a weird world. So.

fantastic gems. Yeah.

I think mentoring is so important but so misunderstood. I think you're not alone. In fact, I know you're not alone. work with...

dozens of entrepreneurs every week and they'll come into my office and be like, hey, I need to find a mentor. you know, I think I've got this great start to my business, but like, I really just need a mentor to help me get to the next level. And the reality is I think we all operate with this idea in our heads that...

There's this champion out there that's going to be like, like we're boxers in a ring and we got to have that person in the corner that's going to like mop us up and clean us up and slap us on the butt and get us back out there for round six. and, and I, I honestly have come to realize after doing this for a long time and helping hundreds of entrepreneurs that the mega mentor we're all hoping for is a myth. It just doesn't exist. And I don't know exactly where this concept started.

Maybe it's these reality TV shows with the mentor coming in to teach him how to sing or whatever, or maybe it's these kind of legendary figures in business. Yeah, yeah.

Yeah.

Maybe, yeah, the legendary angel investors that come in and swoop in and save a business and believe in

the Google or whatever it is, right?

And often the stories we hear about mentors are coming from mega successful people. And their stories about the mentor that changed their life fit a nice narrative in retrospect, but aren't as all encompassing, I think in the actual history as it feels like in retrospect, right? they'll talk a bit, they'll like pay homage to this mentor that came and was so instrumental. But if you actually look at the day-to-day buildings like,

⁓ It's a much more specific contribution that mentors give rather than this general kind of, you know, guardian angel type situation. Anyway, all that's to say, if you're a young entrepreneur, don't go, you know, on the quest to find the mythical mega mentor.

Because the reality is most people don't have time to volunteer dozens of hours every month to help some young person, right? Like that's just not likely. They've got their own lives and businesses to run. And so kind of not very many people just waiting to take some little person under their wing. And the reality is people might even try to be that for you, but

If they're not getting paid to do it, there's other things happening in their life they're gonna eat away at that good desire they had. They've got families that need their attention, they've got businesses, all of these different things. And so unless you're paying them for that service, it's unlikely they're gonna deliver even what they would like to deliver for you. So step one, give up on the myth of the mega mentor. And then step two is instead build...

a portfolio of little mentors that help you do specific tasks and answer specific questions. So what's better than one person that honestly doesn't have all the answers even if they pretend to is having a portfolio of dozens of people. We've talked about this in the social capital episode, but having lots of relationships with people that can answer specific issues with your problem, with your business. Freudian slip here. Problem or business, maybe the same thing.

you

Oftentimes they are.

And so it's a paradigm shift, but I think it's an important one.

So this brings up an interesting question too. So I am in a mastermind program, or a mastermind group I should say, not a program.

And I love my mastermind group. They're fantastic. None of them are accountants. None of them fit at all of what I'm doing. And so in some ways they can be helpful in marketing, networking, and that side of it. They're actually very helpful. And I think they've been a huge help on accounting and business side. They haven't been helpful, but would you consider them mentors, even though they're kind of more like peers?

absolutely. Yeah. And you've got to open up the concept of what a mentor is and maybe even get rid of it. Maybe you don't even need to think about it in terms of mentoring. But in just the reason a mentor exists is to help curate information for you so that you can get progress in your business. Right. That's what it is boiled down to its essence. And the reality is it's kind of a club.

And you don't need a club for your business. Your business needs surgical tools. so taking a more surgical approach to getting the information your business needs is more productive. And so your mentor, your mastermind group are going to be good at maybe three things. And so when you have questions about those three topics, it might be ad spend, it might be client relationships, it might be the emotional aspect of building a business. You can go to them and get answers in those three.

specific

categories and find the scalpel here and the shoot I don't know any surgical scalpel is literally only surgical instrument I know you can find the scalpel there the bigger scalpel here the the mini scalpel yeah the clamp so you find those specific instruments instead of just trying to find the big club that's gonna fix everything for you

The clamp.

And then you're gonna look elsewhere for other things. And so your competitors might be willing to share one's very specific answer. Like, hey, what software do you use to get this thing done, right? Like, that's not gonna change their business or feel like they're gonna give you a leg up or anything like that. So you might be able to use competitors, your peer competitors, for that specific question. So that's the way you should approach this is...

Instead of focusing on some external person as being this genie in a bottle, focus on investing yourself in your ability to exercise a large portfolio of contributors and get really good at reaching out and getting specific answers from a wide variety of people. So that's investing yourself instead of going on the search for the Holy Grail mentor.

And let's be honest, it's more work. That doesn't feel as good. We want a little guardian on our shoulder. But the reality is you're gonna waste a lot of time and there's no such thing. There's not one person, even if you had Mark Cuban, just like you could shrink him down and just perch little Mark Cuban on your shoulder all day, he's never built an accounting firm. He doesn't know what software accountings people use. He doesn't have advice on how to build your small, medium sized business.

good at a lot of things but he doesn't have all the answers and so do the better thing and invest in yourself and in a portfolio of contributors.

So this brings up a question for me, because I have very specific questions, but oftentimes I think my questions are wrong. And what I'm trying to figure out is probably the wrong thing to try and figure out. So who do you go to when I'm trying to think of a good example?

Ooh, yeah.

Mmm, that's next level.

I'm, let's say I'm just struggling on time and having the right people in. And so I think the solution is to hire another person, but they think the solution is to get a software or, or what the real solution is to get a software, right? But I don't know that because I don't know my actual issues. But then I go to an HR specialist and I'm like, I'm thinking about doing this. Like, how do you know when to do, when to hire someone?

Mm-hmm.

Mm-hmm.

And they're not going to know the answer to like, how do you know what questions to bring to who?

Ooh, I like that. This is why we're besties, Charlie. That's such a good question. And if I understand it right, you're asking, you know, what if I don't know what I don't know, right? And so, you know, and...

Yeah, that's a better way to

word it.

And the reality is that's gonna be true all the time. And the fact that you're self-reflective enough to be aware of that potential issue says a lot about you and the way you operate your business, because most entrepreneurs aren't self-aware enough to realize they don't know what they don't know. They just assume the thing in front of them that they're thinking about now is the right thing to be focusing on. So again, there's obviously not, there's a couple things here. There's not,

the right answer to any question in business. There's not the optimal prime, you know.

know, platonic ideal to any question you're asking. And I think we've all got to come to grips with that as entrepreneurs. The right answer is the one that gets the job done. And different entrepreneurs are going to use different tactics. And if they're getting the job done, it's the right answer for them in their business, right? And so that's the other thing is that's another reason there can't be the perfect mentor, because there aren't perfect answers to the questions. so what I...

Invite entrepreneurs to do is to seek context.

and to try to understand the bigger picture of the questions they're asking. And there's lots of different ways to do that. Sometimes, you know, Google and AI can help provide context, but ⁓ often it involves going and talking to people about their businesses and how they're running and seeing a little bit of the big picture and experiencing a variety of perspectives as well, right? Because you're going to piece together the context, not from a singular perspective, but from a variety of perspectives. So it's yet another reason to try to incorporate

lots of small mentors in your process. But at the end of the day, you'll never arrive at the perfect question.

And as long as you're focused on the fundamentals and core of your business and making sure that it's thriving, you're providing that core value to your customers and you know who those customers are, then you don't need to stress too much about it. And you can just have that open learning mindset and again, slowly get more context, which will help you ask better questions. But it's work. Again, that's why I talk a lot about entrepreneurs being experts. There's no...

There is no, you can't hack your way and skip the expertise gaining process. And which is nice because it means there's no such thing as wasted time. You might go invite someone to lunch that you'd like to learn from and you go asking a specific question and then you realize, well, they don't really have much to say about that, but they did bring up this interesting thing I hadn't thought about before. They have a very different approach and maybe I don't like their approach, but it has made me think differently about this thing, right? Like it's, there's no wasted effort.

It's all just increasing your context, increasing your expertise, and that's gonna ultimately benefit your business accordingly. But it's such a great question, Charlie.

Yeah,

it's interesting because I'm now thinking of mentorships as almost contractors, right? So like a really, really common problem I see with businesses I work with, they'll come to me and they'll say, my cash flow is miserable. I need more clients or I need more sales. And then when I look at their cash flow, I'm like, well, you're spending all this money on worthless software. You're not using your

spending twice as much on on labor as your competitors. Like clearly something is going on here. People aren't working or you know something along those lines. And so we can we can go to a marketing expert and say and ask what's like I need more clients and they'll say absolutely and then they'll suddenly help you find more clients but it's not fixing the underlying issues. And so that's

Yeah.

It's interesting to think of it like that, right? Because you're going to these mentors, they don't really know the whole picture. They might not have expertise in every area. so it's just like hiring someone else. And boy, it just even more issues, right? Like mentorship is kind of free consulting in some ways. If you can get lucky with good mentors.

Yeah, absolutely. it's funny because this works both ways, right? So this is important to understand as you're seeking mentorship, but also when people come to you for mentorship, right? Both of us have people reaching out to us and asking us, we have successful businesses, we have some expertise in this area. We have to be humble as mentors to realize we don't have all the answers. We don't have all the context. And so I give...

less advice than I used to when I was early in this journey, but it's better advice, it's more targeted advice. And I always try to give the context to my advice to the person I'm working with so they can see whether it applies to their specific circumstances or not. Because I work with lots of mentors, or rather, lots of mentors work with my entrepreneurs. And...

You can tell the experienced ones from the inexperienced ones because the inexperienced ones will try to have an answer for every question they're asked.

and the experienced ones will know and they don't have the answer and they'll just own it and be like, I have no idea, I've never dealt with that before. But here's someone that comes to mind that might know something about it, right? Or here's one way you could look at that and get your own answers. So when you, and every entrepreneur will eventually become a mentor because that's kind of how this ecosystem works, but remember that, bring that humility and you know.

Be good at what you're good at, but don't try to be that guardian angel with all the answers because nobody can do that.

Yeah, it's interesting. get reached out to by other CPAs that are starting their firms pretty often now. I don't know how that's happened, but for some reason people think that... I guess so. But it's been interesting because they always ask me, do you find that first client? How do you do these things? And boy, all I can say is this is how I did it. This worked for me.

Because you're a big deal, Charlie. You're a big freaking deal.

Yep. And that's valuable. Yeah.

just gotta start putting yourself out there and see what works.

yeah, and I think it's the right answer. But I can't say post on LinkedIn for seven days and you'll get your first client. I can't do that. That doesn't work. Even though...

Yeah.

Personally, I can guarantee I'll get a client in a month by posting on LinkedIn every day. I can't guarantee that for another accounting firm. It's very interesting to kind of realize how specific and targeted advice I'd give myself versus advice I'd give others is.

Mm-hmm. Yeah.

Yeah, it's cheap. Advice is cheap, right? And so sometimes it's tempting to just blurt out something that sounds really good and makes you look really wise. But at the end of the day, know, again, it's not necessarily the full breadth of how you even feel about that, right? advice is cheap, so you've got to think about it as valuable in proportion to what it costs.

I'm in an interesting situation because I am, by definition, an expert in entrepreneurship. Like I have read the academic literature, I've contributed to the science of entrepreneurship, I've worked with, at this point, thousands of early stage entrepreneurs, I've been in the weeds with them, I've built my own successful consulting practice. Like I should be the person with the answers if there is a person. And yet,

I'm often, when I'm working with young entrepreneurs, all I can give you is a process. I can't give you an answer, but here's the process to get the answers you need. Because entrepreneurship is so idiosyncratic. Your specific journey, I've worked with hundreds, I mean thousands of entrepreneurs.

But I might never have worked with one exactly in your situation. In fact, I probably haven't because everyone's situation is so different. Everyone's clientele is so different. The market is vast. The economy is ginormous. And so even myself being with, you know, I've got my PhD in strategy on the wall and again, all this, all these hours and hours I've worked with people.

I still cannot be anything close to the guy with all the answers. And so that should tell everybody that they shouldn't be looking for that because I've spent a decade trying to have as many answers as possible. And so.

But again, I think this is actually good news because again, instead of me, an invite system, instead of looking outward for the silver bullet, look inward, develop your expertise, get really good at asking for help from a lot of different people and let your questions guide who you reach out to. You're not seeking some amorphous mentor. You're seeking the person that's going to help, you know, know, boost your sales. So you're sitting there trying to solve that specific problem. You're asking that question yourself and the universe will start showing you people along your path that

have sales experience and know how to build sales processes and sales teams because you're asking yourself that question, you're gonna find it in your environment. That's just psychology, that's just the biology of problem solving. let your questions guide you and then you'll find those mini mentors in the dozens.

So, boy, I've already come up with a few dozen people that I should reach out to and talk to, which is helpful. it's funny because I think I probably already have some mentors. I mentioned my mastermind group. I would consider you one, my father who has some great experience. yeah.

haha

And likewise, we ping each other all the time. Like, if I've got an accounting

question, you get a text from me and it probably, hopefully, you know, doesn't drive you nuts, but we ping each other on little stuff all the time, right?

No, no, no.

So, but there are other people that I know. So how do you get them to mentor you? So I'm thinking of a direct competitor who I would love to mentor me and we're competitors, but there's enough people in the space and we have similar niches, but still I don't feel, I don't know.

you think there's an opening to have a relationship.

she probably would never give me

clients. She would never give me clients. She'd take them instead. But it seems like, boy, maybe I could get her to mentor me and that would be awesome. How do I do that?

huh.

Yeah.

Yeah. So again, I think you want to make it easy for them to say yes, right? And so finding out the right way to do that, right? Like it could be a trip for coffee or a lunch or, again, people want to, the nice thing about this is people want to feel like their expertise is being seen.

and recognized. And so it's really easy to go and, you know, I always tell students when they're crafting these emails or these texts or reaching out to someone, be honest with.

your respect for what they're able to offer. Like you're going to them for a reason. It's because you're impressed with the clientele they've built, the firm that they've crafted. And so leading with that and being like, hey, I love what you do and I want to be more like you. And I have this question and I really think you're the perfect person to ask. Could I take you to lunch and pick your brain about this? That's hard to say no to, right? People will and that's fine, right? It's just like in sales, you're going to get nos and that's

That's fine, you keep going until you get yeses, but it's honestly hard to say no to something like that when someone's really sincerely and in a genuine way acknowledging the work you put into what you're doing and wanting to learn from you. So I think that's the formula.

Yeah, nos are easy.

I feel like

an idiot. I've been doing this already. And that's the funny part, right? Like I'm thinking of even this competitor that I thought of, right? I had already reached out. We've already had a meeting just to chat and talk. And I didn't ask any specific questions, but it's very easy to follow up with a question. So yeah, I've already kind of gotten a mentor, right? Like it's just not a formal name.

Haha

Yeah, it's not rocket science.

Yep, exactly. And again, this is the Unsexy Entrepreneurship podcast, right? So like the mega mentor, that guardian angel, that's the sexy idea of what mentoring is. And the reality is it's unsexy. It's just lots of little conversations with people that have the answers. It's investing in yourselves and your expertise. But it's not complicated.

Interesting.

You

and being able to reach

out to the right people with the right questions at the right time.

Yeah.

And we talked about this in the Social Capital episode.

But the magic 15 minute Zoom call is a huge unlock, right? That was the gift of COVID is that now it's totally normal to be like, hey, could I just hop on a Zoom for 10 minutes with you? You know, again, that's easy to say yes to. Everyone's got 10 minutes to, they're already sitting at their computer. All they have to do is click the invite link and then you've got this rich conversation that can happen. So definitely it's not sexy.

Yeah.

but it's powerful and it's real and it's how the work gets done. So build that shadow board, that kitchen cabinet, that portfolio of little mini mentors that can answer specific questions and get you what your business needs and just leave that the holy grail. Let it rest in the cave of wonders with the other myths of entrepreneurship and don't go chasing that mega mentor.

happen upon the Holy Grail, drink it. You know, like I'm not saying there's anything against having mentors that are going to champion you or whatever. That's totally fine. But they're not as valuable in my opinion as this approach most of the time. So

Awesome, yeah.

Interesting. Well, thanks for this topic, Seth. This was really, really interesting and I got a lot out of it. Hopefully everyone else did too. And we'll see you next time on the Unsexy Entrepreneurship Podcast. Thanks, y'all.